In this Goal Getter episode, Stacy’s executive coach, Charles Holmes, is in The Legal Department to explore how asking the right questions can lead you to the career you really want. He shares the three questions that can help you identify what you want and how to get there. Stacy and Charles also explore how “tolerable conflict” keeps us stuck between what we want and where we are today.
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Goal Getter: Ask Big Questions To Get Big Goals: Charles Holmes, Executive Coach
Charles Holmes, baseball stats.
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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On this episode, I’m beyond thrilled to welcome my friend and my Executive Coach, who is a Cultural Anthropologist and Organizational Facilitator, Charles Holmes. Charles, how are you?
I love being introduced by someone who says beyond thrilled.
I like to warm up the crowd here, pandering to the audience a little bit. I am both excited and a little nervous to do an episode with my actual coach, but I have surfaced you to the world through my goal-getter newsletter where I added another accolade to your title, I called you the magician. In this episode, we’re going to explore a topic that we do quite frequently in our sessions, which is the power of questions. I was framing this just after our prep session around like how big questions can lead to big goals. Getting started, I just want to lead off with you actually showed me the power of questions. Why are questions so important to goal setting and figuring out what we want?
The Power Of Questions
It’s a great question to start with a question like that. Questions, in my experience, open one to possibility, they open one to potential. Jumping too quickly to action or how, and I think it’s one of the most common questions is how will I do this? 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.
Questions open one to possibility; they open one to potential. Share on XHis 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 now.
The Core Framework: Why, What, Where Now
You’re already giving me goosebumps with this. I just love it. I love the title of that book. I’m going to try to check that out. How is definitely a step, and actually we’ve talked about you have a three-part framework of questions around goal setting. Let’s talk about what those are.
Sure. These questions have evolved through my work, both in doing executive coaching, but also in working with organizations on strategy. You could apply these questions to organizational strategy or almost personal strategy, if you will. The first one is why. In the context of an organization, why do we exist? Why are we here? It’s more than to just make money.
On a personal basis, what is my why? That could be a big why, like why am I here, an existential question, but it could also be why does fill-in-the-blank 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?
Question number one is pretty tightly tied to question number two, which is what. What do I really care about? What do I care enough about to want to see exist? That might sound strange, to want to see exist. I’m a huge fan of the work of Robert Fritz. He wrote a book called The Path of Least Resistance. It’s all about the creative process. I firmly believe that our lives are about creating desired futures. 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 show, 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? What is the impact I want this to have on my listeners? 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 goal? In our conversations you have shared with me that you find the what to be one of the harder questions, what do I really 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.
The where am I now is like the current reality. Robert 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. This is where coaching actually can be really helpful is to help people think through, is that really true that you don’t have the skills or that you are so fearful that you can’t actually take an action or to have someone challenge you around that where you now.
Why, what, where now and the fourth question is how. The how is how am I going to bridge the gap between my aspiration, what I want to create or bring into existence and where I am now. One of the shortcomings of strategic planning many years ago was organizations would put together a gap analysis and say, what do we want to achieve in the next 2, 3, 4 years, where are we now, now 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. That actually might make step C redundant or even potentially inappropriate. 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?
I’ve watched you with the creation of your show and your Substack and what I’m observing and it’s just such a delight to work with you and to be here now talking about it is you’re constantly adjusting. You’re thinking. 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. There’s this process of constantly adjusting as you go based on re-evaluating the question, where am I now?
Thank you for always building me up. I really value your feedback, positive and negative, and I love of course the positive the best. I am now stuck thinking about where am I now and your observation that we’re not always accurate about that. In particular, what occurred to me was well, isn’t that always going to be a subjective state? We talk about you say is that a fact? What story are you telling me? All those sorts of things. It just strikes me as like how will we ever know what is the real where?
Yeah, it’s like asking what’s truth. Is that really true? 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 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. The not-so-technical articulation of MSU is make stuff up.
We make stories up. We make up stories about other people, we make up stories about ourselves, we make up stories about the context or the situation. The ability to recognize that wait a second, that’s a story. It’s a story I’m telling myself . Is all of it true? Well, actually some of it is, yes. If I swallow the entire thing as fact, it has huge power in limiting or the other side, some of our stories can actually manipulate or help us towards what we want.
You might think things are better than they actually are or you might have a blind spot about things.
I really appreciate you bringing that up, what is my blind spot? That’s where, again, I think coaching and therapy has been really helpful to me to recognize where some of my blind spots are.
The Risk Of Climbing The Wrong Ladder
We’ll get into more the limited thinking and moving past that, and you did call me out and I appreciate this. 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 about? Where do I want to go? As we’ve talked before, the legal training and the profession is very linear. I’ve written about this. You can get locked into this momentum that I need to keep doing the thing, the next thing, the next thing, and I think we talked about this in prep, there’s a big identity that goes along with the profession. 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 conditioned to care about what everybody else is caring about.
I don’t think it’s unique to the legal profession. I think this belief that I need to climb the ladder to get to the next thing. What’s that old adage? You spend thirty 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. Look back and go, “I missed all the soccer games, I missed the ballet performances, I did these things in service of supporting family or other things but what happened to the things that I thought this ladder might lead to? That’s one. It’s a sad situation to consider.
You spend thirty years climbing the ladder, only to reach the top and discover it’s not what you expected or wanted it to be. Share on XThe 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 fire and say, “I’m doing it in service of this.” What do they want? They want stability, they want situations for their family, they want maybe it’s the car, the house, the material things.
There’s nothing wrong with that, just be really honest with yourself. This is what really matters, but then there are people who are really bitter about that. “I’m doing this and I’m not happy.” I think this 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 around the question what is it that really lights you up? What is it that makes you happy? What was the question that I asked you, you reminded me that I asked you years ago?
What would you run screaming to get?
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. You thought about it. I think this piece of hitting the pause button. It’s like, “I’m on this ladder, I’ve swallowed that linear mindset, I might not even be aware of it.” To just pause and say. “Is this the linear approach to what I’ve been told, what I really want.”
I think that again, lawyers tend to be achievers, high-functioning people tend to be achievers. To your point about getting somewhere and realizing you didn’t really want it. In leadership, 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. 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. Those are different skillsets, it might look shiny and new and exciting but it is different. That leads me to like how do we test assumptions about what the next thing is or what our goals look like?
When you were talking about what makes your heart sing, I think back to like I was a first grader and our school had a writing program and I loved it. I have been in writing my whole life and I thought I wanted to be a writer. Writers work by themselves a lot. They’re alone a lot. It’s a really long time, even if you write articles, even if you do reporting, to actually have a result.
While I might enjoy the creative process and writing, I like being around people and I like having wins, I like seeing points on the board. Would that be something that I would really enjoy as a career? I don’t think so. Both as an achievement mindset and then just the grass is greener for the non-corporate career, how do you test those assumptions?
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? I’d totally forgotten about that until I was listening to you and I remember one of the exercises in that book was to write down all the things that are important to you and the things that you love and the things that you care about. You just demonstrated it. “I love writing. I also love being around people, I love engaging people, I love learning.”
There’s almost this picture that even in the thirty seconds that you described yourself, that it articulates what’s important. I think that’s one piece, the individual reflective exercise of what are the things that really matter to me? 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 I’m not going to fool myself by saying I want to be in that leadership role.”
I think the other piece in that is talk to people. Just finding out so what’s it like being a managing 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. Don’t fool yourself to making up again a story that that’s what you really want.
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 readers. 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. I felt that if I didn’t keep the plates spinning, if I didn’t keep running and doing the same thing, that things would fail, the world would end, and you asked the question what are you willing to give up to prove that they need you? That still just gives me shivers because it challenged that belief that this superhero complex I think that I certainly had at that time.
I think many of us, and I’m guessing many of your readers will probably resonate with that belief that people are dependent on me and if I stop spinning one of those plates, and you were spinning a lot of plates, if I let one of them fall, it’s going to be catastrophic. Guess what, there’s your make stuff up again. That’s not to say that it’s not important at all. Really being intentional, thoughtful and conscious. In a way, we’re coming full circle to your initial question why are questions important? What you’ve illustrated is those two examples were questions that caused you to pause. Is this in fact a reasonably accurate to say that if I let a plate fall, things will go to hell in a handbasket?
I think the other piece is and I won’t look good. You can then extend, I’ve had this happen, the story like 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 I can go very quickly to selling pencils under the bridge. That is an irrational fear that feels real. Has felt real many times in my life.
I think if I’m zooming out the overall advice here and going back to the start of our conversation is that you need to take time and ask yourself these questions and validate is it true that I want this? Why do I want this? Again, I love that question about what are you willing to give up. It was very pivotal for me.
I’m going to throw two others just because they’re 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? It’s so easy to point our fingers at others and context and what’s that old adage when you’re pointing a finger somewhere then look at where the other three are pointing. Asking yourself what’s my contribution to this situation? That’s about accountability, it’s about ownership, it’s about being an adult. The other question that I really like is what’s the question that if you had an answer to would set you free?
I think I need to go on a quest to go figure that out. That’s so good.
That one you might need to 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? We’re part of a system in every work context.
Accountability Over Blame
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 natural just to look outward but it takes two to tango.
Brene 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 let me see if I can 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.
Blame is about casting doubt and aspersions on others rather than looking in the mirror at yourself. It’s easier to do that than to look in the mirror. Share on XGoing back, the question about where am I now and what’s the gap I need to fill? It makes me think about even if people think they know what they want. What one thing I find really frustrating is people who are like, “I would love to be this, I would love to do this,” but they don’t act. As you know, I’m almost overly wired towards action, like I shoot very quickly and decisively which is maybe another show. I would like to talk about why people stay put. Why do they stay in something, and we talked about the fear of change which you have said is overstated versus resisting the sense of losing something.
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?” People often stay referred to not moving forward as the comfort zone. They 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 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 my concern or fear that I can’t create or get. One of the answers to your questions is fear. Tied around our waist is a rubber band attached to what I want and another rubber band attached to the fear. I start going for what I want. The tension in that band is getting less and less because I’m getting there.
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-figure salary, I really want my own business. I’m going for my own business. No, I can’t have that.” You end up in this back and forth and after a while, a system like that seeks equilibrium. I’m just going to stay here and climb the ladder or take a linear approach. It’s just easier. It’s easier that doesn’t mean it’s painless because there will always be that little bit of, “I wish I could have been a contender, I wish I’d done it.”
That’s what you say is the tolerable conflict, like I’m living with this unease anyway and the other unease, the fear to do your own thing is really scary because I don’t know it, it’s unknown.
On the other side of it is you actually don’t know what’s possible. You and I have had this conversation about when you started this show. You didn’t think it would be possible to get some of the people that you wanted. Now it’s extraordinary, like this world that’s opening up by stepping into. I know you were afraid, there was a fear, it was like, “Is anybody going to listen? Is this going to matter to anyone?” You did it anyway. Why? It’s because you care enough about it. Yes, you have a predilection towards doing things, absolutely. Not just anything, it’s something that matters to you.
Facing Fear Honestly
Thank you, again. One 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?
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 dive into it and very quickly you discover that it’s fear of imaginary negative consequences. That’s where we make up the story. If I do this then this is going to happen. We play that tape over and over again and this is where when you say reality is subjective. Yes, and recognizing when that the subjective expression of reality is like an old 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 give up everything and go willy-nilly. If you’ve got a family, if you’ve got obligations, obviously you’re thoughtful about this. Really check out what exactly is the fear. 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 the context of organizational change. 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 the university, and I couldn’t give up a reliable source of income to pay the mortgage.
Yeah, that is a real actual thing. That’s a fact, not a story.
Exactly, and I wanted to create my own business. I negotiated a halftime role. 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 trappings, and for me, they’re trappings. For other people they may be absolutely what they want and they would never do what I did because those things are more important than the freedom and the creation of the of the job. I had one foot solidly in a role that paid in gave me enough money for the foundational stuff and then I started doing other things. I couldn’t lose that. Over time, and it took about five years, I realized I don’t need that anymore. Since 2025, I have had my own business.
Identity, Values, & Questioning What Truly Matters
It goes back to testing those assumptions, like what is it that I actually need or what are the core things. 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?” I wonder about questioning more intangibles like status. I’ve talked before on this show or I’ve interviewed other folks where we talk about status going along with certain of these roles. How would you peel back that?
Therapy. In a way, and you just did it and I would say do the same thing, you actually took the first question. Why? Why is private school important? Why is the car important? Why are these things important? That’s a very personal question because they may be extremely important. Similarly, why is being executive. Why does that really matter to you? That’s where having someone help you through that and really push you a little bit on that. Me and you have been there.
The answer may be because. It’s something I have always aspired since grade one. I’ve thought about leading a big organization. Great. At the same time, it’s a really interesting potential and dangerous trap because it becomes so much about you. Those who have pursued that high-level position aspiration because of what they think it says about them, are they actually really good leaders? In many cases, the focus is on them.
I would say many times. That just gets me back to this 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 carried with them this for a while. I don’t know if it’s where you are in the organization but certain jobs carry more identity, I think.
I think it’s a really powerful and important exploration for people to think about. I have coached a lot of ceos who are in their early mid-60s, looking at and on things like succession. I have one person. 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 and he’s spending a year around this very question. Who am I? What is my identity now that I’m not a husband, I’m not a CEO? Who am I in the world?
One of my early episodes was with another coach and actually I was exploring the thing and this was a realization I had after that question, what am I willing to give up to prove they need me, was I am not my job.
I think that it is so important to acknowledge that first and foremost.
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, to quote the Ferris Bueller movie, life might just pass you by. As we’re as we’re winding down here, I wonder because we’ve woven in how coaching can help people get through some of these big questions. Do you have recommendations for people on how they would find a coach? We were very lucky to collide in a certain situation and I thank my lucky stars all the time that that happened. I could see I’d be quite overwhelmed if I wanted to get a coach, how I would find the right fit.
Thank you. I like hearing that, by the way. My friend Peter Block often says that when someone pays you a compliment say thank you, and if you’re really courageous, say, “I like hearing that.” If you’re really courageous, say, “Tell me more.” I think there are a couple of things. Talk to others. I’m sure your readers know people who work with executive coaches, talk to them. It’s funny, there is the International Coaching Federation, ICF, and there are rosters of coaches out there. I hear you. It’s like, “That’s overwhelming to go look at a list and how would I choose.” I’ve actually never been asked that question before.
When someone pays you a compliment, say thank you. If you’re really courageous, say, 'I like hearing that.' If you’re even more courageous, say, 'Tell me more.' Share on XI think my answer would be talk to other people. Who are you working with? It’s interesting because 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. All three of us agreed that I wasn’t the right person for her. Years ago, I would have taken that really personally. It’s like my identity’s tied up with being accepted. No. You know it pretty quickly after having a conversation with someone. Is this someone that is going to challenge me enough but not too much? Is this someone who’s going to be too easy on me? Do I feel like I’m going to be appropriately stretched and challenged and do I feel a connection? Is there a match?
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 more challenging in terms of its inquiry. That’s really the bottom line which I think people may not realize.
I don’t know if 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. What are three possibilities? Again, it’s pushing that reflective muscle.
That’s what the whole thing is about. Thank you again. This is the Goal Getter series. I usually ask people about their pump-up song which is fun but, in this series, I ask the question what is a goal that has eluded you? If so, do you still want to achieve it and what are you what’s your plan to do it?
I had the incredible privilege in 2006 of organizing a global conference with the Dalai Lama. It was called Connecting for Change.
That’s a mic drop right there. Let’s not let’s not gloss over that.
I’ve literally had the privilege of spending three full days with him sitting in a room holding his hand. Anyway, we’ll save that for another conversation. The genesis of that gathering, I won’t get into the details, there’s a whole story behind it, but we brought together 70 ceos and 70 executive directors of nonprofit organizations and we paired corporate and nonprofit leaders with each other 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. What that gathering evoked for me was a deep and powerful recognition that we are all connected. We tend to polarize and right now in the world. I think it’s so painful to see the polarization.
This is a crazy, wild goal, but at the time I talked about the concept of six degrees of separation and my aspiration or hope is that 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. 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.
Perfect period to the end of this amazing conversation. Charles, thanks for being here. I really appreciate it.
Such a delight, really, and kudos to you for doing this and leaning into what you love and care about.
Thank you.
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About Charles Holmes
Charles Holmes is a cultural anthropologist by education and an executive coach, facilitator, and educator by vocation. He is passionate about coaching people who care deeply about pursuing their aspirations and dreams. For the past 30 years he has honed a passion for helping leaders to build and strengthen high performing cultures. He has co-created and taught leadership, strategy, facilitation and negotiation workshops for many organizations and university executive programs. He has facilitated dialogues with the Dalai Lama, and with many multi-national corporations, non-profits and government agencies around the world.
