Alisa Cohn - Prenups for Startup Founders, Reinventing Your Career, and More | The Tim Ferriss Show | Transcription

Transcription for the video titled "Alisa Cohn - Prenups for Startup Founders, Reinventing Your Career, and More | The Tim Ferriss Show".


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Intro (00:00)

This episode is brought to you by Kettle & Fire. Do love me my Kettle & Fire. I believe I first heard about Kettle & Fire when it was originally recommended to me by one of your favorites. Fan favorite podcast guest and ketogenesis expert, among many other things, Dr. Dominic D'Agostino. So, what is Kettle & Fire? Kettle & Fire offers premium bone broth made with bones from 100% grass fed and grass-finished cows and organic free-range chickens. They can buy bones with organic herbs and vegetables and filtered water and steel kettles. Then, the mixture is slow-seemered for 14+ hours at 130 degrees Fahrenheit to ensure that as many nutrients, collagen, and amino acids as possible are able to soak into the broth. And all that goodness is fantastic for supporting your gut health, immune system, weight loss, your fasting regimen, whatever it might be, and they make it extremely convenient. Just heat and eat. Five minutes on the stovetop or one minute in the microwave. 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I have two of them upstairs from where I'm sitting at this moment. And now Helix has gone beyond the bedroom and started making sofas. They just launched a new company called All Form, A-L-L-F-O-R-M, and they're making premium, customizable sofas and chairs shipped right to your door at a fraction of the cost of traditional stores. So I'm sitting at my living room right now, and it's entirely All Form furniture. I've got two chairs, I've got an ottoman, and I have an L-sectional couch. And I'll come back to that. You can pick your fabric. They're all spill, stain, and scratch resistant. The sofa color, the color of the legs, the sofa size, the shape to make sure it's perfect for you in your home. Also, All Form arrives in just three to seven days, and you can assemble it all yourself in a few minutes. No tools needed. They're quite astonished by how modular and easy these things fit together, kind of like Lego pieces. They've got armchairs, love seats, all the way up to an eight seat sectional, so there's something for everyone. You can also start small and kind of build on top of it if you wanted to get a smaller couch and then build out on it, which is actually in a way what I did, because I can turn my L-sectional couch into a normal straight couch and then with a separate ottoman in a matter of about 60 seconds. It's pretty rad. So I mentioned I have all of these different things in this room. I used the natural leg finish, which is their lightest color, and I dig it. I mean, I've been using these things hours and hours and hours every single day. So I am using what I am sharing with you guys. And if getting a sofa without trying it in store sounds risky, you don't need to worry. All form sofas are delivered directly to your home with fast, free shipping, and you get 100 days to decide if you want to keep it. That's more than three months, and if you don't love it, they'll pick it up for free and give you a full refund. Your sofa frame also has a forever warranty that's literally forever. So check it out. Take a look. They've got all sorts of cool stuff to choose from. I was skeptical and actually worked. It worked much better than I could have imagined, and I'm very, very happy. So to find your perfect sofa, check out That's Allform is offering 20% off all orders to you, my dear listeners, at Make sure you use the code TIM at checkout. At and use code TIM at checkout. Optimal minimal. Make this altitude like in one flat out for a half mile before my hands start shaking. Can I also do a personal question? Now we're the same. I've got a pet time. What if I did the algorithm? I'm a cybernetic organism living tissue of a metal antoscour. Me, Tim, Paris, show. And Aktung, everyone. Just a quick note, stay around until the end of the episode. In fact, listen past the end of the interview to hear Alyssa's word for word scripts she's put together just for you and this episode. That was a follow-up after our entire conversation. They're not in our book, not on the website. First she offers you a set of scripts that lead up to firing someone. Next, a script to help you get feedback in your job so you can increase the likelihood of getting promoted. Even a few scripts to foster great one-on-one conversations of different types including career coaching with your employees and many more. So keep listening after we end the interview.

Transition From Management To Coaching

Alisas journey and when it took a turn from management to entrepreneurship to coaching (05:18)

Hello boys and girls, ladies and germs. This is Tim Ferriss and welcome to another episode of The Tim Ferriss Show. My guest today, we're going to skip the preamble, is Alyssa Cone, C-O-H-N. You can find her on Twitter @AlyssaCone. She's been coaching entrepreneurs for nearly 20 years including many people I know including yours truly. We've done quite a bit of work together. She has advised founders and executives at Venmo, Etsy, DraftKings, Wirecutter, Mac Weldon, Envision and Tori Birch. Among others, she has also coached CEOs and C-suite executives at enterprises such as Dell, Hitachi, Sony, Google, Microsoft, Bloomberg, The New York Times Company, Calvin Klein, and on and on. She's the author of brand new book from Startup to Grown Up, a guide book for entrepreneurs on the leadership journey from founder to CEO. Her articles have appeared in Harvard Business Review, Forbes, and Inc. magazines and she's been featured as an expert on Bloomberg TV, the BBC World News, and in The New York Times. A recovering CPA, we're going to talk about that and one time startup CFO and strategy consultant. She is now in addition to being a coach, an angel investor and advisory board member. Outside of work, she is a very amateur rap artist. I was privileged enough to think view one of the first recordings of said rap and an investor in Broadway shows, two of which have won Tony Awards. You can find her everywhere online on all of the social media platforms just about @alissacone. That's Twitter, Instagram, LinkedIn, Facebook, and of course, at her website, Alissacone, Alissa, nice to see you again and nice to hear you again. Great to see you, Tim, and thanks so much for having me today. It's really great to see you. I am excited to dig in. We are going to as per usual run out of time before we run out of material, but I thought we would start somewhere we have not spent much time previously, which is usually me asking you questions and for help on various issues, weaknesses of mine, challenges, whatever it might be. I thought we would begin with the background, some of your story, because honestly, I'm embarrassed to say that I don't know more of it.

Origins and first steps (07:23)

Could you just paint a picture for us of where you grew up and then the professional journey that led you to coaching, because I know that's not where you started? I grew up in a small town, Hollister, Massachusetts, which is right next to Hopkinton, which is where the Boston Marathon starts. That's kind of my definition, 26.2 miles southwest of Boston. I barely left Holliston until I went to my undergrad college, Boston University, and I was journalism major. I worked in the nonprofit world for a little while. I was a chief of staff to the Provost at North East University, and we were doing strategic planning. The Provost at some point said you can't manage faculty because they have tenure. Even that I was super young, and I thought, "What do you mean? How can it be that people will only do what you want them to do in service of the organization, because otherwise you'll fire them?" I thought a lot about that, and I wanted to go explore that. I did a little stint in strategy consulting at Monitor, and then I went to business school. I went to Cornell, and at Cornell, I got all turned around, and I was no longer focused on people and organizations. I was focused on finance and accounting of all things, and also strategy. I exited business school into PwC into the so-called advanced development program. It's five years to partner, so fast track to partner. I thought, "Hey, this is great." As I got into my life, I will say that I told one of my professors, "I'm going to PwC," and he said, "Well, that will be very refreshing for the profession." I didn't quite know what he meant, but as I went through, I just realized this is not necessarily my tribe. Also, PwC was so big that I just felt like, "Oh, I can't really make a difference here." It was a fantastic firm, and a fantastic experience, but after two and a half years, I'm happy to tell you about it. I had a dramatic moment that I realized this is not for me. I went off to try to figure out what's for me, what do I want to do? I met a coach at that point, and that's when I realized, "Oh, that's what I want to do." Let's talk about two things real quick, Tintra Jax. First, with the provost and the comment that you can't manage faculty because they have tenure, or if they have tenure, that was meant to convey that, "Oh, I'm not going to do it." If we don't have the looming shadow of possible punishment by firing, you can't get people to do what you want them to do. Was that the gist of it? It's what he meant. Then, the dramatic moment, rather than gloss over that, let's go right into it because a lot of people stick around in this walking dead sentiment in some professional job. They don't like for a very, very long time. What happened, I guess, at that time, it would have been at PWC. Yeah. What was the catalyst? I was at PWC. Again, it is a great firm. Also, for me, I just felt like this is not feeding my soul. This is a big four, big five accounting firm for PQ, don't know. I woke up one morning and I just thought to myself spontaneously, "I hope I get the flu, so I don't have to go into work tomorrow." Life goes on. To be honest, with me, 18 hours later, I was being rushed to the emergency room by my boyfriend at the time with the flu. I showed up at the emergency room and I was in Boston. They took one look at me and they wheeled me into this room and they pumped me up with saline. I had a really bad flu. I just thought at that time, that night, as I spent the night there and for the days that followed, I just thought, "I can't do this anymore. It's not me. I can't do it." I thought, "I'd rather be a waitress. I can't handle this experience of not feeling nourished and satisfied." I guess, for me, that moment of realizing I'd actually rather have the flu. I'd rather get sick, so I don't have to go into work. It was almost scary. It was like, "Oh, my body's trying to tell me something." I was wondering, "How often have I not listened to my body?" Because I've sort of head down, forced March, like you can do it because I was very goal oriented. This is one of the first times in my life. I just went off my plant and thought, "Well, what am I going to do now?" I was down for the count for like two weeks and every time I thought about going back to work, my fever went back up and I thought, "Oh, but what am I going to do now?" Like, washed up at 27. What am I going to do now? In my head, I kept thinking these words kept coming through my mind to make a difference, to make a difference, that the work of my hands matters in the world. That's what I set out to try to figure out, "How can I do something that was going to help me make a difference?" What happened?

Goodbye Goldman Sachs, hello new possibilities (12:20)

What did you do? I would imagine a lot of people have that desire, but then they're going to go around in the dark or they never quite arrive at an answer. How did you arrive at an answer? That's why I went through a number of dead ends. I interviewed with Goldman, I interviewed, I was looking for what is the thing that is going to make me happy. I looked into financial planning. I can help people buy a house or go to college. I went down a number of dead ends and then I went to this conference. I was a volunteer at this conference. It was not really like me. It's called the Body and Soul Conference. Okay, hold on. Pause real quick. Yeah. This is just my nature with these conversations. I think the internal process is really important here or lack thereof. PWC, huge firm. Yeah. I would rather be a waitress. Why then interview or consider Goldman Sachs? What led you to consider Goldman? I went to an Ivy League school. I invested all this time and energy into the MBA. All my peers were like on Wall Street or doing some sort of corporate finance job inside of a company. There wasn't a lot of context for getting off track. I didn't know at the time. I didn't have a lot of ideas like, "What are you going to do?" I really didn't know what I was going to do. When you have a pedigree, you have a lot of pressure, I guess I would say, to focus your efforts that only a set of things are good enough, only a set of things are the right things. Yeah. It's not so easy to go off path. Yeah. I think also, if your experience mirrors mine at all early on, there's also a very limited, or at least I had, and I think a lot of my classmates had, very limited awareness of options outside of a few things, very few things. Right. I've been banking, management consulting, big five accounting, that's expanded a little bit, but at the time, really law, perhaps, if you continue with a professional degree. But the types of companies that were recruiting and the types of stories you heard tended to be, at least in my case, from really a tiny, tiny, tiny slice of the total spectrum of possibilities. Definitely. A tiny slice, and again, it was like a sense of you could only do things which were sort of in some way worthy of all that time and energy spent in your education, and again, building kind of this pedigree. And so there's a lot of, to your point, you didn't always know what was out there, but also if you strayed from this tight, narrow list of things you could possibly do, it felt like somehow you were not being successful, you were giving up, you were not fulfilling the promise that you had thought about in business school.

The tipping point and selfapparent authenticity (15:00)

That's how it felt. Why did Goldman not happen? There was three things that happened at once. I interviewed with a number of folks, again, I interviewed a financial planning firms, and I got this interview at Goldman, and I did that interview. And in the meantime, I had gone to this conference, this Body and Soul Conference as a volunteer, and they said, "Sharroll Richardson is now going to, we did this orientation." And then, "Okay, Cheryl Richardson is now going to speak to the volunteers." And I'm like, "Okay, who is that?" And Body and Soul Conference, just to reiterate, not what I would envision the immediate native habitat to be for you. I'll do respect. Right, this is more of a cultural comment than a judgment of any type. So you ended up there because your boyfriend at the time was like, you're striking out, so you might as well come here, or just if you were behind your back, or thought it'd be helpful. He was a yogi type, my boyfriend at the time. And so, he did me the favor of kind of dragging me. Like we should go to this yoga-y conference, and I'm thinking, "Oh, this is not my thing." But I was, Tim, you get the flu, I realized for me, something's got to change. So at that moment, I was more open to something like, "Yeah, I'm a little, I think I'm more touchy-feely or whatever you want to call it now, I'm going to be spiritual now." At the time, it was definitely not my thing. And I would say it was kind of off-plan and off-path. But what the heck? He said, "We look at this conference. Okay, let's volunteer so we can go for free." Okay, that sounds like a great idea. I was sort of in seeking mode. That's when I met Cheryl Richardson, who spoke to the volunteers, and she just spoke, and she was so dynamic. And I just thought, "What's that? I want to do that. I could do that. I saw myself in her." So I was sort of following her around the whole conference, and I thought, "I want to become a coach." In the meantime, this Goldman thing was still happening. In the meantime, I was being recruited by a startup. And so in the end, I got the offer from Goldman to do private client services or private wealth management or whatever it was called. And I ended up taking the job with a startup. And I was the fourth employee into the startup. And after a week or two, I just thought, "Uh-oh, this was such a bad idea." It was sort of chaotic. I didn't know what I was doing. They didn't know what they were doing. I just thought, "Oh, this was like a bad decision." It's quite a transition from PwC to... Yeah. And by the way, I just... The handful of employees. Yeah, I just want to say that was also before the startup world was so mythologized. It was before the startup world was, "Oh, the sexy startup. It was a startup. Why would you go do that?" Even I didn't know why I would do that. And I just thought, "I can't become a coach yet. I'm not experienced enough. I got to take coach training."

Wasting time (18:13)

And I thought, "Oh, startup, I can make a difference there. A small company, I can make a difference." So week or two went by. And I just thought, "Oh, what a mistake. Such a mistake." So I screwed up. This did not happen easily. I screwed up my courage. And I got back in touch with the guy who I talked to at Goldman. And I said, "I just said straight up on the phone. I made a mistake. I should have taken your job offer. This was a bad idea. I would like to now reconsider." And he said, "No." He said, "No, that was the opportunity you had. You made your choice." We had actually a very cordial, quite lovely conversation. And he gave me two gifts in that call. He said, "You know, Alyssa, you have a superpower. Your superpower is that you are very credible. You show up instantly credible." I didn't know that because I was feeling pretty insecure, I'll tell you. And like I didn't know what I was doing. And the second thing he said was, "The reason I thought you'd be great for this job is not because of your background, not because of your MBA, but it was because you've done stand-up comedy. And I know that you have had to deal with rejection. And so I thought that that would be a good attribute for this job."

Sustained comedy fit, Authority and Credible Consulting (19:26)

Let me ask about those two real quick. Yeah. The sustained comedy fit because in a sense you'd be responsible for building your own book of clients. Yeah. Right. Got it. And then credible, why do you think he said that? What does that mean that you immediately came off as credible? I think I have a way of building rapport with people quickly and kind of showcasing, I guess I would say, confidence. I still, as I say to my clients all the time, I don't know what it's like to be with me. I only know what it's like to be me. However, I do know that throughout my life I have been able to exhibit a certain kind of energy that makes people follow me. I mean, I remember actually in fourth or fifth grade, we were in home room and we were doing a play. So we were just kind of, it's like a free-for-all and the teacher wasn't really involved. So we, the kids were all putting together this play. And suddenly everybody came over to me one at a time and said, "Can I play this part? Can I play this part? Can I play this part?" And I was really, literally consciously thinking, "Why are you guys asking me?" I don't quite know what it is, but there are times that people will come to me, I guess because of my energy or maybe the way I speak, I'm really not sure. But he pointed that out to me and that was helpful. I love that the teacher was absent from the play planning. It's like Lord of the Flies. And then Alyssa decides who's piggy and who gets crucified as piggy and so mutiny. Yeah. Luckily I was there, Tim. Luckily I was there. Luckily you were there to hold the ship together. You maintain order. Well, I think as I reflect on our conversations and the time we spent together that you have a very no bullshit demeanor. And I think that probably translates to people feeling confidence in what you say because if you don't like something or you disagree with something, you're very open about that. So I think that gives people, at least some people, a degree of relaxation and comfort, which might sound strange, but because they don't second guess what you're saying. If that makes any type of sense. Thank you for saying that, Tim. And I feel like you said it very different radically. I'm trying to face you. You're welcome. I'm working on that diplomacy. That's good. But I do think it's no bullshit and people say you're very direct. And I don't even think I'm being direct. I sometimes think I'm trying to be less direct, but I guess I come across as direct. That does seem to be a thing. Cheryl Richardson, let's return to this because for me, if I think about temperament, direct quantitative with comfort with the numbers through business school and training for PWC, what was it that appealed to you about coaching? Why did it seem right at first blush in encountering Cheryl Richardson to appeal to you?

Early mentors and The Inner Drive (22:42)

Because that wouldn't be something. Had I looked at your trajectory up to that point, it's not something I would have, at least from what you've told me, I wouldn't immediately have guessed that. I have to be honest, and I've thought about this quite a bit. I always think, what did she say? And I don't know what she said. I have no idea, but she stood in front of the room and she gave off this incredible energy. And it felt like you felt empowered after that energy, after that talk. And then I followed her around for the rest of the conference and at some point she was in a room of like 500 people and she said, "Okay, who wants to stand up right now and get coached?" And I thought, "Oh, what's going to happen?" So someone stood up and she coached this person there in front of everybody for 20 minutes. And I do remember vividly thinking, "Oh, I could never do that." But I also thought, "Oh, I could do that." I saw that in myself and I remembered, I sort of realized that throughout my life, people have come to ask me for advice about networking, about careers, about problems they were having. So I sort of saw myself in that supportive problem solver and definitely to be someone who really makes people feel like you can do it. I sort of recognize that I had that energy inside of me. Let me, for people who are wondering, give people a concrete example of one way that you do this. Because there are coaches who disempower in the sense that they might even be effective, but they take the agency of, like the locus of control, the agency from the athlete, the client, the fill in the blank and sort of become the person who helps fix the other person. And while you are very helpful, I know in our conversations and certainly I've seen you do this elsewhere, if somebody asks you for advice on a given situation, very often you'll respond with, "Well, what do you think?" And they'll say, "I don't know." And then you'll respond with, "Well, what if you did know?" What might you say? It's incredible how far people can get on their own with just a little prodding and no side exit with that type of reframing, if that makes sense to people listening. I was just going to say thank you for bringing that up. And I really try to, to your point, give agency to other people. And the truth is inside of you, inside of anybody. There's a whole chorus going on. There's a whole music in your head going on and how you're feeling. And the person across from me, you, whoever it is, knows more than they think they know. And I think people sort of say almost by habit, "Well, what do you think? Somehow you're the expert. You're the coach." But actually, you do have a lot more internal wisdom than you allow yourself to express. And I think part of my role is to encourage you to tap into that and not let you take side exits, especially at first. There's a sense of, "Hey, there's more there.

An unexpected answer leads to invaluable clarity. (25:51)

Let's be quiet for a minute and reflect and see what's there if you let it arise." Okay. So as we flash forward and flash back, we're doing this memento style architecture in this conversation. So Mr. Goldman, I know, obviously not called Mr. Goldman, but Mr. Goldman says, "Well, actually that was your window." So my answer is now no. But here are two observations. Within the startup, you've realized, "Uh-oh, this was supposed to take a right turn and I took a left turn. This is probably not the best fit right now." And shortly, I guess beforehand, you had had this encounter with Cheryl Richardson. What did you do then? First of all, it was actually extremely helpful that he said that to me because I can get this way and I don't think I'm alone. It's like, "Should I have done that? Should I do that? This was a bad idea. Should I go back? Should I ask him all these questions which can be kind of draining?" So I was actually very happy and proud of myself that I had gone back and asked. I was disappointed by his answer. I was actually quite crushed. Oh no. What am I going to do? But the clarity was so helpful. I don't have to now wonder, "Should I have done that? Oh, I don't know. Did I make a bad decision?" Or also, "Should I have asked him if I could reconfigure this job offer?" I was like, "Nope. That door is closed. All right. Now I know." So I went back to the startup. And to be honest with you, it was fantastic. It was a great experience. It was interesting and fun and engaging. It was the first time I ever met investors. It was the first time I saw what does a CEO do. So I have a proactive nature and I was able to express my proactive nature. All these things needed to get done. And so I kind of figured a lot of things out by myself and with the company, with the rest of the employees. And so actually it was fantastic. It was so good I joined a science startup. What did the first startup do? It was called Corporate Alumni. So it was a very early precursor of LinkedIn. Amazing. Yeah, which means timing is everything. Yeah. Timing, timing, timing. It is important. Yeah, I don't think you're alone in the questioning yourself and decisions and so on. I was joking with somebody last night. They were talking about their on-sitting, and I was like, "Oh, you mean when you lay down to go to sleep?" And your mind is like, "Oh, thank God. We have some time. I've been waiting all day to talk to you. Here we go." Yeah, yeah, exactly. Yeah.

Was Jessica on a collision course with coaching all along? (28:23)

Okay. So I don't know if there are other dots to connect beforehand, but at what point did you take your pilgrimage to San Diego? Was that years later? Was that shortly thereafter? And also I should ask, while you're working at these startups, were you exploring in your off time the world of coaching or did you really just chalk it up to a weird, interesting experience that grabbed your attention? And that was that end of story. Let me move on to my real career in startups. No. In my mind's eye, whether it was conscious or not, I was on the path to coaching, definitely. And Cheryl, what should I do? I followed around the conference. What should I do? Should I take coach training? So I took coach training, and I coached all my friends. I insisted on coaching all my friends. And I even at some point, I don't remember exactly what, but I hired my own coach. But in the meantime, I left the first startup. I went to the second startup. I was the CFO for a little while because the CEO came to hire me to be the GM of the Boston office. He was in California. And he saw on my resume, he hadn't seen my resume yet. He saw on my resume that I was a CPA. And he said, "I see you're a CPA." And I said, "Yeah." And he said, "You want to be the CFO?" And I said, "No, I really don't." And he said, "Listen, I have a rent to CFO. She's robbing us blind. I need you to come to California and be the CFO for a while. You can hire a replacement and then come back here to Boston and be the GM." That was what they hired me for. And I said, "All right. That's what I'll do." So that's what I did. So I spent some time there as a CFO. I kind of got things sorted out. And it was of course a very good experience. And then I came back to Boston and I was the head of the Boston office. And it was an incredibly good experience because I kept telling myself, "You can't be a coach yet. You're too young. You're too young. You don't have leadership experience. Who's going to believe in you?" Well, after a couple of years of the startup world, you have leadership experience. So that was in 2000 timeframe, 2001. And then of course, it got exploded. And bloody waters. Exactly. So everything exploded or imploded, I should say. And they said, "They shut down the Boston office." And they said, "Come to California. We'll have a job for you here." And I said, "No. I'm going to become a coach now." And that was like, "Boom. I had done all the things. I'd taken coach training. I'd hired my own coach. I coached all my friends." And it was on Friday. I'm going to become a coach. And on Monday, I became a coach. That was my panel.

Adding value by coaching at the top and bottom of the ladder. (31:08)

Couple of things to double click on. Coaching your friends. Does this mean coaching for free? Did you charge them? Or are you like, "Let me just get in reps. I'm going to learn over the bodies of my early students, just the battlefield. How did you approach that?" I coached them all for free. In fact, they did not want the coaching. I insisted on coaching them. I pushed myself on them. So I should have paid them actually. It's the truth. I got in reps to your point. And then after-- I mean, I would say probably it was after I became a coach. I began to coach strangers for free. So it was no longer friends. It was, "How do I start with somebody who I've never met before?" Did you just panhandle with a little coach for change? Or how did you find these strangers? I asked my friends, "Do you know anybody who might want to coach for a period of time? I'm just a beginner, so I'm not going to be charging." And so I got referrals through that. And you get something out of it. First of all, you get the experience. Also, if you do a good job with them and they're happy, they refer you to other people, which they did, who ultimately pay. Right? You can't make a living, actually, coaching for free. It turns out. And I went to a vendor fair at my gym. I remember vividly and had people sign up to do an introductory session with me. So a lot of people did this introductory session with me. And that was also, to your point, getting in reps. It was a feeling of practicing. How do you practice with somebody? That's also when I saw that you can add a lot of value very quickly for people. Just by listening to what's going on with them and responding and sort of helping them sort out all the things they're struggling with in their lives. OK, so if we look at kind of present day, recent times, we met through, I don't know if we should mention his name explicitly, but we met through a mutual friend, an old friend of mine who was in the process, I guess, when you met him of building up his company, while you were together, sold it for five, no idea, nine figures somewhere. So you went from vendor fair gym to working with people like that, C-suite, et cetera. By the way, I do want to talk about pilgrimage to San Diego.

A pilgrimage to San Diego (33:23)

Let's go directly to pilgrimage to San Diego. So after I had become a coach and coach all these people, my vendor fairs, and finally found someone to-- some people have started paying me. I started coaching. I actually started teaching and facilitating inside of a large company. And so from there, I was able to coach a lot of executives inside of this large company. And I was like, awesome. It was fantastic. And I read about this in the New Yorker magazine, this incredible coach, Marshall Goldsmith, who is well known as the number one coach in the world and all the trappings that come with that. Sixteen years ago when I met him, he was sort of a big deal from this New Yorker article. I was flying to Ireland. And I grabbed a book that he had edited. And I read the whole book. And I was upset about something. And I read the book like, OK. And I sort of remembered, oh, yeah, this is why I love coaching. Oh, yeah, this is what I can do. And I flipped to the back of the book. And I thought, hey, he's in San Diego. I had been anyway toying with the idea of going to San Diego. And I thought, I'm going to find him. I'm going to find him while I'm in San Diego. So when I got to San Diego, I was going to be there for three months in the winter. And I networked everywhere to try to find him. Nobody knew him.

How to pitch yourself (34:40)

So I finally just sent him an email. And I said, Marshall, I'm in San Diego for this period. I would love to meet with you, even if it's just for a little period of time, even if it's for a long time away. But I really would love to just come and spend some time with you. And a week later, he emailed me back. And I was able to kind of do my pilgrimage to go see Marshall Goldsmith, the great Marshall Goldsmith in his home in Rancho Santa Fe, California. Tell me more about this email pitch, because I bet he received a lot of those. And I can't imagine he said yes to them all. So what else was in there? Why would he reply to that? Why would he say yes? You know, Marshall is indeed a very generous person. And it turns out I'm not the only one who met him through a cold email. It was a short email. And I'm sure I described myself as in, you know, I'm a coach. Oh, I know. I'm sure I said, I'm a coach. I saw the New Yorker article that was written about you. I saw myself in that. And I'd love to come and meet with you and see you. And then I kind of let him off the hook under any conditions that will work for you. A short period of time, any time you want. So I think that that prob, all the combination of those things was probably very helpful. - Is there any credibility line that you think helped that email or was that absence? Where you were like, I have done work with A, B, and C or I have a belonging block, nothing like that. - No, nothing like that. - That's incredible. - Yeah. I wonder, even if he is generous, I wonder if you caught him in a good window just because there's a point where you just can't physically respond to all of those if you get a lot of them. So that's great that it worked out. - I think you're right about timing. I think you can catch people in a good window to your point. And probably, I mean, certainly he travels a lot. So as it happens, he was around during this particular period that was gonna work for both of us. - So what happened with Marshall?

Strategies For Personal Growth And Improvement

A sunrise walk around Lauren San Diego (36:31)

- So with Marshall, we took this walk. He even said, come early in the morning. So I said, okay, I'll come early in the morning. He also suggested I bring a dog treat for his dog bow, which I follow in instruction. Good idea. And he walked me around this lake that they had in Rancher Santa Fe. And it was this beautiful lake, this beautiful day. And we were talking, talking, talking. Marshall's a great talker. And at some point, he said, "Alissa, how can I make your life better?" And I thought, oh, I don't know which, I'm not prepared for this question.

Ways to make peoples lives better (37:00)

I don't know what to say. So I said, oh, Marshall, I just wanna spend more time with you. Marshall has himself benefited from a lot of other people taking an interest in him and giving him a chance. So he was talking about that. And it just goes back to your question. Why would he see me? And so I think he sees himself in other people. So he was talking about Paul Hersey and how he'd spent time with him. We get back to the driveway. I'm about to get in the car. And I thought, oh, I know he's the big mentor, but you have to step up right now. So I said, "Well, Marshall, how can I make your life better?" And he said, "Well, there's a project you could work on with me." I was like, oh, that's fantastic. That's wonderful. I'd love to do that. And he said, "Oh, but it's in New York." And I said, "Perfect, 'cause I live in Boston." I don't think he quite realized I was only intending for the stream of fear. So I was like, that's great. He said, "Okay, send me your resume and wait for further instructions, which I did." And next thing I know, I was in the executive dining room of this big bank in New York City. - And meeting with the Illuminati? What happened there? - Yeah, well, I was meeting with the COO of this big bank and the three of us, it was me and him and the COO. And he pretty much said, this is Alyssa. She's gonna be working with me and she's gonna be part of the coaching team. So that was the first time I did anything with him and we worked together pretty closely for a couple of years.

Dont miss the best podcasts (38:21)

And he would bring me into engagements he was working on and I would do this, we call it stakeholder centered feedback. So it's stakeholder centered coaching, which means 360 feedback from the folks around the executive and I would do that. - Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by Wealth Front. Did you know if you missed 10 of the best performing days after the 2008 crisis, you would have missed out on 50% five, zero percent of your returns. Don't miss out on the best days in the market. Stay invested in a long-term automated investment portfolio. Wealth Front pioneered the automated investing movement, sometimes referred to as robo advising and they currently oversee $20 billion of assets for their clients. Wealth Front can help you diversify your portfolio, minimize fees and lower your taxes. Takes about three minutes to sign up and then Wealth Front will build you a globally diversified portfolio of ETFs based on your risk appetite and manage it for you at an incredibly low cost. Wealth Front's software constantly monitors your portfolio day in and day out so you don't have to. They look for opportunities to rebalance and tax loss harvests to lower the amount of taxes you pay on your investment gains. Their newest service is called Autopilot and it can monitor any checking account for excess cash to move into savings or an investment account.

Valuable yet confronting (39:42)

They've really thought of a ton, they've checked a lot of boxes. Smart investing should not feel like a roller coaster ride. Let the professionals do the work for you. Go to and open a Wealth Front investment account today and you'll get your first $5,000 managed for free for life. That's Wealth Front will automate your investments for the long-term and you can get started today at This is a good time to pause and expand on 360 feedback. So you facilitated this for me and I found it both valuable and absolutely crushing. It was like panic attack level crushing. I've had Joe Gebia, co-founder of Airbnb on this podcast before he after his 360 feedback. I think he went to his car in the parking lot and just cried his car. I think you have a story, I don't know the full story, but I think you have a story about a CEO in India, which I'd love to hear about. Within the context of describing what 360 feedback is. - I will describe it. And then Tim, I'd love to ask you actually double-click on what you just said in terms of valuable and then also of course very confronting. But all it is is when I'm working with somebody, like in your case for you, I went to a number of your employees and also business associates and I asked people three or four questions, but the basic questions are what is Tim great at? What is his strongest strengths? What is Tim needed to get better at? What has developed opportunities? And then what specific behavioral suggestions do you have for Tim to help him be a better leader, about professional, kind of whatever that is? And then we talk, you know, when I'm talking with somebody, of course, I probe and ask for very specific as I can get because you can say all day long, this person needs to be more collaborative or the person needs to be more strategic or the person should work on whatever. And I'm always interested in what behaviorally would make you think that because people have very different definitions of what we think are common words. - Right. - Right. So I gather all that together and I put together common themes and specific quotes from people so people can hear it. So the executives I work with can hear it in their own words and the people around them. And then we sit down and talk through what they found out. So like in your case, we sat down and we talked it through what you found out about yourself in terms of your strong and strengths and also your development opportunities. And then I love the suggestions 'cause it really gives you a roadmap about what you should start doing and stop doing behaviorally to make changes in the eyes of the stakeholders. - I think one of the mistakes I made, if I remember correctly, because I know you sent me and we talked about the feedback, which is all anonymized.

The most common response. (42:31)

This is a really important point. And I think I was headed on a trip where I can't remember exactly what was happening, but I said something that I've said a lot before that I now take to be untrue, which is well, the good stuff takes care of itself. So just send me all like the critical, send me the hard stuff. Just like front load, front load all the critical stuff, the good stuff will just take care of itself. It's already happening. I don't need to fluff up my ego or puff up my chest. Like just front load all the development opportunities, which is like really putting a monkey in a suit, but it is better phrasing. And I was not prepared for the level of brutal honesty and detail. I don't think anyone is. Even if they say they aren't, at least none of my friends who have gone through this process seem to quite be prepared for what they receive. And it's valuable, especially when there are themes, which almost inadvertently there are, but very, very challenging. And I am curious about the CEO in India that you've mentioned, but not elaborated on what are the most common responses to 360 feedback? - Yeah, so first of all, the most common response is just what you said, which is I don't care about the good stuff. No, no, I don't care about that. And I have to sometimes force it on people. I don't think I had to force it on you. Well, I think you paid, you were sort of like, all right, fine, we're gonna do it your way. So you patiently waited for me to get through the good stuff, the strengths. It's very common that people wanna just get to the part where they can sort of need to change or fix something. The second is to your point, it's extremely common to be like upset, basically, to be confronted, right? It's very confronting when you see that kind of stuff in black and white. The CEO I worked with in India, we were sitting in a conference room together and I gave him the 360 and he was quite impatient with the strengths, like, oh, you're good at this and you're smart and you're a great motivator and you're able to lead with influence, which is not always common for a CEO. I mean, it was fantastic. And then also the difficult stuff, which was, I remember he was sort of motioning, yeah, yeah, yeah, let's go, let's get to the difficult stuff. Let's get to the development opportunities. Okay, so turned out he was kind of a bully at times. He was sort of overreacting many things and we had a list of things and he listened to me, he looked at the papers and he threw them down and he said, this is bullshit. I'm giving it to the bottom of this. And he walked out of the conference, which has never happened to me either before or since. - Which part was bullshit?

Triangulating and handling anonymous feedback (45:28)

Was it the anonymizing or was it something else? The feedback, what did getting to the bottom of it mean in his mind, do you think? - Good question, because I was thinking, if he goes back to his people and confronts them with, you said this about me or you said that about me, we are sunk. The reason we give confidentiality to people, the reason I say to people, I'm not gonna say who said what is for safety. So they don't feel like I can talk about the boss and they don't feel like they're gonna get fired. So what if he goes out and starts asking people, did you say this, did you say this? So I did not know what that meant. I was pretty freaked out. I really was like, I don't know what's gonna happen now. So I kind of waited. He came back and he said, I just called my wife and she said it's all true. So that was going to sink through. - That's really funny. - Yeah. - One of the challenges I had was, well, there were two of them. On one hand, there were some outliers, I would say, with the understanding that my team is not huge, right? I don't have a large team, but there was some feedback that was highly specific, really uncomfortable, that I wanted to address, but it was not across the board for the team. And since it was anonymized and I didn't know who it provided the feedback, I felt paralyzed in a sense because here is an individual with a specific complaint and I can't fix it because I don't know who it is. Or at least that was how I felt. The other issue was being able to identify to triangulate somehow, be like, okay, I actually do know who this is, but I still don't feel like I can bring this up with them directly because it was provided under the promise of confidentiality. Right, so I was like, well, what the fuck do I do with this then? I had a lot of trouble emotionally with it and ultimately there were actionable things and we could put together a plan, but man, I'm sure you remember I really had a very, very tough time with it, which I guess going into it, if the expectation is set that by the way, most people or a lot of people have a lot of trouble with this, then I don't feel quite as judgmental about my response to it. Well, there's a lot here.

Corporate Management Techniques

One CEOs journey through confidential feedback to action items (47:32)

It's fascinating what you're saying. And of course I remember that and I remember that with a lot of compassion, especially because to your point, just it's very confronting for most people and they have their different ways of reacting to it. Many people get quite defensive at first. I remember your reaction was definitely just quite kind of a broad of love anxiety for you as I recall. Yeah, I was just like, well, what the fuck do I do with all this? Because it was with a lot of feedback. I was like, I can't remember 15, 20 pages. I don't know. It felt like 15 or 20 pages, but I think it was. I mean, there was a lot of feedback, positive and negative, but for me, and this is a weakness of mine, I don't think I've received a lot of positive feedback in my life. So I discount it. I just like, yeah, I don't need that. I don't need that, right? Like just if I'm scoring 97 on the test, I need to fix the other three points, not the other 97. So what's the negative feedback or the, I want to know the development of opportunities. And it wasn't immediately clear to me that I could do anything without being able to correlate and discuss the feedback to specific people, if that makes sense. So it was, I had a lot of anxiety. I definitely did. - And I remember that was sort of the day after, in particular, that we talked about it. And maybe a couple of things also. I don't think that we were as rigorous about this with you as I typically am with the COs I work with, which is to send them back to the stakeholders and to say, here's what I found out and to send back to all the stakeholders, because again, it's anonymous. So you can talk about the themes that I found out and then here's what I'm going to do about it. And that actually is a connective tissue. Okay, so I got all this feedback. So now what do I do with it? And opening up the dialogue with the stakeholders is actually very healing. It takes taboo topics off the table. It actually then helps people say in their own words what's going on. It helps the CEO if this was really not a topic for you, but it helps the CEO if necessary apologize to people. Like I didn't realize I was coming across that way. So in many ways that process, it's a starting point of getting the feedback itself and then sending them back to the stakeholders to have open ended conversations about what they found out, what they're going to do about it, bridges the gap between the feedback and then the response. But I guess I'm wondering about you, Tim, could you talk about what was valuable about it? And what did you change as a result of it? - Well, I think that there are certain themes that came back, not surprisingly. So since I have not historically received a lot of positive feedback, I tend not to give a lot of positive feedback. There were a number of themes like that that were self-evident in their importance. It just took the reinforcement of multiple people saying something similar to really drive the point home that something needed to be done about that. Also, I think that as someone who has worked remotely most of his life, it's easy for me to forget how helpful team cohesion can be. - Yeah, yeah. - And with a distributed team also, I think it's easy for me to take that for granted because I just, I tend to, I think, do better than most in an isolated environment. I just don't need as much, I think I'm bizarre in that way. I just have some mutation where I don't require as much socially, I require quite a bit of environmentally, but not socially. - So seeing those things as themes as opposed to one off comments by individuals distributed over a long period of time was helpful to then sit down and say, okay, what am I gonna put in my calendar? Because if it's not my calendar, it's just not real. What am I gonna put in my calendar to block out time to start to address some of these things or develop certain habits that counterbalance other things. - So I think in those ways it was very helpful. I required a cooling off period before I could get there. - Yeah. - And to be clear, it wasn't so much anger at employees or team members, it was, it wasn't obvious to me immediately how to fix these problems or even that they were fixable since I couldn't have specific conversations with specific people. I think that is where I had the most struggle at the time. And I think that's from speaking with friends who have done this, I think that's pretty common feeling. Maybe it's magnified or maybe it's lessened by having a smaller team, I don't know. And there's certainly other things that we've done that I've found helpful that perhaps you could speak to like the pre-mortem as opposed to the post-mortem.

Performing pre-mortems. (52:35)

Could you speak to what that is? People know what a post-mortem is, like let's debrief how this went. But I work with my clients and also thinking about and pre-mortem, so thinking about, let's assume that this doesn't go well, this fails in some way or it doesn't fulfill the promise. One of the things that we did that made it fail. And if you can anticipate those in advance, you have a much better way, a much better hope of planning to not have those things. One of my clients did this, they were doing a partnership with a larger company and the pre-mortem was all the things that are gonna prevent us from winning, from doing it right. And one was lack of communication. So my client that I was coaching from the startup, she realized, ah, okay, I need to proactively make sure that I'm gonna put meetings on the calendar that are gonna contain all of us. Project meetings I contain all of us on a regular basis. Now, what normally happens in any kind of company, oh, we're too busy, we're good, we don't need those meetings, you know, we're all set, but she really insisted because she sort of saw, it's gonna be easy for us to get off track on this project and it really helped them all stay on the same page and also helped them build relationships so that when things got bad and the, you know, when things sort of got rough and they did, the relationship amongst all the team members who were working together was much better. So that's an example of the way you can use a pre-mortem. - I think the phrasing is really important as always 'cause, you know, the words reflect, the questions we ask reflect the precision or lack of precision in our thinking, rather than saying what could go wrong? What could go wrong? Saying, let's assume six months from now the project has failed. - Yeah. - First of all, that forces you to define what failure is and what success is. - Totally. - Respectively. So let's assume six months from now this project has failed. What does that look like? And then what are the most likely causes? What are the things that most likely contribute to that? And walking through, if you were to create the perfect recipe for producing this failure, what would the steps look like? What would the ingredients be? - Right. - It's super, super, super helpful. I wanna touch on a couple of other points.

How to host a productive meeting. (55:13)

We can digress, I should say. We can weave. We can weave this conversation in any nonlinear way that we like, but you are very good at keeping people on point, which presupposes there is a point, in conversations and meetings. Could you speak to establishing agendas or goals for meetings? - How do people actually ensure that meetings are valuable? Because there are also many people listening to this, no doubt, who look at their calendar for the week and they're like, for fuck's sake. I have 80% of my time blocked out from meetings. What is happening in these meetings? - Yeah. - Or I wish I could not be at some of these meetings. How do you make a productive meeting? - I am always astounded at meetings and how inefficiently they're run and how much we waste our time in meetings. I'm always like, guys, it's an expensive room. Like actually, it matters that we're all here and kind of me entering off course. So when I'm there, or what I always try to do is get people to do this. Hopefully, you know, when I'm not there, to get into the habit of saying, what's the goal of this meeting? What is the purpose of this meeting specifically? And what does success look like? We're gonna come out of this meeting with and then some definition of success. And then how are we gonna get there? So when I often will say to people, what's the goal of the meeting? They kind of list out an agenda. First, we're gonna talk about this, then we're gonna talk about this. And actually, what's interesting to me is that it takes a minute for me to have them step back and say, no, really, what's the goal of this meeting? Like what is the outcome you're looking for? Not just the tools, we're not just the sort of agenda you're gonna go through. - Yeah, we're making pound cake or carrot cake. Don't just list the ingredients. Like what do we make in here? - Right, right, right, exactly. That's right, or we're making pound cake or spaghetti. - Right. - It's like two different things. So what they'll say is, what we're trying to make decisions on the set and the other. And I'll say, okay, so you've got 20 people in this meeting. Are you really gonna make a decision in this meeting? Is that really what you're gonna do? Are you set up to make a decision? Has everyone thought about it? Oh, no, not really. Okay, who do you actually need to make a decision? Well, these five people. Oh, okay, great. And what do they need to make a decision? Well, they need this kind of material, this kind of insight, fantastic. So the decision making meeting, the sort of we're gonna decide this thing is a different meeting. By the way, Tim, if that meeting's happening now, then what we can do is shift the goal of this meeting. It doesn't have to be irrelevant. The goal of this meeting maybe is to lay the table for that decision. How's that? So maybe it's to get everyone on the same page. Maybe it's to prime everybody that decision's about to be made. Maybe it's to have everybody go off and do some more work to come back to the table to think about the decision. That's okay, but then we have to be clear. The purpose of this meeting is to communicate and prime people. And that's a different meeting is gonna happen. This is a different meeting is gonna happen to make a decision. I'm obsessed with meetings, as you can see. I love meetings. Yeah, good meetings are great. Well, that's part of the reason that I have hired you to help with off-sights before. My favorite thing in the world.

Offsites. (58:27)

Could you speak to off-sights? And let's frame it for people because perhaps if they work in a large company, chances are that off-sights have either been figured out or they haven't. But if we're talking about smaller teams, just for the sake of argument to make it, not argument, but for the sake of discussion, to make it concrete, let's just say it's teams of 10 to 20 people, startups. Fast-growing startups, right currently 10 to 20 employees. How do you encourage people to think about two off-sights or not to off-sights? Let's just assume we are post-COVID concern. Right, right. And then if the decision is two off-sights, how to think about formatting? Such a thing. Well, I like to think of myself as somebody who doesn't overprescribe. As a coach, I don't walk into a situation and say, let's do an off-site. We need to have an off-site. No, no, no, no. First of all, I'm involved. So what I'm finding are a few symptoms. The symptoms might be people are not on the same page, people don't understand the goals, there's not maybe a strong relationship between key people. To your point about team cohesion, there's just not in the spree to core. So what that means is, all of those things get in the way of work and get in the way of kind of rowing in the same direction. So that's what I would say to the CEO, I'm working with a leader I'm working with, let's do an off-site. Now, as I recall, Tim, you were a little skeptical. Yeah, I was, I was, I was. I mean, this just comes back to not recognizing that my norm is not normal. Right, I mean, I have certain mutations and don't get me wrong, they're not all enabling, I have some crippling deficits, but I was skeptical. I was like, yeah, do we really need this? I mean, we live in a digital distributed world, people are doing their work, we have the SANA, we have Slack, we have these tools. What are we gonna do in the off-site? I mean, it's this, I don't quite understand the value. So yes, I was very skeptical. Yeah, but. So you were actually not not wrong. To my credit, I did it. You did it. What made you agree to do it? Do you remember? You know, I think that for a lot of things like this, ultimately it came down to what's the max downside and is there a possible upside? If so, what might those upsides be? And then just looking at it and concluding that it's an experiment worth conducting. I hadn't decided that it was a bad idea. I hadn't decided either that it was a good idea, but I came to the conclusion kind of weighing the pros and cons that it was a worthwhile experiment. Yeah, like what the heck. So let's just try it. Yeah. And I think that actually you are not alone. So many of the CEOs I work with or any of the leaders I work with, if they haven't experienced off-sites or people may have experienced as a negative either waste of time or weird trust falls or uncomfortable or not productive, I typically have a little ways to go to help persuade them, influence them, that it's a good idea to your point to try. So for me, what I like to do is I use data as in this is my experience of the team. So the team doesn't know, as I said before, the things going on, it'll be really helpful to get everybody on the same page. It'll be helpful to do this one particular working session in where we step outside the day-to-day and do it together in a concentrated period of time but at the end of the day, Tim, just like you, they're like, all right, let's try it. So then we try it and to me, it's the same thing, what's the goal of this off-site? So one day off-site, a two day off-site, what's the specific goal that we wanna get out of this? And by the way, team cohesion, having some laughs together, enjoying being together, that's perfect, that's a fantastic goal. Especially by the way, coming out of COVID, that's a fantastical right now, just to kind of reconnect. But then it may also be to plan the year or it may also be to think through how we're working as a team and to improve the way we're working together as a team. And it may also be specific projects that the team is working on that'll just, again, benefit from a quiet, reflective space together. - It really struck me after the fact.

Additional Benefits. (01:02:44)

It's so clearly valuable also in establishing a feeling of team, four distributed team who individually otherwise can feel very, very isolated. - Right. - And this is particularly true, I think, in my team where there's not a whole lot of overlap. It's not like I have five people working in one division, 20 people working in another. I have very clearly defined roles and they don't overlap very much and therefore people can kind of feel like they're on an island interacting with me on a somewhat minimal level via phone and certainly via FaceTime in person or otherwise and that can be really hard for people, really, really hard for people. And I also found it really enjoyable. Surprise, surprise. Tim also likes to be social sometimes. And breaking bread and having meals and bullshitting and cracking jokes and having interaction that is not limited to, all right, what's the status on X? What are the next steps on Y? Was really helpful to the fortify the health of the collective, so to speak. That was surprised. - Yeah, I remember you were surprised. I even remember this feeling of, oh, you're having fun, that's good, that's good. I think your team was way into it and no one knew it to expect really. But I appreciate that you have come to see the value of the feeling of enjoying being together as being actually tangibly helpful for the team to work together. Yeah. - Yeah, absolutely.

On dealing with mismanagement of meeting time appropriately. (01:04:25)

- That's great. - Yeah. - That was fun. - It was fun. And I wanted to read something that, speaking of my team, so that was just sent by someone on my team 'cause I asked them for it, that is related to wasted time in meetings. And this is from John Arnold, who's an incredible, incredible investor, very, very effective philanthropist also. In 2000, I think 2007, he became the youngest billionaire in the US and has a fascinating story. And in fact, my friend, Peter Tia, Dr. Peter Tia interviewed John Arnold on his podcast and I encourage people to listen to it. He started a firm called Sintourist Advisors in a long time ago, which was a Houston-based hedge fund specializing in trading energy products. An amazing story, really, really fascinating guy. And he was in "Triba Mentors" and I think the question he was responding to is something, what have you come to appreciate or do more or think more about as you've grown older? And here's his answer, it's pretty short. I had not appreciated the maximum time as money until recently, which is surprising, right? Coming from someone of this level of accomplishment. So he continues, but for those whose time is a scarce resource, learning to say no to meetings is a necessary skill. Sitting through an unproductive meeting has huge opportunity cost. It seems obvious, but people struggle with equilibrating time and money. And this is the part that really stuck out for me. It actually still kind of pains me to read this because I recognize it also in myself. There are many organizations that fret over small direct expenses yet have no misgivings about keeping superfluous staff tied up in a conference room for hours. And in recent years, I've become better at judging the opportunity cost of time. But it's true, right? So it's easy to scrutinize and expense rapport and be like, wait a second, why the hell did such and such cost to Grant? In the meantime, the calendar is just clogged full of meetings where staff time is just spinning at an alarming rate and racking up incredible time costs. And that was in his profile and tribe of mentors. But yeah, so I appreciate and I value how you are able to help extract an assure high value from meetings. 'Cause it's another thing that I've had. I think in many cases, a reasonable bias against, but I have come to appreciate that there are times in places where they can be run very effectively. And there are techniques, there are tools for doing that. - Yes, can I say one thing about that quote, which was fantastic? - Yes. - It's that we have, so you're holding these people hostage. You're holding the staff hostage in these meetings. And of course, your hoarding time that should be unlocked to have them go do other things. But also, it's like you're crushing their soul 'cause they know that they shouldn't be in this meeting because they're like, oh, I have so much work to do and I'm in this meeting and it's just draining. People don't feel burned out because they're working long hours or they're working hard. People feel burned out when they're wasting their time. When things are hard to do or when they're spending their time in these endless meetings that don't feel relevant to them. So I think that's part of the unlock is also, it's to be efficient and effective in your meetings. And it's also to recognize that people should be freed and unlocked to go do their work and they're gonna be happier when they're putting their time and effort into things that matter. - Yeah, for sure, for sure. I mean, if I look at the times when I am energetically under resourced and exhausted, it's not when I'm working really hard on something I care about or something I'm excited about. It's when I'm dying to death by a thousand paper cuts. - Right. - Right. - Or locked into something that I'd prefer not to be doing. Thankfully, not very often, but it does happen.

Workplace Feedback And Communication

Making unpopular workplace feedback more productive. (01:08:28)

So let's also talk about one of your strengths which I have personally benefited from. I know a lot of my friends who've worked with you also benefit from and that is Scripps. And my friend from Meet Setty has scripts for all sorts of things, really, to personal finance and they work, right? So if you wanna renegotiate your credit card fees or whatever it might be or you wanna ask for a certain favor from your bank, there are simply scripts that work better than others. And I'd like to talk about a couple of them. You have Scripps for a million different things and you actually have these scripts in your book. So for people who want a full repository of these scripts that have been refined over time from startup to grown up is the book. So pick that up. Well, let's talk about an uncomfortable situation in the work context. And for my team who's listening to this is not because any of you are falling in this category, just to be clear, how to give someone feedback about the fact that they're not addressing feedback you've already given them. Yeah. Or that you've given them multiple times. So what I think oftentimes the clients I work with and really any, let's give a CEO of a startup that I work with, his point of view to me is I keep telling him, I've told him, I've told him multiple times, I've told him, he's not doing it. So then I'm like, let's step back because your job is not to nag people. That's terrible. This feeling of like, oh, I'm the nag now. Now, to me, it gets interesting. And I like to give people a framework which is content, pattern, and relationship. So content, pattern, and relationship. So content is- CPR. CPR, exactly. Exactly. So the content is the thing that they're doing. Let's assume that your vice president of product is not communicating with the people around him. He's kind of like living in a silo. And we need your information to feed into sales, to feed into marketing, even to feed into engineering. And you're not proactively telling people what you're thinking and what's going on. So that's the feedback. And I need you to proactively tell your people. Tell your peers what's going on. And then life goes on and he doesn't do it. And the CEO is back and says, "Hey, I really need you to proactively tell you peers what's going on. It's really, I need this information. It's really important." So it doesn't happen again. And rather than keep going back, it's really helpful to say, "Hey, I've been seeing a pattern." So I've been asking you to proactively reach out with your peers and tell them what's going on. It's actually really important because they need the input. And you've told me, "Yes, yes, yes, a couple of times." But I'm seeing this pattern, which is that I ask you to do it and maybe you get better for a day or two, but it doesn't stick. What's going on? And that's the conversation to have with people. Not this constant sort of, "Do this, okay, do this, okay, do this." It doesn't help.

Firing conversations (01:11:25)

At some point, they're not doing it. What's going on? - Yeah. How do you see those conversations unfold? What do people say? - Actually, the first reaction is usually, "I know, I know, I'm sorry, I know, I know." But that's the problem is that we're focusing again on content. Then I ask my clients to actually the role play with me, "Let's talk about the pattern, what's going on?" And do you think it's important? "Yeah, I know it's important. I get busy, I forget." And then let's talk about strategies that I actually need you to use. And I'm here to help you, but I actually need you to use the strategies to remind yourself to coordinate better with them. Do you need to have sort of a small peer team meeting periodically every day or once a week? Do you need to put on your calendar that you need to kind of let people know on Mondays and Thursdays what's going on? Do you need to have more one on ones with these folks? Whatever it takes, but I can't have you keep forgetting if that's what's going on. Okay, let's say strike one, strike two, strike three. This conversation, strike 37, flash forward. What do the firing conversations look like? After a period of time, if this person is not performing, they're just not performing, they're either not communicating in this way, they're not managing their area. So for example, a lot of people inside of startups, they start out as a product manager as an example, and then they turn into the head of product, which means they're no longer a product manager, that's not their job anymore. Their job is to lead higher and lead a team of people, very different skillset. And it's very common for someone who's a great product manager to get promoted into this head of product, and then bad things happen. So... Problems, problems everywhere, as you also see. Exactly, exactly. Problems, problems everywhere. Well, the problems everywhere is like, "Yep, soon as you solve this problem, you have to solve another problem. So let's solve this problem first. You don't ever graduate from problems." So then look at this person and you say, "Listen, and maybe you've had a few more conversations, and I'll talk about sort of, you're not building and leading your team. I've asked you a couple of times to really focus on building and leading your team, to make sure that everybody's coordinating together, and that we're launching two or three products, not just this one product. I've asked you to learn to delegate more, to get people more involved, and I've asked you to communicate around to people. Let's assume that this person has not addressed any of your feedback, or has not adequately addressed it. Maybe they're trying, maybe they're not trying. It needs to be a different conversation, which is, "Listen, I've asked you to do these things. It hasn't been working. I need to let you know that we're going to part ways with you." We can talk all about why and how, and I want to make sure it's going to be a good transition. I think you're a great person. It's just that you're not able to meet the job requirements right now, and it's really necessary to have the people in place to meet the job requirements. I want to talk to you about the transition plan. The thing is that I assume that you've had a lot of conversations in advance of that, because it should not be a surprise for somebody when they ultimately get fired if that's what happens. It's because you've had the conversations with them time and time again, content, pattern, and you're able to then say, "We've had this conversation multiple times. It's not working. I need to make a different decision. We need to part ways."

Are there any books or resources that you recommend for getting better at having difficult conversations or uncomfortable conversations? I should say, because not all uncomfortable conversations are difficult aside from the fact that most people will avoid and would prefer not to feel discomfort, but they're not necessarily complex. They're just very uncomfortable. Uncomfortable, exactly. I think a fantastic resource is crucial conversations, which is then followed up by crucial confrontations. It's a companion book. Actually, I often think that people think that confrontations are like, "Oh, I don't want to confront him." Well, I think you're just saying, "Here's what's going on." It's not about confronting people. I think sometimes people confuse direct talk and straight talk with confrontations. Nonetheless, crucial conversations and crucial confrontations give you a lot of tools into how to address those conversations. I would add Radical Cander by Kim Scott is also a great book from that point of view, because it also makes the case about why it's so important to give feedback for people. Radical Cander is really clear in you need to build a solid relationship with people, which is absolutely true. Conversations go better when you have a solid relationship with someone and they know that you're on their side and that you're doing this because you want to help them, give them the feedback because you want to help them. And then it helps you really have the tools to actually say what there is to say in a comfortable way. Well, not in a comfortable way, but in a less uncomfortable way. Radical Cander has a lot of people. And I think that's the author one more time, please. Kim Scott. Kim Scott. Yeah. She's a grid and I don't remember all the parts of her grid, but one of her grid, the place you do not want to be, is ruinous empathy. You feel so bad for them, so you don't want to say, and then 20 years go by and their career doesn't get better because you were not comfortable telling them what had to be said. So Radical Cander, not to be confused with Radical Honesty, although they sound very similar. They're very, very different. I think they're actually both worth kind of digging into, but it made me think for a second just for a little comedic relief of an article that a friend of mine, AJ Jacobs wrote for Esquire magazine, which is actually a really good article called, "The headline is, 'I Think You're Fat'". And then the subtitle is, "This story is about something called Radical Honesty. It may change your life, but honestly, we don't really care by AJ Jacobs." And AJ, for those who don't know, will undertake these often absurd, often also profound in some ways experiments of sorts, much to the suffering of his poor wife. It was great, but it's also a good compliment, as it highlights the risks and benefits of Radical, in this case, Radical Honesty, but Radical Cander. I actually haven't heard of that book before, so I'm excited to take a look at it.

Applying Advice (01:17:47)

Kim Scott. I'd like to share a story where this became really real for me. Please? Just from a client a few years ago, he was the CFO of the company that I was working with. And we would talk, and by the way, what a fantastic guy. And also was so empathetic, that it was hard for him to give feedback to people. So he had his direct report, who was never, you know, a number of things that she wasn't doing right. She wasn't owning a process. She wasn't proactively giving updates. She would never speak publicly. So there was all these reasons why she was kind of getting her own way. And we talked about, I said, well, maybe you need to give her that feedback. And he said, oh, no, I know what's going to happen. She's going to cry, no, I don't want to do that. And I said, you know, you're observing this important area for her to grow in her career. And it's so stingy of you to hold back, because you're not comfortable. That's what I hear you saying, I'm going to be uncomfortable, and I'm going to make her uncomfortable. And I just said, you know, you're robbing her of the benefits. So we role play, we role played it. He went and talked to her. They had a very difficult conversation. It was difficult not because she was against the feedback, but because she did cry. And because she did talk about her concerns. It's really hard for me to do this. And it's hard for me to do that. It's hard for me to speak publicly. It's hard for me to remember to keep track of all these things. I don't always feel empowered to kind of go do this thing on my own. They had a long conversation. She was upset. And the next day she came back to him and said, I so appreciate your telling me that. I know that was hard. I so appreciate your telling me that. I wish somebody had told me all this 15 years ago. And I just thought, oh, we have so much work to do. Problems, problems everywhere. Yes. Yes. And you got to pick which problems you're going to solve now. And if you solve the Hyundai of problems, congratulations, now you get the Mercedes of problems. If you solve that, congratulations, you get the Bugatti of problems. But you're still going to have things to work on. It's true. I tell my clients, if you're lucky, you pick your problems. Problems, problems everywhere. But if you're lucky, you get to pick your problems. If you don't like these problems, why don't you go join IBM? Right, because you got all other set of problems. Right, with being in a large company besides being in your startup. So if you like these problems, let's solve these problems. These are the problems you've chosen for yourself. For sure. And as Chris Bosch, legendary basketball player, said recently on the podcast, he said, just imagine you put all your problems on the table with everyone else's problems. You'll probably pick up your problems really quickly. Yeah, that's probably true.

360 Feedback (01:20:43)

So a couple of other things I have in my notes here that I wanted to explore. One is, and I think it extends well beyond personal brand, but the approach to personal brand of asking people, what are the three words you think about when you think about me? Could you elaborate on that, please? I love that. I think that's such a quick and easy 360 feedback a little bit. It's like, how am I showing up? For everybody, Tim, you're the expert on your intention, and everybody around you is the expert on your impact. For all of us, it's so helpful to figure out, how am I showing up? Because we never really know how we're showing up. So these three words activity, first of all, I want to tell everybody, you can always say, oh, I heard a coach, and she told me to do this. Blame me. That's what I always was, because it's a little weird. Yeah. That's a little weird. And if you're not doing it inside your organization, it's going to be like, wait, why are you doing this? I heard a coach. Okay, great. So you can email this to folks. You might want to set it up. I'm gathering information about me. I'm trying to advance my career. One thing that would really help me would be if you could articulate the three words that you think about when you think about me. And now people will regularly say, you mean you're strength and weaknesses? No, no, no. Just looking for the three words. And so if you can email that to folks, or if you can ask them, then they'll give you back three words. So I did this one of my clients, and she had said to me, I'm very strategic. I'm like, great, that's fantastic. And she told me that quite a bit. And I said, well, let's do the three word activity. So I actually did it for her. I went out and I said, when you think about my client, what are the three words that come to mind when you think about her? And a lot of words came back, detailed, critical, thoughtful, analytical, methodical. But strategic did not show, we asked probably eight or ten people, and strategic did not show up. So I said, well, I'm just letting you know, I know that you're strategic in your own head, but I just want you to know that that brand is not getting out there. People are not viewing you as strategic. And I think that's common, Tim, because people think these thoughts in their head, they think, but really what people observe is action. They observe your communication and they observe what you do. So you've got to realize that that's what they have to draw on for you and make sure that you're doing things in which you're in alignment with the three words that you want them to say. I sent this out to ten people recently and no one came back with enlightened. I was very disappointed. Not a one. Keep working.

A simple self-inventory (01:23:22)

Keep working. Keep working. Carry water. Carry water. This type of exercise can be so powerful and it can take many forms, but this type of feedbacks that you can try to compare the image of yourself in your own mind or ego with the image of yourself, the perception of you in the wider world is so valuable. And some are more painful than others. I mean, I think that the 360 feedback is like a 360 sort of psychic colonoscopy. It's not always fun, very valuable. The three words is a pretty sort of lightweight appetizer approach. And I also remember for myself, it only occurred to me right now and popped into my mind, but when I was in high school, I must have been 15 or 16. And I read a book called "Mental Toughness Training for Sports" by someone named Jim Lair, who much, much, much later, decades later, actually had on the podcast, L-O-E-H-R, and he's worked with all sorts of top-level athletes, brand names that everyone would recognize. So I did this inventory in that book, which was similar to 360 feedback in so much as there were maybe 10 or 20 questions and you would give these out to people who knew you really well in different capacities, peers, coaches, et cetera. It was intended for, in this case, sports, so teammates, but that really changed my life. It was even at 15 or 16. It was so shocking and enlightening and actionable to get that kind of feedback. So I love the three words exercise, which is also an easy way for people to kind of dip their toe in the water before they upgrade to the more aggressive possibilities. Right, the nuclear approach. Yeah, yeah, exactly. Tim, can I ask you, what did you find out from that activity and then how did you use it? Way back when I did this, I wish I had a better memory of the exact questions, but it was an assessment of weaknesses and strengths and you would see patterns in terms of weaknesses, but not just weaknesses, but things that you should work on. So, okay, fine, we all have weaknesses. You don't actually need to fix all of them most of the time. And if you look at some incredible athletes, I mean, they have huge weaknesses, but they know how to capitalize on their strengths. But if they have a weakness that is in some way handicapping their strengths, then there might be a bigger issue. So it was really helpful in an unemotional kind of clinical way, almost like they were anthropologists looking at this creature called Tim to simply note, like, yeah, not great at endurance or hasn't developed this physical attribute or in this particular training capacity, but it could do better in this following way in practice. And simply to see a consensus of some type was really helpful to me, because I had a few blind spots and for all of those reasons found it really, really valuable. I love that, you know, as you know, I'm very into fitness and I'm into kettlebells.

Self-Help Techniques And Resources

Why "gap analysis" can be useful (01:26:42)

And so my coach who works with me on my strength training and my kettlebells, one time I failed to lift and he looked at me so kindly and he said so almost like joyfully, oh good, now we know where the gaps are. Yeah. And I thought that was so beautiful that he looked at my failure, right, my weakness that way. And it changed actually my way to think about as much as possible. I try to give people a lot of tools to handle it to your point kind of clinically or even as, oh good, now we have something to do. Yeah, these reframs are really helpful because life can be such a disaster sometimes or it can just be seen as such like an unrelenting barrage of like a hailstorm of bullshit that when you have these experiences, these reframes can make all the difference. Yeah.

How you can embrace obstacles and overcome short-term setbacks (01:27:40)

And I wanted to also because this came up to my mind earlier, but a quote from Jan 11 who's an astrophysicist. And here's her quote, "I used to resent obstacles along the path thinking if only that hadn't happened, life would be so good, then I suddenly realized life is the obstacles. There is no underlying path." And I just find that very reassuring. And you know, another reframe that I found helpful, maybe a lens through which to look at these experiences like a failed lift or something else came from Jim Detmer, who's great and has been really helpful to me. And when I will have some blow up or what I perceive as just a miserable failure or just some complete D minus report card grade back on whatever I attempted to do or I'll lose my temper or I'll get really sad or I'll start beating myself up and describe that to him and he'll say, "Great, that's a pop quiz from the universe. Like all this stuff we've been working on, like great, you just had a test. And I look at what happened." And it's like, "Oh yeah, I'm not in the dojo so I can practice karate kicks in the dojo." This is actually supposed to be used for something like, "Okay, yeah, let's look at the pop quiz from the universe and the report card." And exactly as you said, like, "Great, now we know what the gaps are." Okay, let's work on that. The pop quiz from the universe, I love that. Yeah, yeah. I didn't study, I'm not ready. Sorry, sorry. You called me the red and big quizzes as well. Yeah, you caught me. Yeah, I didn't read up on that math.

Tools for transforming self-talk (01:29:12)

Could you speak to self-talk? And specifically, how do you move from, and why should you move from, some of the more critical self-talk to, let's just say, and this is in my nose here, you know, I will be okay no matter what. And when did that become important to you personally? And I realize there's a lot packed into that one compound question, so take it wherever you'd like. You know, I am somebody, to your point before, like, I'm on the forced march of my life many times. And so my self-talk can be, "Oh, you didn't do that right. You screwed that up. My woe is me, self-talk is what will become of me." Right. And I began to realize that that, you know, you think it's nothing. You think it doesn't matter. It's not in the physical world. "Who cares what you say to yourself or, no, I don't really talk to myself or whatever." But once you become aware of it, actually, I have my clients do this and I do this myself. In the middle of the day, you could journal what has motivated me and energized me so far and what has demoralized me and made me feel bad so far today and de-energized me. And very often, it's self-talk. So it's like, I did this thing and I told myself I did this great job. It's fantastic. That was energizing. And then coming to terms with what you tell yourself when you screw something up or you got a D minus or something on the test. So I think just coming to terms with the fact that self-talk is real and I began to study a little bit about it. And I saw research articles that said that athletes, athletes talk to themselves and they see that when they say motivating things to themselves, they perform better. And when they say demotivating things to themselves, they perform worse. And I thought, "Well, I don't need much more information than that. I'm convinced." And then I see it in myself and in my clients. And so I just want to say to everybody, many people I work with are critical and are very hard on themselves. And I think that they think it gives them an edge. I know you've talked about that a lot before on your podcast. You think it gives you an edge, but actually self-compassion and transforming that negative self-talk into something more positive, into reframes, finding ways to reframe it into more positive, telling yourself positive things even in the face of that negative self-talk. It's actually very helpful because it gives you a ton more energy. And I found that for myself. Totally. And maybe it gives you an edge, but it's like trying to chop vegetables, holding the kitchen knife by the blade. It's like, "Yeah, you're pointing it the wrong way. You're not doing it right." Right. I think it leads to a downward spiral at times. You think it gives you an edge, but I am not sure if that edge is helpful in performance. Because what do you care about? Success. Whatever that your domain is, you want to be successful.

WHY you should be mindful of negative self-talk (01:32:10)

So the problem is when you talk down to yourself, when you criticize yourself, especially harshly, you're actually burning up calories, which you could have used to actually solve the problem. Not your most resourceful, you're not your most creative and best self when you're... Yeah. And you can still have really high standards. If we look objectively at any type of mammalian training, whether it's dog training, dolphin training, human training, overwhelming negative feedback, generally does not work very well. And there's a great book called Don't Shoot the Dog, Terrible Title, Great Book by Karen Pryor that I recommend to everybody. Self talk is one sort of pillar of not just mental health, but mental performance that I've tried to pay more and more attention to. A friend of mine, a very well-known guy who people would know, has worked with therapists and used... I want to say it's dialectic or dialectical behavioral therapy. And as part of that, done an exercise where when he catches himself, berating himself with self talk, he stops, pulls out his phone to use voice memo, records self talk as if he were talking to his best friend or say a younger child and then sends it to his therapist. And that's more for accountability than feedback, although there is feedback also. And did this for a number of weeks, and it changed how he spoke to himself. And in terms of the degree of harshness versus kind of support and encouragement, it makes a huge difference. Wow. Wow. That is a huge difference. Self talk is... And I just want to mention this because I think it's a useful framework or just a mnemonic device is one of what you refer to as the three selves or the three selves. You have self-awareness, self-compassion, and self-talk. And I think if you're checking those off, kind of like you check off the food groups for a given day or more exercises you need to do, we would all be better off, not just individually but collectively. So I did want to mention that. I don't know if there's anything you want to add to that, but the self-awareness, self-compassion, self-talk. You can't have any of those without self-awareness. That's kind of a prerequisite for the other two. But is there anything you'd like to add to that? I just want to add the bridge of self-compassion, which I think is so important. Again, it's like people are like, "Oh, no, I don't want to waste that time. I just want to fix the problem." I actually think internally... Gosh, the image is coming to mind. It's like internally hugging yourself, actually knowing, "Hey, I'm doing the best part of self-talk really. I'm doing the best I can. I don't mean to be screwing up whatever is I think I'm screwing up. I'm going to keep trying until I get it right." The compassionate parent looking into that self and giving some comfort, that lets you move to the next stage, which is self-talk. It's becoming aware of it. It's then giving yourself the healing power of compassion, just knowing, "Hey, we're all here doing the best we can and so are you." That allows you and gives you the space to open up and transform yourself. By the way, if you're hard on yourself, as CEO, as I work with, they can be very hard on themselves, they can be very critical, the problem is, in addition to taking up your time and energy, it leaks into your team. It leaks into the people that you actually want to encourage and you want them to do a good job and you want to encourage them. Regularly, if I say to somebody, "What are you saying to yourself?" They say, "All these horrible things." I feel like, "Would you ever say it to your best friend? Would you actually ever say, "Oh, you jerk. I can't believe you did totally screwed up." They always would give their best friend much more of a break and they even would give their employees much more of a break. The problem is, when they don't give themselves the break, with self-compassion, it leaks out and it pollutes the environment. Yes. Within, without, it's very difficult to have one not affect the other. Where does I will be okay no matter what that sentiment or that feeling come into this, if it does? I think that a lot of, I'll say a lot of people, a lot of people, but certainly a lot of people in the workplace and my clients, they have this underlying fear and concern.

Self-compassion. (01:36:40)

What if this happens? What if that happens? In large companies, it might be, "Oh, what if I get fired or what if these layoffs affect me?" Or whatever. If it might be, "Oh, what if we fail? What if we don't make it? What if we can't raise this funding?" There's just a lot of fear and worry that shows up every day in the workplace. It's really very difficult to think about. What I try to get them to remember is, this one thing is not definitive of your entire life. Not only that, back to problems, problems everywhere. You're always going to have problems. If you can approach this particular problem about maybe getting funding and having trouble doing it or maybe concerns about your job, realizing, "I will be okay no matter what." That helps you have some agency and some empowerment in this matter, whatever it is. I always want to encourage them to remember who are you really?

You have a lot of resources (01:37:40)

You have a lot of resources. You have a lot of creativity. You will figure your way out of this problem just like you always have because you will be okay no matter what. I want people to take that on, take on the mantle of, "I will be okay no matter what." That's been another one that has taken. I shouldn't even put it in past tense. Takes me quite a bit of reminder work to remain present to. It's part of the reason why I spend so much more time in and around nature now because the further my life is abstracted away from that, the more manufactured need and therefore anxiety seems to pervade my day-to-day existence. That's so important. It's really, really... Yeah. Notice how it's actually divorced from circumstances. I'll speak for myself. My life's changed quite a bit in the past 20 years. I know that your life has changed too. The anxiety is ever-present. It just changes what it attaches to. You've got to find ways to counteract the anxiety because the anxiety isn't going away just because some circumstance, you think, "Oh, that thing that I finally get will somehow cure my anxiety." Not really. I've spoken for myself. Not if you have some anxiety embedded inside of you.

Books And Resources For Business Growth

The thing you are so worried about (01:38:56)

Absolutely. There's a piece I can't recall the exact title, but it's from School of Life. It's a really short article called, and I'm paraphrasing. I'll put the link in the show notes, but on finding something to worry about, I think is the title. And again, I'm paraphrasing, but there's an excellent line in there that really struck me, which is something along the lines of, "Perhaps the thing you're so worried about already happened." Yeah. Alluding to the fact that we're so informed by our experiences in childhood and so on, that perhaps the thing that we are so, so worried is going to happen is actually something that already happened and that we can, like, go of great peace. Alandibatong-A-L-A-I-N-Space-D-E in the middle. B-O-T-T-O-N, I think, is the spelling. All those things should help you find it, but we'll put it in the show notes. So let's talk about, from startup to grown up, great title, by the way. I'm really excited about this. It's got three sections, managing you, managing them, managing the business. The appendix contains what we mentioned earlier. These scripts for delicate situations, which I think is in and of themselves, makes the book worth it in terms of picking up, like, just to have a desk reference for delicate situations. I'm kind of a sucker, warm audience for scripts of any type, so I'm super excited about that.

Creating the book From Startup To Grownup (01:40:23)

And I would love to just know more about the journey of creating the book and why you decided to write a book, because writing books turns out pretty hard. It takes a while, so I don't actually know all the backstory here, so I would love for you to just tell the story of how this book came to be and why. So first of all, in my case, the book took 10 years to write, 10 years plus six months. The first 10 years were like, "Oh, I can't do it. I'm not good at this. I can't do it." So that was extremely frustrating. I knew I had something to say, and I wanted to say it. And also, as I got more and more involved with startups, I really saw, "Oh, there are these common things that happen in startups. I'll say, like, where's your leadership team?" And they'll say, "Wait, what's a leadership team?" Or I'll say, "Well, did you give them a step?" You're like, "Exactly." You're right. Exactly. Exactly. Or they'll say, "This person isn't doing this job." And I'll say, "Well, did you hire for that job?" "Oh, well, we sort of just like that person." Or whatever. So I see these things over and over, and I really wanted to write a book. And I'll just tell you, I was just kind of in my own way. All my reasons. I'm not sure if I can do it. Every time I sit down to write, I go blank. I'm not sure how to structure it. All of these things. And then I wouldn't necessarily devote the time to it because it was very uncomfortable. So I'd rather do the things that were comfortable for me. So it took me quite a long time to get over that. And it was actually during the pandemic that I just thought, "If you don't take this time to write your book, you're going to be so disappointed in yourself." Coming out of this pandemic, what's going to make you feel like I did not use my time appropriately, did not use my time well? And the answer was that you didn't write this book. So I talked to a number of friends. I got a lot of moral support. I shed many tears. And I had anyway already had a contact at a publisher. And so the wonderful Cathy Sweeney and I talked together about this book and we sort of finalized what I was going to do. And then I don't know what happened, but everything just kind of changed. Like I began to kind of tell my stories. And I was able to just talk about in writing the experiences I had in startups. And amazingly, the words, I don't want to say they float out of me. There was plenty of difficulty and butt in share and discipline around it. But I no longer, back to self talk, I no longer had this, I can't do it in my head. I had instead, I'm going to do this. I'm going to get this done. What changed? I have to ask, what changed? What the hell changed? If you knew, if you knew what changed, what would it be? Love what it be. Okay. The turning point, I think, was my good friend and fellow coach and one of the Marshall Goldsmith 100 coaches also, Michael Bungis, Daniel, he was kind enough. We were going to do it in person when we were in London together, but we ended up doing it on Zoom. He was kind enough to do this process called immunity to change. Do you know what that is? I don't. I read the book. I'm like, I know that already. I read the book. I know. What I actually am doing. It was very helpful. So it's, I think his name is Robert Keegan, but the process is there's a reason you say you want to do this thing. You say you want to change. You're not changing. So it's like one foot is on the accelerator and one foot is on the break. What's on the break? And Michael was kind enough to sit with me as I talked about all my concerns and issues, turned out there were a lot of them. You say you want to write a book? Yeah, I want to write a book. What's in the way? I don't know. What if you did know? I was able to reveal to myself with Michael's, you know, supportive help what was in my way and all my associations with how hard it was going to be. All my associations with what if I, it's really a lot of ego stuff, like what if it's not a good book? What if nobody likes it? I don't want to be that kind of person who's always talking about my book. You know, in my book, I say, I also knew writing it was one thing and then sort of the year after, you know, when helping people learn about it and promoting it was another thing. And as we talked, it was like I laid them all out on the table and I saw really pretty physically, pretty physically, all the things that were in my way. What's interesting is that sometimes just surfacing the things that are in your way help you.

The book is Immunity to Change. Letting previous versions of Kelly go. (01:44:59)

I'm not saying they don't go away like, oh, magically. But every time now resistance comes up, you're like, oh, yeah, I think it's going to be hard work. Oh, yeah, I don't want to be that person. Oh, yeah. Hi, hi resistance. I get it. And I was able to overcome it in service of my bigger goal, which is basically feeling proud, feeling proud of contributing this, which I think is going to be helpful to founders. And also putting together my stories in a way that makes me feel proud and completing this project and this work. And again, hoping it contributes to people. That was going to make me proud. And so I saw the resistance for what it was and I was able to move forward anyway. Wow. Kudos to you and Michael, of course, taking you through the process. Immunity to Change is by Robert Keegan, K-E-G-A, and subtitle How to Overcome and Unlock Potential in Yourself and your organizations. That's also easy to find. And you know what, here, with the exercise and your description of it reminded me of in terms of identifying the resistance and sort of a, well, it reminded me of two things. It reminded me of, I think it's John Dewey who said a problem well stated is a problem have solved something like that, but then it also reminded me of another famous thinker. And let's see if I can see if I can do it justice.

Three sections of the book: Managing You, Managing Them, Managing the Business. (01:46:39)

Like, name to your fear be before banish it you can. That's Yoda. You got to name your fears. And in applying the name, oftentimes, not all the time, right? This isn't, like you said, this isn't intended to be magical thinking, but as soon as it is kind of put in the light, you're like, oh, okay. Now it's like this thing that is sitting in front of me that I can look squarely in the eye as opposed to this like bump in the middle of the night that is preventing me from sleeping. Okay. They sort of get reduced. They loom so large inside of you. And by the way, there's also some shame there. Like I can't tell anybody. Shame also kind of looms large and we're able to get it on the table. It kind of neutralizes it and it whittles it down to size. It reduces it down to size. So can you elaborate on the three sections in the book? So from startup to grown up, do you have a subtitle? Yes. It is grow your leadership while growing your business. Mm hmm. Take it. Take it. All right. And then the sections, managing you, managing them, managing the business. How do those further break down? You know, if I think about it, if I come in and approach a startup and I approach a founder, my first question is always like, what's going on around here? And what the hell is going on around here? Yeah. So I want to kind of get some perspective and context. And it always comes down. You know, founders always start with me with something strong in the business or we're not achieving our numbers or I'm having these problems with my people, whatever they are. But it always comes down to you. But it starts with you. And that really means you beginning to think about your self awareness or 360 feedback that we talked about, but other self awareness, getting to know your natural swing. Are you a natural communicator? Do you tend to clam up? Do you shut down in the face of stress or do you get, let's say, overly passionate and explosive with your team? So it's about you kind of doing an inventory of your overly passionate. That's a great way to put it. Yeah. Yeah. So it's like coming to terms with that, but it's also about recognizing back to what we talked about in terms of self talk. It's about realizing that you as a founder are going to go through a lot of ups and downs in this journey, which you might think is going to take three years or five years, but it is not going to take three years or five years. That is like a mythical story. It's going to take a long time. You're devoting a lot of time to this. And how are you going to take care of yourself? How are you going to have the right regimens of nutrition and sleeping? How are we going to transform your self talk when you have inevitable imposter syndrome and like what's going on? So that's the first section. It's about you, you, you, you. And then once you figure out you, then let's talk about them, the employee. So it's about hiring. It's about onboarding. It's about sadly firing, which does happen. It's about setting up the right systems inside of your company to help you scale. You can no longer do everything at some point once you grow. So you've got to find the ways and the tools and the allies, the other employees who come on board to help you figure out what are the structures that are right that are going to help you scale. One thing is delegation. Many founders have a lot of trouble delegating because it's like their baby. So it's about teaching you how to give away the core elements of your baby and trust that they can be done. And then ultimately using all of that to manage the business. And then I want to say a special, I realize that this may not be in the right section. Nonetheless, that's my book. And the two pieces that are also in the managing the company section, managing the business section are about managing your board, which people always have questions about and also managing the special relationship known as your co-founder. Yes, that marriage, including prenups and checklist questions.

What questions can founders ask potential co-founders ahead of time? (01:50:15)

And I just want to mention some of yours, then I'd love to hear others that you had. The three that jumped out to me because this is, I have invested in a lot of companies. I've advised a bunch of companies and not all marriages turn out to be picture perfect. You know, riding off into the sunset, there are lots of divorces and some of the questions that can help in advance so that you have some type of agreement, which could be called a disagreement, right? Because it's really to contend with situations that are problematic. What if one of us isn't scaling? How will we know and what we do about it? And these are your questions, just to give a proper credit. You know, what will happen if we get into a massive disagreement that we can't resolve? How do we resolve it? And what are the kind of rules of engagement? What does success look like and how will we know? These are all so important because even if the company does well, let's take that as a case, the company is actually developing some degree of traction. Customers are paying. And you have one founder who wants to get out at a certain price, a certain value. And then you have another who wants to get out at a hundred times that value or ten times that value or two times that value. That's a big problem. That could be a big problem. These are so, so, so important. Are there any other pre-nup checklist questions or other questions that you think founders should pay particular attention? And you have many. So to be fair, they're quite comprehensive. But any that perhaps people tend to neglect or omit. Definitely. What kind of company do you want to build? What's the culture of the company? What kinds of people do we want to hire? What are the important values we want to have inside of this company? Because when you don't come to terms with that, one co-founder is busy kind of hiring for his group, a certain kind of person. And then the other co-founder is hiring for her group, a different kind of person. So ultimately, you're almost like hiring two companies. So coming to terms with the culture we're trying to build is super important. And I also think that I want to go back to what you said about when do we want to, as we say, exit. What do we want to do with this company? It's amazing to me how people just don't talk about that at the beginning of their relationship, the co-founder relationship. What they do is, and I understand this, they're so excited about building the company, but they assume they have the same music in their heads together, right? They assume they're on the same page with, let's say, building a massive business or building a manageable business, building a lifestyle business, whatever it is. And I just think it's so important to have these difficult conversations in advance because I promise you they're going to rear their ugly heads at some point. And so having the conversation in advance may not even resolve anything, but at least it brings up topics. Also getting used to having sort of difficult conversations or real top conversations with your co-founder, I think is the key to the whole thing. Whether or not you resolve anything, it's about getting in the habit of bringing up uncomfortable attacks. Yeah, for sure. And an answer that isn't an answer, by the way, is we're going to build a hundred-year company. Yeah, this is going to be huge. We're going to be giant publicly traded companies. Okay, no, no, but let's talk about, in addition to that, what each person specifically hopes to achieve financially and otherwise, because there will be opportunities, even if you're going to do that, there are going to be opportunities along the way. There will be seductions along the way.

Exploring the goals of Randi's book, The Unicorn in the Woods. (01:53:54)

There will be offers along the way. And so it's really critical to have those conversations. Early, what do you hope the book to do? What would a home run look like for you? I hope that the book inspires founders to do more self-reflection, for sure. I hope it helps founders prevent avoidable mistakes. That's what I really am. And also, by the way, new leaders. There's a lot of material that's just kind of, if you're going from individual contributor to manager to leader, there's a lot of the same journey you go through. So I'm hoping that it helps people solve those problems before they become problems and give them language and tools and insights to help them on their journey, basically. I'd love to coach everybody. I hope this serves as a beacon for some people. I'm really excited about it. And also because I feel that entrepreneurship, however you define that, but this kind of undertaking to create something from nothing and things that often go along with that, let's just say, really good product sense. Seeing a gap in the market, some of those things come very, very instinctively to people. And they have good water feel. They just out of the box for whatever reason they take to these types of things very easily. And they can then, on top of that, build a company, but it's really a company in name. It's a legal entity of some type. But leadership, in my experience, having observed, God knows, hundreds of entrepreneurs at this point, and having been really involved with a lot of them, is not instinctive. Leadership and management are not really instinctive. Some aspects of leadership may be, but really, there's a point where you need training. Even if you're a good swimmer out of the box, you're not going to end up in the Olympics on accident. You're not going to end there deciding what you want to do based on how you feel every morning. And having a playbook that is informed by a lot of repetitions and also a spectrum of exposure, like what you have in working with everyone from the startup names that people will recognize, Venmo, Etsy, etc. And also larger companies, the Dell, Satachi, Sony, Google, and Microsofts of the world. There are principles that work, and they're not all intuitive. In fact, a lot of them are quite counterintuitive. So I'm excited to see what the book does. So congratulations. Thank you, Tim. I do want to say, and I hate to be like this, because I said I didn't want to be this kind of person. But I will say, the first line of my book is leadership is an unnatural act. Okay. And it gets to you. Yeah.

Final Thoughts And Useful Scripts

Why is Randi's book a great read for founders and wannabes alike? (01:56:48)

It gets to your point of, you know, this stuff has to be learned. Giving feedback has to be learned. Even having sort of uncomfortable conversations, most of us didn't grow up in a house where it was like, we all learned to do this. And then even if we did, it just changes in the professional context. So I appreciate what you just said, and I appreciate your kind words. My pleasure. I made it.

So I have to ask before we wrap up, I'll ask a few things. Yeah. Broadway shows, an investor in Broadway shows. I know nothing about Broadway. I've been to a few shows, really enjoyed it. I have very narrow investment experience. I invest in highly speculative, high-risk, early-stage tech companies. And I know how to do that on some level because people have shared their rules. Are there any resources or books for people who would want to learn more about the economics and just the ecosystem of Broadway? And what comes to mind for me for the contemporary art world is a book. I think it's called the $12 million stuffed shark, which was written by an economist who is familiar with the contemporary art world. There are a number of other books like that for people who want to kind of peer into the black box and get a better understanding of how it actually works. Do you have any recommendations for how one might learn more about that? Well, I think meeting people is the best way to learn, but there is a book. I'm going to butcher the name so you're going to have to find it later. It's how to make a killing on Broadway or something like that. Yeah. Yeah. And it's actually a very helpful book. There are a few other resources out there that I have to think about. But mostly my best learning came from sitting down with a number of co-producers and just hearing about their experiences. And I think like everything learning from other people's mistakes is like the best way to learn about anything, certainly about the world of Broadway. One thing I just want to say is that originally people would send us a budget. So here's the capitalization of the show. Here's much money we're going to raise. Here's the budget and here's the break-even analysis. And then as you, luckily, I am a recovering CPA. So I can kind of dig into those numbers and say, do your assumptions make sense here? Why is this so expensive? Or why isn't this expensive? When you see enough shows and you do pattern recognition, you say, well, you should be allocating more money for this. What's going on? It helps you ask better questions. And I think that seeing a lot of deals, seeing a lot of packages is very helpful. Yeah, that makes sense to me. That's true, certainly for the startup tech show up as well. The book, I think, maybe confirm, is I want to be a producer, subtitle, how to make a killing on get killed by John Reglio. Yes, yes, thanks to him, yes.

What Alisa would display on a billboard. (01:59:43)

All right, found it. Okay, last few questions. And this one is sometimes a dead end, but I'll give it a shot and I'll take all the blame if it is. If you could put any quote message, word, question, anything at all, non-commercial, on a billboard, metaphorically speaking, to get something out to everyone in the United States, for instance, a political, what might you put on that billboard? Okay. What comes to mind is, okay, it's two-sided, two-sided billboard. Believe in yourself is the first side. An act like it is on the other side. Act like you believe in yourself. Yeah, believe in yourself and then act like it.

Where to find Alisa online. (02:00:31)

Roger that. And people can find you everywhere online. Do you have a preferred social that people should pay the most attention to? Cross Twitter, Instagram, LinkedIn, Facebook and so on. Do you have a preferred handle somewhere? Following me on LinkedIn is a good place to find me and certainly coming to my website, The new book is from Startup to Grown Up, a guide book, also including scripts. I'm just going to hit that again for entrepreneurs on leadership journey from founder and CEO.

Parting thoughts. (02:01:09)

Super excited about that. Is there anything else you would like to say, any closing comments, anything you'd like to add before we wrap up for today? Tim, two things. One is thank you for having me today. It's been really great to catch up with you and to talk to you in this conversation. I really appreciate it. The second thing is just I want to say thank you for all the work you've done over the years for sharing certainly world-class practices and tactics. Also for your recent, I think really courageous work and revelations about your trauma from childhood and also about your exposing this new world of psychedelic science. I know it's been helpful to a lot of people and I just really want you to know what a difference it's made. Thank you, Alisa. I really appreciate that. It's so nice to reconnect and we have much more to catch up on, which we'll do offline. That's to be continued. This has been so much fun. I'm really excited for you and the new book and for the ongoing career of K-Bell, for those who don't know. The stage name for her rap is in Kettlebell. I'm really looking forward to watching this all unfold with this new chapter pun intended with from startup to grown up. Thank you for taking the time today. For everybody listening, believe in yourself and then act like you believe in yourself, two-sided billboard. Thank you for tuning in. You can find show notes, links to everything we have discussed at. Until next time, thanks for listening. Hi everyone.

Scripts that leaders find most useful in terms of handling difficult situations (02:02:52)

Tim asked me to give you guys a few scripts. I'm going to share with you some of the ones the leaders I coach find most useful. The founders and leaders I work with, they find scripts super helpful. When I walked them through how I would say something as we're talking, they scribbled down furiously and they asked me to repeat it. And they made me realize that people struggle with the actual words to say. So I began to develop scripts that people can use to handle delegate situations, difficult conversations, difficult situations. Now remember, all of these scripts are just guides. You're going to have to tailor them to your own situation, but they should give you a running start. I'm going to give you a selection of scripts here. I created this set just for Tim's listeners. They're not in my book or on my website. There are a few categories for you based on what my clients have found the most helpful. First I'm going to share a set of five feedback scripts that lead up to firing someone, since this is naturally a very difficult conversation and you need help for that. Next I'll give you a script to help you get feedback in your job so you can get promoted. Then a few scripts about how to have great one-on-ones, including how to use your one-on-one to give career coaching to your employees, followed by how to tell someone you're bringing a new leader in to manage them. The last ones will be about my favorite topic, networking. I'll give you some easy ways for you to network, including a script you can use to reach out to someone you've been out of touch with for a long time. When I ask people what's the most common script, they wish they could have. The number one answer by far is how to fire someone, which I can totally understand since firing someone sucks, but you have to do it sometimes. That's your job, sometimes as a manager. I'm going to give you five feedback scripts here, ending with how to fire someone. These are for founders. They're really for any leader or manager or for anybody who is responsible for hiring people, working with them to help them together. Your job's right, doing coaching and feedback with them, and then ultimately again, if the time comes, firing them if they have to. The one I'm going to start with is positive feedback script. That may surprise you. This is the script that nobody asks for, but almost every manager needs. I'm starting with positive feedback because I think people underestimate how really important it is to give your people positive feedback on a regular basis. We always talk about feedback as if it's negative, but actually, many managers have to learn the skill of making sure that they praise their people. They give them positive feedback on a regular basis. That helps motivate your employees. It helps them be more confident and take more risks, and ultimately it builds up goodwill between you and your employees so that you can deliver a difficult message in the future if you need to because they already have the experience of being complimented by you and being appreciated by you so they know you're on their side. Now I think what gets in the way for managers is, first of all, they're not thinking about it.

Feedback Mechanisms In Workplace

The importance of positive feedback and how to give it (02:05:34)

Second of all, it can actually be a little uncomfortable, almost a little embarrassing for some people to give positive feedback, especially if they didn't grow up with their own positive feedback from other people. It's like the workplace version of "I love you." So having a script will help you, and practice will help you too. So first of all, what you need to do is find something to compliment. It doesn't have to be the Nobel Prize of activities that they do to make you realize that you can compliment them. Did they do a good job planning a meeting? Did they do a solid draft of a deck for you? Are they doing a great job getting up to speed on something? It can really be anything that you're really proactively noticing to give them positive feedback. So next is be specific. Now here are some examples. Here are some specific scripts that you can take to just give quick positive feedback. Bill, that spreadsheet you gave you was so clear and well formatted, well done. Andrea, I know that your counterpart in marketing can sometimes be overly emotional. I really appreciate that you go to the extra mile to maintain a productive relationship with him. Chris, I'm so impressed with how you handled yourself in that board meeting. Your presentation was excellent, really well structured, and you de-escalate in the tense moment which could have derailed us. Now there's another spin on this which is encouraging even when someone is struggling. Jennifer, I know you're behind on that project. I just want to make sure you're okay. I see how hard you're working and I know some issues came up that none of us anticipated. It's super frustrating, but I appreciate your hanging in there and I know you'll solve the issues and get it behind you. It's really nice when you express confidence in someone's ability to solve problems even when something's going wrong. Now if you are like many leaders and managers, you know you need to give more positive feedback. I would suggest you literally put it on your calendar or make a spreadsheet to remind you to do this because it's important for you to integrate that into your day to day and week to week. So I promise it'll make a massive difference to your employees and it'll increase their productivity and loyalty. Now very often it's great for you to give positive feedback and just leave it right there, have them have the experience of just being praised. Then sometimes it's important to take the positive feedback and use it as a spring board to help them build a new skill or think about something differently. So I'm calling this one developmental feedback. This is not constructive criticism.

What is development feedback (02:08:14)

That will come later. When you think about development feedback, it has to do with somebody understanding what they're doing well and then what they can build on top of it to be even better. Most employees actually think this is good news. They understand they're doing well and good employees always want to know how to improve. So when you set it up with positivity and then also be specific, you can create that bridge to you're doing great and then do more of this. So now here's a script you can use and there are two examples. One is for a more junior employee. Chris, I love how you jump into all your projects so enthusiastically and move so fast again in your work done and your cheerful attitude towards everything is so refreshing and it's even infectious. I'd love you to advance your game in this one area. When you complete a project, rather than just send it off, pause for a minute and think about how to make sure it's really finished. For example, sometimes when you send me a spreadsheet there are some mistakes that I bet you would catch if you looked it over or when you send emails, I think they'd have more impact if you proofread them. Could I ask you to give your finished products a second look to try to catch errors before you send them off? Let's check in about this in a few weeks and see how it's going. Here's a script for a manager, someone a little more senior. Tammy, you're doing a great job managing your team. They love you and your whole group is getting more productive every month. I love the systems you implemented. Now that you've gotten your arms around your team, I'd like you to prioritize building relationships and coordinating with your peers. We need to be synced up at the leadership level and I have the impression that not everybody knows what your team is doing. So can I ask you to make sure your priorities getting to know your peers better and sharing your goals with them and getting them to share theirs with you? Let's touch base next month to see how it's going. What help do you need for me? Notice that the whole tone of this is positive. It's clear that you appreciate your employee. It's clear that you see what they're doing well and it's clear the specific thing you're asking them to change or to fine tune and there's even a bit of a follow-up plan with a date. That is perfect and the hope is that they're going to take that and run with it and continue to improve. If they don't take it and run with it and continue to improve, you then want to have the next conversation, which is the difficult feedback conversation. This actually is constructive criticism.

Asking Employees to Take Ownership (02:10:37)

The issue here is that often you've seen the same problems over and over with your executive or employee and they need to make changes and they haven't made these changes. That's when you really need to address them in a more specific and maybe intensive way. Here's a script for you to do that. Matthew, in the past month, you've made two major decisions that touch the product team and the marketing team without consulting them or even letting them know. You've missed the opportunity to get their feedback, which would be valuable, and their input, which is essential to the success of our project. Now I'm concerned that because they haven't been in the loop, they're not going to co-own the process with you, so it's going to be much harder for us to finish this project. We've talked about this before and you told me that you'd make sure to get people's input before you made decisions. I need you to fix this one problem by going and talking to these folks right now and then even more critically, I need you to operate differently from now on. We're not going to be successful and we won't be successful as a business if you don't collaborate a lot more closely. I'd love to hear back from you by the end of the week about your plan to solve this once and for all. I'm here to help you if you need me. I'm more than happy to talk through your plan, but I need you to take ownership of this issue and fix it. Harry, you've communicated to them the seriousness of the issue, the specific thing you want them to go and fix, and the timeline that you want to hear back from them. It's not just going to fall off the radar that you've actually agreed on a timeframe that they're going to come back and give you a plan. That's important to make a forward motion. My suggestion to you is that you role play this. I know you don't want to role play it. Nobody wants to role play it, but I really encourage you to do that because first of all, it's going to help you get your tone neutral and that's going to possibly reduce defensiveness and set up actually a good dialogue after this conversation, which is important. The second is that when you get a little nervous, it's hard to have your mouth around the words and when you role play it, it forces you to say the words out loud. Let's assume that you've had a couple of these conversations and things have not improved. That is disappointing, but we have to get to the conversation before the fire in conversation. You never want people to be surprised when they get fired. You also want to tell yourself, "I did everything I could to help this person make changes, and I communicated to this person and the person should not be surprised." That's why it's important just for you and your own sanity and also to give them a chance to make sure that you have the conversation before the fire in conversation. Again, I really encourage you to role play this.

Be Humane and Be Compassionate, But Also Be Clear (02:13:16)

It's hard to land, but it's super important. Also they're going to be upset. This is an upsetting conversation. Be humane and be compassionate, but also be clear. The issue might be performance, or it might be leadership or cultural qualities. I'm going to give you two scripts. I'll start with performance. Camilia, we need to have a serious conversation. You and your team have consistently not met your goals or even come close, and as a result, we've had to move the new product launch twice at the last minute. I know things come up, but your job is to anticipate what those things are, manage your team to deal with them and work with your peers to coordinate all of it. And I don't see you doing that. What I need you to do is immediately, debrief with your team and your peers, pull together a launch schedule that will meet our business goals and then make that date. If you can't do that within the next two months, I'm sorry to tell you I'm going to have to find a new leader to take your role, and we're going to have to part ways. I'm telling you this because I want you to know where I stand on this, and I want you to take it seriously. If there's anything you need for me to help you improve, let me know. I want to hear back from you by the end of the week about how you're approaching this. And here's your second version related to leadership and culture. Matthew, we need to have a serious conversation. We've talked in the past about my concerns about you're making unilateral decisions about areas that affect other areas of the business. Collaboration and transparency are super important values here, and if you keep making decisions in a vacuum, you aren't being collaborative or transparent.

Transparency is Super Important Values Here (02:14:51)

You're also not getting good ideas from others. You're surprising people, and you're not getting buy-in from the people that you need. You're also making people feel dismissed. It's not a sustainable way to work. I need you to know that if you can't fix this issue, we're going to have to part ways. I'm telling you this because I want you to know where I stand, and I want you to take it seriously. I need you to fix this immediately by mending fences with your peers and employees and be taking into account their input before key decisions. If there's anything you need for me to help you, let me know. I want to hear back from you by the end of the week about how you're approaching this, and I need to see improvement within 30 days. Now this is definitely one you're going to want to roleplay. I remember to stay even-keeled and be ready for a discussion after this. I can't give you a script for an unscripted dialogue that's going to take place after you land this one. So in your roleplay, think through how your employee might respond, and what you might say during the discussion that will follow, when you prepare for what they say in response and practice getting your mouth around the words of the script, it will make you feel much more confident. And then you can stay present and listening and also continue to reiterate your intention clearly, which is that this is a serious problem and your employee has to fix it. You've tried to work with them to help them improve. You've told them in no uncertain terms what you do them to do, and they haven't done it, and now it is time to have the conversation in which you fire them. So even though you've already discussed it with them, even though you've given them plenty of signals, they still may be surprised because they didn't really think you were going to fire them. We all have a high capacity to deceive ourselves when we want to. Make sure you use decisive language so there's no question and that there's no sort of wiggling around it. And again, be humane.

Firing someone (02:16:44)

It sucks for you, but it's actually worse for them. So before you fire someone, think about your plan. Tell your board or whoever your boss is that you're going to fire this person and why. Hopefully you've already given them a heads up about the issue. Tell your HR person and help them help. Make sure you have a transition plan ready, and you have to think about the things like severance and termination agreement already lined up. And then after you do this, you tell the person's peers, the person's direct reports, then the rest of the company. So remember to be compassionate and also clear. And here is the script to fire somebody. Camille, yeah, when we talked about six weeks ago, I told you I needed you to get your arms around the issues with your team and work with them and your peers to get the launch back on track to meet our business goals. So far, you still don't have a realistic date. Your team is not clear on what's going on and neither are your peers. It's time to part ways. I know that's hard to hear, but that's my decision. Let me tie with the transition plan and the severance plan. So of course, after that, Camille may want more of an explanation and she may protest, but you know that you've had a whole bunch of feedback conversations with her and that she couldn't be completely surprised. You also know that specifically you've had the conversation before the firing conversation so although this may still be difficult, you've gotten your words out. You've been clear on what's going to happen and now it's just the details of sorting all that out. So I hope that was helpful. All the conversations leading up to having the fire in conversation and then ultimately the fire in conversation. Let's move away from that, shall we? And move on to some different topics.

Workplace Hierarchy And Interaction

Get more feedback from your manager (02:18:30)

I'm actually now going to put you on the other side of the feedback conversation, how you can get more feedback. Maybe you're not getting promoted, but nobody's telling you why. It's actually hard to get feedback at work. So I'm going to give you a sense of script for how you can get more feedback from your manager to help you get promoted. But before you do this, do some prep work first. Look around your company. What kinds of people are getting promoted? What characteristics do they have? What sets them apart? So I would encourage you to do like an anthropological study. You begin to get a sense of what's valued around your company and then you can adapt your own behavior to what's valued. Now once you've done that, you can definitely and you should definitely go and ask your manager for feedback. The reason you're not getting feedback is that people don't enjoy giving feedback. They don't know how to. They're squeamish. They also don't know how you're going to react. So you might have to insist on this and that will you'll get useful feedback from your manager. Here's a script you can use. Suzanne, I've been thinking about my career. As you know, I want to be able to have more impact and I want to progress in my career. So it's important to me to know if I'm on track on getting promoted. Now I've seen a few of my peers get promotions lately and I'd love to talk to you about my performance and what it will take for me to get to the next step. Your manager might say, "You're doing great. Keep doing what you're doing." And then you can say, "I appreciate that. That's really nice to hear." But I've realized that I need more guidance to help me get where I'm going. Do you have any suggestions for me? Asking for suggestions can be easier for them to respond to than feedback. Then she might say, "I don't see you being proactive." Or you need to show up more as a leader. And that's annoying because what the heck does that mean? But don't say that. Say, "Thank you" because you want them to give you feedback regularly and you've got to reward that behavior when you actually rest something out of your boss. So here's what you can say in response to that. Thank you for sharing that. I appreciate it. Would you mind if we spent a few minutes talking about what it would look like if I was showing up more as a leader? Are there behaviors you can point me to? Then you might find out that you may seem dismissive of your peers if they can't keep up, which is not good. Or you might find out that you don't proactively coach more junior employees so you're not showing up as a leader. Now, you may not agree with that, but at least now you know what's in your boss's mind's eye. You've got to listen to what she says, ask questions in a neutral tone of voice and overall make it a positive experience for whoever's giving you this feedback. That way they'll give you more feedback and then you'll have a better sense of how you're showing up and what you need to do to get that promotion. At the end of the conversation, ask if you can check in in about a month and then make sure you do that. So if you'll be consistent and be pleasant to deal with, you're much more likely to get the feedback that you need to get ahead.

One on Ones (02:21:39)

Now let's go back to you and your role as a leader and we can talk about one-on-ones. One-on-ones are a foundation of how you can build the right relationship with your employees and also it's a way for you to hear what's going on with them. So here's a script you can use to either set or reset expectations for your employees. If this is the first time you're doing one-on-ones, you can set the expectations, but if you've been doing them for a while a different way, then you can use this conversation and you can just adapt it to reset the expectations. Donnie, I wanted to give you a sense of how I view one-on-ones and also to get your take. I think of our one-on-ones as mostly your meeting. Whatever you want to bring up is definitely on point. Let's not just do status updates. If you have questions about what's going on in the company, if you have a great idea you want to share, or if there's something you want my advice on, bring them up here. We can also talk about your career path. I'm sure I'll have things on my mind and let's check in every once in a while to make sure they're working for both of us, okay? Then when you do your one-on-ones, ask your employee to prepare by thinking about the topics that they'd like to discuss. Now they may not do this very well at first, but that's okay. They'll learn. If you stick with it, you'll both get the hang of this and you'll adapt your one-on-ones to be more satisfying for both of you. Here are some questions you can ask your employees so that you can have a deeper conversation about work in your one-on-one. What do you like best and what do you dislike the most about your job? Where do you see yourself going your career and how can I help you get there? Do you know where we're headed big picture as a company and do you have any questions about it? Do you know what your top priorities are? Are you having any problems working things out with any coworker and do you need my help? What suggestions do you have for me? These are great questions to start you off. Remember that you don't have to solve all of their problems. In fact, a really good role for you of this one-on-one is for you to coach them, to help them solve their own problems. Also, it's just get a handle on what's going on with your employees and also certainly if they have specific asks of you, this is a good moment for them to tell you so that you can help them in the way that they want help. You can also use your one-on-one for career coaching and I absolutely encourage you to do this. So, a few times a year, make sure your employee knows this in advance that you're going to do this career coaching. Remember that your job is to coach and support not to do all the work for them. You can tell them straight up that you think it's a good idea to do career coaching now and again and here's a script that you can use to introduce this topic. I think it's a good idea to sit down regularly and talk about your career development. Let's do that a few times a year so I know what you want to do and I can help you achieve those goals. First of all, you just get a ton of points as a manager. Just even bringing that up because most employees do not have the experience of having their managers come and proactively talk about their careers. Now, again, all you have to do is ask them questions and then be supportive and help them problem solve to get where they're going. Here are some questions you can ask. Do you have a sense of where you'd like to go in your career in the next few steps? By the way, it's okay if they don't but I would encourage you to keep asking them to help make sure they're pointing in the right direction. What parts of your job right now do you like the most and what do you like the least? What kinds of training or experiences will help you move in the direction you're interested in? If you don't know, how should we find out? Is there anyone inside or outside the company you think you could learn a lot from and want to spend more time with? What would you specifically like to commit to so that you can make sure that you're moving forward on your career growth and how can I help you? Then you can close this discussion by saying, "I'm here to help you with your career growth and of course to help you do a great job at your job." If you ever want to discuss these topics with me, just come to me. You don't have to wait until I initiate them. If you ever think we need to discuss this more, please just tell me, don't wait for me to figure it out for myself. So that puts the responsibility on your employee, not just you the manager. So it's really a joint responsibility to have these conversations but your employee can feel free to take ownership. Here's another one on one that's not so fun but it's really important to be able to tell employees this.

How to Tell Someone You're Bringing in a Manager on Top of Them. (02:26:10)

How to tell someone you're bringing in a manager on top of them. We often call it layering because it's about putting a layer of management on top of your employees. It's actually very common in the startup world because what happens is the company is successful which is great. And what that means is you need to bring in more seasoned executives to help manage the company at the new scale. So it's great news but employees really don't like this. They see it's unfair because they've been there for so long and they're not getting the opportunity and they might even see it's a demotion. It's not a demotion and it's actually again good news, not bad news but not to them. So you have to help them understand it and you have to be transparent about it. So here's a script to address it. Elena, I'm making some changes and I want to discuss them with you. You've done a tremendous job bringing your department to where it is now. What you've accomplished has been amazing and we literally could not have gotten where we are without you. Because of your hard work and everybody else's hard work, we're hitting our milestones and we're growing and that's awesome. To help us get to the next level, I'm going to be bringing in some seasoned leaders who have scaled companies like ours before. They'll have the experience and the context to bring us to the next level. What that means for you is that I'll be bringing an executive into run your department and you'll report to this new person. I want you to know I'll be looking for the right leader who will also mentor you and help build your skills and your career so that you can continue to grow. If you want to talk about this, I'm happy to discuss it. I want you to be happy but I also want you to know this is what I've decided to do. Now as I said, many employees are not going to like this but it's one of the tough decisions that you have to make as a CEO or as any leader. And in fact, I'm sure it's the right decision because you're looking at the business, you're assessing what the business needs and you're making decisions based on what the business needs. Some employees might leave. Now most will stay and if you tell them straight up your plan, they'll appreciate that you're being honest. It is definitely important to bring in a great leader and if people see they can learn a lot from the new executive, that will reinforce your decision and they'll ultimately be happy with their role and the overall success of the company. I'm going to end this with one of my favorite topics, networking.

Tool 11 Networking 101 (02:28:37)

I was inspired a long time ago by a book called Dig Your Well Before You're Thirsty by Harvey McKay and more recently by the book SuperConnect by Richard Kosh and Greg Lockwood. The point of these books is to understand the power of building and nourishing a network and doing this before you actually need anything. Your network is important because through your network you can get the best job opportunities, the best advice and frankly it's just fun to have interesting people in your life and you get them through your network. Keep in touch with your network and give first. When you think about how you can add value to the people around you, you're built up a tribe and they'll be willing to help you when you need it. So I'm going to give you a few super simple networking scripts and also suggestions. The first suggestion is to keep in touch with your old friends and colleagues. Now that can be hard to do especially when we're all busy. The best way to handle this is to keep a spreadsheet or a list of people who are important to you personally and professionally. You can list out 10 people or you can list out 50 people or 100 whatever feels manageable for you and then regularly scan your environment for opportunities to be in touch with them. So an example is you might see on LinkedIn that one of your contacts got promoted or just wrote a book or changed jobs or got quoted in some newspaper or whatever. This doesn't have to be their biggest achievement ever. You can just write a quick note of congratulations. In my network, I recently read that one of the Broadway producers that I know got named to a prestigious committee. So I sent him a note and I said, "Hi Brian, I just saw that you got named to the XYZ committee. Congratulations. They're lucky to have you. I hope everything else in your world is also going great." That's it. It took 20 seconds. He wrote back to me in 30 minutes and he was so happy to hear from me because people love being congratulated and acknowledged for an honor. So be on the lookout for that. You might also see an article or a book that would interest them or come across a memory of some sort. I have a former client who is embarking on a sabbatical and I recently saw an article about things to do on your sabbatical. I sent her a quick email, "Hi Kayla. I saw this article and I thought it might help you as you start your sabbatical. Let me know if you like to brainstorm how to get the most out of your downtime and also enjoy it. Hope it's starting off great." Again, 20 seconds. Super easy. Offering to help is a great way to cultivate your network. As you communicate with people or seem on social media, you'll get a sense of what's going on with them. Maybe they're moving and you might know people in their new city. Maybe their kid is looking for an internship and you know of a good program for her. You can just send a quick note offering to help. I'll give you an example. Sam, the son of a friend of mine, was trying to transition out of being a lawyer and looking for a job in the startup world. I happen to know the founder of a startup who was building a legal platform. It was very quick and very simple to write her a note that said, "Hi Mandy. Looks like your company is doing great. I know someone who's trying to transition from being a lawyer into the startup world. He's super smart, proactive and can juggle multiple balls and obviously he knows all about the legal profession. Do you want an intro?" She said, "Yes, I connected them and then she hired him and they both thanked me. It felt great. That's a moment that reminds me how fruitful networking is and how satisfying it is." Remember to dig your well before your thirsty and stay in touch with key people. But if you do need a favor from someone you haven't talked to in a while, just reach out, be warm and be direct. Don't pretend that you were just thinking about them. They're going to find out that you actually need something. So just be honest and upfront and give them an out to say no. Here's an email you can write to someone you know whom you've lost touch with. "Hi Brian. I hope you've been well. I saw him linked in that you moved to Denver. I'm sure it's wonderful for you to be there since I know you always love to ski. I'm sorry we've lost touch over the years. I'd love to get reconnected anyway and hear how you're doing. The reason though that I'm reaching out right now is that I have a specific ask. I'm looking for a new job in marketing and your company is on my dream list. I'm wondering if you'd consider connecting me to some of the folks in your marketing department not to ask them for a job but just to begin to get to know some people there. If it's not a good time, I totally understand and no worries at all. Either way it would be great to get in touch.

Outro (02:33:04)

Then send it and don't think about it. They'll either write back or they won't. Either way, let it inspire you to stay in touch with your network consistently." That's it. I hope that you find this material as helpful as my clients do. I absolutely hope that you take one or two things away from this Scripps Masterclass and practice them so that you can gain real dexterity and real mastery over the way you can handle sensitive topics and sensitive conversations and be able to say the right thing to the right people at the right time. Feel free to reach out to me through my website, and I'd love to hear how you use this material and what difference it made for you. Thank you. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is 5-bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little more soul of fun before the weekend? And 5-bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to That's

5 Bullet Friday (02:34:46)

All is spelled out and just drop in your email and you'll get the very next one. And if you sign up, I hope you enjoy it.

Sponsors And Advertisements

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Introduction Of Guest

Intro to Klara. (02:39:04)


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