The Art of Coaching with Alisa Cohn

It's not about like, 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 and 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 safe space where you can brainstorm and what you think? What would come out? There is much fruit that comes out of that. Much better than me saying, here's your template.

Hello and welcome to the Conversation Factory. I'm your host, Daniel Stillman. Our lives are literally built one conversation at a time, in teams, in our work and in our lives. We all work to make conversations better. But what are conversations made of? How do they really work? Each episode, I'll talk to an amazing leader about the conversations in their lives and how they make them sing. In this episode, Alyssa Cohen and I talk through the art of coaching and also one of my favorite ways of looking at leadership as the art of showing up on purpose. A coaching mindset is a transformative way to show up for others yourself. So I'm excited to share these insights from Alyssa 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 thinking about coaching or bringing on a coach, 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. A coaching mindset can be powerfully transformative. So even if you don't have a startup, even if you're not a coach looking to improve your practice, or if you're even not an official leader, if you just want to be a better friend, you will find lessons in this conversation with Alyssa that you can use in your life every day. Because coaching is a conversational process that works with someone to help them improve from the inside out. Alyssa shares some of her most powerful coaching questions and I got her to even unpack her most powerful, impactful coaching conversation that she's ever had, which was only eight minutes long. Alyssa and I go into the heart of coaching with her, sharing some of her most essential, fundamental approaches to the coaching process, like firm and gentle inquiry, or moving from the presenting problem to the context, trusting your curiosity, staying loose, and to trust that they have an answer and that the work is in Them. As Alyssa said, all of 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? I loved your question, what if you did know? And getting her clients to sit with the question to sit with. Reflecting. The act of reflecting is helpful. No matter what springs up, the ability to reflect will help with one of the absolute most key executive skills, choosing a response versus having a reaction. Alyssa actually quotes Viktor Frankl's amazing blockbuster quotes 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. I mean, you'll also find as we will unpack, a coach isn't all warm and fuzzy listening. My coach actually calls his approach to this tapping someone's bottle, pointing out the limits to someone's thinking. When Alyssa wants to push back. I heard her use this phrase in another interview. Well, that's how I invite you to think about it. Alyssa 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. And if you are thinking about coaching, this interview will help you know and feel what to expect in a coaching relationship. And also to think about why you might want to bring a coach into your work. Alyssa and I talked together a bit about one of my favorite ideas, leadership as the art of showing up on purpose. And she shared the challenge. As a leader grows and their startup grows, we have to learn to communicate differently and behave differently. We talk about how to find new ways of tapping into your inner humanity and showing up authentically no matter the situation. Just because the board says you need to have more conviction, it 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 found that as a coach and as a coachee, a powerful conversation can help me find my own authentic path forward through having a conversation with my own inner parts. It is hard to do that on your own, not impossible. Having a coach as part of that conversation can be transformative. Alyssa also points that coaching has to be three dimensional because we are three 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. I know you'll enjoy this conversation as much as I did in having it. Do make sure to head over to theconversationfactory.com listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over to theconversationfactory.com listen to become a monthly supporter of the show. For as little as $8 a month, you'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. I certainly welcome the support and welcome spending more time with you. Enjoy the show and I'll talk to you next time. Alyssa Cohen, thank you for making the time to be on the Conversation Factory. I'm really glad to have this conversation with you.

I'm so excited to be here with you.

Thanks. Thanks for saying. I appreciate it.

So.

Okay, I'm really curious. Let's start close in. You've been a coach for a long time, and I'm curious about how you approach your craft because you're crafting conversations with people. That's. I mean, that's the. I would presume it's the core of your business is the conversations that you're having with the coaches that you are caring for. And I'm just like, have your. Has your craft changed over the almost two decades that you've been doing this? Like, what have you noticed about your growth and transformation as a coach?

Well, I love it. You just dive right in. I love that.

Let's not screw around.

Yeah, exactly. No small talk. Let's go. Let's get serious. Well, I just want to. I want to pick up on what you just said about the conversations. Absolutely. What I tell my clients all the time is the work of coaching happens in conversation. We're not digging ditches. We're not doing spreadsheets. We are having conversation. That is exactly the work of coaching. I think for me, if I think about how I have, you know, sort of how I think about coaching, first of all, is that most people bring me in one way or the other where there's a problem.

Yeah.

And the problem may be this thing happened. Right. So some people bring me in like there's a. An employee I'm dealing with, and I can't, you know, I can't manage the situation. I'm not sure what to do. I'm having issues. My co founder, whatever it is. Sometimes the problem is I'm a new CEO and I know I don't. I know I don't know what I don't know. So that's okay, right? But that's also still kind of the sense of a problem, and that's okay. My first, you know, sort of entry point is for me to think about what's going on around here. That's all I'm thinking, like, what's going on? To try to understand who this person is, who's 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 and our makeup, and we're also our environment. So it's a marriage of those two together. So for me, kind of assessing that and thinking about that and being with the person that I'm coaching is 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, you know, and when I first became a coach, I was nervous and I had a lot of performance anxiety, and I wanted to do it right, and that made me tight. And 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.

There's so many threads to pick up on, and 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. And I was like, what a great way to put it. So that's. 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?

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. But the way people feel guided and supported is if you could be firm. So it's both of those things together, and sometimes it's a little more gentle and sometimes a little more firm, and I definitely have that in me. I think for any, if anything, I have to tone down my firmness sometimes. But that's probably also a way that I have grown over the years.

In which way, like using the firmness more or knowing how to hold your firmness lightly.

Yeah, hold the firmness. Yeah. Probably both. Probably both. I'm definitely known for being quite direct, for being pretty blunt, and 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.

Sure.

And so 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. But you need to have both and more in your toolkit.

So this is so interesting, hear you talking about the way you're crafting and chiseling at this, because I think of the conversation as a craft. And 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.

Exactly right. Because you're having a bad day.

Because you're right. And it's about what you're bringing. It's also so interesting to 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. And I think it's such an interesting question of how you are holding the space for the conversation.

Yeah, definitely. Yeah. And I think also just, you know, I'm a fitness fanatic, which I'm sure, you know, on my Facebook, I do kettlebell quarantine on the weekends, and I, you know, I do a little kettlebell movement, but I have. So my fitness coach, who's incredible, he's taught me a lot about strength training. And strength training turns out to be the sort of the polarity between tension and relaxation. When you need to be tense, you need to go all intense. When you need to be relaxed, you need to go all in. Relaxation. And 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.

I'm sure that that is also an applicable lesson to the startup founders, for sure, that you work with.

Yeah.

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 so of course they don't know what they don't know because they're doing things that they've never done before. You have this video where you talk about the work is in you. And there's this idea of, Alyssa, 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 conversational space of like, I want to know how to do X, Y.

And Z. I know all my clients want me to tell them how to do it or what to do, and 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. And 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? And how do you want to be known for it, even in this difficult moment? But there's also just a set of 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. Like, 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. But also, here's your onboarding plan. Right. Here's the form.

Right.

And the form is actually very helpful to structure a step by step process. So I'm not the kind of coach that will say, you got to figure everything out. We got to wander together in the wilderness until you figure out what the onboarding plan is. But I think that the deep inquiry inside of yourself is very powerful for all of us.

Yeah, well, I mean, so it sounds like at some point you'll be like, there is a best practice and here's some of it, but you want them to wander a little bit.

It's not that I want them to wander. I want them to. First thing is that people will say, what should I do?

Right.

I'm going to exaggerate. Just not really a dialogue, 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. So Sorry to be so coachy, but the reason that's important is because you might know if you sat and reflected for five minutes. And the act of reflecting will actually be very helpful for you, no matter what springs up. But I promise you, something will spring up if we sit together and allow you some time to reflect. That is actually very good. It's not about, like, 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 and 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 safe space where you can brainstorm on what you think? What would come out? There is much fruit that comes out of that. Much better than me saying, here's your template. Yes, but at the end, sure, I'll give you the template.

So if you're Alyssa's client, know that. Just struggle a little bit. And then, I mean, I'm joking, but it's because if we go back to what you said earlier, what I really loved was, and this is work that I think I do, which is name how you want it to feel. Yeah, right. Like, no, I can't tell you what kind of a CEO you want to be. Like, maybe you just want to rip the band aid off and tell everyone, hey, everyone, we're out of money. Right. Or maybe you want to make it into a more of a dance or more of a conversation. That's something you can't decide for them how they want to play it.

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, you know, 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? Where am I? What are the things which are important to me. Right. What are my values? Where are we going with all this? That's actually super important. And then in general, like, I worked with a CEO and people would say, he needs to have more conviction. And 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? Because 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.

So this is interesting because I've been noodling on this, this idea of leadership as the art of showing up on purpose. And I think sometimes there's this idea that we have to assume a virtue that we have. Now. I was coaching somebody recently who said, I'm a workhorse and I want to be a show horse so that I can get promoted. And she was resented. She was really holding that. She was like this resentment against the structure she was in, in her organization, that she had to turn herself inside out in order to rise up. That was the narrative she was telling herself. And we discovered that there were 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 and she's like, I know how to call the shots, that I see and see the system and own what I know. And so for me, I was like, you don't have to become a show horse. Maybe you just need to become the coach. And she lit up, finding it inside of herself. And I guess I'm just wondering where, because I think this is 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 amplify? I mean, how do you help people tap into what's native?

Well, right. I mean, what's native is exactly right. I mean, it's the idea that you have some internal drivers and you have a personality at the same time. The truth is, and again, I'll talk about the CEOs that I tend to work with. You're on stage. You have to grow and learn to communicate differently and behave differently as your company grows. And 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 they ultimately do feel authentic. So I told you, I'm writing this book from Startup to Grownup, and. 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.

I think it's a beautiful idea because, you know, when we think about the journey of a startup, there's I, I have an idea. I'm making some experiments. Maybe I've launched something. I have product market fit. And now it's like I have to build a Business. And it seems like. And I'm just curious because it seems like the ideal client for you is somebody who's 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 and they need to catch up with it.

It's funny because people sort of say, who's 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. I tend to work with folks who have already. So first of all, I work also with people in large companies. So that's a whole different dynamic. And helping them, you know, CEOs of large public companies or a C suite executives of large public companies could help them build their leadership skills inside of a certain context. Yeah, I also work with. I do still work with a few individuals who are trying to, you know, think about their careers probably differently and in a more impactful way. So, you know, 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. And part of what I think about leadership is that the first person you lead every day is yourself. And if you're going into the office or remote office these days to lead a group of people, that's where one way or the other, you need help and support and thinking about that. Because leadership is an unnatural act. It is learned, and so you need to learn it.

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

Yes.

Because I'm surprised because 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.

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. So 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, like, they're doing what I want them to do. So that's annoying. And so if how you are being naturally is, I'm annoyed at you, that is not going to motivate that person. Right. And so 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. 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 and, and 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. That's one example. I give you many, many examples of why leadership is an unnatural act. You must check yourself, you must understand your own trust triggers, your own sort of things that set you off, your own makeup. And then you pause and reflect and think before acting. And then you have a fighting chance of being a good leader.

Well, so it's interesting because I want to hold this intention with. And 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, I must be completed with before you wreck yourself. It's just a surrounding.

That's very good.

That's just a total aside and 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.

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

Yeah, yeah. In my language, that's designed. Right. It's intentionality and it's choice.

Intentionality. Yes.

How do people build the capacity to be able to make that choice? I mean, how do you coach people to be able to build that capacity?

It's a great question. So first of all, it's taking on a reflective practice, whether it's journaling, meditation, even talking to a friend, that kind of thing. And part of the journaling, in addition to just stepping back and reflecting, it's also assessment of how am I feeling right now, what has set me off today, what has energized me today. Right. Like so getting in the habit of that. 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. And that's where your freedom is. And so it's looking for that freedom relating to it, like freedom. And then the very basic and simple count to ten. Someone once told me he can only get to five. I'll take it.

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

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. So I'm feeling frustrated. Not really. I'm feeling anxious.

Yeah. So becoming aware of your emotional state. What's your reflective practice?

Well, my fitness practice is definitely a reflective practice. It may not sound like it is, but it definitely is. I also do journaling. I meditate, not regularly, but times or 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 sort of check in and see how I'm feeling. Those kinds of things.

Yeah, spaces.

Yeah, spaces.

It's so important. My wife has been going for.

Of course.

Well, my wife has been going for long walks in the mornings, which actually gives me space. You know, I do a seven minute workout and I stopped playing music with it. And so then it becomes more of a. More of a reflective like just to be present with the sensation.

Yeah.

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 a more of a mindfulness experience.

Definitely.

Thanks for asking. And I agree it's, I think it's this, it's like table stakes because if somebody's not doing that, it's very hard to help them with the next step. Like if they lack all self awareness. Hey everyone, we're at the halfway point. Now is a great time to stretch your legs, refill your popcorn and head over to TheConversationFactory.com to check out the show notes for this episode. And while you're there, explore the other amazing episodes or visit the resources page for handy templates and activity guides to transform your collaborations and your communications. It's really interesting. So 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. And it was really interesting to watch you step in with your perspective, but without force, with gentleness. And I just. I don't know, I just wanted to highlight that and sort of unpack this way in which you help people see themselves as a coach, mirror person thing.

Yeah. I was just in this retreat center, and somebody there said to me, you know, he also works with. With founders and startups. And he said, I do a test. So 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 the right answer or with an answer, I know they're coachable. And if they don't, I know they're not coachable. It's my test. I'm like, okay, well, I'm a coach, so I don't see it that way. Right. Because it doesn't. You know, you can't. 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. 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. And so he was only 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. But 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 insights, and then we see how coachable people are.

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

Yeah, well, of course, you know, But I don't know if it shows up right away. So people will say to me, oh, that guy will never change. Oh, she's not coachable, or whatever. I'm like, okay, please don't speak to me. I can't. You know, like, you have your. Everyone's got their opinions about whatever, and 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.

Yeah, right.

Oh, they have been maybe put down. Well, no wonder they're not changing. I wouldn't change either. So for me, it takes a little while to really figure out what's going on. And again, will this person change?

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

Yes.

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

Definitely. That is definitely important. And also coachability is important. And for him in particular, there is this sort of index, like, he doesn't get paid if they don't change. But Marshall also knows that people don't always show up immediately the way they really are.

It takes.

Takes. It takes a while for defenses to get down, to go down.

Yeah. And I think I've noticed with people in my coaching circle who are, it's like we as coaches can make stories of, like, you know, oh, they didn't respond to my email. They must be not into this enough versus, like, everybody.

Everybody makes up stories. Exactly.

Yeah.

Yes.

So I want to really try to peel back another couple of layers on this startup to grown up idea, because not for you to develop. The book's coming out in a while, but when we think about this arc from product to building a product to building a culture and 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 Alyssa has? Or just when should they start thinking about having a partner in the process?

You mean like a partner isn't a coach?

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

So I just, 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. So the framework is to think about where am I inside of managing myself, managing them. Right. The people around me and managing the business.

Yeah.

But in terms of how do people know it's time to bring a partner? As I said, you have to have something to coach. Right. Something to manage. And also, it depends how interested you are in this 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. They may get into trouble with a situation going on that feels dysfunctional. I don't know what to do. Or 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, and he got angry, as in, like, don't tell me what I need and don't tell me what. But 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 need a coach. I think I need a coach because I want to learn. And different people come from different directions. And then, you know, 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.

Yeah, that's pretty mature of him to.

Yeah, very mature.

Because, I mean, the idea of being voluntold, I mean, as somebody who does training and developing groups of people and cultures, the early stages, 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 voluntold to, like, okay, this is how you need to work. I imagine working with somebody who is being forced or pushed to be coached. Okay. I'm so glad to be in this conference. You're like, I can handle that. Yeah.

I tell everybody, they say, oh, I don't think he's gonna want. I'm like, I welcome skeptics. I welcome skeptics. I mean, come on and talk to me. It's not about, like, oh, you need to be coached. It's about, how can I help you? And, like, how can I like, genuinely, like, legit help you get more of what you want? Who wants to say no to that? But coaching's not framed that way. How does gonna fix you? Let's not talk about that. Let's talk about you. People like that also. You know, it's funny, because I was. I've been put into shotgun marriages many times, actually. This one person, after he was a large company I was working inside of, and he came to me right 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. So 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.

Strap in.

Yeah, let's go.

Let's go baby.

You know, because, because that is what it's about, right? I have to align with my clients so that we can figure out where are we going. And it's like, where are you, where are you going and how are you going to get there? That's all I care about.

Yes.

And if somebody doesn't want to, who doesn't want to engage with that? Right. And then part of that, then there's trust. And then part of that is a 360 feedback process. Very often where people around say, you know, 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 feeling my heart. Okay, now there's something to work on, but we've already established that we have an alliance here and I'm going to help you get better.

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 hour, 30 minutes. Marshall talks about 15 minute sessions with people.

Yeah. The most powerful coaching conversation I ever had was eight minutes on a Friday night. Cell phone to cell phone. We were both driving. That was the most impactful coaching conversation ever. Who knows now that all said, you have to have some structure.

Okay.

So I tend to 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.

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

So there was a president of a division I was working with and she had some important changes to make. This is like a Friday, Friday night. And she had to go in on Monday, make these important changes. And she was thinking about it very tactically like I'm going to do this, I'm going to do that. And 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? And she would hesitate. So then it's like, why are you hesitating? Right. So what's. What aren't you not saying? Right. So 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 and so it's not even 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. Secondly, she was thinking about the org structure and various people in a way which was very superficial. And 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. And she was able to immediately communicate differently on Monday, which set the tone for the whole process.

Boom. What I love about this story, I mean, and I assume you were some weeks or months into your relationship. Right.

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

Eight minutes. Kapow. But what's amazing, I've been sitting with this question of like, what's the value of a coaching conversation? Because people ask all the time, well, how much do you charge? You're like, well, I don't know, how much change are you trying to make? And if you measure it by the value you created in that eight minute conversation, the value is priceless.

Yeah. I tell people I want to spend the least time with them as possible. Listen, 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.

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

I love my HR colleagues who are excellent.

But here's the interesting thing, and this is something that my coach has coached me on in my coaching, which is as mad as 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 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.

Totally. And that's where the value comes from. And that's where, you know, I think the joy of self discovery comes from. Definitely.

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

Well, I think one question is how is this situation serving you? Because people complain about whatever and the question is, how is it serving you? What are you Contributing to this situation. That's a very important and powerful question. And I think, what are you afraid of? And that's again, with a trusting relationship. That's where a lot of the fruit is.

Yeah. Taking ownership.

Yeah. And also that sort of self inquiry, the depths of the self inquiry.

It's really interesting because there are these two points in the journey. Where it's at the beginning is like, where are we now? And these questions are like, where do you want to get to? What can draw you forward? 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? And I just wanted to say, like, I love that question. It was a beautiful question.

Thank you.

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

Of course. Well, that's also. That's sort of entering the. So, like, that's the initial stage of the coaching conversation. So even that we talked about people who are like, skeptical or you said voluntold. You know, 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? Yeah, that's just a better question or a better conversation than like, I'm not happy. I don't like this. They shouldn't, you know. Okay, whatever. Those are boring. Let's talk about what's, like, really interesting, which is what you actually want to get done in your life.

Yeah. Because here you are in the conversation, you, somebody potentially has paid for your time already, and here we are. What do you. What do you want to do? Yeah, it's a great question. 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?

Well, I think maybe one thing that I would just say it's not so much a question. Well, maybe it's. The question is, what's the entrepreneurial journey like and why is it so hard? And 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? So just the sort of the, 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 founder is boss for the entry level position. So you don't know what you're doing necessarily. You may not have had any other management leadership experiences before. So you've got to learn all that piece together and then you've got to do all the other things that a founder has to do, like raise money, like, you know, sort of pull them, like figure out the market, figure out the strategy, you know, 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.

Yeah.

And so just to say that like I'm in awe constantly of the founders I work with and their ability to deal with that struggle.

The Yiddish word that's coming to mind that my dad loves is rachmunis, which is like deep empathy. And I can feel that you really get and relate to their journey and their struggle.

Yeah, yeah, that is true. I feel really allied and aligned.

So there's some parting things that we should make sure we places where people can learn about all things Alyssa 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. So where can people go to learn more about you? In the Internet places.

Great. On the Internet people can always find me on my website, alyssacon.com and all the socials. So lyssacohn or LinkedIn. Alyssacohne A L I S a C O H N Everywhere you find your social.

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

HBR and Inc and Forbes. Find me on Clubhouse. Follow me on Clubhouse. Lyssacohn yeah. Okay, so all of that and the thing I want to say is that when you come to my website or look for me on LinkedIn, you will see I'm doing a program for coaches to teach coaches how to build their businesses, how to get more clients. So it's called the Business Development Academy for Coaches and it's got two parts to it. April, we're going to do a 30 day quick start challenge to help you gain traction after this year coming out of the pandemic. And then a 10 month program which is called Build you'd business program which is how do you build a sustainable business? So that is with W Beccs W B E C s go there or come to my website. But then the thing I'm also particularly excited about October 2021 this year coming to a bookstore near you. From Startup to grown up. And it's about growing your leadership while growing your business.

That's a good subtitle. When the, when there's a galley ready, I would love to read it and have you back on to talk about. To talk about those issues. I think these are, it's important. You know, I had an old boss who's talked about zero the zero to one idea and and this is what startup founders are doing. They're trying to make something truly new, which is true. Truly hard.

Totally truly hard. It is.

And also truly important. So I mean it's. I honor the work that you do with them and I hope you can. I'll find links to all that. There will be links to all of that in the show notes.

I will help you fill out the show notes.

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

I love it.

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

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

That's very kind of you to say. Well then I'll call scene and we'll leave it right there. If you made it this far, you're a rock star. Subscribe on itunes, Google Play or Spotify to never miss an episode. And if you want to help spread the word about the show, head over to itunes on your desktop and leave the show a review. It only takes a few minutes and really helps.