Defining Leadership and What Makes for a Good Leadership Coach
An interview with Bob Stapleton of Live Oak Leadership, a leadership development executive coaching and human resource consulting practice.
Cris Cohen: What made you decide to make the leap into coaching after being on the corporate end of things for so long, where you managed large numbers of people to switch into something where it’s just you in a very one-on-one situation?
Bob Stapelton: It was really an easy decision for me. When I left corporate, I knew I was going to continue to do something. So, I wasn’t going to hang up my business suit and jump on a golf course or learn how to play pickleball. I knew that I had a lot more to give, and I had a lot more to do, and a lot more to learn.
And so, when I looked at those things in my career that I enjoyed doing, and if I looked at those things in my career that I felt that I was pretty good at, it made every bit of sense to look at pursuing coaching.
If I look at my work as a leader, whether I’m managing a store or a district or a function, a key element of my leadership was my coaching.
And if I look at my background in Human Resources (HR)… it’s not always the smartest thing to do, but people have a tendency to look at HR for the answers, right? We’re the ones who are the conscience of the company. And while a coach doesn’t tell people what to do, we’re often there to help guide people through a decision.
So, I took all of the things that I loved most about my career, and that I felt that I was pretty good at. And I knew that, as a coach, I could still enjoy those things going forward. Knowing that I had to start over. Because there’s being a coach in name. And then there’s having a modality and credibility through the certification process.
Cris Cohen: Yeah, although I’ll say, and this has been a pet peeve of mine, at least you’ve got the experience. I’ve just come across so many “coaches” online who… that’s the only thing that they have done. And you just want some sort of proof of purchase that they’ve experienced the trenches in the real world.
So I, personally, like that aspect. You’ve been in the position that your clients are theoretically in. And so you’ve a) had success in that area, and b) you can really speak from that perspective.
Bob Stapleton: I call it empathy. If you’re dealing with a totally crazed executive, who is crazed because they’ve got a ton coming at them — challenges, dealing with the pandemic, and how it’s shifting their business — having been in those kinds of situations (not a pandemic, but other circumstances), I get that I may not be the most important person in their lives, or our work may not be the most important element of what they have going.
So, I think it gives me a perspective, at least of understanding kind of where a person is based on where I’ve been. But at the same time, coming at it without judgment. I can’t assume that my experience and how I approach things would be how the person across from me is. But yeah, it’s helpful.
Cris Cohen: And you break it down. What you offer on your website are three different kinds of coaching: Life coaching, leadership coaching, and career coaching. First off, how often are those distinct silos and how often do those just kind of bleed into one another?
Life Coaching
Bob Stapleton: I’ll start with life coaching. Because life coaching is in the context of a person and what they want. So, it’s kind of an open agenda. It’s a matter of fact, in life coaching, the client comes with the agenda. I don’t, as a coach, look at them and say, “You need to do more of this or less of that.”
They clearly come with an openness about what they want in their life. If you’re a leadership coach, it’s the same thing. It’s life coaching, but it’s in a context of who they want to become as a leader or how they want to influence and show up in the world.
So the topic or the subject, if you will, is in the context of being a leader. But it’s life coaching.
I typically won’t go into it, but I can tell someone how to write a resume, how to do a good interview, how to network better than they are now. But career coaching isn’t job search coaching. It can be a part of it, but it isn’t. And if I think about life coaching, it’s really coming at them as the person coming into the relationship, the coaching relationship, through the context of who they want to be professionally.
I say that I never thought that being a life coach, because I wasn’t a life coach until I became certified. I now see that being a life coach with the discipline and following their methodology really enhances my capabilities as a leadership coach and as a career counselor.
And ultimately, going back to life coaching, the person who shows up as a whole, fully resourceful, capable person…
Oh, by the way, they also have to have aspirations of how they want to lead in the world. And I don’t mean lead a store or an organization. How they lead their life.
So, there’s a lot of overlap. But the foundation, if you will, or the secret sauce that is a part of every part of my coaching is life coaching.
Expanding the definition of leadership
Cris Cohen: That’s really interesting. I’ve never heard anyone express leadership coaching like that. Usually people just use the typical, direct definition of “You’re leading a group of people, you’re leading a company, etc.” I find it rare that anyone comes at it from the idea of self-leadership or exploring the different ways that that particular term can be used. Have you always approached it that way, or did that kind of evolve?
Bob Stapleton: If I think about my life, as a leader, or as a manager, or running a function, I always saw the people that I worked with in the context of them being kind of the stewards of their careers, the stewards of how they want to show up.
So, I see them as someone who works for me or a key part of my team. But I also know that person has a life beyond the business. And they perhaps lead as a family member, as a parent. So, I think I’ve always assumed that inherent in all of us, regardless of what we’re doing, is the sense of being a leader. To me, it’s “How do I show up in a way that I represent the best part of me? And how do I show up so that I can help whatever situation I’m in? Whether it’s me, as a teacher, me as parent, me as a son, me as a father… how do I want to show up in a way that I can be a good influence?”
And at the end of the day, that’s really what leadership is in my opinion.
What makes for a good client
Cris Cohen: And as you alluded to before, you don’t come in with any preconceived notions about who you’re working with or what they want to accomplish. To me this begs the question: What makes for a good client? What do people need to bring to the table personally with you, so that you can really hit the ground running with them?
Bob Stapleton: That’s a great question. And what I would tell you is: It’s being fully in. It’s having a stake in the outcome, seeing the work as important. And it’s all kind of inner driven, a passion to accomplish something that they have never, prior to this, been able to accomplish and have a strong passion and desire for that. That is the ideal client.
That person makes my job so easy. And that isn’t always the case, particularly in a corporate environment. People don’t go to their boss and say, “I want a coach.” The organization goes to them and says, “We think it would be good for your development to have a coach.”
The first question is usually, “What’s wrong?” And oftentimes, if I end up with a potential client that comes in a little bit apprehensive or wondering, “Why am I here? I know my boss wants me here, but why am I here?”, we can work with that in the first meeting. But at the end of the day, I can’t in good conscience be a good coach for someone who isn’t bringing their passion and interest and curiosity into that relationship.
And that kind of goes back to: Don’t come in with any preconceived notions. That’s the hardest part of coaching.
Because as human, particularly in Western culture, we’re always judging. We walk up the aisle in the grocery store, we look at people, and we judge them. We don’t consciously, but we kind of put people in categories. And as a coach, you can’t do that.
Helping those who have no direction
Cris Cohen: That’s a good point that. That must take a bit of work on your part, just being able to come in and say, “Okay, this is a blank slate.”
Although, I would think a lot of people come in not necessarily knowing which road they want to go down. Especially in today’s times, with the pandemic and all the madness that has been 2020, it would seem like people would come to you with a distinct lack of direction, not really knowing what’s even possible anymore. How do you — without getting specific about individual people — how do you help them with that?
Bob Stapleton: I have a good example. Oftentimes, I’ll work with someone who is right out of school, or a year out of college. And they don’t have a clue what they want to do. They’re lost. And they have either a side hustle or what I call “a survivor job.”
And so, they will bring me into their lives, and the assumption is that I’m going to have the answer. Or the assumption is that I’m going to give them a number of assessments, which I’ve got in my toolbox, and that somehow, through those assessments, the answer of what is the end game of their life that they want to pursue (will emerge). And if any coach ever tells you that that exists, run.
So oftentimes, in the first session, which is complimentary, I just want to give people the opportunity to know how I think and how I approach coaching. In a situation like what I’ve described, I will clearly say to the person, “You and I are going on a journey. And right now, I totally accept the fact that you’re like, ‘I don’t know what’s next. I don’t know what I want to do.’ And that’s fine.
“Ultimately, through conversation, questions, and curiosity. We’re going to figure it out together.”
Usually (there is) a little bit of disappointment. “You mean, you’re not going to tell me what to do after two meetings?”
I say, “If I were to do that… 1) Chances are, I’ll be wrong. 2) It shows such a lack of respect for you. That somehow you don’t know enough about who you are and where you’ve been that you need me to tell you what to do.”
That is an example, but it applies in so many different aspects of coaching a leader.
“So you’re a coach. You’re going to tell me how to be a better leader?”
Hell, no. It’s getting people to see that my job isn’t to tell them what to do or to fix them. My job is to be almost like a Sherpa or someone who’s got one of those miner helmets with a light. And I guide them through, asking the right questions, being curious, and going places with them that no one probably would go, even people who are… whether it’s a parent, whether it’s a significant relationship. Part of it is the courage to have the conversation that ultimately unlocks the door for him or her.
Cris Cohen: And it’s interesting that you say that you work with a lot of people who are one year out of college. This is something I’ve talked about with friends a lot. I’ve had some great education myself, but I don’t necessarily believe that it gave me the tools for figuring out my path post college.
Also, I got pretty good at school itself. You learn what is expected of you, what you need to accomplish. They set a path for you. And then you get out into the real world and suddenly you’re somewhat ill prepared for it.
I’m wondering, is it even possible for schools to give people this kind of direction? Or are they just not necessarily built for that?
Bob Stapleton: I think primarily schools that teach you a vocation — so if it’s business school, law school — there can be a lot more in the process of having people go through an exploration of what may be the next step. Most don’t. And those that do are too formulaic. I think they can do a better job here.
People know a lot more than they think they know
So I’m going to bring you behind the curtain. And this is where I go from being a coach and I get curious to tell you what my experience is. So, I’m kind of consulting now, showing you what I think people should know about what you’ve described as “I’m out a year, and I’m lost, and I don’t know what to do.”
1) People know a lot more than they think they know. Always.
They can look at their lives and say, “Here’s what I enjoy. Here’s what I hate. Oh, I love that. I hate that. Here’s the kind of situations I’d like to put myself in.”
People think of work as kind of the construct of a role, a job description, or a position inside a company. And that is one perspective. But if I look at someone who is in career chaos, and doesn’t know what’s next… They know more than they think they know.
2) It’s not easy.
And what do I mean by that? I think people look at examples. They’ll say, “Gosh, I read this thing. I saw this on TV about this person who said, ‘At the age of five, I knew I wanted to be a doctor.”
Those people are so rare. They’re like, literally, 0.00001% of the world. So, people see that and they say, “What’s wrong with me? Why am I so lost?”
The bottom line is: For most of us, if we follow those things that we enjoy and that give us satisfaction or happiness or a sense of making a difference… If we follow that lead and look at what’s possible in terms of different roles, or different kinds of companies, or different industries, I tell people “You can’t make a mistake at this point.”
You don’t have to have THE answer in my opinion of “Here’s the industry. Here’s the job. Here’s the kind of discipline that I want to get into.” I see it as more of an exploration, where they try something. And if it doesn’t work, they pivot. But at the point where they pivot — one of our favorite words, right? — they have so much more data.
And to try to make a decision right out of school without a lot of data, other than the data looking in the rearview mirror… There’s a little bit of trial and error.
Another thing that people don’t really believe me, when I meet them for the first time, using the example of someone coming out of school. I say, “You know, chances are you can’t make a mistake at this point. So, take a deep breath. The decision you make with us working together isn’t going to be a make it or break it.”
Cris Cohen: But that’s funny because, back when I worked in the corporate world, inevitably during a job interview, there would come the standard question of “Where do you see yourself in five years?”
And my typical answer was, “When I was in college, the internet didn’t exist. So, I’ve given up predicting where anything is going.”
Our perception of reality is an illusion
And kind of along the same lines of what we’ve been talking about, you had a really cool line in your latest blog post where you wrote, “Our perception of reality is an illusion.” Which I thought was really quite fascinating. And I’m wondering, how much of your work with your clients is about changing their perception?
Bob Stapleton: I would say, if it’s not close to 100%, it’s at least somewhere between 90% and 100%. Because ultimately, it kind of goes back to our conversation around we’re all the architects of our life. We’re leaders, in the context of how we want to show up. How we show up is more often than not our perception of how we see ourselves, or how we see others, or how we see a situation. And, at the same time, there are other people’s perceptions of us.
So, we walk in with kind of our perception of how we see things. And then others, who know us or don’t know us, they walk into the situation with their preconceived notions of how we show up. It’s like being the youngest brother or the oldest brother. You have a sense of how you are to be. And the illusion part of it is: It’s all made up. We all make it up. The people who are judging us make it up.
And we walk in and say, “Okay, I’m the youngest person here. I’m the lowest, most junior person here. I better act in accordance with that.”
So, as a coach, my job is, through conversation, to have them see those hidden rules about who they’re supposed to be and how they’re supposed to show up, those preconceived notions. And then what I do, much like a mirror, is I put it in front of them and say, “You and I talked about your goals, your coaching goals. How do these perceptions measure towards you getting to that goal?”
Almost all of coaching is helping people see who they are, through their eyes, and asking the question, “Is that who you want to be? And to the extent that you have aspirations, how is it working for you?”
Am I speaking of too theoretical?
Cris Cohen: No, I don’t think so. Because I think it has to be a radical shift in how you think. And also, as you pointed out, a lot of people have more tools in their toolbox than they really realize.
So, I think that’s a misconception with coaching, that they come in and say, “Okay, you’re going to do this.” Something really down to the detail of, you know, “Do this 5 times. Do this 10 times. And then you’ll get to X.”
So, yeah, I can see how it would be a shift in perception. And that’s a challenging thing to explain.
Bob Stapleton: Yes. I mentioned earlier about modality of coaching. And there are buckets. Whenever you’re coaching someone, you have to have a sense, “What is the conversation I’m having right here with this human being?” And one of those buckets is perspective. Perspective is: How does the person see the world? How do they see the situation? It’s like when I talked about the first meeting and coaching. Their perspective is that Bob’s going to have the answer. And then we have to look at that. Is that really what we want? You want me to tell you? I might as well have like a crystal ball, right?
Measuring progress
Cris Cohen: And then, finally, so many businesses, so many people in the business world are obsessed with measuring progress in every field. How do you measure progress in the work that you do? Is it even possible to measure it?
Bob Stapleton: That is a profound and great question. Measuring progress is really important. I think it’s the dynamic that motivates us as humans. It’s a sense that we can find out where we are, where we want to go, and where we’ve been.
Measuring progress, while important, should only be seen through the eyes of the client.
Let me say that again. Because it’s kind of a radical thought. Typically, it’s the boss who measures the progress. But if I think of me as a coach… and this kind of goes with what I said earlier about coming in with neither a preconceived notion nor a judgment. It doesn’t really matter what I think. It matters what the person, the human being across from you, sees as progress. Because so often — we call it kind of self-regulating — if I don’t see someone making “progress,” I go into my head and say, “What’s wrong with me? I must not be a good coach. It’s not happening here.” Or “What’s wrong with them?” That will destroy. It’s the most toxic thinking.
And so, if I think about progress, it’s clearly in the eyes of the person who’s across from you, the client, and having them be able to see it. And this kind of slides back to perspective. Measuring progress is a perspective on how you’re doing. And I think the job as a coach, is to recognize and have the person see where they are through their own lens. Because as humans, we typically are pretty hard on ourselves. We don’t give ourselves enough credit. Where if we were thinking we want to shoot to the moon, or solve world hunger, that any progress short of that is failure. And that’s a perspective, but it’s one that prevails too often.
