Design Matters: Alisa Cohn

Alisa Cohn—named Top Startup Coach in the World—shares her secrets, insights and strategies from nearly 20 years of turning startup founders into world-class CEOs.

Alisa Cohn—named Top Startup Coach in the World—shares her secrets, insights and strategies from nearly 20 years of turning startup founders into world-class CEOs.


Transcript

Debbie Millman:

How do you take a sprout of an idea and grow it into a billion dollar business? The conventional wisdom about startups is that they’re all about brilliant products and long, long hours. There may be some truth in that, but according to Alisa Cohn, it’s also about you, the starter-upper. Alisa is an executive coach who specializes in getting new businesses off the ground. She’s worked with companies like Venmo, Etsy and Wirecutter. And now she has distilled her wisdom into a brand new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business. Alisa Cohn, welcome to Design Matters.

Alisa Cohn:

Thank you so much, Debbie. It’s such a joy to be here with you.

Debbie Millman:

Alisa, is it true you won Scott, the rapper Jelly Donut to freestyle about meetings?

Alisa Cohn:

That is true. That is true. I was interviewing him for my Forbes column. What he does is he’s a rapper, he’s also an improv artist and we were talking about what improv can add to business and to start ups. And so, yep, I got him to rap about meetings at the very end of our discussion. What is there to rap about meetings?

Debbie Millman:

Meetings give you a beatings. Yeah.

Alisa Cohn:

Yeah. He was like me and you in the Zoom. I’m not sure if he would call it the best rap ever, but he’s extremely talented. He’s one of the members of the Freestyle Love Supreme coming back to Broadway now. And he’s so talented and that’s what I loved about him. And again, the notion of what improv brings to business and what improv brings to startups. The idea that you have to make do with what you have, and what he had right then was meetings.

Debbie Millman:

Alisa, you grew up in Massachusetts, and I understand you were quite good at algebra so much so that you competed with the boys in your class in sixth grade, but as you made your way through school that changed and your confidence plummeted, what happened?

Alisa Cohn:

Debbie, it’s true what they say about you, that you go deep in your research. My goodness, that is absolutely true. And what did happen? I got into geometry in high school and for whatever reason I got intimidated. And I think that there is a meme, which in my case was true and I think is true at times where girls have a fall off in math. And it took me, frankly, a long time to get over that fall off. I mean, I was. I loved algebra. I excelled at algebra. Somehow after that moment in high school, I lost all my confidence in math. And I never really regained it until I went to business school and I had to attend math camp before I was allowed into business school. And not only that, but to prep for that, I took calculus.

Debbie Millman:

Whoo.

Alisa Cohn:

I know. Right. And then I also stats, statistics and actually I thought, “Huh, this actually isn’t that hard after all.”

Debbie Millman:

You said that your coaching imprint really began when you were 13 years old. What happened at that point to create that imprint?

Alisa Cohn:

So I was part of a youth group, a Jewish youth group called Young Judaea. And it turned out it was a peer-led youth group. I didn’t even know what that was. I was only 13 years old, but what I did know is that I and all of us were facilitating discussions for the rest of our peers, for the rest of the people in the youth group. Other youth groups went to the movies or they went bowling or something. What we did was we had intense intellectual discussions and I started facilitating when I was 13. And I got a lot of practice from that period. And I can see that the roots of my profession now and my joy and love for, and my skill and facilitation started then.

Debbie Millman:

Despite your interest, your early interest in musical theater and your experiments and stand up comedy, you went to Boston University and studied journalism. What did you think you wanted to do professionally at that point?

Alisa Cohn:

I had no idea, but I do know that I love to read. And what I really wanted to do was to be an English major. And my parents were like, “You’re not going to be an English major. We are not sending you to college to go get a liberal arts degree. What are you going to do with that?” So we all decided that journalism was close enough. So that’s what I ended up doing. And I didn’t know what I wanted to do, but I did a number of internships in journalism during that period to know that I probably did not want to be a journalist. At the time, I was quite shy. I know.

Debbie Millman:

I’m shocked by that. Shocked.

Alisa Cohn:

I know. I was very shy. I grew up a shy kid, which is by the way, why it was so helpful to find this youth group, more so to find my tribe of people. But when I was doing my few internships as a journalist, I had a lot of trouble asking strangers questions. And then I had a lot of trouble going back to them and asking them follow up questions. So that was very difficult for me. So I just knew that wasn’t my thing, but I did like education and I did like the university environment. So my next two jobs kind of reflected that. And I’d sort of, until I really found my way, I just made up a bunch of stuff.

Debbie Millman:

What made you decide to go on and get an MBA in strategy and organizational development from Cornell?

Alisa Cohn:

Well, I worked at Northeastern and I was the chief of staff to the provost and we were doing strategic planning. And so at some point the provost has made this offhand comment, he just said, “Oh, you can’t manage faculty because they have tenure.” And by the way, even I was quite young and I didn’t even quite get it. But I began to understand that what he meant was because you can’t fire them. And I thought, “Well, that day can’t be that people will only do what you want them to do for the organization if you fire them.” Sort of this weapon you have.

Alisa Cohn:

And I wanted to go off to business school to think about that and to learn more about why people did things for organizations or sadly didn’t do them. But I got there and I got all turned around. I went to Cornell. And the focus at Cornell was very much finance. It’s very much Wall Street. So actually, I ended up focusing in finance and strategy and accounting of all things.

Debbie Millman:

You’re a CPA, I understand.

Alisa Cohn:

I’m a CPA. And I loved accounting. I loved it. In some ways, it’s just like journalism. It’s kind of storytelling for business and it’s the language of business. And so I loved the analytical approach. I loved figuring things out and I just really enjoyed it. And I saw it as a triumph over the past.

Debbie Millman:

Now, I understand that when you went to Cornell, you felt that you had something to prove. Why did you feel you had something to prove? What were you looking to prove?

Alisa Cohn:

Well, I think that’s about two things. It’s like identity. That I was this little girl from a small town. I’m from Holliston, Massachusetts. And that’s this rural place and I just didn’t think that I could go off and achieve like, “Wow.” Get my MBA or something like that. Also, I was from a nonprofit world. So I was journalism major from the nonprofit world. And I had to go to math camp before they let me in. So I felt like I had to overcome certain challenges to prove that I belong there. And so that was identity.

Alisa Cohn:

And second, I was still dealing with his lack of confidence in terms of my ability to do the so-called hard stuff of business. So again, numbers and finance and analysis. And even I had gone there to do the so-called soft stuff of business, more of the organizational and development stuff. So it took me time to unravel all that. But in the meantime, I was on a mission to be successful at business school.

Debbie Millman:

After graduation, you became a strategy consultant at Pricewaterhouse Coopers where you were on a fast track to become a partner, and ordinarily it takes 12 to 14 years at PwC to become a partner. You were going to be doing it in five. What were the specifics of the fast track program?

Alisa Cohn:

It was called the advanced development program. And they took a number of graduates from so-called top business schools. And the program, the ADP program was rotational. So they showed you a whole bunch of sides of the firm, which was an incredible experience for me to be part of that and they gave you a mentor. They really put a lot of resources behind you to help you achieve and succeed on that speed level.

Debbie Millman:

Two and a half years in, you wake up one morning, hoping that you have the flu so you didn’t have to go to work. What happened in that two and a half years culminating in that moment to create such a sense of doom?

Alisa Cohn:

Yeah. So when I was graduating from Cornell, and I went and talked to my professor, my accounting professor, Mark Nelson, I said, “I’m going to join PwC.” He said, “That’s great.” I said, “I’m going to be an auditor.” And he said, “That would be very refreshing for the audit profession.” I thought, “Oh, what do you mean?” And then I found out what he meant, in the sense that… By the way, PwC is a fantastic firm and was great to me through and through. But for me, I just didn’t quite realize that I was really getting into a system, a very large system that was sort of hierarchical, that you had to do certain things, sequential, first you did this, and then you did this.

Alisa Cohn:

And that it felt to me very regimented. And I guess I also just have to acknowledge, I was not passionate about the work. I was passionate about the client service. I was the only one who figured out that my client from this company and my client from the other company shared a passion for synchronized skating and knew each other because they were on the same synchronized skating team.

Debbie Millman:

What are the odds?

Alisa Cohn:

I know. I was the kind of person who was very interested in the people and also their jobs. I loved controls work because we interviewed people about their jobs, but I just didn’t find the work itself engaging. And I felt like it was a lot of routines over and over. And didn’t leave a lot of room for creativity for me at my level.

Debbie Millman:

18 hours after you woke up that day hoping you had the flu, you got the flu.

Alisa Cohn:

I got the flu. Can I just tell everybody be careful of what you wish for.

Debbie Millman:

Right? You ended up being rushed to the emergency room. You were in bed for two weeks. And every time you thought about going back to work, your fever would spike back up. I guess it was then that you decided that PwC was not your calling and to leave that particular fast track. How hard was that for you to do?

Alisa Cohn:

Extremely hard. Very, very hard. I had a lot invested in this fast track program and I had a lot invested in my future is all set. I’m good. And also, there were a lot of people who mentored me at the firm and who were fantastic to me. And just this notion of, what am I going to do next? I have no idea. And I’m now going to leave for no good reason was not my path. That was not the way I was sort of raised. Although actually, I’m going to talk about the path because it reminds me of my favorite Joseph Campbell quote, which is, if you can see your path all the way through to the end, you are following someone else’s path. Your path only becomes clear step by step as each foot hits the ground. That might be a paraphrase of the quote.

Debbie Millman:

Good enough.

Alisa Cohn:

But that’s how I think of it. And I know that at that time I saw my path all the way through to the end. And the only thing I had to go on then was the music in my head said to make a difference. It just kept repeating, to make a difference, to make a difference. That the work of my hands matters. And I tried to go out and see what is going to be the thing that’s going to let me know that the work I do makes a difference.

Debbie Millman:

When you started telling people that you were leaving, people at PwC, people in your family, what was the response?

Alisa Cohn:

The people at PwC were quite gracious, extremely gracious. And one of them actually, the head partner, Jay Mattie, he pulled me into his office and he said, “If you are going to leave to go to a different firm, or even to a large company, I would try to talk you out of it, but I can see that you just want something different. So what we’ll do is we’ll give you a few weeks and maybe even a few months and we’ll introduce you to some clients and we’ll let you think about what you want to do. And so you have a little time.” So gracious.

Debbie Millman:

That’s incredible. That’s unheard of.

Alisa Cohn:

It was incredible. I know. Actually, he said, “I always tell people if they think about leaving, they should come and talk to me. And they don’t.” But telling my parents was difficult as in like, “What am I going to do?” But they were used to me by then making some moves that they didn’t necessarily agree with or want for me. Telling my friends was confronting because the next years were a lot of my imagining them saying, “Oh, what is she doing now?” In this kind of judgy way. It took me a little while to find myself.

Debbie Millman:

You ended up getting two different offers. One was from Goldman Sachs and their private client services. One was from a startup. You decided to take the role with the startup. Why?

Alisa Cohn:

When I met with the folks at Goldman, it was the same thing as PwC. You walk in, it’s a big office, there’s a lot of glass, there’s a conference room. And even though it was like, “Goldman Sachs, wow.” I knew it was the same thing. I went to the startup and it was this little rental space on the third floor of some place in Boston. And it was kind of a mess and it was tables everywhere and we were all in the same room and it was different and it was vibrant. And I just thought, “Well, if you want something different, this is the thing.” And also, I even knew at the time, why was I even talking to Goldman? Like, “You want to make a difference? You want to make a difference.”

Alisa Cohn:

And so I realized even then vaguely, that I was getting caught up in the same thing that I had gotten caught up in, “Oh, your career, make the smart choice. You didn’t go to business school to throw it away. You’ve got to do something with pedigree.” And so I’m glad that I had the courage to then say yes to the startup, even though it was a difficult choice and I certainly have regrets about it initially.

Debbie Millman:

Well, after one week at the startup, you decided you made the wrong decision and then went crawling back to Goldman. So tell us about that. What happened?

Alisa Cohn:

It was chaotic at the startup. I did not realize what chaos was until experiencing it there. It felt it was a stretch for me. It was uncomfortable. And there was a way in which I was like, “Oh man, this is not going anywhere. I can’t believe I threw that thing.” It was like, “I threw that away. How could you throw that away? Anyone in your shoes that had your pedigree and your background would have wanted that?” One thing about me, Debbie, and I have learned to do this more often than not is that I will go back. I will go back and swallow my pride and even swallow my fear and call him back up and we made an appointment to talk and I just laid out for him. And I said, “Well, I think I made a mistake. I’d really like to revisit the job offer that you made.”

Debbie Millman:

Revisit in quotes.

Alisa Cohn:

Yeah, exactly. And he said, “No.” It was really a week or two later. It was very, very recent. And he said, “No, that was your chance. And I don’t think this is right for you if you didn’t want this initial.” He said something like that.

Debbie Millman:

That’s incredible. That’s incredible that he said no just one week later. But it’s smart because I remember when I turned down my, you know the story. When I turned down my CEO offer, the CEO position at Sterling Brands. It took me four months to make that decision. And at which point, before even having said no, my partner came to me and said, “Just to put this in your bonnet, anything that takes you four months to decide is probably something you don’t want to do.” But he knew that after a week. That’s pretty cool.

Alisa Cohn:

Yeah. It was pretty cool. I mean, whatever he knew or thought, I don’t know, because the truth is that, I’m sure he had just kind of already moved on. However, he gave me two real gifts in that conversation. He said, “The reason I offered this job to you is not because of your pedigree. The reason I offered this job was because you had done standup comedy.” As you said, I had done standup comedy in Boston. And he said, “And I knew that somebody who could do that would be somebody who’d be successful here.” He also said, “You should know that you have a superpower. You can get people to get on your side or to believe in you. You’ve credibility.” And I was very young and inexperienced in the world of work still and quite unsure.

Alisa Cohn:

And so I wrote it down. I had this little book, I would write down to inspire myself and to comfort myself. And I wrote down, “Alisa, you have a superpower.” And I still have it. And I still think about it sometimes because he was right, I didn’t belong to Goldman. And I knew that. So I went back to the startup and I was more confident because I thought, “You got to make this work. And also you don’t have another option for the moment.” And I’m glad I did that because I was not wondering.

Debbie Millman:

How did you make your experience at the startup better? Because it seems like that was really entirely something self-directed?

Alisa Cohn:

Yes. I think I just embraced the chaos. That is what startups often are initially. And I don’t mean chaos like nobody knows what’s going on. I mean, chaos, like there’s way too much to do. It’s not always clear how to get it done and you’re really trying to lay the tracks and ride the train at the same time. So it’s just overwhelming. But with a new attitude, to be honest with you, that’s good for me. That’s where I shine. And I enjoyed people I worked with and we were able to team really well and we were able to build a lot of cool stuff and I had incredible experiences there. I’m so happy that I was able to have those experiences early on.

Debbie Millman:

You’ve declared that this was when your love affair with startups really began, but it wasn’t until you volunteered at a [woo-woo 00:18:56] Body and Soul Conference, a conference you ordinarily would not have gone to, that you heard what you referred to as violence.

Alisa Cohn:

That’s right.

Debbie Millman:

What happened?

Alisa Cohn:

So at the time I was going out with my boyfriend who, he was a yoga guy, like a yogi. So I was seeking. I probably was still working at PwC, but I was seeking. And he dragged me to this body and, even just saying it, Body and Soul. That was the name of the conference and the magazine, which is Body and Soul. But not only do we go to the conference, we volunteered for the conference so that we could go for free. That was his game. I was like, “That’s great idea.” So we went to the orientation for the volunteers and at the end they said, “Okay, now Cheryl Richardson is going to speak to the volunteers.” And I’m thinking, “Who is Cheryl Richardson? And do I have to stay for this? Can I leave there?”

Alisa Cohn:

There she was in the front of the room and she was so dynamic. And I don’t remember what she said, but she was so dynamic and so inspirational. And like, “You can do it.” And it felt like, you could make a difference and you can shine your light. I thought, “What? Who is this? What is that? I want that.” And literally in my mind’s eye, I’m like, “That’s it. I want to be a coach.” And that’s where I say violence played. It was this moment of understanding and knowing, “This is me. That’s what I want to do.”

Debbie Millman:

Did you train to become a coach?

Alisa Cohn:

Yes. So I followed her around in the conference and she was very nice to me. And I said, “I want to be a coach.” And she said, “You do coach training.” “Okay. Tell me what to do.” So she sent me to a coach training. Actually, the first coach training place or organization there was called Coach U, and I did training through Coach U. And I coached all my friends for free and I hired my own coach. And so when the startup world didn’t quite work out, I was ready to make my way as a coach.

Debbie Millman:

You decided to pitch your coaching business at a vendor fair at your local gym. You were still in Boston at the time. It was an evening in February. It was sleeting outside. You didn’t want to go, but you pulled yourself together and told yourself that it wasn’t the sleet or the vendor fair that you wanted. What you wanted was the life of your dreams. And you stated that if you wanted the life of your dreams, you were going to walk through the sleet to go down and present yourself at the vendor fair at the gym, which you did. And you offered complimentary lessons to the attendees. And your first coaching client was a man named Rick Samuels. Tell us about Rick. Tell us all about Rick.

Alisa Cohn:

Wow. Debbie, all of that’s true. Rick Samuels, he was, I guess a member of my gym. This is a long time ago. But he like many people signed up for this free complimentary session, which half of them did not show up for on the phone. But Rick did. And Rick and I had a long talk about him feeling stuck in his career. And I spent time just asking him a bunch of questions. And I gave him some insight about himself that no one had ever shared with him before. And also, I gave him specific steps, that we talked together and agreed on specific next steps about what he needs to do to make the changes in his career that he wanted to make.

Alisa Cohn:

And for me, it was like breathing in and breathing out. I was made to do this and for him it was a revelation. He said, “Oh, I’ve been in therapy for years. We’ve never gotten here.” And I felt that’s fantastic. And then he hired me on the spot.

Debbie Millman:

What is the difference between coaching and psychotherapy?

Alisa Cohn:

I think increasingly they may be converging in a way, because I think that psychotherapists have become a little more so-called directive. But I would say that therapists really, first of all, they are trained of course, to handle all sorts of things, which are, not just the regular normal, I’m stuck at work. They’re trained to handle moods and panic attacks and things that might be going on inside you. Also, I think that therapists dive deep and think a lot about the scar tissue that may prevent you from doing the things you want to do and help you at that level.

Alisa Cohn:

Coaching, deep coaches, and I think I’m a deep coach. We definitely go back in time and think about experiences and times that you had in the past that are leading to this moment. But coaching always ends in action. And coaching always ends with this notion of what are you going to do differently? What behavioral activity are you going to take away from this to help you make progress? So I think a lot about coaching being about forward motion. And I think therapy helps you also gain the understanding of the architecture of how you got to be this way.

Debbie Millman:

This is a question I probably should have asked at the top of the show, because as you’re talking, I’m realizing that some of my listeners might not even know what a coach actually does and might think we’re talking about sports. So talk about what it means to be a business coach or an executive coach.

Alisa Cohn:

Coaching is its own domain. And so when I think about coaching, the way I describe it to people is I help you think about where are you, where are you going and how are you going to get there? And so what that means is we do self-awareness and self-assessment, your situation. And then if it was perfect, if you were acting as a professional or in your personal life in a way that is exactly ideal, how you want to be acting, describe that. What would that look like? And then what are the specific tools? What are the specific behaviors? What are the specific structures you need to have in your work and in your life to then help you achieve that ideal state?

Alisa Cohn:

So I hope that gives you a sense of coaching. And then there’s also a context of coaching being a sounding board, because the CEOs I work with and senior executives that I work with, don’t have anyone else to talk to. So sometimes the best use of a coach is to have somebody who’s safe and nonjudgmental. And they’re listening to you get through the things that you’re stuck on, because then you can come out the other side with better thinking and a better plan forward.

Debbie Millman:

30 years ago, having a coach was primarily kept a secret. It was something that people weren’t quite as forthright about. Now, people are proud to have a coach, talk about their coaches. It’s a badge of honor in a lot of ways. Things have really changed. What would you say is the primary driver of that cultural shift?

Alisa Cohn:

There is definitely, especially in the past, 5 or 10 years more and understanding of what it’s really like to be a leader in a company. In my world of startups, there’s a lot more light shined on what founders and CEOs have to go through and how difficult it is. There’s more permission to be vulnerable and real. So in light of all that, people are just more open about having a coach and other kinds of tools to help them just like successful athletes have a coach.

Debbie Millman:

We know how you got your first client, Rick Samuels. How did you get your second and third and fourth?

Alisa Cohn:

First of all, I just want to say that the reason I was able to focus on the life of my dreams is because I had actually gone to the trouble of making a vision board.

Debbie Millman:

Wow. Wow.

Alisa Cohn:

Yeah. Which I still have. Talk about body and soul.

Debbie Millman:

Woo-woo.

Alisa Cohn:

Talk about woo-woo. I did. It was uncharacteristic of me to think, “I’m going to make a vision board. I’m going to make a collage of my ideal life.” So I had a pictorial representation of my ideal life, which was my guiding light in all the things that I did, like getting my first client, going down to the gym that day, but also getting my first client. So one thing I did was I taught adult ed. This was the Boston Center for Adult Ed, and I pitched them a course on money coaching. I was very passionate about-

Debbie Millman:

You got your CPA, girl. Let make use of it.

Alisa Cohn:

Exactly. I was very passionate of making a difference. So they could buy their first home, they could put their kid through college, they could retire. So I thought, “Well, the issue is people are confused about money.” And a friend of mine called me and I was leaving for the class, my friend, Doris. And she said, “Oh, what are you doing?” “I got to go. I’m running late.” “Oh, what are you running late for?” “I’m teaching a class. I got to go.” And she said, “Oh, what class?” “It’s on money coaching. I got to go.” “One of my clients is looking for someone to teach business acumen in their curriculum. Are you available for that?” I was like, “Huh, I got plenty of time. Plenty of time to talk to your doors.”

Debbie Millman:

Easy is a decision.

Alisa Cohn:

Yes, that’s right. That’s right. It’s a very good point. So I began hustling as much as I can and telling people, and eventually, this is a life lesson. When you tell enough people what you’re up to, actually people want to help. And Doris put me in touch with EMC which is a fantastic company. They got bought by Dell about three years ago. And I thought, well, if I start teaching in the business acumen curriculum, I will very quickly work my way into leadership curriculum. That’s what’s going to happen. And that’s exactly what happened.

Alisa Cohn:

And then once I was working at EMC, that became an opening for other referrals. It became an opening just to have the credibility, of working with EMC. So a lot of things flowed from there.

Debbie Millman:

Why startups?

Alisa Cohn:

I moved to New York probably about 14 years ago. Part of what was happening in New York was the tech startup scene was nascent in those days. And I was excited to be part of that building process, of being part of this tech scene that we were building here, the startup scene. And I met the GM of Foursquare at this, actually, it was a musical theater event through a Harvard Alumni group. So like, “What?” And also, “Why was I there?” But he was there, Evan Cohen, and we talked and we just became friends. And we would meet for coffee now and again, and he would just sort of share what was going on with him and what was going on at Foursquare.

Alisa Cohn:

And then about a year later, he introduced me to the HR person and I started doing manager training there. And then from there, I started coaching a number of the executives there, including Dennis Crowley, the founder, and at the time CEO of Foursquare. And I remembered it was like a flash back to Boston and that startup life that I loved. And so it was a combination of being thrown into the startup world and realizing that I could make a difference in New York. And that was very exciting.

Debbie Millman:

Since then, you’ve been named as the number one top startup coach in the world. You were also named the number one Global Guru of startups, and you’ve worked with startups, including Venmo, Etsy, the Wirecutter, Tory Burch, you’ve coached CEOs and C-suite executives at companies, including Sony, IBM, Google, Microsoft, Bloomberg, The New York Times, Calvin Klein. The list goes on and on. You’ve also just published your first book, it’s titled, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business. Alisa, congratulations. I know you’ve been working on this for a long time.

Alisa Cohn:

Thank you, Debbie. Thank you so much. And I have been working on this for a long time. It’s nice to hear all that. Thank you.

Debbie Millman:

You start your book by declaring that leadership is an unnatural act. Tell me more.

Alisa Cohn:

A client said that to me once with this quizzical look and I had to agree, giving feedback to other adults is not natural. Praising someone who has just done a bad job, which sometimes you have to do is not natural. Managing yourself when you’re freaking out, when you’re feeling irritated, where you have to be smooth and polished, these are not natural things. These are all learned behaviors. And I think it’s important that we recognize that leadership overall is a learned behavior.

Debbie Millman:

You said that you know that leadership is an unnatural act because you’ve witnessed it helping CEOs commit the unnatural act of leadership for now over two decades. Based on what you know now, what is the biggest challenge founders and startup leaders face?

Alisa Cohn:

Startup founders have to face the challenge of the scale of their business being extremely rapid. The velocity of the scale of their business that requires them to grow their own leadership style, their own behavioral style, their change and adaptation at a velocity which is just enormously hard to do. So there’s a lot embedded in that, the different things you have to change and adjust and learn and grow. But ultimately, you have to do that in concert with the ups and downs of the business which are challenging. And then also, hopefully if you’re successful, the rapid scale, the rapid velocity of scale of the company.

Debbie Millman:

You write that while your title may make you the boss, your people make you a leader. Can you talk a little bit more about what that means?

Alisa Cohn:

What that means is that people will follow you because you’re the boss and they’ll do what you tell them to if that’s your style, because you’re the boss. But as a startup founder, growing into a leader, and really as any leader or CEO, you have to earn the right for people to follow you, for people to trust you, for people to agree with you or see your direction and believe in your direction, even though they may not actually have any evidence themselves. To follow you even when they disagree with your direction. You need to sort of earn that leadership through influence, through appreciating them, through them knowing that you care, both about them and also about ultimately the success of the business, more than you care about yourself.

Alisa Cohn:

And so all of those elements are in play that you have to activate to get people to really get behind you in a fulsome insignificant way that you need when you’re trying to do something hard.

Debbie Millman:

Leadership feels like a real privilege, but it has a lot of responsibilities. And it feels to me that there’s a lot of accountability to your people when you’re a leader. One of the things that really struck me in your book was a quote that you include from chip Conley, the founder of Joie de Vivre, the hotel chain, who states in the book, “Don’t mistake activity for achievement.” I want to make that a tattoo for a couple of reasons. One, it could have applied to anything. I remember one time sitting with one of my graduate students who was on the verge of failing out. We were sitting with the provost and he was saying, how hard he worked, how hard he worked, how hard he worked. And the provost said sort of the same thing, don’t mistake working hard for working smart.

Debbie Millman:

And I also think it applies in another area where people want to appear busy or want to feel busy. So they feel like they matter, or that they’re important, or that they’re distracting themselves from whatever it is that they don’t want to face. Why do humans seek out so much activity to keep themselves afloat?

Alisa Cohn:

I think that actually both of those ways of framing, mistaking activity for achievement have to do with our capacity for self-denial. So the question you ask is, why do people stay so busy even if they’re not getting anywhere? I think the answer is they don’t want to face that still inner voice. They don’t want to maybe face always the hard work that they have to do or the hard personal work, or the hard professional work. It’s easier to answer email all day than to really think about strategy of where we’re going, which is difficult intellectual labor.

Alisa Cohn:

But the second thing is also true that people do feel like if I’m working and working and working on this treadmill, at least I won’t get fired, at least I’m doing something. And in a large company, sometimes that’s true, you can hide more easily. I will say inside of a startup, it’s just not going to work that way because with startups, they are lean and also they require everyone to give discretionary effort. And that’s what startup people do. And if you’re not able to make that activity count and make it worthwhile and achieve things based on it, ultimately, you’re just falling behind and you’re keeping the team behind. And that’s not sustainable for a startup, which is either fighting for its life or growing with a massive velocity.

Debbie Millman:

When you start with a new client, the first question you ask them is simply, “What’s going on?” Why do you start with that question?

Alisa Cohn:

Because first of all, I really want to know. I want to know, it’s like, “Why are we here?” I try not to wait it, especially if I have some background information about why someone else thinks that we’re here or why they originally called me, because I want to know what’s up right now. And that’s where we’re going to enter the discussion.

Debbie Millman:

You talk about how the act of reflection needs to become a reflex and that founders and all leaders need to learn to reflect, get in the habit of reflecting and turn to reflection rather than reaction when bad things happen. And that really surprised me because it was really the first time I became really aware of the inner workings of what it means to be or have an executive coach and I wasn’t expecting it to be so sort of philosophical and self-reflective.

Alisa Cohn:

Yes. Well, I think it’s important, two things come to mind. One is that, if you’re a leader… I just spoke to one of my clients two weeks ago. And she said to me, “I knew that the startup was going to have ups and downs, but I didn’t realize they would come within five minutes of each other times 10 a day.” And I was like, “Yep, that’s the life you signed up for?” And the issue is that people just get caught up in their own emotions and then they have to address the all hands or have the customer call or sort out this difficult situation going on in marketing.

Alisa Cohn:

So they have to really stop and reflect and think about, “What am I trying to get done here?” And they need to find a way to compartmentalize all that baggage from the past three hours of whatever that was in order to put themselves in the mind’s eye to be effective, to be amazing, to be the leader here and now. So that’s one reason that reflection is so critical. And the second is because, it’s an incredible tool. I was working with a founder one time and he was telling me about his many complaints, many problems, many complaints. And he’s not wrong, because there’s always a lot of complaints inside of a startup and things are usually not working ideally.

Alisa Cohn:

So he was expressing to me all the things that were going wrong. And I just got this [inaudible 00:38:59] and I said, “I’d love you to write that down. All of those things and spend a few days journaling every day about all the problems and concerns and what they bring up for you.” And so to his credit, took that assignment away and three days later, he actually scanned his journal and sent it to me. And we talked it through and the whole journal was this complaint, this complaint, this complaint. And it came back to, my people aren’t doing the right thing. But then he realized, I haven’t told them what I’m expecting, what the context is. It always came back to him in terms of what he had missed inside of communication, inside of context.

Alisa Cohn:

And I think that reflection is the most powerful tool to recognize that and realize that. So if you really will go deep and you do the work, you see the root cause of some of these things. Otherwise, you just walk around saying, “Oh, they’re not good. I should fire them.” No, no. You should give them context, “Let’s try that,” or coach them, “Let’s try that.” But you can’t get there unless you’re willing to unpeel some of these layers inside of you.

Debbie Millman:

Let’s talk about the role of authenticity in leadership. It’s a big word. We hear a lot now. And I think just the idea of saying something needs to be authentic means it already stops being authentic.

Alisa Cohn:

It’s true.

Debbie Millman:

But on the one hand you have the notion that a leader is supposed to be authentic and on the other hand, there’s the platitude, never let them see you sweat. So it seems like authenticity is both complicated and polarizing. How do you understand what it means to be authentic and how do you coach your clients on the role of authenticity and leadership?

Alisa Cohn:

Yeah. It’s a good question and something that I think about all the time, because listen, of course you should be authentic, whatever that means. The problem is that it means a lot of different things at a lot of different times. Walt Whitman said, “We are multitudes.” And it is so true, we are multitudes. So your authentic self can change at any given moment. At the same time, you need to actually take on the mantle and the role of the leader. And you need to do so in a way that feels more or less genuine to you.

Alisa Cohn:

So if you are a quiet, more solitary type and you try to go out and be a big extrovert, that’s going to be weird for everybody. However, if you are a quiet solitary type and your authentic way of doing things is to be silent. Actually, the role of the CEO, it requires you to communicate in different contexts. So you’ve got to find the way to learn to do that in a way that feels more or less comfortable to you. And that you do it, even if you don’t want to do it. And the way I think of all of that is ultimately you get to let your humanity show, which is certainly important because I would just add vulnerability is an important tool of leadership because when you’re vulnerable, other people recognize they can be vulnerable and safe with you and inside of your company. So that’s really good.

Alisa Cohn:

But if you start freaking out in an authentic way, that’s not going to really inspire confidence in the people around you. So the way I land on authenticity is that you have to show your humanity and you have to learn the tools that you need to be an effective leader in your role, a CEO or whatever leader you are, in your role in a way that’s going to feel ultimately natural and genuine to you. By the way, the last thing is that, when you start a new skill, just like with everything, you’re going to be uncomfortable. You’re going to be all elbows and knees. You’re not going to do it. So you also need to be able to tolerate the learning curve that’s necessary as you try on new behaviors.

Debbie Millman:

It’s so interesting because high achievement people don’t like to do anything that they’re not good of right out of the gate. And I don’t know that that’s ever possible, ever. We can’t do very much well without being taught. And so it’s an interesting conundrum being a leader when you’re expected to be excellent at everything, but still have to learn new skills.

Alisa Cohn:

Yeah. It’s really true. And I think that’s the other thing about, as we, you said high achieving people and it’s so true. And when you’re kids, it’s acceptable to learn something, but somehow when we get to be adults, it’s somehow not acceptable anymore. That’s why I think culture is so important. If you’re the CEO and you say, “Listen, I’m going to make mistakes. We’re going to make mistakes. And we’re going to have a learning organization culture.” That’s going to help everybody recognize that learning is valued around here.

Debbie Millman:

I want to talk to you about imposter syndrome. You talk a lot about it. You write a lot of really important things in your book about imposter syndrome. And you have a ridiculously successful executive quoted in your book that states, “The more successful I am, the more I have imposter syndrome.” How common is that? And how do you view imposter syndrome? How do you define imposter syndrome? Just the whole thing.

Alisa Cohn:

The whole thing. Yeah. Well, so imposter syndrome is simply this notion that you’re a fake, you’re a fraud. They’re going to find you out and the game is over. The jig is up. That is imposter syndrome. Your luck is going to run out. And so I would say that, I’m not going to say all, there’s no such thing as all, every single one, but most founders at some point along the way have imposter syndrome. And it might be little and it might be big.

Alisa Cohn:

It might be like, “I just screwed up that board meeting. The board is going to think that I’m an idiot. The board’s going to fire me.” That might just be a little momentary panic as compared to, “I’m trying to raise a round. It’s not working. I’m not going to be able to raise this round. We’re going to have to close up shop. TechCrunch is going to write about it and all things are going to go bad.” All this catastrophizing. And it’s quite debilitating, imposter syndrome. And if you ever experienced it you know that it’s just a very difficult feeling to come up against your failings and this notion like, “The jig is up.”

Alisa Cohn:

So it’s helpful to find tools to get over it. Because chances are, if you’re at that stage, you’ve done something right. And you have done enough things in your life to know it’s not just luck. So the best tool that I’ve ever offered people, that people find very helpful is called a highlight reel. It’s the idea that you look to your past and you find your successes, your accomplishments, the things you’re proud of from your past. And if you write them down a couple of times, that kind of grooves them into your brain. And if you read them over daily as a practice, it reminds you, “Hey, I’ve actually accomplished a lot of things.”

Alisa Cohn:

And then if you’re actually having an imposter syndrome attack right now, you can pull up your list of accomplishments, your highlight reel, and you can read it just to give yourself a little more perspective and a little more evidence that actually you’ve done a couple of important things in your life.

Debbie Millman:

You write that the phrase imposter syndrome is not a single monolithic thing. It takes many forms and flavors of self-doubt that get triggered in founders in certain situations. Now, you talked about the highlight reel. What about for people that are not founders or have reached the pinnacle of their careers yet? For those that are struggling with even just feeling like they’re not a fraud, is there anything that can be done to help people, just one thing that they can do differently in thinking about that?

Alisa Cohn:

Well, I think the highlight reel is helpful for them too. And then I would add that self-compassion, that’s actually, back to reflection, tuning into these voices in your head and then asking the voices in your head that’s being critical or self-doubt, or jeering at you or telling you, your luck is going to run out. You could say, “Huh? Who are you? And what do you have to teach me?” And then listen to the answer and see if anything shows up. And if you can get into dialogue with that part of you, it’s healing. It’s also quite interesting what comes up. As in there’s something here for me to learn.

Alisa Cohn:

So I’ll give you an example. One of the founders I work with, he came up against this imposter syndrome and he couldn’t shake it. He couldn’t sleep, he was having panic attacks. And we just talked it through. And I asked him to do this writing exercise, who are you and what do you have to teach me? And he scoffed at it, but he was willing to do it. And he realized that even though his board had never called him out on this and even though he was running a, what was then a successful business, which got even more successful, he realized that he did not feel like he really understood his metrics and he really understood his business enough.

Alisa Cohn:

But the truth is, he had more work to do in understanding his business. He had more work to do in digging deeper in terms of what the metrics should be, what some of the industry norms and practices were. And even maybe understanding what some of the old timers in the industry had to add, because a lot of times the startups are like, “Oh, we’re disrupting the old timers.” But actually he was missing some of that knowledge. And he went and did that work. It didn’t take that long. But it really solved his, I’m an imposter in this industry problem. And he wouldn’t have gotten there if we hadn’t done this woo-woo writing exercise.

Debbie Millman:

Well, another thing that you include it in the book, that’s actually been really helpful to me is the idea of vaporizing imposter syndrome by coming to terms with your underlying fears and concerns about who you think you are. And that’s been really helpful for me. I think that’s a wonderful exercise. Can you talk a little bit more about that for our listeners that might be suffering from their own imposter syndrome?

Alisa Cohn:

So actually, I just want to first mention that I spoke to Suzy Batiz, who is the founder and former CEO of Poo-Pourr. Poo-Pourr is this amazing breakthrough product that took off virally. And Suzy Batiz told me, “I don’t have imposter syndrome. I am an imposter. I’ve never done this before.” And I love that she said that. And I think that young people should recognize that they don’t need to know everything in order to be successful. And that there’s lots of different ways to learn. So if you’re feeling this insecurity, this self-doubt, again, I would go back to tuning into, what are you afraid of? What are you concerned about? What are you thinking about yourself and how are you judging yourself?

Alisa Cohn:

And then go out and find answers. You need more education? Often, young people need more mentorship. Maybe people who have been successful in your field that you want to be successful in, or maybe just people that you admire and that they live their life in a great way. If you can find those mentors, they will help you find your way, but they will also give you in doing so, amazing positive feedback about what you’re already doing. And that’s going to help both, you feel confident about where you are now and help you feel confident in the steps that you walk along your path.

Debbie Millman:

I have to urge people listening to make sure that they play that part that Alisa just said again and then go out and ask people to be your mentors. Because people are not going to approach you and say, “Hey, can I mentor you?” Unless you’re really lucky. Most of the time it comes from asking. And one thing that you do talk about quite eloquently in your book is the role of asking for the things that you want.

Alisa Cohn:

Yeah. Asking for the things that you want is the way you’re going to get the things that you want. And as my mentor, Marshall Goldsmith told me one day, “You don’t ask, you don’t get.” And Debbie, I just want to also mention that I, myself have two or three peer coaches. So we’re mutual mentors for each other. And there’s one peer coach I have who’s inside of my field who’s also a fellow coach and we kind of coach each other and mentor other. And then there’s somebody I have who’s more in the startup world and actually in the investing world.

Alisa Cohn:

And we both mentor each other and coach each other. And it’s a very fruitful relationship. It’s also a way to get to know somebody in a different environment. And it’s a way where you can both benefit from the relationship very clearly and specifically. And I just would say, everybody can find five different people to peer coach with each other because you can always benefit from the perspective of somebody else.

Debbie Millman:

Alisa, I want to talk to you a little bit about the difference between leading and managing. And you write in your book that leaders are always seen as not so subtly as better. People say, as if bragging, “I’m a great leader, but I’m a terrible manager.” Talk about the difference between leading and managing and why both roles are so critical to running not just a successful startup to running a successful company.

Alisa Cohn:

Yes, for sure. So it is true that leaders bring a lot of important qualities. So we think about leadership and that brings the vision, that brings the charisma, the speaking ability, the ability to galvanize people around you, probably the strategy. Also, we think about leaders as looking into the future or three or more years. So that is super important. But if you’re just doing that, then who is doing the execution.

Alisa Cohn:

The managers are the ones that are on the day-to-day, hand-to-hand combat of making sure everyone understands their goals, setting goals, learning how to delegate and delegating work to other people. Helping people by giving them specific clear feedback, helping people resolve problems with each other. That is the day-to-day work of management and nothing happens without that work. I think we need to celebrate that work much more and give them equal status in the eyes of people as we do leaders.

Debbie Millman:

I have a few more questions for you. And then I’m going to ask if you can share one of the most remarkable things in your book, which are scripts. You have scripts in the appendix of the book that allow people to see samples of what you might say in particularly difficult situation. But before we do that, what is your ultimate goal as a coach?

Alisa Cohn:

My ultimate goal in my life is to make a difference. My mission is to light 10,000 candles. And I think a lot about lighting the candle of the person I’m with right now. Making someone’s day right now. So that’s my overall mission. When I think about my goal as a coach, I’m really focused on helping this person do more of the things that will make him or her more successful and the company more successful and doing fewer of the things that get in their way. So it’s addition and its subtraction.

Alisa Cohn:

And my ultimate goal as a coach, I love of having deep conversations, but I want them to be able to take a different tactic, a more effective tactic on a random Tuesday afternoon. I know that I’m successful when two years later, eight years later, 15 years later, someone comes to me and says, “Yeah, then I heard your voice in my head and I realized I shouldn’t do this, I should do that. So then I did that and then good things happened.” So that always makes my day. And my goal is to enable people to achieve the things that they want to achieve.

Debbie Millman:

For someone thinking of starting a company, what advice would you give them?

Alisa Cohn:

My advice is, do it and know in advance what you’re getting yourself into. People think about the product or the service or the thing they want to offer and they don’t recognize the path they have to be on and the personal growth journey they have to be on as they build a thriving business. So when you start a company, you’re not just building a product, you’re building a business. And all the things that come along with that are going to be important for you to master and to be able to adapt as you go. So recognize that and find good mentors and other helpmates to help you through that journey.

Debbie Millman:

What would you caution them against?

Alisa Cohn:

I would caution anyone starting a company against believing the meme that’s in life right now about the Mark Zuckerbergs or even the Jeff Bezos, as in like, “Oh, it’s so easy for them. And they were on this just direct path towards success.” Recognize it’s a lot of hard work. It’s a lot of unglamorous hard work. So don’t buy into the Silicon Valley, “We’re crushing it,” kind of mentality. And don’t get distracted by a lot of the hype around startups, focus on what you want to do and what you want to build and that will help guide you.

Debbie Millman:

Let’s talk about the scripts.

Alisa Cohn:

Yes.

Debbie Millman:

The scripts in the appendix of your book, what made you decide to include them?

Alisa Cohn:

When I’m talking with my clients, they’ll say, “I’m not sure what to do about this.” And I’ll say, “Well, how come you just don’t say,” and then I’ll say what they should say. And then I see them writing it down furiously. And I say, “Oh, do you want to record this?” He’s like, “No, no, just say it again.” I’m like, “Okay.”

Debbie Millman:

Slower.

Alisa Cohn:

Right. So I say it again. And it dawned on me after years of this happening that these scripts were actually extremely useful for people. And so, as I was writing the book, it just occurred to me, people like scripts and they find them very helpful. And so I’m going to put some in the back that my clients have found very helpful.

Debbie Millman:

Will you share a few with us?

Alisa Cohn:

Yes. I’m going to share two scripts. These are two very common scripts that I think people find very helpful. The first is giving difficult feedback to people. People hate that. And the leaders I coach say, “How do I hold people accountable? What am I supposed to fire them?” And I’m like, “No, no, no. There’s a lot of different ways to hold people accountable. But first of all, what discussion have you had with them already? Have you set clear goals?” “Yeah. We have set clear goals.” “Okay, good. So what have you already told them?” “Well, they should know that…” I’m like, “Well, no, no, they probably don’t know because that’s why we’re having this conversation. What have you already told them?” And it turns out they haven’t shared any feedback with them. And I understand that, it’s really difficult to give feedback.

Debbie Millman:

Yeah. People avoid conflict almost more than anything.

Alisa Cohn:

Totally. Totally. And not even conflict, even just straight talk. And so I am going to share this script and I want to talk about a concept that I use regularly, which is called labeling. So first of all, this is not a bad person, but we’re just going to label a few things to call them out. So we’re going to make some observations here. That’s first of all. And second is, I’m going to give difficult feedback, but I’m going to get into it with what I call an emotional payment. As in, you are not a problem. And also, and you add a lot to the table, but there’re some things that you need to work on.

Alisa Cohn:

The reason I think it’s important to make that emotional payment is because you want to signal good intent. And if you’ve not been giving them positive feedback for the past couple of years, you might really need to signal good intent right here and right now. So I’m going to give that as context. I want to distinguish this also from the so-called feedback sandwich. Have you heard of the feedback sandwich?

Debbie Millman:

No, no.

Alisa Cohn:

What people think about is the feedback sandwich is you tell people something good, then you tell them what you really want to tell them and then you tell them something good to soften the blow. I do not encourage that. Do not do that. However, you do need to signal good intent. And if you haven’t done that regularly, let’s start off by giving the positive so the person understands where you’re coming from.

Debbie Millman:

Why do you recommend not giving a feedback sandwich? It sounds like the big difference between what you’re going to share with us and a feedback sandwich is that you don’t come back to the bottom half of the sandwich bread.

Alisa Cohn:

Yeah. The problem with the feedback sandwich is its technique. It’s not coming from a philosophy. It’s just a technique. Like, “How do I give someone a feedback?” Well, you tell them something good and then you tell them something bad and then you tell them something good. There’s no depth to that. Also, people see through it. So it doesn’t land in the way that you’re hoping for it to land. So I think it’s almost a spiritual difference.

Alisa Cohn:

What I’m asking you to do is not give a feedback sandwich, I’m asking you to actually think about, for yourself, all the good things this person does bring to the table so that when you have the conversation, your tone is connoting the approval, those good things. Also, so that your employee understands that you’re coming from a place of wanting to be helpful to them and appreciating what they bring to the table. So I think it’s a difference of almost philosophy and depth.

Alisa Cohn:

So I’m going to ask you all to really think about, what does this person do well? Because you’re going to start with that and also you want to bring that to the conversation as you have a difficult feedback. Is that helpful?

Debbie Millman:

Absolutely.

Alisa Cohn:

Okay, great. So I’m going to get right into it. “Debbie. I want to talk to you today because I’ve noticed a few things that I think we should address. First of all, I appreciate everything you do. I know you’re one of the hardest workers here and your sense of humor brings everyone up. That’s great. That said, I want to make sure you’re getting great results with all your work. What I often see from you is a number of projects, a lot of activity, but I often see the projects are delayed and remain unfinished. Also, you don’t always let everyone know with the delays so they come as a surprise. That’s a problem for your coworkers who are counting on you to do what you say you’ll do. Then other things get delayed waiting on you.

Alisa Cohn:

I’m sure you have your reasons. Things are not perfect here. Maybe you’re waiting on other people, but I expect you as a leader here to work constructively with your peers to fix process problems as they come up and to raise flags early if things will be late. I also expect you to make sure that you’re communicating regular with your peers and all the things you guys are working on jointly. I know you’re super talented and you have much to contribute to our company. I want your efforts to have the right impact and I want you to be able to move forward in your career. That’s why I’m working on this with you.

Alisa Cohn:

We can discuss some of this right now, and I’d love you to think about this and come back to me in three or four days with what you see is the problems and how you propose to fix them. What day should we plan to sync up again so you can share your plan with me and let me know what help you need from me?”

Debbie Millman:

So do you recommend that that’s something that be said face-to-face or should that be in an email? Could that be in an email?

Alisa Cohn:

I really prefer face-to-face or these days video. It’s important to have the conversation because they’re going to have a response. When I write these scripts, by the way, obviously you’re going to tailor it to your own circumstances, but also, they might interrupt you. That’s okay. You’re trying to get your mouth around the words. Also, you’re trying to get your mindset right. And so practicing it is very helpful. Having a script to practice it is very helpful. But once you’ve thought through what you want to say, when and if they interrupt you, and also share their point of view, which you certainly want to hear, it’ll help you listen to them and not worry about you getting through your message.

Debbie Millman:

What happens when somebody responds defensive?

Alisa Cohn:

I know. I have a script for that on my website actually. When someone responds defensively, so first of all, I think it’s important to step back and remind them, “I’m only sharing this with you because I care about you and your success.” Also, that’s where labeling comes in too. “Listen, I see that you’re having in kind of an emotional reaction. I understand that. I don’t like getting difficult feedback either. So let me just see if we can calm down for a second.” And we might need a minute. The other thing you can do when someone acts defensively is you can just be quiet and you can also say, “Listen, I don’t want to upset you. Tell me more about how this is the landing for you.”

Alisa Cohn:

By the way, I just did this with a client the other day, I was giving him the feedback and he got super explosive with me, quite defensive. And so I just let him talk and let him talk and let him talk. By the way, we think coaches don’t take it personally, I took it personally.

Debbie Millman:

You’re a person. Why wouldn’t you take… I take everything personally, I’m a person.

Alisa Cohn:

Yeah. But I let him vent and vent and vent and vent and vent. And then I said, “I see that I touched a nerve here,” which I think was accurate. I was just labeling that. And also, what I said to him was, “I really didn’t mean to upset you. That’s not why I brought this up. Tell me more about what’s coming up for you or what’s going on with you.” And as a leader, you can say that too and you can, this is another woo-woo term in coaching. We say holding space. You can hold space for somebody to have a difficult and emotional reaction. And that can go on for 5 minutes or 10 minutes. And it’s not their final answer. And also, you don’t have to take it personally. You can get to a place where you realize they’re having an emotional reaction, let them talk it out and it’s not going to hurt you. And now you can together explore that emotional reaction that they’ve just had. And it can be actually enormously healing.

Alisa Cohn:

And in the case of the person I was just mentioning, he got upset, he had this emotional reaction. And then we got through it and he calmed down and said, “I really understand what you’re saying and I want to think more about it.” And I said, “That’s great. Why don’t you think more about it?” And then we had a follow-up conversation and he came to the table with a lot more sophisticated commentary on what was going on. And I think that leaders get alarmed and shut down themselves by someone else’s defensiveness. And I would say a lot of people have a defensive reaction at first, before they have a more, let’s say, enlightened reaction.

Debbie Millman:

You included one story, one anecdote with a client that left the room. He was so aghast by what you said and you didn’t know what to do. You’re just sitting there kind of like, “Should I leave? Should I stay?” Eventually 45 minutes, he comes back in a completely different mood and says, “You’re right. I spoke to my wife. She said that I do all of those things.”

Alisa Cohn:

That’s right.

Debbie Millman:

I love that story.

Alisa Cohn:

Yeah, that’s right.

Debbie Millman:

Share one more script with us.

Alisa Cohn:

Okay. I’m going to share one more script. This is going to be a simple script. And I think that people don’t think enough about this. So as a manager, one of your roles is to do career development with your people. And I think that managers and startups definitely don’t think about that. And also, they think they may not have something to add because like, I’m in marketing and that person’s in product management or whatever. So this is a very short and simple script that you can bring up to your people, three, four times a year, which is about their career development. “Debbie, 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 these goals.” And that’s it.

Alisa Cohn:

Now, here’s I have some questions. I’m going to give you a few questions you can ask. You can ask, “What parts of your job right now, do you like the most and what parts do you like the least? Has anything about your career aspirations or goals changed since the last time we talked? What are you doing now that points you in the direction of what you think you’d like to do? What kinds of training or experiences do you need to get there?” And then on and on and on. There’s a number of other questions in the book, but you will see that actually your job as a manager is to ask a bunch of thought-provoking questions. If they can’t answer them, that’s okay. You’ll talk again in three, four months, it’s fine.

Alisa Cohn:

But let them receive that you care about their career development. And then when people say, “What’s she like as a manager? Does she care about your career?” They’ll say, “Yes, she does.” And that will be amazing for them and for you.

Debbie Millman:

One of the things that I like very much about that script, I didn’t know you were going to read that one is that that’s also something that people reading the book can do self-directively. You can answer those questions for yourself as a way to gauge how you’re feeling about what you’re doing and how satisfied you or may not be.

Alisa Cohn:

Yes. So true. That’s right.

Debbie Millman:

I have one last question for you, Alisa. You start the book with a question that you sort of leave us hanging with throughout the entirety of your book and don’t answer until the end. And so spoiler alert for anybody that might be listening that doesn’t want know the answer to the question. I’m going to ask it. Hope you’ll answer. Should startups have a ping pong table in the office, and if so, why?

Alisa Cohn:

The age-old ping pong question. Here we go. Well, like any good coach, I’m going to say, well, it depends.

Debbie Millman:

Not fair.

Alisa Cohn:

I know. I want to say briefly that when you’re building culture in your company, you’ve got to think about what kind of company do you want to build? What kind of people do you want to be in that company? Let’s hire are those people. Now, let’s train them, let’s onboard them, let’s give them training and let’s communicate and doctrine them into that culture. And now you probably want to have a place as part of that culture people feel cared about.

Alisa Cohn:

So do the things that you need to do to make people feel cared about, ask them about themselves, get to know them, try to commiserate with their trouble and give them positive feedback for when they’re doing a good job. And at the end of all, that you can think about a few perks that you want to give your people. And if one of them is ping pong, God bless.

Debbie Millman:

Alisa Cohn, thank you so much for putting so much important work in the world, for helping so many people become better at who they want to be. And thank you for joining me today on Design Matters.

Alisa Cohn:

Debbie, it has been an honor to be here with you and thank you so much for the work that you put into the world and everything that you do. It’s amazing and this has been a joy to be here.

Debbie Millman:

Thank you. Thank you. Thank you. Alisa Cohn’s brand new book is titled, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business. To find out more about Alisa Cohn and all of her extraordinary coaching work, go to alisacohn.com, that’s A-L-I-S-A-C-O-H-N.com. This is the 17th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.