The Art of Coaching with Alisa Cohn

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In this episode, Alisa Cohn and I talk through the Art of Coaching and also one of my favorite ways of looking at Leadership: The Art of Showing up on Purpose. A Coaching mindset is a transformative way to show up for others and yourself, so I’m excited to share these insights from Alisa, since she was named the Top Startup Coach in the World, and she has been coaching startup founders to grow into world-class CEOs for nearly 20 years. If you’re stepping up as a leader, or are thinking about coaching, this interview will help you know what to expect in a coaching relationship and why you might want to bring a coach into your work.

Everyday Coaching

A coaching mindset can be powerfully transformative, so even if you don’t have a startup, even if you’re not a coach... if you’re not even an official leader, or even if you just want to be a good friend, you’ll find lessons in this conversation with Alisa that you can use in your work and life, every day. 

Coaching is a conversational process that works with someone to help them improve, from the inside out. Alisa shares some of her most powerful coaching questions and all about how the most impactful coaching conversation she’s ever had was only 8 minutes long.

Alisa and I got right into the heart of coaching, with her sharing some essential, fundamental conversational approaches to the coaching process like: 

>>firm and gentle inquiry
>>moving from the presenting problem to the context
>>Trusting your curiosity
>>Staying Loose!
>>Trust that they have an answer...that the work is in them. 

As Alisa said:

“All my clients want me to tell them how to do it or what to do. They'll ask me a question and my answer is, "Well, listen, I wouldn't be any kind of a coach if I didn't get a chance to say, 'What do you think?"

>>Alisa will ask “What if you did know?” and push her clients to sit with the question. The act of reflecting is helpful no matter what springs up.

>>The ability to reflect will help with one of the absolute key executive skills: choosing a response versus having a reaction. 

Alisa actually quotes Victor Frankl’s blockbuster thoughts on this capacity:

Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.

A coach isn’t all warm and fuzzy listening though…My coach calls his approach “tapping someone’s bottle”...pointing out the limits to someone’s thinking. When Alisa wants to push back I heard her use the phrase:

"Well, that's how I invite you to think about it." 

Alisa will step in with her perspective but without force. A tap isn’t a shove!

Asking “How is this situation serving you?” is a gentle challenge.

What to Expect in a Coaching Relationship...and why you might need a coach

If you are thinking about coaching, this interview will help you know what to expect in a coaching relationship and why you might want to bring a coach into your work.

Alisa and I talked through one of my favorite ideas: The Art of Showing up on Purpose. One huge challenge of being a leader is that, as she says “You have to grow and learn to communicate differently and behave differently as your company grows.” Alisa and I talk about how to find new ways of tapping into your inner humanity and show up authentically, no matter the situation. Just because the board says “you need to have more conviction” doesn’t mean you have to become a jerk, or invert how you want to be. It’s about finding ways to be passionate and firm that work for you. 

In my own experience, I’ve found that, as a coach and a coachee, a powerful conversation can help me find my own, authentic path forward, through having a conversation with my own inner parts. It’s hard to do that on your own...having a coach as part of the conversation can be transformative.

Alisa also points out that coaching has to be 3-Dimensional, because we are 3-Dimensional. As we grow as leaders, she thinks of three dimensions of growth: we have to grow in our self-management, our skill in managing others, and, of course, in managing the business. A powerful coach is going to make you look at all three.

LINKS, QUOTES, NOTES AND RESOURCES

Alisa's website

Alisa on LinkedIn

Alisa on Twitter

Alisa on Jeff Gothelf’s Forever Employable series

Alisa Rapping!

Check yourself before you Wreck yourself

Minute 4

The way people feel safe is if you can be gentle with them and with the questions. The way people feel guided and supported is if you can be firm. It's both of those things together and sometimes it's a little more gentle and sometimes a little more firm.

Minute 4

I think for all of us, it's important to have dexterity and a set of tools so that we can use a fine chisel when we need one and sometimes a sledgehammer when we need that too. You need to have both and more in your toolkit.

Minute 7

All my clients want me to tell them how to do it or what to do. They'll ask me a question and my answer is, "Well, listen, I wouldn't be any kind of a coach if I didn't get a chance to say, 'What do you think?" Because the work is in you and the answers are in you.

Minute 8

Let me ask you to actually think deeply about what you want out of this onboarding plan and think deeply about how you want this person to integrate into your culture and your highest and best hopes for this new person and what they can bring to the table and what we can all do together. That is the work is in you.

Also, here's your onboarding plan, here's the form. Right? The form is actually very helpful to structure a step by step process. I'm not the kind of coach that will say, "You've got to figure everything out and we've got to wander together in the wilderness until you figure out what the onboarding plan is." I think that the deep inquiry inside of yourself is very powerful for all of us.

Minute 9

It's not about I want you to wander. It's that I want you to have the fruit of the labor that it takes to actually reflect and to think about it and to gather your thoughts. Also, to let yourself be unedited and explore these ideas and the reason you think you don't know is because you got to get it right. What if you don't got to get it right? What if we're just having a safe space where you can brainstorm on what you think? What would come out?

Minute 11

Certainly, a startup founder and, increasingly, as he or she builds a company to scale, they need to do that self-awareness and that self-inquiry to figure out what are my triggers? What are my strengths? What are the things which are important to me? What are my values? Where are we going with all of this?

It's actually super important. Then, in general, I work for the CEO and people would say, "He needs to have more conviction." He would say, "Listen, I am not the kind of sales guy that pounds my fist on the table." No, absolutely not. But how can you in your quiet way express more conviction? What they're looking for is something a little more firm from you or something a little more awake or passionate from you? How can you do that? That is the question.

Minute 13

Again, I'll talk about the CEOs that I tend to work with, you're onstage. You have to grow and learn to communicate differently and behave differently as your company grows.

You have to practice things that don't always feel authentic. In order to expand your ability and your repertoire of skills and behaviors so that ultimately do feel authentic.

Minute 15

Part of what I think about leadership is that the first people you lead every day is yourself and if you're going into the office or a remote office these days to lead a group of people, that's where one way or the other you need help and support in thinking about that because leadership is an unnatural act. It is learned. You need to learn it.

Minute 34

Well, I think one question is how is this situation serving you? Right? Because people complain about whatever and this question is how is this serving you? What are you contributing to this situation? That's a very important and powerful question. I think what are you afraid of?

Minute 35

That's the initial stage of the coaching conversation. Even that, we talked about people who are skeptical or you said volun-told. It's like, "I don't want to be here." Okay, fine. Okay, great. I love your skepticism. Let's put it aside. If you had a secret weapon dedicated entirely to your success for six months, what would you want to get done? That's just a better question or a better conversation than I'm not happy, I don't like this.

Minute 37

Well, maybe the question is what's the entrepreneurial journey like? Why is it so hard? I would just say that founders are like the most incredible, courageous, crazy people who are risking everything against all odds to build something when they could just get a job at IBM if they wanted to. Right? It's like why are you doing this?

Just maybe to hold with reverence what a founder is and then what a hard job that is because you're learning as you go, the entry level position for a founder is boss, right? The entry level position. You don't know what you're doing necessarily. You may not have had any other management leadership experiences before. You've got to learn all of that pieced together and then you've got to do all the other things that a founder has to do like raise money, like figure out the market, figure out the strategy, run an operational business, hire people, fire people, hire your friends, fire your friends, handle conflict, all those things are very difficult to orchestrate together.

MORE ABOUT ALISA

Named the Top Startup Coach in the World at the Thinkers50/Marshall Goldsmith Global Coaches Awards in London, Alisa Cohn has been coaching startup founders to grow into world-class CEOs for nearly 20 years. A onetime startup CFO, strategy consultant, and current angel investor and advisor, she was named a top 30 “Global Guru” and has worked with startups such as Venmo, Etsy, The Wirecutter, Mack Weldon, and Tory Burch. She has also coached CEOs and C-Suite executives at enterprise clients such as  Dell, Hitachi, Sony, IBM, Google, Microsoft, Bloomberg, The New York Times, and Calvin Klein.

Marshall Goldsmith selected Alisa as one of his Marshall Goldsmith 100 Coaches – a gathering of the top coaches in the world – and Inc named Alisa one of the top 100 leadership speakers, and also been named one of the top voices of thought leadership by PeopleHum for 2021.

Alisa is a guest lecturer at Harvard and Cornell Universities, Henley Business School and the Naval War College. She is the executive coach for Runway–the incubator at Cornell NYC Tech that helps post-docs commercialize their technology and build companies. She serves on the board of the Cornell Advisory Council. She has coached public and political figures including the former Supreme Court Chief Justice of Sri Lanka and the first female minister in the transitional government of Afghanistan.

Her articles have appeared in HBR, Forbes, and Inc and she has been featured as an expert on Bloomberg TV, the BBC World News and in the New York Times. A recovering CPA, she is also a Broadway investor in productions which have won two Tony Awards and is prone to burst into song at the slightest provocation.

She is also an amateur rap artist.

FULL TRANSCRIPT

Daniel Stillman:

Alisa Cohn, thank you for making the time to be on the Conversation Factory. I'm really glad to have this conversation with you.

Alisa Cohn:

I'm so excited to be here with you.

Daniel Stillman:

Thanks.

Alisa Cohn:

It's great.

Daniel Stillman:

Thanks for saying. I appreciate it. Okay. I'm really curious, let's start close in. You've been a coach for a long time. I'm curious about how you approach your craft. Because you're crafting conversations with people. I mean, I would presume that's the core of your business is the conversations that you're having with the coachees that you are caring for. Has your craft changed over the almost two decades that you've been doing this? What have you noticed about your growth and transformation as a coach?

Alisa Cohn:

Boy, I love that you just dive right in. I love that.

Daniel Stillman:

Let's not screw around.

Alisa Cohn:

Exactly. No small talk. Let's go. Let's get serious. I want to pick up on what you just said about the conversations. Absolutely. What I tell my clients all of the time is the work of coaching happens in conversation. We're not digging ditches. We're not doing spreadsheets. We are having conversations. That is exactly the work of coaching.

Alisa Cohn:

I think, for me, if I think about how I think about coaching, first of all, is that most people bring me in when there's a problem. The problem may be this thing happened, right? So some people bring me in, "There's an employee I'm dealing with and I can't manage the situation. I'm not sure what to do. I'm having an issue with my co-founder. Whatever it is."

Alisa Cohn:

Sometimes the problem is I'm a new CEO and I know I don't know what I don't know. That's okay, right? That's also still kind of a sensitive problem and that's okay. My first entry point is for me to think about what's going on around here? Right? That's all I really think about. What's going on? To try to understand who this person is who is sitting in front of me. Who this person is and what is their environment and their context like? Because for all of us, we are ourselves in our makeup and we're also our environment. It's a marriage of those two together.

Alisa Cohn:

For me, assessing that and thinking about that and being with the person that I'm coaching as we explore that together in the initial meeting and then going forward but then the last question being how have I grown? I mean, oh my God. I've changed a lot. When I first became a coach, I was nervous and I had a lot of performance anxiety and I wanted to do it right. That made me tight.

Alisa Cohn:

Over the years, I've loosened up a lot and I've let it go the way it's going to go and I would say that the most important thing is that I feel much more empowered personally to follow my curiosity and to go deep with a client and also to help them feel safe in going deep with me.

Daniel Stillman:

There's so many threads to pick up on. I think that's ... This question of what you are curious about is such an interesting question because as a coach, there's so many directions you can take a conversation just through questioning. The phrase you used in the conversation with Jeff on his Forever Employable series was firmly and gently inquire. I was like, "What a great way to put it." I mean, in a way if we're talking about heuristics by which you would judge the design, the way you're shaping the conversation, are you holding those words in mind? Like the firm and the gentle.

Alisa Cohn:

I'm not holding those words in mind. I'm trying to hold that space in my heart. I'm trying to ... The way people feel safe is if you can be gentle with them and with the questions. The way people feel guided and supported is if you can be firm. It's both of those things together and sometimes it's a little more gentle and sometimes a little more firm.

Daniel Stillman:

Yeah.

Alisa Cohn:

You know? I definitely have that in me. I think if anything, I have to tone down my firmness sometimes. That's probably also a way that I have grown over the years.

Daniel Stillman:

In which way? Like using the firmness more or knowing how to hold your firmness lightly?

Alisa Cohn:

Yeah. Right. Yeah. Probably both. Probably both. I'm definitely known for being quite direct, for being kind of blunt. I think that in the wrong moment for me, that can look a little ... I don't want to say dismissive but maybe peremptory or something, abrupt maybe.

Daniel Stillman:

Sure.

Alisa Cohn:

I think it's important to be able ... I think for all of us, it's important to have dexterity and a set of tools so that we can use a fine chisel when we need one and sometimes a sledgehammer when we need that too. You need to have both and more in your toolkit.

Daniel Stillman:

This is so interesting to hear you talk about the way you're crafting and chiseling at this because I think of the conversation as a craft. For you to pick up a sledgehammer on purpose is very different than you picking up a sledgehammer because you're frustrated with your client. That's control.

Alisa Cohn:

Exactly. Right. Or because you're having a bad day.

Daniel Stillman:

You're right. It's about what you're bringing ... It's also so interesting that you use tight and loose. In design school, one of my teachers said that this is the only criticism that anybody will give you of your work, that it's either too tight or that it's too loose. I think it's such an interesting question of how you were holding the space for the conversation.

Alisa Cohn:

Yeah. Definitely. Yeah. I'm a fitness fanatic, which I'm sure you know. On my Facebook, I do kettlebell quarantine on the weekends. I do a little kettlebell movement. My fitness coach is incredible. He's taught me a lot about strength training and strength training turns out to be the polarity between tension and relaxation. When you need to be tense, you need to go all in tense. When you need to be relaxed, you need to go all in relaxation. The play, the play between tension and relaxation is a dynamic. It's a natural system that plays out in all of our lives and, certainly, in conversation.

Daniel Stillman:

I'm sure that that is also an applicable lesson to the startup founders.

Alisa Cohn:

Oh, yeah. For sure.

Daniel Stillman:

That you work with.

Alisa Cohn:

Yeah.

Daniel Stillman:

I feel like one of the things that I want to pick at is this, "I don't know what I don't know" feeling that people feel when they are rising in their work. Of course, they don't know what they don't know because they're doing things that they've never done before.

Daniel Stillman:

You have this video where you talk about the work is in you. I mean, there's this idea of like, "Alisa, please tell me what I don't know about being a founder" versus bringing it out of them and maybe this is the tight and loose. How do you handle this shaping of that conversation space of I want to know how to do X, Y, and Z?

Alisa Cohn:

I know. All my clients want me to tell them how to do it or what to do. They'll ask me a question and my answer is, "Well, listen, I wouldn't be any kind of a coach if I didn't get a chance to say, 'What do you think?"

Daniel Stillman:

Right.

Alisa Cohn:

Because the work is in you and the answers are in you. That's not always true when it comes to, sadly, we have to lay people off, how should I do it? In part, there's a how do you want to do it? How do you want to be known for it? Even in this difficult moment. But there's also just certain mechanics that have to do with a communication plan and have to do with a messaging and the same is true of an onboarding plan, right? Let me ask you to actually think deeply about what you want out of this onboarding plan and think deeply about how you want this person to integrate into your culture and your highest and best hopes for this new person and what they can bring to the table and what we can all do together. That is the work is in you.

Alisa Cohn:

Also, here's your onboarding plan, here's the form. Right? The form is actually very helpful to structure a step by step process. I'm not the kind of coach that will say, "You've got to figure everything out and we've got to wander together in the wilderness until you figure out what the onboarding plan is." I think that the deep inquiry inside of yourself is very powerful for all of us.

Daniel Stillman:

Yeah. Well, I mean, it sounds like at some point you'll be like there is a best practice and here's some of it.

Alisa Cohn:

Yes.

Daniel Stillman:

But you want them to wander a little bit.

Alisa Cohn:

It's not that I want them to wander. I want them to ... The first thing is that people will say, "What should I do?" Right? I'm going to exaggerate. This is not really a dialog but I'm going to exaggerate. "What should I do?" "What do you think you should do?" "I don't know." "What if you did know?" Right?

Alisa Cohn:

Sorry to be so coach-y but the reason that's important is because you might know if you sat and reflected for five minutes. The act of reflecting will actually be very helpful for you no matter what springs up. I promise you something will spring up if we sit together and allow you some time to reflect. That is actually very good.

Alisa Cohn:

It's not about I want you to wander. It's that I want you to have the fruit of the labor that it takes to actually reflect and to think about it and to gather your thoughts. Also, to let yourself be unedited and explore these ideas and the reason you think you don't know is because you got to get it right. What if you don't got to get it right? What if we're just having a safe space where you can brainstorm on what you think? What would come out?

Alisa Cohn:

There is much fruit that comes out of that. Much better than me saying, "Here is your template."

Daniel Stillman:

Yes.

Alisa Cohn:

At the end, sure, I'll give you the template.

Daniel Stillman:

If you're Alisa's client, know that ... Just struggle a little bit and then ... I mean, I'm joking but if we go back to what you said earlier, what I really loved was ... This is work that I think I do, which is name how you want it to feel.

Alisa Cohn:

Yeah.

Daniel Stillman:

Right? I can't tell you what kind of a CEO you want to be. Maybe you just want to rip the band-aid off and tell everyone, "Hey, everyone. We're out of money." Or maybe you want to make it into more of a dance, more of a conversation. That's something you can't decide for them, how they want to play it.

Alisa Cohn:

Yeah. That's also true. I think it's important also for all of us to bring ourselves to the table and I think a CEO needs to ... Certainly, a startup founder and, increasingly, as he or she builds a company to scale, they need to do that self-awareness and that self-inquiry to figure out what are my triggers? What are my strengths? What are the things which are important to me? What are my values? Where are we going with all of this?

Alisa Cohn:

It's actually super important. Then, in general, I work for the CEO and people would say, "He needs to have more conviction." He would say, "Listen, I am not the kind of sales guy that pounds my fist on the table." No, absolutely not. But how can you in your quiet way express more conviction? What they're looking for is something a little more firm from you or something a little more awake or passionate from you? How can you do that? That is the question.

Daniel Stillman:

This is interesting because I've been noodling on this, this idea of leadership as the art of showing up on purpose. I think sometimes there's this idea that we have to assume a virtue that we have ... I was coaching somebody recently who said, "I'm a work horse and I want to be a show horse so that I can get promoted." She resented it. She was really holding that she was like ... This resentment against the structure she was in and the organization that she had to turn herself inside out in order to rise up. That was the narrative she was telling herself.

Daniel Stillman:

What we discover is that there are parts of her life where she knew how to be in charge. It was in sports actually. She coaches a team that she's part of. She's like, "I know how to call the shots that I see and see the system and own what I know." For me, I was like you don't have to become a show horse. Maybe you just need to become the coach.

Daniel Stillman:

She lit up finding it inside of herself. I guess I'm just wondering ... I think there's this idea of like I have to become something I'm not versus the work is in me, I have to find it in myself and how do I ... How do you help people tap into what's native to them?

Alisa Cohn:

Right. What's native is that [inaudible 00:13:18]. It's the idea that you have some internal drivers and you have a personality. At the same time, the truth is ... Again, I'll talk about the CEOs that I tend to work with, you're onstage. You have to grow and learn to communicate differently and behave differently as your company grows.

Alisa Cohn:

You have to practice things that don't always feel authentic. In order to expand your ability and your repertoire of skills and behaviors so that ultimately do feel authentic. I told you I'm writing this book From Startup to Grownup and it's the idea of how do you activate both your internal nature in a way that does feel authentic but learn the counterintuitive skills sometimes that you're required to to become a successful leader, a successful CEO.

Daniel Stillman:

I think that's a beautiful idea because when we think about the journey of a startup, there's I have an idea, I'm making some experiments, maybe I've launched something, I've product market fit, and now it's like I have to build a business.

Alisa Cohn:

Yeah. Exactly.

Daniel Stillman:

I'm just curious because it seems like the ideal client for you is somebody who is not way in the beginning of their journey and saying, "I'm thinking about starting something up. I'm still in the corporate and I haven't made the leap." They are starting up. There's acceleration. We need to catch up with it.

Alisa Cohn:

You know, it's funny because people sort of say, "Who is the ideal client?" And whatnot. I didn't really think about that but it is true. I don't tend to work with folks in that stage. That is true.

Daniel Stillman:

Yeah.

Alisa Cohn:

I tend to work with folks who have already ... First of all, I work also with people in large companies. That's a whole different dynamic in helping them, CEOs of large public companies or C suite executives of large public companies, but help them build their leadership skills inside of a certain context.

Alisa Cohn:

I also work with ... I do still work with a few individuals who are trying to think about their careers probably differently in a more impactful way. Yeah. It's like I work with all kinds of folks but when I think about founders and I just focus on founders, there's no question that I work with people who have something to work with.

Daniel Stillman:

Yeah.

Alisa Cohn:

Part of what I think about leadership is that the first people you lead every day is yourself and if you're going into the office or a remote office these days to lead a group of people, that's where one way or the other you need help and support in thinking about that because leadership is an unnatural act. It is learned. You need to learn it.

Daniel Stillman:

Can we unpack that? That's so interesting, this idea that leadership is an unnatural act and people have to learn it.

Alisa Cohn:

Yes.

Daniel Stillman:

I mean, I'm surprised because a part of me feels like, "Oh, leadership is an innate skill" or it's a human skill. That it's unnatural, tell me more about that.

Alisa Cohn:

Well, I think that we sort of think it's supposed to come naturally and that gets in the way of learning it but here's a very good example of what you have to do as a leader. If someone, let's say, a CEO is looking at their executive team and there's one person, one of their executives is not doing it right, so they're not doing what I want them to do.

Alisa Cohn:

That's annoying. If how you are being naturally is, "I'm annoyed at you." That is not going to motivate that person. Right? Sometimes counterintuitively, you have to compliment this person and praise them for what they've already done for their attempts. You have to take sometimes the blame as in, "I probably wasn't very clear. Maybe I've given you misdirection. Maybe we all together haven't thought through the whole process" or whatever.

Alisa Cohn:

Even though, how you're feeling and what is actually possibly true is, "You're doing it wrong." Now why? Because people get defensive, because people get demotivated. In the fast-paced world, pressure cooker of startups, you can control yourself and if you get irritated, impatient, frustrated with somebody in that fast-paced world, they may very well shut down and that will be counterproductive.

Alisa Cohn:

That's one example. I can give you many, many examples of why leadership is an unnatural act. You must check yourself. You must understand your own triggers, your own things that set you off, your own makeup and then you pause and reflect and think before acting. Then you have a fighting chance of being a good leader.

Daniel Stillman:

Well, it's interesting because I want to hold this intention with ... By the way, the reason I was giggling is because I know you like to rap and when the phrase check yourself, in my mind, must be completed with, before you wreck yourself. It's just a sort of ...

Alisa Cohn:

That's very good.

Daniel Stillman:

That's just a total aside. We can go back around to that later. I want to hold this idea that it's an unnatural act because this is really interesting with the work is in you because it sounds like what you're saying is reactivity and impulsivity are at odds with scaling leadership.

Alisa Cohn:

So true. Yes. You want to be in a position where you can choose a response versus have a reaction.

Daniel Stillman:

Yeah. Yeah. In my language, that's design. Right? It's intentionality and it's choice.

Alisa Cohn:

Intentionality. Yes.

Daniel Stillman:

How do people build the capacity to be able to make that choice? How do you coach people to be able to build that capacity?

Alisa Cohn:

It's a great question. First of all, it's taking on a reflective practice, whether it's journaling, meditation, even talking to a friend. That kind of thing. Part of the journaling, in addition to just [inaudible 00:19:29] and reflecting, it's also assessment of how am I feeling right now? What has set me off today? What has energized me today? Getting in the habit of that.

Alisa Cohn:

Also recognizing that you have a choice, right? Viktor Frankl said in the period between action and reaction there's a space and in that space there is your freedom. That's where your freedom is. It's looking for that freedom, relating to it like freedom, and then the very basic and simple, count to 10.

Daniel Stillman:

Yeah.

Alisa Cohn:

Someone once told me he could only get to five. I'll take it.

Daniel Stillman:

Yeah. It's so true. I'm so glad that Viktor Frankl is in the room. I mean, it's such a small space sometimes between action and reaction. I think the difference is between, "You made me" blank versus, "I am feeling blank."

Alisa Cohn:

Definitely. That's part of it. Yeah. That's not the only thing, though. I think it's also we together are creating blank. Right? Or also maybe it's an even deeper experience of what I'm really feeling. I'm feeling frustrated. Not really. I'm feeling anxious.

Daniel Stillman:

Yeah. Becoming aware of your emotional state, what's your reflective practice?

Alisa Cohn:

Well, my fitness practice is definitely reflective practice. It may not sound like it is but it definitely is. I also do journaling. I meditate not regularly but times. I take a walk. Without any headphones or whatever. Those kinds of things. Also, I'll do a pause in the middle of the day and check in and see how I'm feeling. Those kinds of things.

Daniel Stillman:

Yeah. Spaces.

Alisa Cohn:

Yes. Spaces.

Daniel Stillman:

It's so important. My wife has been [crosstalk 00:21:15].

Alisa Cohn:

What's yours?

Daniel Stillman:

Well, my wife has been going for long walks in the mornings, which actually gives me space. I do a seven minute workout. I stopped playing music with it. Then it becomes more of a reflective ... Like just to be present with the sensation than like I'm going to listen to some '80s hip hop while I get through this. It's a big difference. I think, for me, that's what makes it more of a mindfulness experience.

Alisa Cohn:

Definitely.

Daniel Stillman:

Thanks for asking. I agree. I think it's like table stakes. If somebody is not doing that, it's very hard to help them with the next step if they lack all self-awareness. It's really interesting. There was a phrase I heard you use in the conversation with Jeff as you did a little micro coaching for him where you offered him a different way of thinking about something. You pushed back on his belief system and then you said, "Well, that's how I invite you to think about it." It was really interesting to watch you step in with your perspective but without force. With gentleness.

Daniel Stillman:

I don't know. I just wanted to highlight that and unpack this way in which you help people see themselves as a coach mirror person thing.

Alisa Cohn:

Yeah. I was just in this retreat center and somebody there said to me ... He also works with founders and startups. He said, "I do a test." Already I'm like, "All right. I don't know ... Where are we going with this?" "I do a test. When I talk to them, I ask them this question and then I give them some material and if they get back to me, I know they're coachable. If they get back to me with a right answer or with an answer, I know they're coachable. If they don't, I know they're not coachable. That's my test." I'm like, "Okay, well, I'm a coach. I don't see it that way."

Alisa Cohn:

You know, it's not one and done. It's not, "Oh, here's the thing. Fill it out. If you don't fill it out, you're not coachable. If you do fill it out, you are coachable." It does not work that way.

Alisa Cohn:

What I told him and what I know is true is that very often people need an invitation, an invitation to change, an invitation to think about something differently. Sometimes it's more than one invitation that they need. He was talking about something else, which is here's my lens about how I decide if I want to work with someone or not. Not a problem. That's fine.

Alisa Cohn:

The notion of coachability, to me, is very ... It's very interesting that people think they can tell by looking at someone's outsides and what I try to do is get on people's insides and then we see how coachable people are.

Daniel Stillman:

I presume that coachability is an important heuristic for someone you want to work with.

Alisa Cohn:

Yeah. Well, of course. I don't know if it shows up right away. People will say to me, "That guy will never change", "She's not coachable" or whatever. I'm like, please don't speak to me. Everyone's got their opinions about whatever.

Alisa Cohn:

I approach somebody as in they have not been powerfully invited to change. They have not seen a what's in it for me? About any kind of change. They have been judged. They have been assessed. They have been demotivated. They have been made put down? "Well, no wonder you're not changing. I wouldn't change either."

Alisa Cohn:

For me, it takes a little while to really figure out what's going on and, again, will this person change?

Daniel Stillman:

Yeah. Also, it's whether you're willing to engage in that conversation with them, which means you have to be excited. Marshall Goldsmith talks about how important choosing your clients is.

Alisa Cohn:

Yes.

Daniel Stillman:

In the process of do you believe that they've got what it takes to do it with you?

Alisa Cohn:

Definitely. That is definitely important and, also, coachability is important and for him, it's particular. There is this sort of index. Like he doesn't get paid if they don't change. Marshall also knows that people don't always show up immediately the way they really are. It takes a while for defenses to go down.

Daniel Stillman:

Yeah. I think I've noticed with people in my coaching circle who are like ... We, as coaches, can make stories of, "They didn't respond to my email. They must be not into this enough" versus like ...

Alisa Cohn:

Everybody makes up stories. Exactly. Yes.

Daniel Stillman:

I want to really try to peel back another couple of layers on this Startup to Grownup idea, because not for you to ... The book is coming out in a while but when you think about this arc from building a product to building a culture, this transition from that arc in their life cycle ... Part of me is sort of like, "Okay, well, what do they need to learn at each phase?" Is there a beautiful framework that Alisa has? Or just when should they start thinking about having a partner in the process?

Alisa Cohn:

You mean like a partner as in a coach?

Daniel Stillman:

You. Yeah. When should they start thinking about having a coach?

Alisa Cohn:

I do want to say, if you think about a framework, the way I think about the framework is you have to grow in three dimensions. You've got to grow managing yourself, managing others, and managing the business. The framework is to think about where am I inside of managing myself, managing them, the people around me, and managing the business?

Daniel Stillman:

Yeah.

Alisa Cohn:

In terms of how do people know it's time to bring a partner ... As I said, you have to have something to coach, something to manage. Also, it depends how interested you are in this sort of journey, in this process. I think that some people get a little bit tripped up at different parts in the way. They may, again, recognize they know what they don't know or they don't know what they don't know.

Alisa Cohn:

They may get into trouble with a situation going on that feels dysfunctional and they don't know what to do. They may have people tell them, "You've got some issues." One of my clients had a board member who said, "You need a coach." You know? He got angry as in like don't tell me what I need.

Alisa Cohn:

They had some harsh words together and my client, ultimately, came to me saying, "I don't think I need a coach because he thinks I need a coach. I think I need a coach because I want to learn." Different people come from different directions. At times, it's also more about how do I scale up because now that my company is getting bigger, I need to change my ways.

Daniel Stillman:

Yeah. That's pretty mature of him.

Alisa Cohn:

Yeah. Very mature.

Daniel Stillman:

Because the idea of being volun-told. I mean, as somebody who does training and developing groups of people and cultures, the early stage is when people are there because they're the first responders to this new way of working, they're the most fun to work with, and then there's the people who are volun-told.

Alisa Cohn:

Yeah.

Daniel Stillman:

To like, "Okay, this is how you need to work." I imagine working with somebody who is being forced or pushed to be coached ... I'm so glad to be in this [inaudible 00:28:42] like, "I can handle that."

Alisa Cohn:

Yeah. I tell everybody [inaudible 00:28:47]. I welcome skeptics. I welcome skeptics. I mean, come on and talk to me. It's not about like, "You need to be coached." It's about how can I help you?

Daniel Stillman:

Yeah.

Alisa Cohn:

How can I genuinely, legit, help you get more of what you want? Who wants to say no to that? Coaching is not framed that way. [inaudible 00:29:06] fix you. Well, let's not talk about that. Let's talk about you. People like that.

Alisa Cohn:

Also, it's funny because I was ... I've been put into shotgun marriages many times actually. This one person after ... It was a large company I was working inside of and he came to me on our first meeting and he said, "I've been asking for a coach for two years and now suddenly there's a problem and I get a coach. I'm mad but I don't care because I'm going to get the most out of this experience." I was like, "Okay, me too."

Daniel Stillman:

Strap in.

Alisa Cohn:

Yeah. Let's go. Let's go, baby. That is what it's about. Right? I have to align with my clients so that we can figure out where are we going? It's like where are you? Where are you going? How are you going to get there? That's all I care about.

Daniel Stillman:

Yes.

Alisa Cohn:

If somebody doesn't want to ... Who doesn't want to engage with that? Right? Then part of that, then there's trust and then part of that is a 360 feedback process very often where people around say, "He's not influencing. He throws bombshells into meetings. I don't know what he's thinking. He doesn't share. I can feel him in my head but not feel him in my heart." Okay. Now there's something to work on.

Alisa Cohn:

We've already established that we have an alliance here and I'm going to help you get better one way or the other.

Daniel Stillman:

What's your favorite way to contain the coaching conversation? Do you have a periodicity, a rhythm that you prefer to work with people? Some people are two hours, some an hour, 30 minutes. Marshall talks about 15 minute sessions with people.

Alisa Cohn:

Yeah. The most powerful coaching conversation I ever had was eight minutes on a Friday night, cellphone to cellphone, we're both driving. That was the most impactful coaching conversation ever. Who knows?

Alisa Cohn:

Now that all said, you have to have some structure. Okay? I tend to give my clients more or less, every other week, more or less, for 60 minutes. Also, I'm available as needed. I think that as needed time can be the most important time.

Daniel Stillman:

Yeah. That eight minutes. Can we unpack that? That's leaving a gun in act one. What made that eight minute conversation so impactful?

Alisa Cohn:

There was a president of a division I was working with and she had some important changes to make. This was like a Friday night. She had to go in on Monday and make these important changes. She was thinking about it very tactically. Like, "I'm going to do this. I'm going to do that." I just asked her a few questions like what are you trying to achieve here? What is it going to look like and feel like when you've made these changes?

Alisa Cohn:

She would hesitate so then it's like, "Why are you hesitating? What are you not saying?" Then what we did was we uprooted a number of things and her realization was, number one, I'm the one that's not communicating enough. The reorg has to happen, the changes have to happen, but I see that they will not take root unless I change my communication style definitely.

Alisa Cohn:

Secondly, she was thinking about the org structure and various people in a way, which was very superficial, because she wasn't going deep enough into what was actually going on and, as a result of that conversation, she made changes in the changes she was going to make and that was a better, more resilient, more effective organization. She was able to immediately communicate differently on Monday, which set the tone for the whole process.

Daniel Stillman:

Boom.

Alisa Cohn:

Boom.

Daniel Stillman:

What I love about this story ... I assume you were some weeks or months into your coaching relationship, right?

Alisa Cohn:

Yeah. It wasn't the first time we met.

Daniel Stillman:

Right.

Alisa Cohn:

Hi. Hi.

Daniel Stillman:

Eight minutes. Kapow.

Alisa Cohn:

Yeah. Yeah.

Daniel Stillman:

What's amazing, I've been sitting with this question of like what's the value of a coaching conversation? People ask this all the time, "How much do you charge?" Well, I don't know. How much change are you trying to make? If you measure it by the value you created in that eight minute conversation, the value is priceless.

Alisa Cohn:

Yeah. I tell people I want to spend the least time with them as possible. Your time is valuable. Right? I want to give you maximum change with minimum time. Doesn't that sound better? It's only the HR folks who are asking you how many hours?

Daniel Stillman:

For those of you listening at home, she rolled her eyes when she said that.

Alisa Cohn:

I love my HR colleagues, who are excellent.

Daniel Stillman:

Here's the interesting thing, this is something that my coach has coached me on in my coaching, which is as meta as it can get, is coaching people as much as they need. I think many people, myself included, when I started was like, "Okay, here's your beginner package and this many hours" and it's transactional versus what you're talking about, which is having a relationship with somebody and being there when they need them, which is where the juice comes from.

Alisa Cohn:

Totally. That's where the value comes from. That's where I think the joy of self-discovery comes from. Definitely.

Daniel Stillman:

I'm wondering ... I'm unpacking so many beautiful ways you firmly and gently inquire in the work you do. I'm wondering if you have some other of your favorite conversation hinge points, ways that you unpack, questions that you ask in those moments to get somebody to flip the card over and look at it differently.

Alisa Cohn:

Well, I think one question is how is this situation serving you? Right? Because people complain about whatever and this question is how is this serving you? What are you contributing to this situation? That's a very important and powerful question. I think what are you afraid of?

Daniel Stillman:

Yeah.

Alisa Cohn:

You know, that's ... Again, with a trusting relationship, that's where a lot of the fruit is.

Daniel Stillman:

Yeah. Taking ownership.

Alisa Cohn:

Yeah. Also, that sort of self-inquiry, the depths of the self-inquiry.

Daniel Stillman:

It's really interesting because there are these two points in the journey where the beginning is like where are we now? These questions are like where do you want to get to? What can draw you forward?

Daniel Stillman:

There was one question I heard you use with Jeff, which was if you had a secret weapon that was totally dedicated to your success for three to six months, what would you want to work on? I just wanted to say I love that question. It was a beautiful question.

Alisa Cohn:

Thank you.

Daniel Stillman:

I don't know if you still use that one but I like it.

Alisa Cohn:

Of course. Well, that's entering ... That's the initial stage of the coaching conversation. Even that, we talked about people who are like skeptical or you said volun-told. It's like, "I don't want to be here." Okay, fine. Okay, great. I love your skepticism. Let's put it aside. If you had a secret weapon dedicated entirely to your success for six months, what would you want to get done? That's just a better question or a better conversation than I'm not happy, I don't like this. Okay, whatever. Those are boring. Let's talk about what's really interesting, which is what you actually want to get done in your life.

Daniel Stillman:

Yeah, because here you are in the conversation. Somebody potentially has paid for your time already and here we are, what do you want to do?

Alisa Cohn:

Yeah.

Daniel Stillman:

That's a great question. I mean, we're getting close to the end of our time. What haven't we talked about? What haven't I asked you about that I should ask you about? What's important for us to know about the way you craft coaching conversations and how we can help startups, founders, become leaders? Or anything else we haven't talked about.

Alisa Cohn:

Well, I think maybe one thing that I would just say, it's not so much a question ... Well, maybe the question is what's the entrepreneurial journey like? Why is it so hard? I would just say that founders are like the most incredible, courageous, crazy people who are risking everything against all odds to build something when they could just get a job at IBM if they wanted to. Right? It's like why are you doing this?

Alisa Cohn:

Just maybe to hold with reverence what a founder is and then what a hard job that is because you're learning as you go, the entry level position for a founder is boss, right? The entry level position. You don't know what you're doing necessarily. You may not have had any other management leadership experiences before. You've got to learn all of that pieced together and then you've got to do all the other things that a founder has to do like raise money, like figure out the market, figure out the strategy, run an operational business, hire people, fire people, hire your friends, fire your friends, handle conflict, all those things are very difficult to orchestrate together.

Daniel Stillman:

Yeah.

Alisa Cohn:

Just to say that, I'm in awe constantly of the founders that I work with and their ability to deal with that struggle.

Daniel Stillman:

The Yiddish word that's coming to mind that my dad loves is [Foreign language 00:38:30], which is like a deep empathy. I can feel that you really get and relate to their journey and their struggle.

Alisa Cohn:

Yeah. Yeah. That is true. I feel really alive and aligned.

Daniel Stillman:

There's some parting things that we should make sure we ... Places where people can learn about all things Alisa and the things that you're launching. There's some programs that you have coming up when this conversation will come out, plus just general evergreen things that you're doing. Where can people go to learn more about you in the internet places?

Alisa Cohn:

Right. On the internets. People can always find me on my website, Alisa Cohn dot com, and all the socials. Right? At Alisa Cohn or LinkedIn, Alisa Cohn, A-L-I-S-A C-O-H-N. Everywhere you find your social.

Daniel Stillman:

Yes. We can read you on Forbes and Inc and some other places.

Alisa Cohn:

Exactly. HBR and Inc and Forbes. Find me on Clubhouse. Follow me on Clubhouse at Alisa Cohn. Yeah.

Daniel Stillman:

Okay.

Alisa Cohn:

All of that. The thing I want to say is that when you come to my website or look for me on LinkedIn, you will see I am doing a program for coaches to teach coaches how to build their businesses, how to get more clients. It's called the Business Development Academy for Coaches. It's got two parts to it. April, we're going to do a 30 day quick start challenge and help you gain traction after this year coming out of the pandemic. Then a 10 month program, which is called Build Your Business program, which is how do you build a sustainable business. That is with WBECS, W-B-E-C-S. Go there or come to my website.

Alisa Cohn:

Then the thing I'm also particularly excited about, October 2021, this year, coming to a bookstore near you, From Startup to Grownup. It's about growing your leadership while growing your business.

Daniel Stillman:

That's a good subtitle. When there's a galley ready, I would love to read it and have you back on to talk about [crosstalk 00:40:31].

Alisa Cohn:

Thank you. I would love that.

Daniel Stillman:

I think it's important ... I don't know a boss who has talked about the zero to one idea. This is what startup founders are doing. They're trying to make something truly new, which is truly hard.

Alisa Cohn:

Totally. Truly hard. It is.

Daniel Stillman:

And also truly important.

Alisa Cohn:

Yeah. Super important.

Daniel Stillman:

I honor the work that you do with them. I hope you can ... I'll find links to all that. There will be links to all that in the show notes.

Alisa Cohn:

I will help you fill out those show notes.

Daniel Stillman:

Thank you. We'll create that. We'll create an alliance and those show notes will get made.

Alisa Cohn:

I love it.

Daniel Stillman:

Well, then I will thank you for being part of this conversation. I'm really grateful for the time and for your wisdom.

Alisa Cohn:

Thank you. I love chatting with you and thank you for elegantly steering this conversation.

Daniel Stillman:

That's very kind of you to say. Well, then I'll call scene.