![Goal Getter: Ask Big Questions To Get Big Goals: Charles Holmes, Executive Coach [E91] — The Legal Department cover](https://feeds.podetize.com/WOwR_yfED.jpg)
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I'm Charles Holmes. I'm an executive coach, cultural anthropologist, inside organizations and a fun fact. I had the opportunity to organize a three day conference with the Dalai Lama.
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Welcome to the Legal Department, a podcast for lawyers who want to learn, connect and grow their careers. I'm Stacey Bratcher, I'm a general counsel and I'm excited to share these conversations to help you level up in house. On today's episode of the Legal Department, I'm beyond thrilled to welcome my friend and my executive coach who is a cultural anthropologist and organizational facilitator, Charles Holmes. Hi Charles, how are you?
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I love being introduced by someone who says beyond thrilled.
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Yeah, well I like to warm up the crowd here and pandering to the audience a little bit. Well, you know, I am both excited and a little nervous to do episode with my actual coach, but I have sort of surfaced you to the world through my Goal Getter newsletter where I added another accolade to your title, called you the Magician. And today we're gonna explore a topic that we do quite frequently in our sessions, which is the power of questions. And I was kind of framing this just after our prep session around like how big questions can lead to big goals. So getting started, you know, I just wanna kind of lead off with. You actually showed me the power of questions. And why are questions so important to goal setting and figuring out what we want?
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It's a great question, Stacy, to start with a question like that. Questions in my experience open one to possibility. They open one to potential thinking, jumping too quickly to action or how. And I think one of the most common questions is how will I do this? And people start with how questions. And you'll probably hear me mention one of my mentors in this conversation a few times, Peter Block. He wrote a book called the Answer to How is yes and his premise is asking how is too early. Because a question like how will I do this? How will I grow my career? Or how Will I accomplish the goal actually takes us into potentially premature action versus what I have found personally and with all of the executives I coach. Questions that invite people into reflection, contemplation, and connection to both what matters and where they are.
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Now, you're already giving me goosebumps with this. I mean, I just love it. And I love the title of that book. I'm going to try to check that out. So how is definitely a step. And actually we've talked about, you have sort of a three part framework of questions around goal setting. So let's talk about what those are.
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Sure. And these questions have evolved through my work, both in doing executive coaching, but also in working with organizations on strategy. And so you can apply these questions to organizational strategy or almost personal strategy, if you will. So the first one is why, why do we, in the context of an organization, why do we exist? Why are we here? And it's more than to just make money on a personal basis. What is my why? Why do. And that could be a big why, like why am I here? An existential question. But it could also be why does fill in the gap really matter to me? Why does this job matter to me? Why does accomplishment of whatever, the next phase of my career or the creation of my business or creation of a podcast, why does it matter? So question number one is pretty tightly tied to question number two, which is what? What do I really, really care about? What do I care enough about to want to see exist? And that might sound kind of strange to want to see exist. Yeah, I'm a huge fan of the work of Robert Fritz. He wrote a book called the Path of Least Resistance, and it's all about the creative process. And I firmly believe that our lives are about creating desired futures. So what is it that I want to see exist in the future? Let's say in the context of my job, in the context of my career, in the context of this podcast, what is it I want? You do it consistently. You do these pre interviews around. Okay, so what is it going to look like? What are some of the questions I might ask? So what is the impact I want this to have on my listeners? So that's question two. Question three is, where now? Where are we as an organization or where am I now relative in relation to the aspiration or the what or the. Or the goal. And in our conversations, you have shared with me that you find the the what to be one of the harder questions. Why want? For me, it's being accurate and honest about where I am now that I Often find harder. And I find a lot of people struggle with. Because where am I now? Is sort of like the current reality. And we, Robert, often would often say that reality is an acquired taste. It's not good, it's not bad. But we tend to often misrepresent where we are right now. We make it worse than it really is, or we pretend it's better than it really is, or we just don't accurately assess ourselves. And this is where coaching actually can be really helpful is to help people think through. Is that really true? True that you don't have the skills or that you are so fearful that you can't actually take an action or, you know, to have someone challenge you around that. Where are you now? So why what where now? And the fourth question is how? And the how is how am I going to bridge the gap between my aspiration, what I want to create or bring bring into existence and where I am now? And that is not one of the, I think shortcomings of strategic planning. Many, many years ago was organizations would put together a gap analysis and say, what do we want to achieve in the next two, three, four years where we now know? Let's develop a plan, a railroad plan to get us there. I've seen people do this as well. Now the problem with a railroad type plan which lays out step A, B, C, D, E, F, by the time you take steps A and B, the aspiration isn't necessarily going to change, but the current state is going to change. And that actually might make step C redundant or even potentially inappropriate. So that ability to stay connected to where am I now? What results did that step or that action generate, is that the right thing for me right now? You know, and I've, I've, I've watched you with the creation of your, of your podcast and your substack and what I'm observing and it's just such a delight to, to work with you and to be here now talking about it is you're constantly adjusting and you're thinking, okay, you know, the responses were this on this podcast, the next one, I'm going to change it a little bit. I'm going to interview this person or I'm going to take this approach. So there's this excuse the Canadian pronunciation process of constantly adjusting as you go, based on reevaluating the question, where am I now?
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Well, thank you for always building me up. I appreciate, I really appreciate, value your feedback, positive and negative. And I love, of course, the positive the best. But I am now stuck thinking about where am I now? And your observation that we're not always accurate about that. And in particular, what occurred to me was, well, isn't that always gonna be a subjective state? Like. And we talk about, you say, you know, is that a fact? Are these stories. What story are you telling me? All those sorts of things. And it just strikes me as, like, how will we ever know what is the real where?
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Yeah, it's kind of like asking what's truth?
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Yeah.
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Yep. Is that really true? And I think it's a really good point. Part of, again, having someone, a partner, a friend, a spouse, a coach to push you a little bit on and challenge on that. Yes, it can be subjective. But you actually just a minute ago used story. And every single group, every single person I work with, I acknowledge that we all have advanced master's degrees, msu. And the not so technical articulation of MSU is make shit up. Or we make stories up and we make up stories about other people. We make up stories about ourselves. We make up stories about the context or the situation and the ability to recognize that, you know, oh, wait a second. That's a story. It's a story I'm telling myself that. Is all of it true? Well, actually, some of it is, yes. But if I swallow the entire thing as fact, it has huge power and limiting.
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Or.
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Or the other side. Some of our stories can actually manipulate or help us.
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Yeah.
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Towards what we want.
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Yeah. You might think things are better than they actually are. Or. Or you might have a blind spot about things.
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Yes.
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Yes.
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And I. I really appreciate you bringing that up. What. What are. What is my blind spot? And that's where, again, I think coaching and therapy, you know, it's been really helpful to me to recognize where some of my blind spots are.
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Well, and we'll get into more kind of the limited thinking and moving past that. But. And you did. You called me out. And I appreciate this. And I think that I'm not alone, especially as a lawyer, being a little unclear about what do I really want? What do I really care where about? Where do I want to go? Because as we've talked before, that, you know, the legal training in the profession is very linear. And so you can. And I've written about this. You can get sort of locked into this momentum that I need to keep doing the thing, the next thing, the next thing. And. And I think we talked about this in prep. There's a big identity that goes along with the profession. And so what I was hoping we could get a little more Granular about is how to get to that. What do I really care about? When you are sort of conditioned to care about kind of what everybody else is caring about.
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Yeah. Yeah. And I don't think it's unique to the legal profession. I think this. This belief that I need to climb the ladder to get to the next thing and that, you know, what's that old adage? You know, you spend 30 years climbing the ladder and get to the top only to discover that it's not really what you had expected or wanted it to be.
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Yeah.
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To look back and go, oh, my goodness, you know, I missed all the soccer games. I missed the ballet performances. I did, you know, I did these things in supposedly in service of supporting family or other things. But. But what happened to, you know, the things that I thought this ladder might lead to? So that's. That's one sort of sad, I guess, situation to consider. The other is I firmly believe that most people in their heart of hearts know what it is that they want and care about and want to create. Now, for some people, support and stability for family is above everything else, and they will do anything to ensure that that's in place, including compromising or dampening their inner spark or. Or fire, and say that I'm doing it in service of this. So what do they want? They want stability. They want situations for their family. They want. Maybe it's the car, the house, the. The. The material things. And there's nothing wrong with that. Just be really honest with yourself.
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This is.
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This is what really matters. And I'm doing this. But then there are people who are really bitter about that. I'm, you know, I'm doing this, and. And I'm not happy. So I think this, you know, that question. And I don't mean to sound idealistic in what I'm saying, because I think there's so much evidence to the contrary that. Around the question, what is it that really lights you up? What is it makes you happy? What was. There was a question that I asked you. You reminded me that I asked you years ago.
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Yeah. What would you run screaming to get?
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Yeah.
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Yeah.
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And, you know, and I think. And you. You didn't answer that right away. You sat with that and you contemplated it, and I know you journaled and you wrote about it and you thought about it. Yeah. And so I think this. This piece of kind of hitting the pause button, it's like, okay, I'm on this ladder. I've. I've swallowed the kind of linear. And I don't mean to sound negative in saying, I've swallowed sort of that linear mindset. I might not even be aware of it, but to just pause and say, is this the linear approach to I've been told what I really, really want?
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Yeah, yeah. And I just. To be the latter, it's, it's. I think that again, we're lawyers tend to be achievers, you know, high functioning people tend to be achievers. But then to your point about like getting somewhere and realizing you didn't really want it, you know, like in leadership, right, everyone wants to be the leader because that's the top person. But what you learn is that the leadership job is different, very different from the individual contributor job. So if you loved being the smartest in the room, the technical person, all of a sudden when you're a leader, that's not your job anymore. Your job is getting people on board, keeping the troops excited, and getting the whole organization to accomplish goals. So those are different skill sets. It might look shiny and new and exciting, but it is different. And so that leads me to like, how do we test assumptions about what the next thing is or what our goals look like? Because you know, one thing when you were talking about, you know, what makes your heart sing, I think back to like, I was a first grader and we had like, our school had a writing program and I loved it. And I have been, you know, in writing my whole life and I thought I wanted to be a writer. But you know, writers work by themselves a lot. They're alone a lot, and it's a really long time. Even if you write articles, even if you do reporting to actually have a result. So while I might enjoy the process, the creative process in writing, I like being around people and I like having wins. I like seeing points on the board. And so would that be something that I would really enjoy as a career? I don't think so. So how do you, you know, both as an achievement mindset and then just a sort of the grass is greener for the, you know, non corporate career. Like, how do you test those assumptions?
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Yeah, that's beautiful. And thank you for that example. And I just had this flashback to might have even been in the mid-90s, there was a book called what color is your parachute?
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Yes, yes.
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And I'd totally forgotten about that until I was listening to you. And I remember one of the exercises in that book was to, to write down all the things that are important to you and the things that you love and the things that you care about. And you just demonstrated it you know, I love writing. I also love being around people. I love engaging people. I love learning. I mean, so there's almost this picture that even in the 30 seconds that you described yourself, Stacy, that it articulates what's important. So I think that's one piece, the individual reflective exercise of what are the things that really matter to me. And again, I also like your distinction between the individual contributor and the leader. It's like, I like contributing. I love taking direction from other people. And so that's. I'm not going to fool myself by saying I want to be in that leadership role. So. And then I think the second, the other piece in that is talk to people, just finding out, so what's it like being a management partner? What's it like being a general counsel of whatever size organization it is? That job looks like that flashy, marquee job. I want to find out more about what's involved. And don't fool yourself to making up again a story. That's what you really want.
A
Yeah. That is so good. It's so good. Thank you for that. Let's go back to the. What would you run screaming to get the other thing, the other question. And I'm a little hesitant to share it, but I think it'll be helpful to the listeners. You also asked me because during that time I was feeling like I had a lot of accountability and responsibility to others and to my organization. And I felt that if I didn't keep the plate spinning, if I didn't keep running and doing the same thing, that things would fail, the world would end. And you ask the question, what are you willing to give up to prove that they need you? And like, that still just gives me shivers because it challenged that belief that, you know, this superhero complex I think that I certainly had at that time.
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Yeah, I mean, I think many of us, and I'm guessing many of your listeners will probably resonate with that, that sort of belief that people are dependent on me and if I let them, if I stop spinning one of those plates and you were spinning a lot of plates.
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I was, yeah.
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If I let one of them fall, it's going to be catastrophic. Well, guess what? There's your make shit up. And that's not to say that it's not important at all. And, you know, really being intentional, thoughtful and conscious. And in a way, you know, we're coming full circle to your initial question. Why are questions important? And what you've illustrated is those two examples were questions that caused you to pause and go, oh, Wait a minute. Is this. In fact. I won't use the word true. Is it reasonably accurate to say that if I let a plate fall, things will go to hell in a handbasket? And I think the other piece is. And I won't look good. And you can then extend. I've had this happen. If I don't do this, then I won't get this project or this contract and then that will mean that they don't want me and I won't have income. And. And I can go very quickly to sell. Selling pencils under. Under. Which is an irrational fear that feels real. Has felt real many times in my life.
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Yeah. Well, I think if I'm zooming out, the overall advice here and kind of going back to the start of our conversation is that you need to take time and ask yourself these questions and validate, you know, is it true that I want this? Why do I want this? And again, I love that question about what are you willing to give up? Was. Was pivotal. Actually. It was very pivotal for me.
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I'm going to. I'm going to throw. I'm going to throw two other. Just because they're. They're sort of top of mind in other conversations right now. Really powerful questions. What's your contribution, or what might your contribution be to the thing you complain the most about? So easy.
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Ouch. Ouch.
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It's so easy to point our fingers at others and context. And, you know, what's that old adage when you're pointing a finger somewhere that look at where the other three are pointing. So, you know, asking yourself, what's my contribution to this situation? And that's about accountability, it's about ownership, it's about being an adult. And the other question that I really like is what's the question that if you had an answer to, would set you free?
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My God. I think I need to go on, like a quest to go figure that out.
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That one, that one. That one you might need to sit with. Sit with a little bit. The first one, though, is when you're in a situation where you're complaining and angry, take a breath. What's my contribution to this? Yeah, I can guarantee we're always. I mean, we're always. We're part of a system in every work context.
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And I think that that question makes you a better leader, a better professional, a better person. Because you're right, it's very tempting. It's very sort of natural just to look outward, but takes two to tango.
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Just on that note, Brenny Brown had a Great quote. Because in a way, by pointing the finger, it's blaming, it's blaming others, it's blaming the situation and not. And let me see if I'm going to get this right. Blame is about casting doubts, aspersions on others rather than looking in the mirror at yourself. It's easier to do that than to look in the mirror. Something along those lines.
A
Yeah, no, sure, sure. So kind of going back the question about where am I now and what's the gap I need to fill makes me think about even if people think they know that what they want. One thing I find really frustrating is people who I would love to be, blah, blah, blah, I would love to do this, but they don't act. And as you know, I'm almost overly wired towards action. Like I shoot very quick and decisively, which is maybe another show. But I would like to talk about why people stay put. Why do they stay in something? And you know, we talked about the fear of change, which you have said is sort of overstated versus resisting the sense of losing something. Legal intake shouldn't live in slack and spreadsheets. Streamline AI centralizes requests, manages matters, streamlines collaborations and gives legal leaders real time visibility into their team's work. Built for in house Legal Streamline AI.
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So a few things in that I find it really sad and I hear you because it frustrates you and I think in part I know it frustrates you because you see the potential in people and it's like, why can't you get over yourself? And people often stay refer to not moving forward as the comfort zone. Stay in the comfort zone. For most people, it's not necessarily comfortable. I refer to it as the area of tolerable conflict. It's not so bad or not or the aspiration's not so great. Here's an image. Picture this. On one wall is my aspiration, what I want. And on the other wall is, is my concern or fear that I can't get it. And this is one of the answers to your questions is fear. And tied around our waist is a rubber band attached to what I want and another rubber band attached to the fear. So I start going for what I want and the tension in that band is getting less and less because I'm getting there. But what's happening to the other rubber band? It's pulling me back. I can't do this. I can't accomplish this. I'm going to not have the car, I'm not going to have the big six dollar figure salary. Da Da, da, da, da. I'm not going to get the. No. But I really, really want my own business. I'm going for my own business. No, I can't have. And you end up in this after. Back and forth, back and forth. And after a while, a system like that seeks equilibrium. So I'm just going to stay here and climb the ladder.
A
Just easier approach.
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It's a. It's just easier. Yeah. And it's easier. That doesn't mean it's painless, because there is. There will always be that little bit. I wish I could have been a contender. I wish I'd done it.
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Yeah. Well, that's what you say. That is tolerable.
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Conflict.
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Conflict. Yeah. Like, I'm living with this unease anyway. And the other unease, the fear to, you know, do your own thing, is really scary because I don't know it. It's unknown.
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Right. And on the other side of it is you actually don't know what's possible.
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Yeah.
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Right. I mean, you and I've had this conversation about, you know, when you started this podcast, you didn't think it would be possible to get some of the people that you wanted. And it's. It's extraordinary. Like, you know, this world that's opening up.
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Yeah.
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By stepping into. And I know you were afraid. There was a fear. It was like, oh, is anybody going to listen? Is this going to matter to anyone? You know, and you did it anyway. And why? Because you care enough about it. And. And yes, you have a predilection towards doing things. Absolutely. But not just anything. It's something that matters to you.
A
Yeah. Well, thank you again. So one kind of final question on that fear topic and is really challenging the fear. And the question that we talked about was, what's the courage that's required of me now? Or the courage to step out of what's not serving you?
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One of the ways I often challenge clients that I'm coaching with around the conversation about where am I now? Around the fear is to kind of dive into it. And very quickly you discover that it's fear of imaginary negative consequences. And that's where we make up the story. You know, if I do this, then this is going to happen. And we play that tape over and over again. And this is where, you know when you say reality is subjective. Yes. And recognizing when you know that the subjective expression of reality is like an old, you know, needle stuck in a track on a record, which is constantly telling myself this negative story. It's still a story now, that doesn't mean that you just kind of give up everything and go willy nilly towards. I mean, if you've got a family, if you've got obligations, obviously you know, you're thoughtful about this, but really check out what exactly is the fear. And you said it a minute ago, you referenced people don't resist change. What they fear is loss. I have found that over and over again to be so true, especially in, in, in the context of organizational change. And you apply it to an individual as well. What is it that is absolutely critical for you to not give up or to not lose? In my career path, I had a great good paying job. I was with university and I, I couldn't give up a reliable source of income to pay the mortgage.
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Yeah, that is a real actual thing. That's a fact, not a story exactly.
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And I wanted to create my own business. So I negotiated a halftime role and that halftime role was sufficient to pay the mortgage. It wasn't enough to go on family holidays or to have the super nice car or other sort of trappings. And for me, they're trappings for other people, they may be absolutely what they want and they would never do what, what I did because those things are more important than the freedom and the creation of the, of the job. So I, I had one foot solidly in a role that gave me enough money for the foundational stuff. And then I started doing other things. I couldn't lose that. And over time, and it took about five years, I realized, oh, I don't need that anymore, you know, since 2025, have had my own business.
A
Yeah, well, it goes back to testing those assumptions, right? Like what is it that I actually need? Or what are the sort of the core things, you know, And I think money's almost an easy one because you can say, like, do my kids really need to go to private school? Do we really need to go on a vacation? Do I really need to lease a car? But I wonder about questioning more intangibles like status, you know, and I've talked before on this show or I've interviewed other folks where we talk about status, kind of going along with certain of these roles. So I mean, how would you peel back that therapy
B
in a way, and you just did it. And I would say do the same thing. You actually took the first question. Why? Like why is private school important? Why is the car important? Why, why are these things important? And that's, that's a very personal question because they may be extremely important. Similarly, why is being executive or why does that really matter to you. And that's where having someone help you through that, you know, and really push you a little bit on that. I mean, you and I've been there. Yeah. And the answer may be because I really. It's something I have always aspired since grade one. I've thought about, you know, being leading a big organization. Yeah, great, great. And at the same time, it's a really interesting potential and dangerous trap because it becomes so much about you and those who have pursued that high level position aspiration because of what they think that it says about them. Are they actually really good leaders? Because in many cases the focus is on them.
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I would say many times.
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Yeah.
A
Many times. Yeah. Yeah, yeah. And that just, you know, just gets me back to this kind of core issue that I've not been thinking about for myself but others about how career and identity can get so intertwined. I have a friend who was CEO of a big company and sold it and does a bunch of other things now. And just how unwinding from that identity of being the CEO has, you know, carried with them this for a while. Like it as you. And I don't know if it's where you are in the organization, but certain jobs carry more identity, I think.
B
Yeah, no, I think you're. I think it's a really, really powerful and important, I'll say, exploration for people to think about. I. I've coached a lot of CEOs who are, you know, in their early mid-60s looking at and on things like succession.
A
But then that must be hard.
B
Yeah, big time. I, I have, I have one. This person's become a very dear friend who within six months his wife left him and he left his role as CEO of a global big. And he's spending a year around this very question. Who am I? You know, what is my identity now that I'm not a husband, I'm not a CEO? I'm like, what? Who am I in the world?
A
Yeah. One of my early episodes was with another coach and actually I was exploring the. The thing and it. This was a realization I had kind of after that question, you know, what am I willing to give up to prove they need me was I am not my job.
B
So I think that's. I think that is so important, Stacy, to that and to acknowledge that first and foremost.
A
Yeah. We just spend so much time getting ready for it, investing in it. It's so many waking hours and if you're not careful, you know, to quote the Ferris Bueller movie, you know, life might just pass you by. So as we're winding down here, I wonder, because we've talked about, you know, we've kind of woven in how coaching can help people get through some of these big questions. How do you have recommendations for people on how they would find a coach? We. We were very lucky to collide in a certain situation. And I thank myself, thank my lucky stars all the time that that happened. Um, but, you know, I could see I'd be quite overwhelmed if I wanted to get a coach, how I would find the right fit.
B
Thank you. I like hearing that. By the way, my friend Peter Block often says that when. When someone pays you a compliment, say thank you. Yes, I like hearing that. And if you're really courageous, say, tell me more. So I think, you know, there are a couple things. Talk to others. I'm sure your listeners know people who work with executive coaches. Talk to them. I. It's funny, like, there is the International Coaching Federation, icf, and there are rosters of. Of coaches out there. And I hear you. It's like, oh, my God, that's kind of overwhelming to go, like, look at a list and how would I. How would I choose? I've actually never been asked that question before, so.
A
Oh, sorry. Stump stumps the expert here.
B
But I think my immediate answer would be, talk to other people.
A
Yeah.
B
Who are you working with?
A
Well, the other thing.
B
And, and, and it's interesting because just. Just last week, I had to say to the CEO of an organization that I didn't think I was a match for one of the executives I was working with. And we both agreed, all three of us agreed, that I wasn't the right person for her. And, you know, 10 years ago, I would have taken that really personally. It's like, oh, my God, my identity's tied up with being accepted. No. And so, so that. And you kind of know it pretty quickly after having a conversation with someone. Is, is this someone that is going to challenge me enough, but not too much? Is this someone who's going to be, you know, too easy on me? Do I feel like I'm going to be appropriately stretched and challenged? And I feel a connection? Is there a match?
A
Yeah. Well, and I'll just say, I mean, for people who maybe think a coach tells you what to do, I hope that this conversation has shown that it's really very. It's more challenging in terms of its inquiry. I mean, that's really the bottom line, which I think people may not realize that.
B
I don't know if you. You recognize this, but one of the things I tend to always do in any situation with someone I'm coaching. When it comes to action, I will say, what are three possible actions to get people out of picking the first immediate thing? So what are three possibilities? And again, it's. It's pushing that reflective muscle.
A
Yeah. Yeah. That's what the whole. The whole thing is about. Thank you. So I. This is the Goal Getter series. I usually ask people about their pump up song, which is fun. But in this series, I asked the question, what is a goal that has eluded you? And if so, do you still want to achieve it? And what do you. What's your plan to do it?
B
So I had the incredible privilege in 2006 of organizing a global conference with the Dalai Lama, and it was called Connecting for Change.
A
That's a mic drop right there. Let's not, let's not gloss over that.
B
Yeah, I got to. I've had the. I've literally had the privilege of spending three full days with him, sitting in a room, holding his hand. I mean, it's. Anyway, we'll save that for another conversation. But the genesis of that gathering, I. I won't get into the details of there's a whole story behind it, but we brought together 70 CEOs and 70 executive directors of nonprofit organizations and we paired corporate. Nonprofit leaders with each other to discover. Well, really to discover each other. It was called Connecting for Change because all too often executives of corporations made up stories about nonprofits and vice versa. And what that gathering evoked for me was a deep and powerful recognition that we are all connected and we tend to polarize. And right now in the world, I think it's so painful to see the polarization. So this is a crazy wild ass goal. But at the time, I talked about the concept of six degrees of separation. And my aspiration or hope is that we can. We can create a world where we recognize zero degrees of separation, that what I do has an impact on you, even if I don't know you now, you might say, how in the world would you ever accomplish that goal? It's not something I'll accomplish in my life, but it's something that guides my decisions and what I do to create the conditions for people to connect, to discover possibilities they never realized were possible as a result of connecting people with each other and connecting people with themselves.
A
Perfect period to the end of this amazing conversation. Charles, thanks for being here. Really appreciate it.
B
No, such a delight, really. And kudos to you for doing this and leaning into what you love and care about. Thanks.
A
Hey, before you go, if you want more content from the legal department, check out TLD Goal Getter on Substack. It's a mix of free and subscription based content to help you level up your career. That's TLD Goal Getter on Substack. Hope you check it out.
The Legal Department Podcast
Episode 91: Goal Getter: Ask Big Questions To Get Big Goals
Guest: Charles Holmes, Executive Coach
Host: Stacy Bratcher
Release Date: April 7, 2026
In this engaging and practical episode, host Stacy Bratcher welcomes her own executive coach and renowned cultural anthropologist, Charles Holmes. Together, they explore the transformative power of asking big questions when setting significant goals—both in one's legal career and personal life. The episode delves into frameworks for effective reflection, the influence of professional identity, the tricky territory of ambition, leadership, blind spots, and how to distinguish between narrative and reality. Charles also shares vivid anecdotes, including organizing a conference with the Dalai Lama and his own pivot away from traditional work. Throughout, both guest and host offer actionable tools and probing questions designed to help legal professionals clarify what truly matters, challenge assumptions, and move forward with courage.
For further insights and actionable career tools, Stacy invites listeners to check out her Goal Getter newsletter on Substack.