Leadership Notes #62
Interview with the Top Startup Coach in the World
Alisa Cohn is an Executive Coach who has worked with C-suite executives at prominent startups (such as Venmo, Etsy, Draft Kings, The Wirecutter, Mack Weldon, and Tory Burch) and Fortune 500 companies (including Dell, IBM, Microsoft, Google, Pfizer, Calvin Klein and Hitachi.) She is the author of From Start-up to Grown-up, which won the 2022 Independent Press Award, the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name*,* which provides insights and tools for the journey founders (and all leaders) must go through as they scale their leadership.
She was named the Top Startup Coach in the World at the Thinkers50/Marshall Goldsmith Global Coaches Awards and ranked globally as the #1 Global Guru for the past four years by Global Gurus Research Organization. A sought-after speaker, Alisa was named one of the top 100 leadership speakers by Inc. She has keynoted events for IBM, PwC, Dell, and Citi. She is the executive coach for Runway, the incubator at Cornell’s New York City campus. She is a regular contributor to the Harvard Business Review, Forbes, and Inc, and she's been featured as an expert on BBC World News and in the New York Times and the Wall Street Journal. She is an angel investor and a Broadway investor.
You can download Alisa’s 5 Scripts for Delicate Conversations at www.alisacohn.com/scripts. Buy Alisa’s book here and check out her podcast. You can follow her on twitter & instagram @AlisaCohn.
A condensed transcript of PGLF Virtual Author Series at CIED, Georgetown
Potolicchio: What are some tips that you have for making a good first impression, particularly if we're in a large setting, and we have to stand out with so many other voices in the room?
Cohn: Listen without thinking about your response and take the person in. If you're in a large group situation, it's so often that people are intimidated. They don't know what to do, and just meander around. There are a couple of things to do. Number one - go approach somebody who is not talking to anybody else. In fact, if they're on their phone, even better, because they're on their phone to distract themselves from their own insecurity. You can just sidle over and say, “Hi!”
My opener is typically, “Hi! My name is Alisa!”
If you're in a large group with multiple people who are all chatting together, especially if it's a networking conference or event, they're there to network and so are you. There's nothing wrong with going over to join a group and say: “Hi! Can I join you?”
The biggest thing that gets in people's way is this sense of shyness and the spotlight effect - that everyone is watching them. They are not watching you, they are concerned about themselves. They are self-conscious, and you are doing them a favor by approaching them.
The other thing is listening without an agenda and just being curious, asking people questions about their life, their profession, what they enjoy. That is what will absolutely help you make a strong first impression.
Potolicchio: The best thing you ever told me is when you're going up to somebody that you would like to be a mentor, or somebody who's going to be on your unofficial board of advisors, is you treat them like a peer, you should immediately start equal in status. What is some advice on how we treat those that have august positions and titles or investors as peers and how do we build our relationships?
Cohn: They're people just like you. They have wants, hopes, dreams and needs. Why are you even worried about them? If you think about this person as just another human being, and not get all caught up in your adulation of them, you will do much better. If they are a very famous author, or thinker in your field, you don't pretend you don't know them.
For example, I met Daniel Kahneman, Nobel Prize Laureate for Psychology, a few times while he was still alive. In this case, you can say: “I'm familiar with your work, and I really appreciate the contributions you've given to the world!” Then, you can act like a normal person, asking things such as: “What brought you here tonight?” What are you working on these days?” “What are you most excited about?” That's going to help you calm down and give you better access to that person.
It's always helpful, if you know in advance that you're going to be meeting someone who you admire, to figure out a little-known fact about them. Here's an example for me - I'm a very committed weightlifter, I'm passionate about it. I also love music, singing, and when I can bond with somebody over weightlifting or some other topic, it is very interesting how easily they talk.
Finding something that accesses their humanity is always a good outlet. It might be something you know about them, but it might also be just an interest of yours that you throw out there that helps them to connect to you.
Potolicchio: One of the things that you taught me was that you should always add value, because we often have this fear that when we're networking, it's going to be transactional. One of your close friends who's also in the executive coaching business, has a strict rule, which is, you don't make any request of somebody that you meet for at least 365 days. But if this individual is going to be in your network, presumably, you're going to have three or four touch points with them before you make an ask in that one-year period of time, so you're going to add value three or four times before you make your own ask.
Is there something in your own repertoire, particularly as you look to deepen relationships that you think is useful? And one very specific question I have is, how do you write the follow-up email, what does that look like? Is there a checklist that you personally go to?
Cohn: I sincerely believe that networking is not transactional. I genuinely believe that it's a better world when everyone is on team Alisa and Alisa is on team everybody else. The only way I can be on everybody else’s team is if I know them and have a connection with them. Then, we begin to have an interaction over a period of time.
It's helpful to start with sincere intent, because life is more fun and better that way. When you're interacting with somebody, it's very helpful, as we already talked about, to be interested in them, in what they care about, and what they're excited about. I'm somebody who has a lot of broad interests and usually there's something to connect to. It could be something such as: “I know a book or a podcast for you.” “I think you should meet this person!” That begins the process of following up already.
For the actual follow-up conversation, you get their contact information, and then you follow up with “It was so nice to talk to you!” and then mention something that you sincerely enjoyed about the conversation. Then, you say: “Here's a book, article or podcast for you! Hope that you find that helpful or useful.” or “You should meet this person! Let me send you their LinkedIn profile. Would you like an introduction?” This way, you're positioning yourself to add value.
If you have a dream job that you want, and they're the hirer of that dream job, you have to resist, it cannot be “Can you put me in that dream job or company?” That's just inappropriate to be asking for, you're setting yourself up for failure. Over time, when you build relationships that are wide and deep, you begin to have access to information, connections, jobs and opportunities that other people have. That only happens when you invest that time and energy to showcase that you mean to be sincere in adding value.
Potolicchio: Is there something that you do when you cold email someone that you don't have a connection with?
Cohn: The key is persistence, because when you showcase that you have persistence and are really sincere, after 25, 50, or 100 emails, they will ask themselves, “Who is this person?” They get to know you if you've sent 50 cold emails and they haven't responded to a single one. You're now a presence in their inbox and that is very useful.
The other thing I would say that could be useful is that if someone is very well known and very followed on Twitter and LinkedIn, but not on Instagram, then actually you can go to their direct messages on Instagram and send something compelling there.
Potolicchio: I need to ask about the elephant in the room. If you haven't read this Matt Shumer memo that went completely viral, I want to read a bit so we get everyone on the same page: “If you were paying close attention, you might have noticed a few people talking about a virus spreading overseas. But most of us weren't paying close attention. The stock market was doing great, your kids were in school, you were going to restaurants and shaking hands and planning trips. If someone told you they were stockpiling toilet paper you would have thought they'd been spending too much time on a weird corner of the internet. Then, over the course of about three weeks, the entire world changed. Your office closed, your kids came home, and life rearranged itself into something you wouldn't have believed if you'd described it to yourself a month earlier.
I think we're in the ‘this seems overblown’ phase of something much, much bigger than Covid.
I've spent six years building an AI startup and investing in the space. I live in this world. And I'm writing this for the people in my life who don't... my family, my friends, the people I care about who keep asking me ‘so what's the deal with AI?’”
What is the permanent training regime that we can adopt so that we can be incredibly adaptable for this changing world, especially given emergence of AI?
Cohn: Number one, you cannot predict the future. You have to think about your current state, and what are the habits that you are taking up to get yourself up to speed on AI.
AI is changing faster than you can adjust. You need to practice, get in the habit of keeping abreast of what's going on. Find one or two podcasts or thinkers, and follow them to help you lead the way. Devoting time to it right now is not optional, it's mandatory.
What's interesting to me is that there is definitely a great divide. I just talked to a client today, a very senior executive in an old school legacy space, and I said: “Has anyone been talking about AI?” He said: “Yeah, a little bit.” For him, AI looks like Claude or Chat GPT, and not other sophisticated tools. That is extremely different from when I'm in New York, or in the tech world, in San Francisco, where that's all they're talking about. It's important to be aware of whatever your bubble is. Get curious about other people's bubbles to find out what's really going on in the world.
Potolicchio: We both share a the same affliction on United Airlines, and in reaching that rarefied air, one of the payoffs is you get to talk to the most expert individual that you can possibly imagine when travel goes awry. We get possibly the most impressive problem-solver at the company that will help us with complicated travel plans and adjustments. I found myself realizing now that I would rather interact with the chatbot that United has, than this person with 40 years of experience, and that somehow this AI is now cultivating not just judgment, but also sophisticated taste. 6 months ago I’d swat away the chatbot and talk to this brilliant, experienced crisis-solver. Now the chatbot is not just outperforming, but doing so 60x as fast.
I'm wondering, what do you think the skill is that is going to make us irreplaceable? I think improvisation and having a deep expertise that's not just surface, that's my speculation, but what do you think is going to be most important as AI develops judgment and taste?
Cohn: I think that AI is going to surpass us in taste and judgment. There is something subtle about what I'm calling a “knack”, and I think there is something about the humanity of seeing something over and over again and being able to manage complicated dynamics.
There's something around emotional intelligence, people skills, plus a knack for understanding a vibe. I’m doubling down on in-person experiences and the notion of networking, because at some point, people are going to be the only ones who can give you the insight that is not available on Google or AI-able.
Having your network around you will give you access to stuff that chatbots can't. It's even more important to have a challenging network of people to get you out of your bubble.
Potolicchio: My all-time memorable advice that you gave me is that you need to say the hard thing while it can still have an impact, or while it can still help somebody. Tim Ferriss famously said this about you - that you're so good at being direct in all the feedback.
How do we have difficult conversations? How can we handle them more effectively?
Cohn: It's very challenging because we, as humans, are wired to be together, to cooperate, and not to lean into controversy. People are raised not to say difficult things and shy away from conflict.
As a professional, whether you're a CEO or a professional, aspiring to or moving up the chain, you have to be able to have difficult conversations and to say what is important. We all have a bunch of feelings that we need to, at times, override to be able to do the hard thing.
You need to think - “What is your goal with this conversation?” The goal has to be an action. You want something to be different after this meeting and you've got to really prepare emotionally: “How am I going to have emotional self-control while this may get heated, or when I, myself, may get nervous?” Literally plan, script out what you want to say. It's very helpful to roleplay it. It's hard to do beforehand, but then it makes it easier to do the situation, and then you debrief for yourself what worked and what didn't work.
Your life and your work are proportionally better directly to the number of difficult conversations you have. Practicing and getting better at them will significantly improve your life.
It can be hard and heated, and you can prepare all you want, but you can't prepare for that person's reaction. You've got to be able to improvise, to say: “This may not be the right time.” or “I did not mean to make you upset!”, or “That's a really good point, I didn't think of that!”
We talked about this in the very beginning, but be a listener, so that you're in the moment. These things don't always go well, but your ability to do them will ultimately give you a better outcome.
Potolicchio: What are some strategies for us to become more confident, particularly if you're a founder and there are a lot of things that you don't know? What can we do to be more effective dealing with that insecurity that we may have?
Cohn: Having an avatar is very helpful. Another tool that I give everybody for imposter syndrome is called “the highlight reel”. A highlight reel is where you really sit down and think about all the times that you overcame challenges and what you did about them. If you write down six or seven, you have a highlight reel.
One of my clients, he was a junior partner at a very well-known venture capital firm, was feeling a lot of imposter syndrome. I asked him to do this highlight reel, and he couldn't think of any, so we did them together. I told him to read those every day and it will make him feel better. He said it was ridiculous, but to humor me, he agreed to do this for two weeks.
When I saw him next, he was absolutely transformed. He said: “I took your advice and I read my highlights every day. Not only did I feel better about the imposter syndrome I was having, but it also pumped me up so much that I took care of a very difficult thing, first thing in the day, and all of a sudden, my days got better.”
Mantas: I'd love to get your view on the topic of being a better leader as AI transforms organizations. What would you say is the top habit that you need to almost stop, and the top habit that one should take up to become a better leader in this world shaped by AI?
Cohn: AI changes so quickly. You must get out of the habit of thinking that AI hallucinates or that it doesn't know the thing. You have to unlearn whatever you thought three months ago about AI.
You have to take on the habit of iterating and being open to what's really going on and not what you thought was going on. You need to be flexible and adaptable, and to keep approaching these tools with a beginner's mind.
It's also about leading your people in that direction. Some practical strategies for leaders are to be constantly testing and using AI tools and then showcasing what they're doing and not doing. We need to set time aside, let's say once a month, a week, or a quarter, where we all get together and do AI hackathons or show-and-tells. We need to show what we screwed up, what doesn't work and what does work, and then revisit it to normalize the fact that it didn't work three months ago, but now it does.
For the moment, it's the leaders who are able to sit with their people and meet them where they are, to help bring them along this learning curve, which we have to acknowledge, is very confronting.
Those are some specific tools that will hopefully help, but the notion of taking up a learner's mindset and beginner's mind is the most important thing.
Potolicchio: While we're reading “From Start-Up to Grown-Up”, what's going to be on our brain palette? What are we matching this book with?
Cohn: There are a few books that I love. One is certainly “The Hard Thing About Hard Things” by Ben Horowitz, a classic start-up book. One of the books that I have gotten so much out of is called “Getting More: How You Can Negotiate to Succeed in Work and Life” by Stuart Diamond. I love that book because of all the super practical negotiation tools and tactics that he uses.
I've been reading a lot of biographies lately, and one biography that is fantastic is the biography of Walt Disney by Neil Gabler. He writes about how the entire journey of entrepreneurship played out through Walt Disney.
For what it's worth, we are celebrating our 250th anniversary here in the US, and I just read a biography of John Adams. It turns out that the founding of the United States was very much not expected, unpredictable, and it took the determination of a few people to make sure it did not fall off the radar.
Potolicchio: Is there a founder or a CEO that you would suggest that would be a model of emulation that you're really impressed with, or even somebody that you wish you were their right hand and their counselor?
Cohn: One that comes to mind, who I think is super impressive, is Brian Chesky, the founder of Airbnb. He's gone through the entire journey of being a startup founder for this very improbable idea he could not raise money for, to becoming a public company CEO. He followed a lot of the traditional management advice, and realized it wasn't working for him, so he gave a speech, which then gave rise to the term “founder mode”, which is about how involved you need to be. I really admire him.
This is controversial, think what you want about Elon Musk, but what I like about him is he's got a point of view, and to say the obvious, you have to really run through walls to accomplish what he did and that's inspiring. You don't have to be a jerk, you don't have to be political, but you can be inspired by his drive, determination and vision.
Potolicchio: What's the question that we should have asked you today that we did not ask you? What's the answer to it?
Cohn: Many successful people have moments of imposter syndrome or severe self-doubt. One thing I would invite you to do is to think about a billboard for yourself.
The front of the billboard is “Believe in yourself!”, and the back of the billboard is “And then act like it!” Your beliefs drive your actions.
Put inside of yourself the beliefs you want to embody, and then spend your time and energy devoting yourself to embodying them. That is the key to success for all of us.