Alisa Cohn on How To Take A Startup To The Next Level

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We have a lot of pressure to your point about ego, I just think there's a lot of pressure for founders to want to and have to go all the way. And I think it's a really important several moments, right? Series of moments to step back and wonder and is this the right thing? And is my title the right title? Does it reflect the things that I want to do?

You're listening to the Elevate podcast and I'm your host Robert Glaser. Join me as I talk to world class performers about how they build their.

Capacity and reach greater heights in leadership.

Business and life and how you can do the same. Welcome to the Elevate Podcast. Our quote for today is from Guy Kawasaki. Ideas are easy, implementation is hard. My guest today, Alyssa Cohn, helps founders turn their ideas into thriving companies. She was named the number one startup coach in the world by Thinkers50 and has coached startup founders from companies such as Venmo, DraftKings and Mack Weldon. She's also an investor, strategy consultant and coach to C suite executives at clients such as Microsoft, Google and IBM. And she is the first time author brand new book From Startup to Grownup which publishes the day this episode airs. Alyssa, welcome. Excited to have you join us on the Elevate podcast.

Thank you Bob. I'm so excited to be here.

So you spent a lot of your career coaching others? Coached the stars but I'm sure that wasn't your first job. So what did you major in? And then what was your sort of first job out of school?

I majored in journalism. I wanted to major in English, but my parents would have none of that and they wanted me to get more of a trade thing. So I majored in journalism. And my first job out of college was I worked at EF foundation in Boston. Cambridge, actually. It was a nonprofit that was. Helped exchange students come to the US and send exchange students from the US to other countries.

I have a good friend on my soccer team that works at that company. So, yeah, it's been. It's like a multi generational business, right?

Yes, exactly right. Yep.

And then what'd you do from there?

Well, so there, you know, is again, EF education. And I realized I actually liked education, and so I moved into the world of education more strongly. I was the chief of staff to the provost at Northeastern University, and I did that for a couple of years before I sort of found my calling.

And how did you find your calling?

Well, in the provost's office, it was an amazing experience, and I saw so many different things. And one thing we did was strategic planning. So. So I was the chair of the Dean's Council, and we brought in this facilitator to do strategic planning. And she was so inspiring. And she was like. I remember specifically we were doing this meeting and somebody was getting very upset and like, yelling at her and screaming at her. And at the end of her screaming at this facilitator, she said, jane, I hear you saying two things. I hear you saying that we've made a lot of mistakes, and I hear that you saying that you not feeling included. So I want you to know we have made mistakes, and we will continue making mistakes, and we will fix them as we go. And we very much want you to be included in this process. And I was like, I didn't hear her say that. I heard her screaming at you. So I was so amazed by that. That someone could really hold a room like that and turn this gobbledygook into something very constructive. That was really a moment of truth for me.

And I assume the person reacted positively to that.

Yeah. Well, the screaming stopped and we then had a very productive meeting. So. Yes.

So I think I also read you worked as a CFO at a startup early in your career. So how big did that company get and what did you learn? Was that a functional or dysfunctional startup experience?

Well, I think all experiences are good for the soul. Right. They move you in the long run. Right, exactly. So actually, just to give you a little more background After I left, I went off to business school to focus on people in organizations and I got all turned around and I ended up I was at Cornell. And at Cornell there was a lot of focus on finance and strategy. So I focused on finance and strategy and accounting. We actually had this fantastic accounting faculty at Cornell. And so I then exited into PricewaterhouseCoopers again in Boston. And I was on like the fast track to partner program. And so I did a whole bunch of things at PwC, including getting my CPA. And then I realized this is not it, this is not my thing. So I had to kind of go figure out what was my thing. And that's when I found coaching. But I also found the startup world. So this was my second startup I was hired into. And when the CEO came to Boston to kind of like rubber stamp my hiring, he saw like this little bitty thing on my resume that I was a cpa. He said, you're a cpa? I said, yeah. He said, do you want to come to California and be our cfo? I said, no, not really. And he said, we have a rent a CFO and she's robbing us blind. I need you to come to California and sort that all out and then we can move you back to Boston. So I was like, okay, I guess this is what I'm going to do. So that's what I did. And I did that. I was the CFO of that company for about six or seven months until I did sort it all out, which was a huge learning experience, just like figuring out how do you come in the middle of that thing. And I had never been a CFO before. And then I came back to Boston and I was the GM of the Boston. And the truth is that that and the other startup I worked in taught me a lot about startups, what it takes to do execution, what it takes to bring people together, and certainly about product, market fit.

And so what is it like in that role? Were you providing coaching or what really like drove that spark for you? Did you have a coach or this probably didn't exist at that point.

No, they did. They did exist. Yeah. Yeah. When I was at PwC, my moment of truth was that I woke up one and I thought, I hope I get the flu so I don't have to go to work tomorrow. It was a Sunday and I was rushed to the emergency room 18 hours later with the flu. And I thought, oh, wow, this is really, this is really provocative. It's really powerful.

That could be a sign that's going.

To be a sign. Exactly. And I thought, you got to listen to your body. Here you go. Listen to the sign. So then I was like, very upset, like, well, what am I going to do? Because my life was all set. Five years to partner. I know what I'm doing. My life was all set. And so I had to really come to terms with this is not it. So I just think, what was it? And in the middle of all this, you know, I began the process of thinking about how I'm going to quit PwC, which was a great firm and they were great to me as I was leaving, but I had to figure out what I was going to do next. And I went to this conference called Body and Soul, and my boyfriend, who was a yogi guy, dragged me there and we volunteered. And at the end of the volunteer orientation, they said, cheryl Richardson is going to now speak to the volunteers. And I was like, who is that? And can I leave? This is mandatory. Do I have to stay for this? And she is this coach. I found out. And she was amazing. And she was so dynamic and so motivational. I thought, oh, wow, what is that? And the very next day, I saw her do live coaching in front of 500 people. She said, who wants to stand up right now and get live coaching? And I thought, oh, wow, what is going to happen? Someone stood up. She live coached that person for 20 minutes. And I thought, oh my gosh, I could never do that. But I also thought, oh, I could do that. And that's how I figured it out. And I took coach turn like violence played, and I took coach training, and I did. I hired my own coach and then I coached all my friends, and that's how I kind of got the reps in.

Was it life or business?

At the early stage, it was life. But I've always been interested in people in a career context. I've always been interested in people always came to me for advice, for networking and for what they should do with their careers. And I really think that the way you impact people is through their business life because we spend so much time at work. And when you can also make a difference with yourself at work, you can impact people around you. I always had an interest in the business world, but I would say originally it was sort of life coaching.

So are you hired today? Are you hired by the company because they think someone needs coaching, or are you hired by the individual who wants to do better? Both.

Certainly when the CEO hires me, it's because he or she has met me and they kind of Realize, like, they want some of that or they realize. I know. What are you. What are you going to do?

I was going to say when the board hires you.

Yeah, yeah. Well, it has happened several times where the board has said, here's Alyssa, your new coach. Which doesn't work out that well, actually. No, but sometimes the board will say to me and to them, to them, we think you could benefit from coaching. And we've known Alyssa, and she might be someone for you to talk to, and that is a much better sell.

Yeah. And you know what's interesting that I found? And look, you've coached some of the best executives and companies, and the people that want to be coached are already good. They want to be better. The people that fundamentally don't want to be coached think they know everything. It is almost this opposite scenario.

That's true. Yeah. Actually, the people who want the coaching the most kind of need the least coaching. And they're also. They're the ones who are the most open, for sure, and the most humble.

All right, so I want to dig into your new book. You waved me the COVID It's fun to get it from startup to grown up. What motivated you to write the book now? And who's the target audience? Are you warning people about the road ahead, or is it someone right at that awkward teenage business? Teenage years.

Right. Well, I think both can benefit from it. You know, I was motivated to write the book because I would go into scenarios, but go into startups and other companies, and I would say things like, so how often do you meet with your leadership team? And they would say, what's a leadership team? Or I would say, well, have you delegated this thing to somebody?

Delegation.

Exactly. Well, it must be more like, I tried to do that. Didn't work. I told them what to do, they didn't do it. And so I kind of realized, oh, there are avoidable mistakes that I see all the time that I could solve. And I regularly felt like, I wish I had a book that I could hand you to kind of show you the road ahead and help you avoid preventable mistakes. And so I realized there was not such a book, and so I wrote that book. And I'm very happy that I feel like now it sort of shines a light on, to your point, the road ahead and what to do about it.

So when does a startup founder. I mean, I guess in your experience, we see the Zuckerbergs. We see, like, to me, it's always a little bit like the LeBron James or the Michael Jordan Right. We celebrate the, the once a decade. But for most people in companies, is it going to be one person or is it more likely or not going to be different people along that company journey?

What do you mean different people?

CEO like that a CEO can go from startup to public.

Right. It's sort of the age old question. So first of all, in my book, what I say is first of all you have to really step back and reflect and assess. Do you want to be the CEO at multiple stages?

Right. Do you want the job? Is probably a good first question.

Exactly. In fact, talked to on my new podcast called From Startup to Grownup, I just talked to Greg Gallant who is the CEO and founder of Muckrack and he said to me it's like it shouldn't even be the same title. Like your CEO on day one and your CEO on day 10. And they're so different. Oh sorry, year 10. And they're so different that they shouldn't even be called the same title. So to your point, sort of stepping back at a regular cadence and asking is this the job I want? And then what does it require? So what it requires is your ability to adapt and grow very quickly, to change your leadership style very quickly, to change your communication style very quickly. And so if you want to do that, which is very uncomfortable and often founders like don't want to do that because they're focused on the product and they find it kind of boring to be communicating all the time. But if you genuinely want to do that, then yes, I know for sure that anybody who has enough, you know, kind of get up and go to found a company has enough get up and go to learn how to be the CEO. But I think it's really the desire that. The desire and the willingness to.

The true desire versus the ego aspect.

Right?

Exactly. There's a lot of that ego stuff. I actually talked to a founder last year and he told me I fi after like it's like he's a serial startup founder for startups, I think. And he said after the third I finally got that my sweet spot is 0 to 10 million. Everything after that I just need to find someone else to do. And that self awareness is important, but we have to give yourself permission to really say this is not for me.

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Today's show is brought to you by Vanguard. As we step into a new year, it's the perfect time for all the active advisors listening to think about how to set up your clients for success. One way to do that is to level up your fixed income strategy. But bonds are tricky. The market is huge, rates shift and risks hide in plain sight. That's why having a partner with scale and expertise matters. Vanguard brings both. Vanguard bonds are institutional quality. Institutional quality isn't just a tagline, it's a commitment to your clients. It means top grade products across the board. And the Lineup includes over 80 bond funds actively managed by a 200 person team of sector specialists, analysts and traders. Some managers out there promise big returns, but that comes with big risks and that can mean a rollercoaster ride for investors. Vanguard takes a steadier approach. So if you're looking to give your clients consistent results year in and year out, go see the record for yourself@vanguard.com audio that's vanguard.com audio all investing is subject to risk.

Vanguard Marketing Corporation distributor Patrick Lencioni wrote this book, the Motive, which I think is really good on this and it was insightful for me. I'm always curious too on the title of CEO. I actually didn't take it until much later in our company when it was confusing because I was managing director and we had other managing directors and you know, and when you see a founder who is founder, president and CEO, then you know that there's ego problems. But that's right. The title itself is Chief Executive Officer. Right. Which would mean you are the leader of the executives. And to your point early, if you are the executive team, the CEO is almost a title you should grow into at a certain size then you should have in a three person company when. When there are not other executives that you are leading.

Yeah, that's actually a very good point. I just talked to, literally I got a call yesterday from somebody. He is the COO and his co founder is the CEO. She's a CEO and that's all they have in their company. So they've got these big elevated titles. Yeah. You could do better at the early stage, right?

Yeah. And particularly if you are the CEO and you're then playing all of the other roles. You are the head of sales, the head of marketing, the head of finance. I mean, I think the right title is kind of president at that stage. And you can tell, I think by people that sort of over title early that that is what is important to them.

Yeah, I think that we have a lot of pressure. To your point about ego, I just think there's a lot of pressure for founders to want to and have to go all the way. And I think it's a really important several moments. Right. Series of moments to step back and wonder if is this the right thing and is my title the right title? Does it reflect the things that I want to do?

Yeah. And so when in your experience, do you think that the founder starts getting into the danger zone? Is it a number of people? Is it number of revenue? Like, what are the. I know there's some tried and true sort of inflection points where it's like the. The thing into the valley of death and then it's like the next one. But where do you see when the first change really has to happen?

Yeah, I think of it from the point of view of number of employees because, you know, metrics are so different in different businesses. But if I think about number of employees, I think it starts in the 30 range. You know, 30 is where you definitely can't fit everyone in the same conference room. So you definitely have to think about, okay, so who is supposed to make the decision here? Because like at eight people, we kind of all decide together. Maybe at 20 people, we all decide together. And then at 30 plus, there is just a change in the way you can no longer manage everybody as a direct report. You have to start leveling and layering. You have to figure out who makes what decision and establish decision rights. And that's basic. When you then get to be a hundred and then you have two products happening. Right. Or multiple kind of work streams going on, that's when you have to make a shift again. Because then you probably have managers, managing managers, and you, the CEO also have to adapt.

It's so interesting.

I have seen that 30 number in our industry companies hit it. It's kind of at the point where it can't just be about the product anymore. It's got to be about the company. And they either blow through it and double or they kind of crash back under or they'll just. Five years, they just bounce around that number because you could sell market, you could do all the stuff yourself, I think, up until that point. And then you have to start breaking those things up. And that's the point where it also requires adding the infrastructure and the costs.

Oh, yeah, the infrastructure. I mean, also just like systems and tools and a consistent way of doing things to. In order just to keep everybody sane. But some people don't like that and they don't want to do it that way. And then, you know, I would also say at 60 to 80, you definitely want to have an HR person who can help you figure out the business of managing. Right. The tools and structure about managing other people, because that's going to become important, too.

All right, we're going to take a quick break for a word from our sponsors, and we'll be back with Alyssa.

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And we're back with Alyssa Cohen. All right, so there's something really interesting you talked about in your book that I actually saw, and that's that a CEO suggestions are often interpreted as orders. I remember getting feedback on this, where being in a meeting and saying, hey, what if we did this? Or whatever. And then I said, well, Bob told me we had to go do this. I'm like, I thought we were Having a brainstorming, storming. And it took me a while to realize that people took everything I said literally. How do you coach people to manage that?

Right. It is true. And the way to manage that, it's several things. It's first of all to say, clearly, I think we're just brainstorming and here are some ideas. And also. And then you want to be really overly solicitous. I'm sure you guys would know better. You're in the details more. I suspect you have better ideas.

And.

And then you also want to give positive reinforcement to people who tell you that's a bad idea or tell you they're not going to do that. It's really helpful to celebrate people publicly for giving you pushback and also for taking your idea and explaining why it's not what we're not going to do or taking your idea and building on it.

Thank you for sharing that. My idea was crap. Yeah, exactly.

That's good work for you, Bob.

But, you know, one of the analogies I used when I was training someone is, is sort of the Disney cast model, you know, which is like, when you're underground, you're underground, but like, as soon as you're on stage or in the role, I think people start to realize, you know, even not ideas but, but offhanded comments or casual things like, as they have senior roles, they don't realize the weight that those carry.

Yeah, that is so true. Which means that even a slight little question, not even a reprimand, but a question, falls really heavily on people. And also, to your point, you know, your ide our orders. And so you have to constantly be making sure that people understand that the culture we're trying to build here is where the best idea wins, not where the CEOs idea or the, you know, the executive team's ideas win. And I think that also, you can almost make a game out of like in a meeting, you can say, I want to make sure that there's a challenger here who's a devil's advocate or challenger and assign that as a role.

And then give a person.

Yeah, they give that person a lot of reinforcement again, publicly. And then I know that Ben Horowitz, actually, I heard him on the podcast, this is a great idea, and I've used it with my clients. When you get to be in the executive meeting or other more senior level meetings, the cost of admission is bad news. So it's like, tell me something that I don't want to know.

Is there a 2021 exemption on that rule. Feel like people need good news in meetings now. Last year, we had no demand, and this year we have no supply. Like, that's every meeting I walk into.

Right, Right. Exactly.

Right. But you're trying to encourage dissent and.

Exactly. And push back. And push back.

Right. I like that. If everyone's in love with an idea, then someone try to convince us, talk us out of it.

Right, right. And look for disconfirming evidence. But I think. I really think that the leadership, I mean, when you can bake some of those practices into the culture as rituals or ways we do things around here, you're able to lessen that out of size imprint that the leadership or certainly the founder and CEO has on the company.

Well, let me ask you something that I've heard a lot of people struggling with these days in Rosetta, this sort of onstage thing. And that is like showing up authentically, vulnerably, not scripted, but in a world of instant cancel culture that people are terrified of. And so they're very careful with their words and that the wrong words and they're done. Like, that seems like a difficult straddle.

Yeah, it is. I think when people say, you need to be authentic, what they really mean is, you need to be authentic with air quotes. Right. The idea is that, like, you need to be my version of authentic.

Yeah.

So just like you said, a little bit vulnerable. Not too vulnerable. Don't make us uncomfortable, but a little vulnerable. And also that you, like your authentic self, should care about other people. I just want to say that I want you to care about other people too. But some people authentically don't care about other people. Let's be honest. And so what they're really saying is show some humanity. And also, you as a leader will do better when you can showcase some chinks in the armor and show a little vulnerability, because people are more engaged when they think they can contribute. And if you're all set, you got everything all figured out, you have all the answers, you. Then people get actually shut down because they don't think that they can make a difference.

Interesting.

Humanity, not authenticity.

Humanity, not authenticity.

Yeah.

You know, because Kim Scott talks about this, that people who think they're using radical candor are using the obnoxious aggression. Authentic. Right. But. Well, some of it is not hurting other people, but wanting to express how you really feel about something. But again, it's a world of lots of opinions, and it's complicated. I mean, even seen in our organization saying people saying, oh, the. The messaging sounds more. More Scripted or you know, the town hall used to be, you know, more off the cuff. And that was a town hall with 20 people. A town hall with 300 people. You kind of need to walk in, you know, having a little preparation. So it's always, it's always a hard one for me.

Well, I think that's right. You know, there's a CEO I work with and he's trying to, with my coaching and with like good sense, trying to be more maybe scripted, maybe more polished, maybe professional. The company now has 500 people and the early employees don't like it. They don't like it. And that's something you have to live with too because you could say, oh, they don't like it so I shouldn't do it. Or you can say, you know what, we all need to grow here. And as you well know, all the early employees may not make it to the more established, polished company.

We have seen that a lot and I don't think it's because they can't. I think it's because they're just holding on to the past, you know, get a feedback a lot that it's interesting. Funny as a leader you want, you want to put everyone. They say that no hecklers in the show. You want to take everyone and be like, why don't you come on stage and then see what, see what it looks like from the other side. But we get that, hey, we need more information. We don't know about everything, you know, all this stuff. And then we want to, okay, let's have this call or this, oh, I'm overwhelmed. Too much communication, all this stuff. But I have seen this and I've said to a couple of people on my team and again, as people have been around, they're like, look, there's just a general discomfort with not knowing as much as going on In a almost 300 person company is when it was 40. And my answer is I got there and I don't mean it that way, but I don't know anything. I know one person. I mean everyone at the leadership level had to get comfortable with not knowing what their teams are doing. And you have to change to do that or it just doesn't work.

First of all. Totally. And also I think that the question I would ask is what are you really uncomfortable with you middle manager or you employee or even you more senior manager. And to really, I think that's really helpful will be helpful is if you and your leadership team can in smaller environments, one on ones or small groups really get into what is making you uncomfortable? Because it usually comes down to your point. I don't like change. I like the way it used to be. And so then it's like about, let's just sit with what change feels like and how can I help you change? Not like, oh, we need to shower you with more information.

Come back to the quote. That's the best quote. If you don't like change, you're going to like irrelevance even less. From the general. I thought that was a very good one. Yeah, I think it is. Sometimes it's just, it's too much change and it's different and that's hard.

Yeah. Yeah.

Well, we touched on this before, but, you know, thinking about the transition for a founder that's doing too many things. I mean, what are the core responsibilities of a CEO and. Or I guess that how does that change at some of those delineation points you mentioned earlier?

Right. I mean like the fund, fundamentally the CEO create the environment for people to do the best work of their lives and, and also make sure the company doesn't run out of money. And also context switch all the time because they need to figure out when to zoom in and when to zoom out and enable the ecosystem around them overall. So that's the way I see the role of the CEO. And I think that that is sort of the same as you go, but it looks different. It looks different. I think if you think about enabling employees to do great work in order to serve in service of the business, but also for them to be fulfilled and happy and then they want to stay and not leave a kin with a great resignation. So that looks initially like being involved in everything. And I think later stage employees that looks like feeling like their career is going somewhere. So feeling like there's career training around here and career progression. And I know that my work has meaning. And so that's different in different stages in terms of what you, the CEO has to do. And I would say very often it comes down to not what you, the CEO has to do, but also how do you activate your executive team and your leaders to be out there as more ambassadors and understand their role in dealing with employees.

Can we talk about the great resignation for a second?

How are you feeling about it?

I mean, I get angry when I hear a quote like from monster.com that saying 90% of people are looking for new jobs because it's like, I mean, the grass isn't that greener. I think we've been through a very traumatic two years and it's taken an emotional toll on people. And they've been working at places while they had this emotional toll. And so a lot are associating that with work when work is not the issue. So I'm split. I think that if you thought that you realize that life's too short to be doing what you're doing and you want to do a different career and this was the impetus, that's great. If you're like, I don't want to be in the foxhole with these people. They're terrible. And a leader and stuff, that's great. But I think that just like, I need different or I'm burnt out, so I just need a new job, to me feels very like a product of the helicopter and snowplow parenting, which is, if it's difficult, just move on.

Yeah.

And so I just. I see so many people who just think that the new thing is going to be better.

Yeah.

And it's not. It's just going to be new for like a week.

Yeah. Well, you take yourself wherever you go, right?

Yeah. Or when they say, yeah, I'm just looking for, you know, a job that's a little less work and more pay. And, you know, this recruiter who is desperate to build a job has painted this beautiful picture. And by the way, they need me to start in two days. I'm like, well, how calm do you think it is over there when they. When they can't even wait two weeks for you? So. So that's one piece of it. And then the piece that I'd really like to get your feedback on is what I've heard from a lot of other leaders is that I think this is exacerbated generational leadership stuff that they have not had before. They're like, look, I've never had a Gen Y, Gen Z problem before. And now I feel like Gen Xers and the Gen Y, they're all on like totally different pages with this pressure applied. And I've heard multiple people share something to that sediment.

Yeah, well, it's complicated. There's no question that everybody's talked about this as the pandemic, as the great accelerator, which I think that's right. I think it's also has shined a big light on practices. So if you had leaders in your organization who were actually bad managers, and let's face it, there are many.

A lot.

Yeah, a lot. And also bullies or really controlling or focused on status and power. The truth is that that was probably something you were tolerating for a while, and now because of this churn, you're not able to tolerate that anymore. It's just not acceptable. And I think that that is what is causing more of the disruption in the workforce. But I also think it is absolutely true. We have seen Gen X. Well, it's like what millennials and Gen Z. I think what we have seen is that those generations do feel empowered and they feel they expect to have a voice. They expect to have a voice and they intend to have a voice and they have a voice. And I think that that is a new dynamic in the workplace which we haven't seen before. This.

The thing that I've talked to a lot of CEOs about this and they agree. And again, I think no one is saying, hey, I mean, some people might, I worked 80 hours and I was 20 and you should do the same. But not in that vein. But I think we're seeing this gig economy mentality come into corporations. And I think the empowerment part of it's great if they're bad managers or bad policies and people should speak up in psychological safety. But the self optimization in the context of a company is going to get a little complicated, like real time self optimization, because companies have product goals. You know, someone was telling me that their company is in England and they were launching their core product and you know, they get 100 weeks of vacation over there, whatever, and everyone wanted to take all of August off and the product launched in September and they were having to buy back vacation. They're like, look, someone's kind of got to care that we're launching our product here. And so look, I think it's great, the empowerment, but I think if we get to where it's every man or woman for himself inside of a company, we're not going to like what we see from a culture standpoint, that's for sure.

We're not going to like what we see. But like, what's the solve for that? I really think that people do want their work to have meaning, that they want to work with people that they think care about them, that they feel good about. You know, I'll just talk about burnout for a second. People don't get burned out because they're even working too many hours. They get burned out because it just feels like it's endless. They don't see the results of their work, that their work doesn't have purpose and meaning, and that they're working with people they don't really appreciate that the working style isn't working. And also that there are not systems and tools and processes that help them make their work easier. So all of that together leads to burnout. But also the thing you're talking about, which is apathy. And so the truth is that I think there's a lot more that leaders can do inside the workplace to help their people see purpose and recognize that, like, there's a mission here we're all on. As opposed to, yeah, I'm taking August off.

No, I agree with you in a normal times, but I think again, if you had your three kids and homeschooling for 12 months, I think your work could have been amazing. You're probably still burnt out. So then the question is whether just switching from one pretty good company to another is going to solve that problem. I actually think in some cases, if people said, I want to take three months off, that would make more sense to me.

Yeah, yeah, I could see that. Listen, we all know that we're going through this unprecedented time and I think there's a lot of experiments being done right now, this human experiment, like unintended experiments. And I think we're going to see a year and five years from now, it really happens. But I think there's a lot of pendulum swinging going on here too, and we'll see how the pendulum swings back.

But I agree with you and what I've been telling people and talking about remote work, there's no going back to 2019.

Right.

This is probably five to 10 years of certain dynamics accelerated. And you don't usually put the genie back in the bottle on these things, right?

I think that's right. And also just look and see if you're looking at like, what's being incubated now. Early in the pandemic, I talked to a VC who said, we're incubating a company to help with meetings, make meetings better. And I just thought, like, no one cares. I care about meetings, but nobody cares about meetings. But apparently it's a hot space because now there are like eight startups that I know about at meetings. The way meetings work. I think that what's going to happen now is innovation around meetings as a whole. The way people gather, because we need it, because we're going to gather in different ways. And also, of course, remote workflow tools.

Yeah. I mean, we have always used the traction EOS system. And I think one of the best things is their thing called the L10 meeting, which is at the end of the meeting, you rate it. And if it's not 8 to 10 regularly, why are you having the meeting if it's a 4. Why having the meeting? I mean, that creates some real strong accountability for that was one of the advice I gave people is sort of like when you move, there's always a fight usually between the partners around the stuff you haven't used in four years. Do you throw it out or do you move it to the new house? I think as people have gone flexible, don't take the meeting everyone hates and make it remote. It's a pretty good time to determine whether you even need that meeting.

So true. That's very wise.

So you talk a little bit about authentic leadership styles and I have this belief, I think that new leaders and new managers understandably aren't that good at it. And so what's the first thing they do? They look at best practices of other people they liked and things they do. And I felt this about myself. And you build sort of a patchwork best practice leadership design. You try that on and then after a year or two, some of the things feel right and some of the things feel not right at all. So what does the shift to authentic leadership look like where you are not trying to do the best of other people or the people you've had, but you are trying to really just show up in the way that you are?

Well, I think it is definitely taking the best of what you've been given from the past and noticing how bad the worst was and not doing that right.

There's always an anti thing that people are spending their whole career trying to not. I'm never going to make anyone feel like that person made me felt.

Exactly. I think that's like important. So people kind of bring that. Now, I would add two things to that. First of all, it's really helpful to get some formal training and if your company provides it, that's great. But there's other ways you can find that out online and get some training on management skills. And then there's the practice. So practice is really hard. You know, part of my book is also like having difficult conversations and how do you have delicate and difficult conversations? And they never feel natural. You can put off having difficult conversations for 20 years and then be uncomfortable having your first one 20 years too late. Or you can lean into practicing and you can know about any skill you're going to take on, whether it's delicate conversations, whether it's delegating, whether it's giving feedback, whether it's even just clarifying roles and responsibilities. You can do any of that. And you can realize that the first few times you do it, it's not going to go well and you're going to feel kind of like all elbows and knees and then if you keep doing it, you're going to find a style that actually works for you. So to me the key is to practice and to forgive yourself for feeling like it's not quite in your skill set. I mean, have you found, Bob, I would ask you what have you personally evolved as a style which at first felt really uncomfortable for you but now is kind of in your, in your sweet spot?

So I learned by teaching on this one because. So we actually created a segment for our emerging leaders difficult conversations segment in which it's a role play game where they're each given a very realistic like Law and Order ripped from the headline situation and they, they sit down to have that check in with everyone else watching. And one of them is like, thinks that they are need a raise and the other person is ready to warn them that their job's in jeopardy. And a lot of them are pulled from like real stories. Yeah. And this is a play pretend thing. And we watch how people dance around it. Don't say the direct thing, watch the reaction. It's really uncomfortable. And what we noticed is then we do a freeze and everyone gives their feedback and then they do it again and they don't, you know, they avoid the shit sandwich and they go into whatever it is and not only is it feel like so much more authentic and respectful, the other person like hears it and responds. You actually, even though it's fake, you watch the real reactions on this. And you know, my style generally is I'm founder, like you know, connect with people and elsewhere. And so, you know, the last, after having watched this a bunch and watched coaching and watched that the last time, I had to really have a really difficult conversation. I just got on the phone and someone said this and I said we're about to have a really difficult conversation. And that was just so much easier save so much dancing around it and not trying to set it up or tee it up. And so I was really impactful watching this session four or five times and watching the reaction to the other person of just getting the straight story rather than the dance around story.

Yes, I love that. I love that for so many reasons. I'm a big fan of role playing. And what you got the opportunity to do was to go watch other people role playing and then see their reaction. And that's a rare opportunity. Everybody should do this right now. Everyone should go set up a scenario where they could do that role play. Just like you did in their company, try to sell.

I mean, again, this is a practice telling someone that their job's in jeopardy and people couldn't do it.

It's practice.

Like, it's not. Not even real. And. And you can see the dancing around. I've done this session now four times. So I. I may be mixing the things, but I think the first one is the person thinks that they're doing great, wants to know what they need to do promoted, and the other person's kind of like, giving them a warning that they have one quarter left. And so we've now done this four times, and after 10 minutes of the conversation, the first time, I look to the 20 people, and then we all rotate watching, and I say, how many people in the room think that Alyssa and you're the ambitious person, you're the one being telling me knows after 10 minutes that her job is on the line? No one raises their hand. I say, look, this is why this happens. I hear this all the time. Someone says, I had the check in with Alyssa. You know, you know, we talked about it. And then they say, and I gave Alyssa her performance boom plan. And she was shocked and angry. Like, how is she shocked and angry? You said you talked to her about it. And so I'm like, oh, I get it now.

Yes, yes, it's so helpful. But, Bob, I want to add something else. People won't even have the difficult conversation when it's not like, your job's on the line. So I worked with a CFO one time, and he was talking about his employee, and she, you know, wouldn't do. Wouldn't take ownership and was late on things and didn't, like, speak in meetings or whatever. And I said, well, if you give her the feedback. Oh, no, no, I couldn't give her the feedback because, you know, she'll be too upset. By the way, he was not going to fire her. She was a good employee. But he. These things were really problems. But no, she'll be too upset. She'll cry. I was like, okay, well, I understand that you're compassionate, but at the same time, you're, like, robbing her of the opportunity to really know what's going on and also improve. So he took my advice. We role played it. He went and talked to her, and she cried. She did cry. And then the next day, she came back to him and said, I thought about what you said. It is difficult for me to think about how to improve these things, but I really appreciate your bringing all this up to me. And helping me think about it. I wish somebody had brought this up to me 15 years ago.

Yeah.

It's only a sample size of four cycles through this. But I will tell you that what's most interesting when the group reflects on, through this exercise, because the emotions are almost real, is that when the dancing around and the whole thing's going on, the other, like, the other person feels it and it feels awkward. And when they just tell them the truth and are direct, it's actually more comfortable.

Totally.

It's paradoxical, right?

So true. Yeah.

All right, so last question for you. What is this? Is multivariate. So it could be personal or professional or single or repeated. What is a personal and professional mistake that you made that you've learned the most from?

So many. So many. So many mistakes. I'm going to talk about this book because I'm so happy, because I think this is an absence. The mistake that I made was making such a big deal out of it that in my mind's eye, really, I could have written this five years ago, and I didn't because I had so much negative chatter in my head about it.

Imposter syndrome.

Imposter syndrome. And criticism and. And, you know, sort of internal critics. And I would try and fail and try and fail, and I would make that mean, you can't do it. And what I learned from it in going through the process and coming out the other end, and once I decided I was going to write the book, once I kind of got out of my own way and decided I was going to write it, I'm not going to say it was easy, but it was super clear. And it was so that's. It was easy. It took a lot of work. It took my butt in the chair, and it took, you know, time and energy, but it was easy because I knew this was what I was going to do. And the lesson for me and for everybody is that your identity is what's getting in the way of things that you can't do. So look inside and look at your identity and what you're telling yourself and find ways to upgrade that. And that will help you upgrade the things that you're able to do.

Very good advice. So where can people learn more about your work? Find the book. Where should they go?

Well, they can definitely go to Amazon to find the book From Startup to Grown up, but they can also come to my website, alyssacohn.com scripts to help give you more scripts. Five specific scripts for delicate or difficult conversations.

Ooh, I like that.

Yeah. And so It's a downloadable tool that you can take and use today.

So alyssacon.com Scripps we all need help with those conversations. You could probably use it for family and friend conversations as well. All right. Well Alyssa, thank you for joining us and congrats on the book and wish you the best of luck with it.

Thank you so much for having me today.

To our listeners, thanks for tuning in to the Elevate podcast today. We'll include links to Alyssa and her new book From Startup to Grown up on the detailed episode page@robertglaser.com as always, if you enjoyed today's episode or the Elevate podcast in general, I'd really appreciate it if you could leave us a review or rating because it helps new users discover the show super easy. If you're an Apple podcast, click on the library icon Elevate Podcasts and then scroll down to leave a rating or review. Thanks again for your support. Until next time, keep elevating.