9. From Startup to Grown Up: Coaching for Success with Alisa Cohn

My name is Patrick J. McGinnis, and I coined the term FOMO. That's short for fear or missing out. And it's why some people end up following the crowd. But we're not like them. We're part of a new species that isn't afraid to do things differently. I call us FOMO Sapiens. And this is the show where you'll meet people like us. Phenomenal FOMO sapiens. To learn how they find the courage and the ideas to live exceptional lives. Fomo. Fomo. Welcome to another episode of FOMO Sapiens, the show for people who don't just follow the crowd, but instead take their own path to success in business and in life. I'm your Host, Patrick J. McGinnis, venture capitalist by day, author and podcaster by night, and FOMO sapiens 24 7. And we are continuing with our theme of entrepreneurship here in season seven. And today we're going to talk about how do you go from startup to grownup? Always a challenge. And my guest today is the author of the book called From Startup to Grown Up a Great Grow your leadership to grow your business. And her name is Alyssa Cohn. She's an executive coach who has worked with founders and C suite executives at prominent startups and companies like venmo, Etsy, and DraftKings, as well as Fortune 500 companies like Dell, Microsoft, Google, Pfizer, and the New York Times. She was named one of the top 100 leadership speakers by Inc. And the famed executive coach Marshall Goldsmith named her the top startup coach in the world. Wow. Her articles have appeared in hbr, Forbes, and Inc. And she's been featured as an expert on BBC World News and in the New York Times Wall Street Journal. Now, I wanted to have Alyssa on the show because I got to tell you something, this whole coaching thing, it's. I don't even know. I mean, you hear about coaching, but it feels like there's a lot of people out there and you're like, oh, you're a coach. What exactly do you know? But there's also really impactful coaches. And I've talked to friends who work with coaches, and they say it changes their life. So I just wanted to come on and first of all, just about the coaching industry, what it's all about, who does it, that whole thing. Then I wanted to get her expertise on how she coaches founders and also how can clients get the most out of her talents? Maybe some of you have a coach. What should you be doing to get the most out of the time you spend with that coach, she also gets into some really just tactical, valuable advice, like how to run a meeting. And my favorite topic, which I fail at on a daily basis, how to say no. When you want to do everything, you can't do it all. How do you say no to stuff and just do the things that are important to you? Now, I do have one small ask this week, and the ask is this. Consider having me speak at your company. So, don't know if you know this about me, but I do speaking all the time. I talk about decision making, I talk about entrepreneurship. I've spoken to companies like Google and Viacom. I've spoken at the World bank, the State Department, Axel Springer, ypo. And as you can see there, it's not, not just in the US I do it overseas. I do it over zoom. I do it in all the ways. And so I love speaking to companies. I customize what I talk about to your company's needs. And I've been booking up my calendar for 2022 back on the road, and obviously on some zooms, and it's happening. And so if you're interested in learning about my speaking practice, you can go to my website, patrickmcginnis.com and there you can actually download a speaking kit which talks about the kinds of things I talk about and has some of my credentials and stuff. You can also just reach out to me@Let's Connectatrickmacinnis.com and I can tell you all about it. So thanks for considering me. All right, and now onto the interview. As you know, I like to ask the same question every time. And with Alyssa, it's no different. So I started our interview by asking her this question. What's a formative decision you've had to make to get to where you are today?

Great question. I'm going to say the formative decision was becoming a coach. I was, you know, I was working in the startup world way down in the first Startup World.com version 1. And the crash happened and I got offered a number of jobs, and rather than take any of those jobs, like, actually, my coach at the time said to me, you keep being offered that same job and you keep saying you want to do your own thing. The time is now, and if it doesn't work out, you'll still be offered that same job. And I knew that she was right, even though it was very painful and scary. But I decided that the thing for me to do right now is to become a coach. And that's what I did.

That. I mean, there's a lot in there that to unpack about the fact that so many people have a scarcity mindset. I do. I'll admit it. And that you just kind of swatted away because it's like, listen, that'll still be available to you and so take a risk is really powerful stuff.

Yeah. You know, whether that's scarcity mindset or also, I think tunnel vision. I mean, the same thing I could say is that when I moved to New York about 15 years ago from Boston, I was. I was really scared and I moved to New York and it was only with the realization that actually I could move back to Boston if it didn't work. You know, I think a lot of it, it's more about, like, the notion of reversible decisions and irreversible decisions. And there are a lot of decisions that you actually can undo. But if you kind of get yourself into this it must work or else mindset, then you won't try anything new and you won't take the risk for fear of the failure. So I think the ability to take risks safely is so important for all of us on our journeys.

Now, I have a whole plan for this interview, but I'm going to take a little veer to the rest stop.

Okay.

Like, because. Because, you know, I. Yes, we are. So just before we get into it startup, where you're straight, you know, world's number one startup coach, you, you work with entrepreneurs all the time. You were there for the first crash. So that made my ears peak up a little bit. And I've been looking around, I'm like looking in the air, trying to see if we're gonna get into another crazy crash. And you talk to entrepreneurs all the time. Where's your kind of. What does your Spidey sense tell you about that?

My Spidey sense tells me that there certainly has been a lot of money in the space, which has kind of maybe inflated valuations and also overblown confidence. But there are so many businesses that I personally work with, the CEOs of businesses that I personally work with, which have sustainable businesses and sustainable business models. And it goes without saying that, like, the quality is. If the quality is there and if you're building a sustainable business, you're going to be okay. And I also, we. We both know that there's murky waters and turbulence, maybe in the funding environment and the stock market environment, inflation. But also there's an entire new being created right now before our eyes. It relates to web3vr, the metaverse. And if you you can sort of believe it or not believe it, but I think that we're right now creating the infrastructure for that. So there's a lot to be optimistic about in the startup world. But will there be some fallout from this, you know, current, let's say, environment? I think so, but I don't think it's going to be a massive crash.

Okay, thank you for that. I needed that because, I don't know, I've been worried. So let's get into it now. Now, the first thing, I'll be super honest with you, Alyssa. So I've known Alyssa everybody for. For some years now. You know, we run into each other. We have other guests on the show who are friends in common, like Dory Clark. And so, you know, we know each other well in terms of socially, but, like, we haven't worked together. And I found myself last week recommending a coach to somebody. I said, you need a coach, right? And then I said to them, by the way, I say this to you as somebody who generally has, like, never really understood what coaches do and kind of been skeptical because I think we all know that person who, like, couldn't figure out what they wanted to be. And so then the next day, they're a coach. And which is crazy. It's not like, you know, I'm sure there's certifications and stuff, but, like, it's one of those things that, like, anybody can say they're a coach to some degree. And so the industry, it's kind of like it's hard to figure out from the outside who's real, who's not, and sort of all that stuff. So I'll just put that out there as, like, my. My cognitive bias. Okay? That being said, you know, you are legitimate. We all know that. And so I want you to first just say, like, what is a coach? And, you know, what is a. What is a good coach versus a bad one.

So, first of all, thank you for your faith in me and my credibility. I appreciate that. You're not wrong about the industry, which definitely has people all over the place, including, you know, this notion of not just business coaches and executive coaches and career coaches, but also life coaches, you know, so there's a lot of different elements to it, and there's not a strict certification process. Like, you may or may not know that. I'm also a CPA for my sense. And with the CPA process, let me tell you, there are strict certifications. It doesn't just happen, okay? You have to do a certain amount of training. So compared to the rigor of that. The rigor of coaching as an industry hasn't quite gotten there yet. But if I think about a coach, I would just say this. A coach is someone who helps you get, helps you figure out where are you, where are you going and help you get there and how are you going to get there. And it's important to recognize that a coach is not a consultant, like here tell you what to do and is also not a therapist like oh, tell me how, tell me how it feels to you. It is someone and I'll speak for myself. I as a coach, I look at my clients and I really think about what is your context, what's your business context, what are the most important things that you need to to do, to affect, to activate inside of your business context, to do, to support, to conversations, to have processes to run and then what is in the way of you doing that? It might be a skills gap. I don't know how to delegate. I know how to give feedback. But it might be a mindset or an inner gap, as in I'm uncomfortable, I don't know how to get over it. I'm maybe unsure and don't know how to move forward when I'm unsure. So when I think about a coach, the sort of critical aspect is to be able to really figure out and step into someone's world with them and help them unlock what is locking them up so that their full leadership capacity can be unleashed. FOMO AI is incredible. It can teach you how to fry an egg and even write a poem.

Pirate style, but it knows nothing about your work. Slackbot is different.

It doesn't just know the facts, it knows your schedule.

It can turn a brainstorm into a brief.

And it doesn't need to be taught because Slackbot isn't just another AI. It's AI that knows your work as well as you do. Visit slack.com meetslackbot to learn more.

TaxAct knows filing taxes can be confusing. So we have live experts on hand.

Who can help answer any questions you may have.

Questions like can I claim my SUV is my home office?

If I answer work emails in my car? If I adopted 12 dogs this year, can I list them as dependents and.

Am I doing this right or am.

I doing this very, very wrong? Our experts have the answers to those questions and many others.

Tax act, let's get them over with fomo and then you know, the good ones versus the bad ones. Like I guess if we think about that, how does one tell the difference?

I always recommend to people. When you're choosing a coach, there are two things to look for. Number one, can this person help you? So there's a lot of things around that. What I do with my clients before I start with them is I actually do a little mini coaching session to see if we can actually get traction on something that's meaningful to you right now. And what I know is that it won't take longer than 20 or 30 minutes to do that. And if we can't do that, then maybe I can't help you. But mostly I can do that. And what I think is that coaches should be able to add value very quickly by listening, understanding, and then, you know, helping unlock it. As I said, kind of unlock things which are gummed up. The second thing is you have to figure out, do I want to spend time with this person? Because I used to minimize this, but now I actually think it's super important. You're going to spend a lot of time with this person. The person's going to help. You have to give yourself over to your coach. You have to be able to be willing and able to call your coach or reach out when there's a problem, when you need something. So you better enjoy this person. You better have kind of a rapport together. So that's the way I see it. And I would also say it's obvious that you want to look for references of other people that the coach has helped and hear about scenarios that the coach has, like, worked through to see if you can see yourself inside of that.

Now, you've been at this for more than 20 years, right?

And I'm just curious about 20 years.

Okay. Hey, that's experience. Like, we should. You should be, like, even more. But thinking about, like, you go back in the magic Homo sapiens time machine to, you know, when you started this out. Now, you know, I mean, I'm sure you've made tons of mistakes. You've learned a ton of stuff. Like, what is the big thing you've learned that you wish you could go back and tell yourself in the beginning that would have transformed you kind of earlier on.

It's such a great question. Several things come to mind. One is we are, you know, I've been trained as a coach. I've been, you know, guided and mentored specifically by Marshall Goldz with the legendary executive coach, the number one on the planet. And one thing that I sort of. We were sort of taught that I've experimented with and now realize is so important is to follow your curiosity. So when something pops into my head, like, I wonder if he's getting enough sleep. Right? I mean, I like, literally something like that. I will then ask. Let me just ask you if you're getting enough sleep, because it turns out that we get a lot of information in from people, and it's not just what people are telling us, but it's the kind of gestalt and the way people are relating to us. And I now know that when something pops into my head, there's a reason for it, and it's helpful to put that on the table. And the second thing I would say is that when I'm dealing with my client, I might feel a certain way. So I might feel agitated, I might even feel bored. I might feel energized or de energized. And it turns out that I, as the coach, am having an experience of all of that person's direct reports and employees and team, just like they are. And so if I'm feeling super energized, which is great, then they're feeling super energized. But if I'm feeling de energized, bored, stressed, whatever, dealing with this person, then there's a good chance that his or her employees are feeling that way too. So knowing that you can then do.

Something about that, that is. I like that because I think oftentimes we forget that when you're working with somebody and you're sort of like, in a detached place, you're like, well, we have a different relationship. But if you're feeling like, wow, this person is really obnoxious, then likely you're getting a little, you know, you're getting like a spoonful of what people are eating all day at the office.

Yes, that's well said. Exactly.

Huh. Okay, now you work with. It's cool. Your client list is super cool. So like Venmo and Etsy and DraftKings, we're talking founders and leaders. I mean, just, I would love to hear a story about, you know, just like, give us a war story to show what it is that you do. Because I think again, it's like, yeah, we sort of understand, but, like, what's the kind of impact that you have? What is the stuff that you're dealing with when you. When you meet with clients?

Well, I'm dealing with so many things, but I guess a war story that comes to mind is that there was a situation with one of my clients a few years ago where they were really, they were having a lot of trouble making progress. So, as you know, in a startup, time is your enemy. And you need to execute and move fast. And. And I don't mean move fast to break things. I really mean just move fast in an operationally sound way. And in the company that I worked with, there was a lot of just lag time. Things weren't being done. There was no sense of cadence, of progress. And the conversations I would have with the CEO were, I am being clear and holding everyone accountable. And then I would do 360 feedback with people. So that means I went out and got feedback from all the stakeholders around her and. And I would talk with her to say, it doesn't feel like that's what you're getting from your people. Right. What they're saying is she's not holding us accountable or we're confused about the different pieces that have to come together to make this successful. Right. To sort of mark progress and to achieve the milestones. So there's first of all, the insight that this is what's really going on. You think you're the expert in your intention, but everyone around you is the expert in your impact. And you think you're being clear and holding everyone accountable, but they don't feel that way. So that's like, number one. And then number two, what called out, what really cried out for, was a team meeting where we could get everything on the table to understand what are our expectations for each other, what are we trying to get done. And it turned out that that sounds really, really simple, but actually there was a lot of confusion about that. Once we straightened that out, it was much easier to make progress. Things happened more easily and moved more quickly and. And the business got unlocked. But also the CEO realized, oh, I have to repeat myself. I have to be more clear. I have to bring these people's attention more, more often. And so it's the insight that then allowed her to continue moving down this path as well as, like the initial unlock where everyone just got on the same page.

It sounds very helpful. I feel like I need to just take you around with me all the time. People do find me helpful, but I have another thing I could just do, which is to read your new book, which is called From Startup to Grown Up. And you recently had this book party in New York, which I went to, and it was cool.

Thank you for coming to my book party.

It was my pleasure. Now, for folks who maybe don't know what this book is out or curious about what it's about, tell us what is in the book and why we should read it.

Okay, good. So the book, as you Said is called From Startup to Grownup. And it's really about the journey and what you have to do to go from founder to leader. But it's also about the journey of all leaders and your personal growth journey that you have to do to become a stronger leader. I divided into three sections. Managing you, managing them, and managing the business because it starts with you, right? So the idea is that you probably have your own natural swing, natural strengths and weaknesses, your natural style. And that's great until it's not. And you have to really think about and understand what's my natural style and then how do I need to adapt? And the second thing is you need to manage your psychology. Because, you know, Patrick, as you know, being a leader, being an entrepreneur is really difficult. You have lots of ups and downs. And so you've got to manage your own psychology and manage your inner voices and find different ways to manage yourself so that you can then be effective. So that's managing you. Managing them has to do with the tools of leadership, right? So feedback and coaching and delegation and how to run great meetings and how you motivate people again in experience, where actually there's a lot of ups and downs. It's super hard. And then the third section is about managing the business because at the end of the day, we want to give the coaching and give the feedback and build the team and build the culture and feel good and then accomplish results, which I think sometimes in the muck and mire of startup world, we sometimes forget to do.

Yeah, we do.

Yeah. Or think about.

Oops, broke that. Okay, let's take each one of those. Like, so I have what I want to take away from today for everybody is like, some. We're all gonna change the way we do things. Cause, like, I was like, I was prepping for this and I was like, oh, man. Like, these are all, you know, we're always learning. But, like, I definitely just love the advice. So let's start with the managing yourself. You know, you talk about that. You have sort of a first piece of advice that you give to people. Who's learning how to delegate and delegation. I'm going to tell everybody, FOMO savings. I'm coming clean. I'm bad at it. Okay. Terrible. Getting better.

You're not alone, fomo Rince knows that greatness takes time, but so does laundry. So Rince will take your laundry and hand deliver it to your door, expertly cleaned. And you can take the time pursuing your passions. Time once spent sorting and waiting, folding and cueing, now spent challenging and innovating and pushing your way to greatness. So pick up the Irish flute or those calligraphy pens or that daunting beef Wellington recipe card and leave the laundry to us. Rinse. It's time to be great.

Fomo. Talk to us about how we can be better at delegating.

Better at delegating. One of my favorite topics. So I guess I would say that it, you know, actually it comes back to managing yourself. So, first of all, thinking about yourself, what does done look like? What happens is leaders CEOs will often delegate things, assume that we're all being clear, not have a clear idea what done looks like, and then be disappointed in the results. So be clear yourself. What done looks like, number two, is about communicating that to the other person. Number three, having clear checkpoints. If there are checkpoints or due dates. What happens all the time is CEOs will say, oh, I tried to delegate, but I delegated it. That person didn't get it done. I was so frustrated. Okay, I understand. Frustration's name of the game. I get it. But did you give the person a timeline? No. She should have known. She should have known that it should have been done this week. Well, I guess she didn't know. Right? So it's about real. Like, to me, delegation is about clarity, and it's also about communication. So when you're able to do that, then you can assess. Because sometimes what happens is we forget that this person may not have the skill level that we need them to have to effectively delegate. And if you delegate something with clarity, then the person comes back and doesn't do it right. Or has a different. Different way of doing it. You can decide, maybe the person doesn't have a skill level to do it and I need to delegate differently or I need to upskill this person or I might have the wrong person, which no question is confronting. But either way, as long as you're clear at delegating, you'll be able to assess that as opposed to this sort of cloudiness of like, oh, it just is not working for me.

Okay. It's like, you're in. You just saw me, you see me. Because, no, as you're talking about this, I'm thinking, because I'm not in a corporate world like I used to be. When I am in corporate settings, though, I do consulting work or whatever, and there's always that person who's like the project manager, and they're really good at that bit. And I'm like, God, I would never want to do that. I'm not interested. But, you know, then everything just happens. And it works. Right? And I would. And I just. I guess my insight is, so if you don't like doing that, then outsource it. Delegate it to a person who is skilled at it. Follow your sort of eat your own cooking, and then you won't have to worry about things not getting done.

Yeah, that's literally true in so many aspects. I just literally had a call, a meeting this morning with a CEO, and he. His point was our meetings are not running well. Our meetings are inefficient. And I'm like, okay, I get it. He said, it's my fault. I'm inefficient. I'm honestly not the paragon of efficiency. I'm constantly distracted. I'm never on track. I'm not managing the time. I said, I feel you. I forgive you, and you need to get 1% better at that if you can. Which we talked about that. But secondly, I said, you know, I bet there's someone sitting in your meeting who's great at managing the time, who's great even at managing you to manage the time. Don't you just want to declare a meeting czar before every meeting? And that person can handle it. And that's a delegation right, right there. That's delegation. And then that person's doing their highest and best use, and you're not getting dragged down with trying to be efficient in a meeting when it's just not your skill.

Now, I heard a rumor that you love meetings, which I'm like, okay, there you go. Good for you. I am not. But maybe you can change our mind. I guess I put this in the managing business bucket of the ones that you talked about earlier. So why do you love meetings? And what are you doing that I'm not? To make them work so.

Well, thank you for letting me talk about my favorite topic. I love the potential of meetings. Why shouldn't we have great meetings with these great people in the room? They're super. They're smart, they're engaged, they want to, you know, make progress. So what gets in the way? So if you. If you or anyone could just say, you know what, from now on, before we have a meeting, I'm going to think for 10 minutes about what is the purpose of the meeting, not the agenda of the meeting. What's the purpose of the meeting? We're trying to get on the same page. We're trying to sync up on something. We're trying to make a decision. We're trying to resolve an argument. Whatever it is, the purpose of the meeting and then the agenda of the meeting is how are we going to get there? And then that sometimes brings up pre work. We can't decide in the meeting. People need to prepare in some way. I need to ask them to prepare. If you, the leader will think about that in advance, that's going to help you have a much better meeting, more on point, more clear to everybody. And then also it's going to drive decisions. At the end of the meeting, the thing to do is to ask the three questions to end the meeting, which is what did we decide here? Who will do what by when and who else needs to know? And if you'll just get in the habit of doing the pre work, the pre planning and asking those three questions at the end of the meeting, I promise you, you're going to have much better meetings.

Okay, so it's what did we decide? Who's going to do what, where, why or when and who needs to know what?

What did we decide here? Who will do what by when? Okay, and who else needs to know?

So you know, again, it's like one of these things where like it's so it's, this is not, you know, it's not like a rocket science thing, but nobody does it. So everybody, we're going to try that. Okay.

No, here's what's normal for me. If I'm observing a meeting or walking into a meeting or doing an offset or anything and I haven't prepared it, as soon as we get there and starts, I'll say, oh, let me just check in. What's the goal of this meeting? And everybody201 goes, oh, great question. And I'm thinking not really a great question, but like a kind of a basic question, however, one that has not been asked. So I see how it's going to be valuable to ask that question. Most of what I do does not require a lot of attention to nuance. But in the fast paced business world and certainly fast paced startup world, many steps can get missed. And I'm there to help make sure that steps don't get missed. So it's like, you know, slow down for a minute so we can go faster.

Yeah, I mean people just have this. There's like a popular notion that when you're an entrepreneur that you're just like a ball, you're like the, you know, a ball of chaos and that you sort of just, there's no structure at all, but you're right. Like the reason why you have scaffolding around a Building is so it doesn't fall over. Well, that's being built. Same thing goes with management teams.

Definitely. Wow.

I should write this should be on a pillow somewhere. I think that's right.

Okay, now NFT it and sell it.

Oh boy. Yes, we will. Now I have one final question, which is a one that again, it's something I think Homo sapiens struggle with because like we're all high functioning individuals, but we are also human. And saying no, it's so hard. And so I would love to hear how you work with people like Patrick and probably many of my listeners who are our default setting is yes and yes, please, yes and more. How do you get us to say no?

I know, I could totally relate to that. I'm a recovering overly yes person myself. The answer is this. Listen as much as possible for everyone. And I think with this a lot. What are your priorities in life? What is your mission? What's important to you? And that's professional and that's also personal. And if you're really clear on that and then you look on a regular basis, weekly or even monthly at your calendar to see what you're actually doing, that is like in a good, in a good way, it's like, yes, I'm doing the right thing or in a bad way. Oh, oh, I'm not living with my values or my purpose. So that's one thing to think about. And the second is if you're really clear with your mission and your purpose and things are important to you in your life, when people then ask you to do something, you'll allow yourself to take a breath and ask yourself the question, is this on the most important list? Is this my mission? Is this consistent with my values? So that's the big picture way to think about it. Because every time you say yes to something, you have to be honest with yourself. You say no to something else, including free time, including rejuvenation time, including white space. And the second thing I would say is when people ask you if you want to do something, please get in the habit of thinking about it and not saying yes immediately because you can always pause and then say yes a day later. It's much harder to say yes and then take it back and say no.

You know what? I do actually. So this is. I'm thinking about our friend Martha Beck and the way of integrity, which came on the show a little while ago and just like, okay, do I actually want. Does this like align with what I see as my life? So I love it because it makes tons of sense to me and what I do, actually I've learned to do. This is kind of new is I don't just respond to many emails right away. I put them in a folder and I wait a day or two. Number one, because if you respond too quickly, people assume that you have nothing to do and therefore they just bother you more because email is somebody else's to do list. But second is that I comment like I do get excited. I mean, you guys know me. I am like Mr. Excited about everything. But if I take a beat, then I'm able to assess things in a much more dispassionate way.

That's excellent. Great tool and it's so true. Yes. All right.

The book is From Startup to Grown up. And if you want to find out more about Alyssa's work, you can go to alyssacon.com and very conveniently, all of her social handles, whether it's Twitter, Instagram and LinkedIn, are the same. Lissacohn Alyssa, thank you so much for being here.

Thank you so much for having me, Patrick. It was a great spot to talk to you.

Fomo. All these patients complaining they can't get their medicines. Insurers and PBMs are often owned by the same giant company, so middlemen like me decide what medicines you can get and how much you pay. But don't worry if your prescription gets denied. We know another one that works for us.

I mean you, Washington should stop PBMs and insurers from driving up drug costs. Learn more@phRMA.org insurecosts paid for by PhRMA.

If you like today's show, please be sure to rate it and recommend it to your friends. And as always, you can find me on Instagram @PatrickJMcGinnis, on Twitter jmacginnis, and on the web at fomosapiens.com or patrickmcginnis.com where you can get all kinds of free resources to live a more decisive and entrepreneurial life. FOMO Sapiens is recorded in New York City. Theme music is by Mike McGinnis and editing and post production is by Josh Elstro. If you like to today's show, please be sure to rate it and recommend it to your friends. And as always, you can find me at fomosapiens.com and at patrickmcginnis.com to advertise on FOMO Sapiens, reach out to contactomosapiens.com.