Forever Employable Stories: Alisa Cohn, #1 Startup Coach in the World

Posted on November 8, 2020.

I was lucky enough to meet Alisa Cohn by chance. Dorie Clark, who wrote the forward for Forever Employable, invited me to a virtual cocktail party a few months ago where Alisa was the co-host. We kept in touch over the subsequent months and recently I had a chance to catch up with Alisa one-on-one to get her forever employable story.

Starting in the world of corporate finance Alisa quickly realized that Big 5 consulting was not for her. Dropping out of the corporate world despite being on the fast track to leadership forced Alisa to reconsider what she wanted to do with her life. In our conversation she shares how she discovered the concept of coaching and why she felt it was the right decision for her.

Importantly, we also discuss how she began to build that business and eventually scale it to the point where she’s now the top recognized expert on startup coaching and has been featured in the New York Times, BBC, CNN and many other media outlets.

As with many of our forever employable stories, Alisa and I dove deep into the power of the holy trinity of career success: hustle, focus and writing. Figuring out how to get the word out there about what you do, focusing on that mission relentlessly and hustling in ways to just land that first or second client and then build from there are just some of the techniques Alisa used and which she shares in detail.

Most importantly, Alisa emphasizes that with any coaching engagement (and I’d argue with any business engagement of any kind) you need to deliver value in the first 20 minutes. If you can do that, you imprint on your client and can move out of “sell” mode and into pure “delivery” mode.

Alisa close to releasing here first book called From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business in the coming year and you can always find her on LinkedIn and Twitter.

Watch the full interview here (transcript follows below):


JEFF:    Hey folks, welcome back to another Forever Employable Story. Super excited for my guest this time around. I have executive coach, startup coach, and all around fascinating person, Alisa Cohn joining me from very close to my former hometown in New Jersey. Alisa, how are you today?

ALISA:  I’m fantastic. It’s so great to be here with you today. Thank you for having me.

JEFF:    I’m thrilled to be here. We met a few months ago with Dorie Clark. You and Dorie were hosting a bit of a networking virtual drinks thing that I was lucky enough to get an invitation to. I thought that was super on brand for Dorie wrote the forward for my new book Forever Employable and how do you maintain these networks in a world where we’re all socially distributed? Virtual drinks it was. You and I met.

ALISA:  We also wrote two articles for HBR but I had to do virtual networking during this time. It’s something that has a lot of passion for both of us – the idea of how do you add people to your network and then also continue to get to know people who already know.

JEFF:    It’s super important and super valuable. We’re here today because of that. We didn’t know each other before that. And that was really nice. You’re an executive coach, the number one startup coach in the world which is an amazing feat, but let’s start off with executive coaching. What’s an executive coach?

ALISA:  When I think about coaching, I think about helping people assess where are they? Where are they going? How are they going to get there? You can apply that to any aspect of life. Life coaches do life stuff. Weight loss coaches, weight stuff. I work with executives; specifically, startup founders to help them think about their leadership, to help them get coached inside of their leadership, and help them grow as leaders. Coaching is really about partnering with someone to help them walk the path so they can reach their full expression of leadership.

JEFF:    The startup founders that I met and that I’ve worked for in the past, they all have some element of brilliance. They got to that point by being smart, by being brilliant, by having this spark. A lot of the time, it’s technical brilliance or product brilliance or design brilliance. Leadership is something they typically have to grow into if that brilliance sparks an idea that actually begins to grow. Can you teach that to somebody? Can you teach them leadership?

ALISA:  It’s a great question and the essential question. The answer is absolutely yes, but to your point, a lot of founders start off with the technical expertise, even a sales expertise product, and maybe they’re tinkerers and it’s about how do you go from someone who is busy building a product to someone busy building a business? That is a different thing all together. Then it’s about getting the right people, galvanizing them, motivating, figuring out what’s going to motivate them, and putting together all the aspects that you need to along that way. That requires inner growth. I’m not sure if you remember, but in our cocktail event, I told you about the rap music video that I produced this summer – my summer COVID project. It’s called The Work is in You. That’s what it takes for any founder to grow into a CEO or really, anybody to grow. The work is in you. How do you grow yourself in order to kind of figure out what are the elements that you need to build to build a business in a thriving company?

JEFF:    As you think about being a coach and look at the analogous coaches people know, sports coaches, gymnastic coaches, whatever it is – it feels like a lot of those folks did that thing first and then became coaches. How does one become an executive coach?

ALISA:  The answer is it depends. From my point of view, I was at PWC and I was on the fast track to partner there. I had kind of that corporate expertise. I then joined the startup world and I was the CFO of one startup and the head of strategy for another startup. I kind of got my own leadership chops at a young age. I’m also a CPA. I have found all of those things enormously helpful when it comes to helping people scale because I know what it’s like to be in the trenches. Do you have to be an executive? I can’t say. I think that you have to know the topics that executives deal with and have had some experience of that kind of pressure that CEOs face every day. Without it, you don’t quite have the empathy.

JEFF:    You start off your career as sort of the way we’re all told to start off our career. We get a job. We move from one place to the next. We get a little bit more responsibility. Then you decide to transition out. Why transition out of the corporate world and how did you actually get out?

ALISA:  It’s very difficult. From my experience, I was at PricewaterhouseCoopers and I was on this fast track to partner. It’s like a 12-14 year journey to partnership. The program I was in was supposed to be a five year journey to partnership. I had it all set in some ways. I woke up at 2 ½ years in and I just thought, “This is not for me.” PWC is a fantastic firm. They treated me great the whole time and they treated everybody great. Even as I was leaving, they were amazing to me. It just wasn’t the right fit for me because it was just too big. I just realized this is not for me and I had to go seek out what is for me. How do you tell? Honestly, I got sick. I woke up one morning and I thought, “I hope I get the flu so I don’t have to go to work tomorrow.” Then I got the flu like 18 hours later. Rushed to the emergency room. Important pro-tip: do not ask for the flu. It’s really bad. I was down for the count for two weeks and every time I thought about going back to work, my fever would spike back up and I said, “This is not it.” I kept thinking in my head that it matters to me to make a difference. If the work of my hands matter. PWC, a great firm but with all those people, that did not feel like my calling. I had to seek out my calling. How do you do that? You kind of wander around. In my case, I went to this conference that I would have never gone to. It was called The Body and Soul Conference. My boyfriend, at the time, was a yoga guy. He’s like, “Let’s go volunteer for this Body and Soul Conference.” I’m like, “Seriously?” I didn’t have anything else to do. I was in a seeking mode. At this Body and Soul Conference, I was a volunteer, and they said, “Cheryl Richardson is now going to speak to the volunteers.” I’m like, “Who is Cheryl Richardson? Do I have to stay for this?” It turned out she was amazing. She’s a very well known coach, it turns out and she was amazing. I followed her around in that whole conference. I was like, “That’s what I want to do.” It’s like violins played.

Then it’s mechanics. How do you go become a coach. I asked Cheryl, “How do you become a coach?” She said, “You should get coach training.” I’m like, “Okay, I got some coach training.” They said, “You should coach everyone you meet.” I got my friends who let me coach them for free. In the meantime, I did leave my job at PWC. I joined the startup world. That went on for a  couple of years and when things went south in 2000, I had already kind of gotten myself together to be a coach. I’d taken coach training. I coached everyone I know. To your next question – what do you do? You put one foot in front of the other. My gym had this vendor fair that you could go down and present yourself. I was like, I’m going to go to the vendor fair. It was February. I was in Boston and it was sleeting. It was dark. It was 5:00. I did not want to go but I pulled myself together because I thought this  – it’s not like this sleet and this vendor fair is what I want. What I want is the life of my dreams. If I want the life of my dreams, I’m going to walk through the sleet to go down and present myself at this vendor fair which I did and I had people sign up for complementary sessions which they did. Half of them did not show up for their complementary session but some did. I coached them complementary and then one hired me after that call. That was my first client. Rick Samuels. Thank you, Rick.

JEFF:    Do you still keep in touch?

ALISA:  No. I should track him down because that was my first paying client. I will never forget the gratification of that. Things are hard but if you want this vision of what you say you want, you have to do hard things to go get that.

JEFF:    You say coaching. Specifically, you’re an executive coach and a startup coach. When you’re starting out you said you  met this woman and she was an amazing coach and she said to coach everyone you meet. Can you clarify what that means?

ALISA:  It’s a very good question and it’s a little bit how I kind of perfected, for me, by mistake, the art of adding value in 20 minutes. That’s kind of what I think when I’m meeting with somebody new. My goal is to add value in 20 minutes. To me, it was very simple. I’d say, “What do you want coaching on?” Nobody said shooting baskets. Coaching is a domain. It’s really about how do you think about where are you, where are you going, and how are you going to get there? You can apply that to anything in your life because it’s about sitting down with somebody for an hour. What I’d say to people is if you had a secret weapon for 3-6 months that was totally devoted to you and your success, what would you want to work on? They’d answer me and we’d start to working on it right there and then. It might be weight loss. It might be relationship stuff. It might be I feel stuck in my career. I’ve always bene the person that my friends come to to ask about careers. That is not a surprise to me but the truth is, I may not be a relationship expert but I’m an expert at asking great questions because I’m curious about people. If we sit down together for an hour repeatedly, you’re going to have insight through my questions and my asking you to really dig deep about what’s going on with you. That will unlock a number of things in a number of aspects of your life.

JEFF:    I work with a  business coach. I’m a company of one. I have a part-time assistant but you’re looking at Gothelf Corp and my children, my video production crew, as we call them around here. At the urging of a friend, I ended up hiring a business coach and I’ve been working with her now for a year. I found it to be fascinating. I feel like I’m an expert in my field. I feel I know what I’m doing and I feel like I have really good perspective. Like you said, you sit down with somebody on a regular basis for an hour and you share what’s happening, what you’re challenges are, what you’re trying to get to and the objective, expert opinion that comes back opens up so many new ideas. I found it infinitely valuable.

ALISA:  What specifically have you gotten out of it?

JEFF:    This book. And the reason we’re even having this interview came out of that because the idea for this book was sitting in my backlog for two years. My coach asked me kind of a similar question. What’s sitting around? What do you really want to work on? I said, “I’ve got this thing in my backlog. It’s been sitting there for two years.” She’s like, “What’s stopping you from doing it?” “I don’t have any time. I’m really busy.” She’s like, “Well, do you want to do it?” “Yeah.” We talked about tactics to get it done. Through her and that support, we got it done and now this is out there and it’s a significant amount of my focus at the moment. I don’t think it’d be live now if it wasn’t for my coach.

ALISA:  Yay you. That’s fantastic. And tribute to her. Notice how she wasn’t an expert on publishing books.

JEFF:    She’s not, no.

ALISA:  That’s not what you got out of it. What you got was someone to sit down with you and really gently but firmly inquire into you what’s going on with you. For me, it’s like, “What’s really going on with you?” When you can identify that for yourself and you’re a pretty capable person, as you are, things just change. You  just devote the time to it or you just find the person to help you or whatever it is. I think it’s very powerful.

JEFF:    You transition out and literally walk through sleet to get your first gig. How long ago was that?

ALISA:  Roughly 20 years ago.

JEFF:    How do you start to then build your brand and reputation when you’re transitioning into a new world?

ALISA:  At first I didn’t focus on building my brand. I didn’t know to do that and didn’t have access to that language or those tools. I just hustled. I talked to everybody I knew, everybody I could. I taught adult ed which was a way to build my brand without my realizing it. I built my network maybe more. I really hustled and tried to figure out how I’m going to get clients. I’m pretty tenacious and good at what I do, I got a bunch of clients. That was very helpful as a proof of concept. The way I began to build my brand, later than I probably would have wanted to, is I was working with this one company and it was going great. Then they brought in a new head of leadership and it was not going great anymore. I was so upset. I’m a runner, and so, I’d be running, running, and so upset about this company. By the time I got home, six miles later, it was always the same thing. Diversify your client base, Alisa. I’d be like, “How do I do that?” It’s actually not that hard. Write a newsletter. I was really nervous about it but 14-15 years ago, I began writing my monthly newsletter. It came out between 8-10 times a year for as long as it was monthly. By the way,  I was terrified. It really felt like a year I wrote my additions. In those days, you’d have someone launch it for you. I’d be done with it. I’d give it to him to bury and I’d say, “I’m going to go hide in my closet.” That is literally true. I’d go hide in my closet because I was so nervous about putting this out into the world. It was crazy. Then I got more comfortable and then I got the opportunity to write for Worth because I met the publisher at a dinner I was at. That was about networking and I kind of got my courage up to ask him if I could write for him. He said yes and then I emailed him three times and he didn’t get back to me. Email overload. You have to be persistent with people. Got back to me. Put me off to a more junior person. We organized myself to write for Worth which was great and I used that to start writing for Forbes and then I began to have a track record of content and building my brand. People began to hear about me and they’d come to me and then Inc. found out about me and Inc. asked me to write for them. Now I write for HBR, again, on the back of all that content.

When you start building content and you have your network, as we know from our good friend, Dorie Clark, that’s the way you become a recognized expert and people begin to reach out to me as a result to that. It didn’t happen in the first year. It takes a long time.

JEFF:    I’ve been working on this myself for 12 years. It’s an ongoing work. You said, how do I diversify my client base? Write a newsletter. Connect those dots.

ALISA:  Every time I went for a run and got that in my head, I rediscovered that every single time. The reason is because what I knew, without being an expert in this world and I wish I knew then what I know now, but I knew having a regular cadence with reach out to people that was interesting and engaging to them would somehow come back to me in the form of clients. I didn’t quite know how but then it turned out people I use who used to work with me rehired me or they’d forward it to a friend or they’d say, “Oh, I didn’t know you were a coach,” or “Oh, I forgot about you. Now I remember you.” As it happens, this person needs a coach or referring that way. Even just gathering the people you already know yields current business but it also develops kind of a tribe so people remember you because you’re memorable.

JEFF:    That builds up over the years and starts to snowball into other writing gigs which is terrific. I talk a lot about writing as key skill. Clearly, it’s working for you. Give me a sense, in a month, how much time you invest in writing.

ALISA:  Definitely not typical because it goes up and down for me depending on what else I’m doing. Let’s say I interview 1-3 people in a month and I write up that interview, that’s probably 10-15 hours because it takes me a long time to write. If I then add on doing an Inc. article where I typically don’t interview somebody, that’s another probably 3-4 hours. In a month, I probably spend a good 20 hours on writing.

JEFF:    That’s roughly five hours a week on writing. Clearly, that’s not only diversifying but growing your client base as well. It’s tremendously valuable especially now that you’ve got sort of regular outlets and a roughly diverse set of outlets as well. That starts to broaden it out as well. Are there other ways that you generate business that drives leads?

ALISA:  I made a point of asking for referrals. I think people get uncomfortable. I really think I’ve helped a lot of people and I know that our process is helpful for them. I just think, “Don’t you want to share this with other people?” I’m comfortable asking for referrals. At this point, I’d say people, without my asking – just today, got another referral. Even two today actually. People found me through my website or they just email me and say, “I know somebody who is looking for a coach. Can I refer you?” Track record and existing network. Also, I was just on the BBC last week and that generated. The BBC and the New York Times, whenever I’m in them, “Oh, I saw you…” People I met 12 years ago, “Oh, I saw you in the New York Times. I saw you on the BBC.” That’s cool and it keeps me on people’s radar screens. There’s an alchemy of how you get business and it’s not always clear what’s the one thing that’s going to lead to business. I know that somebody hired me after meeting me eight years ago. You just have to have a sense of the long-term nature of the game.

JEFF:    I saw this illustration about COVID and it was the swiss cheese strategy for managing COVID. It was a bunch of slices of swiss cheese where the holes didn’t line up. Every slice was wearing a mask, social distancing, small groups being outside well-ventilated; that type of thing. Some virus passes through every slice but less passes through multiple slices. By the time you get to the end, there’s very little that gets through. The reason I bring that up is I really like swiss cheese. That’s really it.

ALISA:  He’s like I’m obsessed with COVID and cheese.

JEFF:    The idea is there’s no one strategy that is a silver bullet for driving leads to your business, to yourself, to these opportunities. It’s all of these things together that some leads are going to pass through and others are going to get blocked. It’s writing. It’s giving talks. It’s doing things like this that we’re doing right now. It’s networking. It’s these happy hours, media, etc. Eventually, that starts to  build these consistent leads that come from these very sources. Sometimes those sales cycles will be years’ long. You’ll just wake somebody up. I’ve been teaching a class for the last month with one of the big hardware stores in the United States. The guy who hired me for that, he’s a guy I worked with 14 years ago and lost touch with him. He kind of pops up, “Hey, I’ve been reading your books and I’ve been following along and now I’m ready to hire you.” It’s amazing to me.

ALISA:  And you didn’t even know you were waiting for him.

JEFF:    No, I had no idea. It’s fantastic. Media. You talked about the BBC, New York Times, Inc., Forbes, etc. How do you choose which media to do? Is it paid work typically? Do you ever say no to certain publications?

ALISA:  It’s pretty organic. If I’ve heard of a publication, I’m pretty sure other people have and I think that’s probably a good use of my time. Being nice to reporters is a good use of your time. I just recorded an audio course for Knowable called Learn to Love Networking. Knowable is a new startup that’s doing audio courses. Feel free to check it out. In that, I said it never hurts to have context in the media in terms of who you’re thinking about adding to your network. I followed my own advice on that. Do I turn anything down? Yeah, I turn things down. I turn down a lot of virtual summits.

JEFF:    Why?

ALISA:  They are time consuming and there’s a lot of people doing virtual summits. I’m not so sure if I’m going to get a lot of reach from those virtual summits. May Bush does a virtual summit in January. She’s super well-known, a good friend of mine. Of course, I do her virtual summit. Marshall Goldsmith is doing a virtual summit. Of course, I’m going to be involved in his virtual summit. It’s more people I’ve never heard of maybe. None of it’s paid.

JEFF:    The pay comes from the leads. That’s part of the hustle, part of the work that a lot of folks don’t realize. “Oh, you’re doing another conference, another virtual summit.” Yeah, it’s the work. It’s the sales part of the work itself. In my world, one of the competitive advantages that people have who do what I do for a living is geography. For example, someone is the best or best known agile coach in Amsterdam. Someone is the best product management trainer in New York City. COVID has killed that. The idea of a geography based moat is gone. Everybody is teaching in the same place online, which means I and people like me and everybody else is now competing with literally every single other person in the world who does anything remotely close to what I do for a living which can be really intimidating. For example, I’m expensive. There are people who do exactly what I do for a lot less money than me. I never had to compete with them because we never taught at the same place at the same time. I’d fly and maybe they wouldn’t fly or something along those lines. That’s gone. All of us are playing in the same space. As long as you’re willing to adjust for a time zone, anybody can play in any space at any time. Like today, I spoke at a conference in Scotland. I worked with my client in India. I did work with my business partner in New York. That’s today.

ALISA:  And now you’re conducting an interview with somebody who is in Montclair, New Jersey.

JEFF:    My favorite state in the whole world. How do you stay relevant, in demand with this new added level of competition and the competitive advantage of geography completely gone?

ALISA:  I love this question. I’m definitely going to give you some coaching because I think you need to reframe your attitude. I’m known as the top startup coach in the entire world. Just today, by the way, I spoke to somebody who is based in Belgium. I said the same thing to him which is now is the time to do just what you said which is not have to travel. You’ve democratized and leveled the playing field which means you have 100% access to build your brand and building your brand demands higher feeds, more notoriety, more people coming outreach to you rather than you reaching out to them. All of those things together are totally playing in your favor. I would say to you, don’t think of it as a competition. Think of it is as what do you need to do to be top of everybody’s radar both in terms of brand excitement as well as just knowledge like top of mind as well as knowing so many people that they come to you first? If all of those things are working together for you, then geography, in this time, becomes your friend because you just did all those different things. I know myself just did a keynote in India for 300 Indian CEOs. They would not have flown me in to do that. That would not have been so easy to do. There’s so many virtues of this time. That’s how I want you to think about it.

JEFF:    You’re saying it’s not a competitive disadvantage. It’s a competitive advantage because now you’ve got the whole world and new opportunities and the ability to work in three different countries in one day. Whereas before it would have crushed your soul to be on that many airplanes.

ALISA:  And you wouldn’t have had the time. You can’t do three events in a day in three different locations, but on video, you can.

JEFF:    Thank you so much for sharing your expertise and spending the time with me telling us your Forever Employable Story. It was a ton of fun. I wish you nothing but the best and success in the future.

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