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Kevin Eikenberry is a world‑renowned leadership and remote‑work expert, bestselling author, speaker, consultant, and coach, and proudly serves as Chief Potential Officer of The Kevin Eikenberry Group, which he founded in 1993. With roots on a Michigan farm and a B.S. from Purdue, Kevin learned early lessons in values, work ethic, and trust. He's co‑founder of The Remote Leadership Institute and creator of Signature programs like From Bud to Boss and the Long‑Distance Leader series. Twice named by Inc.com as a Top 100 Leadership Expert, and recognized by Global Gurus and AMA, he empowers leaders to turn potential into impact. A storyteller at heart, Kevin inspires audiences to embrace learning as play.

 

In this episode, Jason and Kevin discuss:

  • What it means to lead with gratitude in uncertain times
  • The core concept behind Kevin’s new book Flexible Leadership
  • Why rigid leadership styles are becoming increasingly ineffective
  • The danger of over-identifying with your leadership "type"
  • Practical ways leaders can flex and adapt based on context

Key Takeaways:

  • Leadership must evolve to keep pace with a rapidly changing and increasingly complex world. What worked yesterday may not work today—adaptation is no longer optional.
  • Flexibility isn’t about compromising your values—it’s about staying rooted while shifting your methods. Just like a tree bends with the wind but stays grounded, effective leaders adjust without losing their core.
  • Locking yourself into a single leadership style can limit your effectiveness. True growth comes when you move beyond your default behaviors and respond to what the moment truly requires.
  • Engaging with your team on a deeper level is essential, especially in uncertain times. Trust and collaboration flourish when leaders listen, involve others, and stay open to feedback.
  • “It depends” can be a leadership superpower. Taking a moment to assess the true context before acting leads to wiser, more impactful decisions.

“We have to be able to think differently about how we lead in any given moment—especially when it challenges our comfort zones, past experiences, or auto-responses. We must move beyond those defaults to lead in a way that fits the moment and gives us the best chance of success, even if it’s not what we prefer, are used to, or feel comfortable with. That’s what flexible leadership is—going beyond our auto-responses.”

 - Kevin Eikenberry

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Kevin Eikenberry- Flexible Leadership

Hello and welcome everybody to this episode of The Insight Interviews. I've got a guest today that, you know, I've interviewed hundreds of people now Kevin, and I don't know, there's a handful of times that it's been like, I don't know that we're competitors, but we're kind of in the same industry, and we do the same thing. I think we help different people, and I get excited that couple times a year when I interview people like you, to rub shoulders with a like-minded professional that's helping people in the leadership space, and so, my guest today is Kevin Eikenberry. Kevin is the Founder and Chief Potential Officer of the Kevin Eikenberry Group, which is a Leadership and Learning Consulting Company that has been helping organizations reach their potential since 1993. ‘93 is when I graduated from college, Kevin, so, you've been doing that quite a long ways.

We just won't comment anymore about that, Jason.

Well, but I’ll tell you what, here's the next part of my intro, which I really found interesting, because there are people that might be further along the road than I am, and when they list their accolades, oh, they're from the 80s and the 90s and the early 2000s. No. Well, that's actually not the case for you. For instance, Inc has named you the top 100 leadership and management experts in, not the country, but the world and all kinds of different awards like that, and these are recent awards. And so, I just want to say, yeah, you've been doing this a long time, but you're doing some really cool things today. Very innovative and creative, and may I say flexible things today. So, Kevin, welcome to the show, my friend.

Jason, it is a pleasure to be with you. And here's the thing, let's just get this out on the table, we're not competitors. There are so many people, including probably everyone who's listening to us that knows that if their leaders are more effective, their organizations will be more effective, and so, yeah. So, we might deliver some of the same kinds of services, but it's not like there’s a limited number of possible clients, right? Like, I live in an abundance mentality, and I think that clearly applies here. So, I would see us more as colleagues than competitors, even though that might not be true on paper.

You and I very much think alike, which I think we figured that out before we hit record, but I was in corporate America, in the mortgage industry, for 21 years, and I would call my direct competitors, you know, the top competitors in my region, and they would all be like, hey, I'm not looking for a job, I'm good. I'm like, dude, I'm not, I'm not calling you to recruit you. Let's go have lunch. Like, you might have some things that I can learn from them, and by the way, I'll teach you everything that we're doing, as well. And man, I had some of my closest, which really were competitors, they became close friends over the years and still remain that way. I just, I like rubbing shoulders. Let's share ideas together. I think we're better. And so, hopefully today is one of those days. So, I do have an opening question for you before we get to leadership, before we get to some of the things that you've done, some of the books that you're working on, and strategies that you have, but towards the beginning of every episode of the Insight Interviews, I just like to ask people, to get us facing in a particular direction, who or what, Kevin, are you especially grateful for today?

Well, that's a long list. I mean, I'm grateful for my Lord and Savior, I'm grateful for my family, I'm grateful to my team, I'm grateful for our clients, I'm grateful for the opportunity that I have, Jason, to do the work I was put on the planet to do. That's a long, long list.

You mean, we could probably talk for half an hour just on that topic? Is that what you're saying?

We could, but that's probably not what everyone else wants to hear. But, let me say this to everyone who's listening. If you haven't asked yourself that question today, do it. That's an important question and we have a day in the United States every year called Thanksgiving Day, and I'm like, it can't just be a day. It just can't be a day. A number of years, and we started this during COVID, we did something called a 45-day gratitude challenge, and you had no way of knowing that you when you asked that question, but we built a process, and we help people give them their 45 days’ worth of prompts. We had a bunch of other stuff that happened during these 45 days. A virtually done sort of blended learning sort of thing, and we did it for like, three years, and it was a great privilege to do it and to help people really think about that question, because, you know, when our heart is full of gratitude, it doesn't have space for a lot of other things that impede us, like worry and anxiety and frustration and all the research says that gratitude is one of the best things that we can do for ourselves.

Yeah, right on. Well, it's one of the main reasons we ask it first, to be honest with you. And, you know, you mentioned Thanksgiving. The week before Thanksgiving, and we've done this three years in a row, and we're already scheduled to do it this year, we take clips of all guests on the show and the answers, and we kind of run, you know, I don't know, a little test of the week before Thanksgiving.

That’s cool.

I tell you, man, it has brought tears to my eyes at times listening to that. So, anyways, thank you for answering that question, and I just love the footing that it gives us as we enter into our conversation today. Leadership, really big topic. You've written books. It seems like when I looked at your profile, your website, the books that you've written, it's almost like you're in this coaching chair or speaker chair and looking at leadership from different angles. And your latest book, “Flexible Leadership” is something that, I don't know. I haven't read the book, and I don't want to act like I have, but give us the big idea of the book. Tell us how it came about and then I just feel like we're going to go in all kinds of different directions from there.

So, I'll ask everyone who's listening a question. Are you leading the same way you were five years ago? If you are, you are like most every other leader on the planet. A lot of things have changed in the world in the last five years, and I'm guessing all those changes have not brought the world closer to your personal approach to leading, which means, however effective you were five years ago, if you're doing it the same way today, you're less effective today. Flexible leadership is the idea that we need to be grounded and consistent and stable on a number of things, like our principles, the principles of human dynamics, group dynamics, leadership, we need to be stable and rooted and consistent in those things, as well as our values and our purpose, but we must be willing to flex our approach. You know, if you look at a tree, it's rooted and it's stable and it's consistent because it's rooted and yet it's also flexible. So, a lot of times people will say, well, Kevin, flexible leadership sounds like a good idea, but aren't I supposed to be consistent? And I say, yes. Both are true. So, one of the big ideas of the book is that the world is much more of a both/and place than an either/or place, and so, we have to start to think in a world of more uncertainty and complexity, we have to be able to think in different ways about how we need to lead in a given moment, which might be different than our comfort zone, our past experience, our auto responses. We have to get past that so that we can lead in a way in that moment that what is required or needed or gives us our best chance of success, not necessarily what we like, are interested in or are comfortable with. That's what flexible leadership is. Going beyond our auto responses.

Yeah, that opening question that you gave to the question that I asked about, are you leading the same way you did five years ago, that's one that I think can hit people between the eyes, because there's really great leaders out there that have been doing great things for a long time, but, man, since the pandemic, I mean things, and even if there wasn't a pandemic, you know, it would still be different today and what worked yesterday may not work today.

Yeah, I think that's really important, if I can just stop you there for one second, that's a really important point. Like, oh yeah, Kevin's talking about the pandemic. Well, I'm not. I mean, that actually makes it kind of an obvious question to ask, but I could have asked that question five years ago, and I can ask that question five years from now, and the timing that I put on doesn't really matter, right?

Right.

It happens to be that as we're having this conversation, we were about two months plus into lockdowns and all that stuff, but the question isn't a pandemic question.

Yeah, understood. Understood. Now, when I hear you talk about the analogy of a tree with the foundation of the roots, and you call that maybe those are principles or maybe values, so it was a word people might use.

Yeah.

But then the trunk of the tree, and I’m looking at a tree right now as I’m talking to you right now. It has the ability to remain flexible, and it gets stronger as the wind pushes against it, and it does different things that makes it stronger, and so, I get the analogy. Meaning, I'm shaking my head, I hear you, I get you. What are you seeing right now out there in organizations, maybe when you're in a boardroom, or when you're in that workshop arena that you and I are both in often, and you're around the table of the decision makers or the stakeholders, and you ask that question, and they go, ugh. What exactly are you seeing the responses are? And then, I'm assuming not all great responses or responses that are working for the organization right now. And then a follow up question that would be okay, what then? What do you end up doing about it?

Yeah, well, there are some people that say, yep, pretty much, right? I am. Okay. So, what I'm really trying to do when I ask that question is number one, to get people to think, and number two, to get a sense, if it is in like a workshop setting, to your point, to start to understand more about people's mindset, right? Because here's one of the traps that we fall into. And, well, I'll just state the trap. Here's the trap. We have all, everyone who's listening, pretty most leaders on the planet, I suppose, at some level, or certainly, many have taken some sort of assessment. Sometimes they've taken many of them. They've taken a Myers, Briggs, they've taken a DISC assessment, they've taken a Strengths finders, they've taken a colors, animals, they've taken all sorts of things, right? They've taken a thing that says, this is my leadership style, not just my communication style, like we've done those things.

Sure.

And those things are useful until they're not, and here's when they become not useful. They become not useful when we take the ideas in the model and translate them into our identity. See if I say, well, you know, I'm trying to be the same leader I've always been because I'm a facilitative leader, well, first of all, there's absolutely nothing wrong with being a facilitative leader, but if that's what I'm calling myself, if that's how I'm describing myself, that's my identity, there's no place for me to move. If the context of a situation would serve us better, I, the team, our organization better, if in that moment I wasn't facilitative, but I was decisive, I'm not going to be decisive, because I've decided I'm a facilitative leader. And so, the idea of being flexible is being able to identify context enough to say, what might I do? And sometimes, whatever that identity is will still be just fine, but not always. But the thing is, once we've said this is who I am, then it's very difficult for us to do something different. Because it's one thing to try to change a habit, it's another thing to try to change your identity. So, it's really important, and that's where we that's where so many leaders get stuck, because organizations have invested in these kinds of tools, and all of these tools have great intention, and all these tools have great value, and organizations have invested in them for those reasons, and then we misuse them, misapply them, mis train them to our ultimate detriment. And in a world that's more uncertain and complex than ever, that's becoming more detrimental all the time.

Yeah, so I'm still nodding my head, because I hear all that, doesn't matter if I have an issue with it or not, but I don't. I am nodding my head to that. Obviously, anonymously, but do you have a story that, you've been in that situation and you've given those examples, and then they go, okay, yeah, Kevin, that's us, you just described our organization, so what do we do?

Practically speaking, data is where we all can start. Here’s where we all can start, and everybody will know exactly what I'm talking about. Someone comes into your office virtually or in person, right? They come into your slack or your team's channel, they come into your text message, they walk into your office, whatever, and they ask you a question, or they're wanting some advice, they're wanting counsel, they're wanting a decision and many times you give them a decision. We can have a conversation about that. But there are times when in the moment you say, well, it depends, or in your head, when you're deciding on something, you say, well, what I should do depends. When you say it depends, if you stop and say what does it depend on and then consider those components, really what you're doing then consider the true context of the situation. When we hear or say it depends and then stop and consider what it depends on before we decide, we're being a flexible leader, even if what we end up doing is what we might have done naturally anyway, because now we've considered the context. When we think about flexible leadership, it's intention plus context plus what we call flexors and we can talk about those if you want, but the idea is that we've got to recognize that being flexible is important, and then we've got to look at the context of our situation, the simplest one being It depends, what does it depend on and then, how do I flex based on that?

Yeah, you answered the question directly. It’s just more thoughtful, more deliberate, more consideration, context. Yeah, flexors, talk to me about those. What are those, man?

Well, I hinted at one already and they are about an idea that usually we think about two things as “or”. I should do this, or I should do that, when really, they are symbiotic. So, I hinted at it, although I wouldn't necessarily call this a flexor, but the idea applies here. Should I be consistent, or should I be flexible? But let's take another example. Should I give positive feedback or corrective feedback? Well, the right answer is yes, and it depends yes on the context, right? Now the thing about a flexor, and in the book, we talk about 19 different ones, and the number of them is somewhat irrelevant to the point, because here's the idea. If you put those two things on a continuum, what is almost always true is that if we lean too far in one direction or the other, it's not going to get us the best results.

That's right.

And our style, our habits, probably lean to one side or the other. And so, if you're a person who tends to lean toward giving positive feedback, awesome. You're in the minority. That doesn't mean there aren't times you need to be on the other internet spectrum, or leaning in the other direction, which might not be what's comfortable for you, may not be what you like to do, might not be sort of how you define yourself, and yet, that's exactly what this situation required. That's being flexible. That's recognizing that both of those things are true. The far extremes at either end are not likely helpful.

Yep.

Here's another example. Someone comes in as a new leader in an organization or a new leader of a team, and I've asked this question of 1000s of leaders. What are the mistakes that new leaders make when they show up, whether they're brand new as leaders or just brand new to this team? And I hear these two mistakes almost every time. I hear a lot of mistakes, but two of the mistakes I hear are they make too much change too fast, and they don't change anything.

Both ends of the spectrum.

Both are mistakes. At the end of that flexor, both of those are mistakes. Now, as individual leaders, you have a tendency that leans one way or the other in that and so recognize the tendency and recognize that you need to be able to flex based on the context. That's the difference. Maybe I need to express a little more urgency with the team right now. Maybe I'm a person that loves change and is fast paced and wants to keep us moving, but in this moment, that's not what this team needs, or I'm going to overwhelm them if I do that. So, even though that's what I'd like to do, I need to do something different right now.

One question that I want to ask is what are you seeing the greatest challenges in leadership? I feel like I've only known you for 20 minutes here now, Kevin, but feel like I can almost answer that, which is, you know, today's leaders, just as information ramps up and technology ramps up, and the world changes, and I know that in every period in history, we've always felt that that's the case. We're just we happen to be in this part of history where we definitely feel that that that's the case. What's the greatest challenge? And it sounds like this flexible leadership idea may be the same solution to the challenge, but I'm still going to ask it anyways. What are you seeing is the greatest challenge these days?


I think the uncertainty and complexity, and I really actually say complexity. The world is more complex on almost every level. I had someone say to me recently, and they were right, that we can all say that the world's more uncertain than ever, and yet we've only ever lived in this time, so really, that's kind of what you were saying. We don't really have a perspective about that, but I think it is safe to say that it's more complex than ever.

Yep.

On a geopolitical framework, on a geographical framework, on how we do work after the pandemic. We could have a long conversation on that, if you want. Like, how society thinks about work is drastically different than it was five years ago.

Yeah.

It just is. And that change happened overnight, where the last time that that changed, I could take you back 70 or 80 years, and those changes usually take about 80 years to come full circle, and this one went from about 10% to 90% in two weeks.

Yeah, that's right.

We would have gotten where we're headed now, but it wouldn't have been for another 30 years.

Right.

And we would have had time to evolve to it. So, like, that's a huge thing. So, we talked earlier, it's not just about the pandemic, and yet, that's a huge thing. And then we've got things like AI, and we could go on and on. So, like, there's tremendous amounts of complexity. And you know, you and I are generally of the same age. We had a little conversation earlier about the difference in our age, but fundamentally, when we both went into the workplace, here's what was true: best practices, reign supreme. Process Improvement was where it’s at. Like, there are clear causes and effects, and if we take those into account and we build strong processes around them, and we have best practices most of the time, we'll get better results. All of those things are still true today, some of the time, but not all of the time, and yet we're leading and working and acting as if that's still the way the world is, and it's just not. There are far more things that are unknown and unknowable than there used to be, and so, recognizing that fact and then leading differently in that context makes all of the difference.

If you're in a cocktail party setting and you've got a leader that you've just met, and because you're engaging as you are, and let's say the leaders is similar, within 10 minutes, you guys are having a deep conversation, and he or she says to you, hey, I haven't done any training, I've just worked my tail off. I've got this organization, but Kevin, I'm just having the hardest time I've ever had because of the world's just changing so quickly, and it's complex and whatever. And I know the answer is it depends, but just for kicks and giggles, as we're talking right now.

That is the best consulting answer of all time.

Yeah, of course. Are you kidding me? I use that with my kids, I use that with my clients, I use that with our team members. Come on. Of course. It's my buffer between whatever we're going to decide and whatever, but it's also the truth, right? It depends.

It is, yeah.

But that person asks you, you know, after kind of going through that preamble, and I know there's no magic buttons, I know there's no silver bullets, but what do you suggest I do right now to just shake myself free of this rut that I'm feeling that I'm in?

Remember that it's not about you. Leadership is about reaching valuable outcomes with and through others, and that's my definition. There's 100 definitions leadership. Many of them are great. That's mine. By the way, a lot of people's definitions of leadership are somehow about the leader. It's not about us. Leadership is about reaching valuable outcomes, goals, objectives, strategies, sales, whatever. Reaching valuable outcomes with and through others. It's not about us. Now, how we show up, the conversations we've been having today, Jason, are absolutely important. Like, how we show up makes a difference, but it's only in the purpose of serving outcomes in others.

Yeah, yeah.

And so, the thing I would say to that earnest and overwhelmed leader would be, it's not about you, and you probably need to lean into your team more, not dump on them, but engage with them and have real conversation in real dialog with them and listen more to them. Like one of the things I tell leaders when they first move into a new role is the first thing you should do is go on a listening tour. You should go listen to everybody on the team, perhaps stakeholders too, depending on the role, but you should go talk to everybody and with the goal of saying very little, asking a few questions and both mostly just taking notes. There's all sorts of good reasons for doing that, and I would say that anytime a leader really feels that moment of overwhelm, of, I don't really know where we need to go, engage your team, because you have blind spots. They see things you don't see and if you do those things, you will build your team, you will build trust, and you'll find better answers.

Yeah, thank you for that. As I listen to you, I’m thinking of just so many clients, former and existing, colleagues that probably fit in the boat that I described to you, and I also think of just some guests on this podcast that have stuck out, and some of our clients. The ones that run the show, call it President, CEO, whatever, and they're the most relaxed ones, and I see the countenance. The happiest ones are the ones that are like, hey, man, I just hire the best people, and I let them do their thing. Those are the ones that it's not about how great they are, the idea that they had, or how hard they worked, but it's all about them, being their team, and so, yeah, I think most people that just heard what you said would go, yeah, that makes sense, I agree, but down deep, are they really living out their leadership in that way? And my observation, Kevin, is the ones that do, boy, they're happy, they're easygoing, yeah, it's cool. I’ve had many leaders tell me, when I'm in the room with my colleagues and the people on my leadership team, I'm dwarfed in the way of intelligence, skill set, leadership skills or whatever, but they've done something where they've assembled this great group of people, and they really take to heart what you just said, which is, you know, yeah, it's not about them. So, I just appreciate your answer there. What are you most excited about these days? As I look around the landscape, man, I see people kind of with their heads down, kind of a little downtrodden. There are some people, but you strike me as a person that is probably excited about a few things, whether it be in industry or in business or leadership. What excites you these days?

Well, it is my countenance, and is sort of my natural proclivity, for sure. And I want to say something here, and what I'm saying is not political, okay? Is it is absolutely not meant to be political. Are there problems in the world? Of course there are. Sure, there are. But if you look at the history of the world, there's always been problems, and if you look at the progression of human civilization, what we have accomplished is amazing, and what we will continue to accomplish is also amazing. Are there things to be worried about? Of course there are. Should we be thinking about those things? Sure, we should. But should we look at the world into the future as if it's full of clouds and dismay? I don't think that serves us, and I also don't think it's accurate. And you know what? We are in the business, in our organization, the Kevin Eikenberry group of helping as many leaders as we can, be the best that they can, because we know that's the best way to make the world a better place, because we know that nothing positive happens without someone leading. So, I get excited about helping leaders grow, because that's helping make the world a better place. Whether that's on a team, whether that's at a micro level, whether it's on a macro level. And so, I'm very excited about the future. I just read today that there are 560,000 new millionaires in the United States since, I don't know, five years ago. That's pretty darn cool. I'm not saying that dollars are the only way we should measure things. I'm not saying that, but I'm saying that's pretty cool. It's a whole lot better than saying, well, there's fewer than there used to be.

Right on, yeah.

And if you're the person, you say, well, yeah, it's just inflation? Like, stop. Yes, that's true, but let's not throw cold water on something that says that people have made good choices, they've done positive things, and they've done one of the things that most people think about in life as valuable, which is to create the ability to care for themselves and their families moving forward. Like, how is that a bad thing? It's just not.

Yeah.

And that's just one of 100 examples that I could give you. It's the one that pops into my head because I read it like an hour ago, right?

Sure, sure.

And so, I get excited about a lot of things. I'm very excited about this new book, “Flexible Leadership.” I think it's the most important thing I've written, and I'm excited about having the chance to talk to you about it. I'm excited about how we can share that in the world and hopefully help more leaders get even more effective, be more confident. In this uncertainty and complexity, the way to navigate it is to know that I don't have to know what to do, but I know that being flexible is part of the solution, and if I'm confident and have a bit of a roadmap on how to do that, I'll be more confident, and if I'd be more confident, then I could build my competence, because those two back and forth and reinforce each other. Confidence and competence.

Is there anything, either about the book or any topic, Kevin, that I have not asked you, that you just kind of secretly wished I would have asked you?

Well, you didn't ask me about my kids. No, I'm just kidding. No, I'm teasing.

I did in my opening question.

You did. You did when we talked about gratitude, that's for sure. Listen, I would say that if you found any of the stuff that we talked about useful, then you can find me on LinkedIn. You can go to our website. KevinEikenberry.com. I would love to have you do that, but I want to give people two specific things they can do, Jason, today. One is, if you go to KevinEikenberry.com/Flexible, you can learn more about the book and you can get a sample chapter the book. And if you go to KevinEikenberry.com/Gift, I have a free gift for you. So, we were just talking about confidence for a second, and so, I created a master class a couple of years ago that we sell every day for $79, but you can get it for free. It's a masterclass on building the confidence in yourself and others, and it's your gift for having joined Jason and I today.

Very kind of you, my friend. Your proactive approach, you skipped my last question, which is, how do people find you, because I have a feeling people are going to want to find you. But you're a pro. Not only are you're a host of a few shows just like this, so you kind of know the drill, so I appreciate you getting there. I do have a sneaky suspicion people are going to want to reach out to you. I know that I'll be getting the book, and I'd love to see your master class as well, so, I hope people do take advantage of that, because, gosh, just really great information and just spending time with you today, I feel improved. I feel better. I don't know that I even needed that today, but it's been a lift. So, thank you for your time, your energy, thanks for what you're doing out in the world, Kevin. I know that I personally appreciate it, and I have a feeling that I can speak on behalf of my audience. We all appreciate it. So, thank you very much, sir.

Jason, thanks for having me. It was absolutely a pleasure. Thanks again.

Oh, well, that was such another good interview. At least I thought so. A good guest. Kevin Eikenberry. Here's some of the insights that I had. Boy, just first what he was grateful for. He just boom, went right into it and was very clear on the things that he's thankful for, and that always fires me up. And then when he talked about leadership, you know, one of the most important things that I think he said during our conversation, or at least to me, was leadership is not about you. And then he explained that which I really appreciated. And just his sense of abundance, as opposed to scarcity, being excited about the future, even in the midst of all the hubbub or whatever is going on that's not so good these days, he just remains optimistic, and just really went through a lot of good things that are happening these days. And one of his last quotes that I just really appreciate was being flexible is often part of the solution. So, those were my insights today from Kevin Eikenberry, but as we say at the end of every episode of The Insight Interviews, it doesn't much matter what my insights were, but dear listeners, what were your insights?

                                                                                                             ---

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