Guiding the Next Generation of Leaders, With Walter Yenkosky
The executive coach and former Marine joins Charlie Guarino to explain what good leadership looks like—in IT or any other industry
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This transcript has been edited for clarity.
Charlie Guarino:
Hi everybody. Welcome to another edition of Tech Talk SMB. Today I have as a guest, an operations executive and executive coach joining me, Walter Yenkosky. Walter is a Marine veteran who has spent a decade in the infantry before making a bold transition into the tech industry, where he then carved out a career in business consulting and nonprofit executive leadership. And now he’s founded his own consultant coaching firm where he specializes in helping mid-level managers and licensed professionals break through career plateaus and step into executive roles or entrepreneurship. Walter truly equips leaders with the tools to excel in strategy, operations and personal effectiveness. Now, you might be asking where’s the IT in that introduction, and the true answer is that it’s all in there. It’s IT. It’s any platform at all, any industry at all, because really, what makes a leader, in my opinion, is not stuck in one industry at all. So Walter, thank you for joining me here today. It’s so great to see you again. Thanks for coming to our podcast.
Walter Yenkosky:
Hey, appreciate the opportunity. Thanks for having me.
Charlie: Absolutely. Thank you very, very much. So I want to start by just asking something that you have on your LinkedIn profile, and right under your name it says, I’m guiding the next generation of leaders. In a nutshell, what does that even mean? I mean, it’s very self-evident, but expand on that for us please.
Walter: Sure. It doesn’t matter if you’re 20 or 50, it just matters. Do you want to lead? You don’t even need to have a leadership role. You just want to have the effect on other people. Let’s get you there. Simple as that.
Charlie: It’s interesting to me because when I first saw that, and maybe many people will think the same thing, the next generation of leaders, I think we might just assume, incorrectly apparently, but we might just assume that we mean that we intend or you intended perhaps somebody who’s maybe fresh out of college, the next generation, but you just said 20 or 50 years old, doesn’t make a difference. But how does that affect what you’re doing, be it a 20-year-old or 50-year-old so anybody can become a leader?
Walter: Absolutely. The skills, the techniques, the behavioral additions that everybody learns as they’re graduating from follower to leader, maybe into the executive roles, maybe they just want to be a leader in their technical field. It’s generally all the same, and mainly it’s interpersonal training, but they’re individuals in their 50s that go, “I need to make a change.” And they may not want a career change, they just want to role change in how they approach their own career.
Charlie: And they may have attended a real university or the school of hard knocks.
Walter: Absolutely. Does not matter.
Charlie: Does not matter. No. So I have to ask you then what, because this consulting company that you now have is still fairly new, but what inspired you to really get into leadership development as a career that you’re doing now?
Walter: Appreciate that. So I left business consulting because I asked the dumb question, “What’s our purpose here?” And the answer was to make money. I go, “Great, for what?” And they said, “To make more money.” Decided to retire. I’m not the guy who stays retired, apparently. Joined a nonprofit and operations. Half of my job is providing counsel to the executives within New York. When I decided it was my time to leave, I had to sit down for quite a while trying to define my own purpose. And I really found giving counsel, providing guidance is where I belong. And I said, “Where would that have the most effect?” And that’s with the individuals that want to achieve leadership roles or leadership skills, and I would counsel them and guide them to be those leaders they truly desire.
Charlie: It almost sounds to me that your own journey has made you a perfect case study, and it’s a point for anybody who you’re going to be working with after that. I mean, it sounds like you took a good hard look in the mirror and you came to this conclusion, and maybe other people who are in the same position perhaps, or even not, may come to the same conclusion that it’s time to become a leader or to get into leadership.
Walter: Maybe introspection is a critical tool for every leader to have, because if you don’t know yourself, how are you supposed to lead somebody else?
Charlie: What do you say to people who are thrust into leadership by whatever reason, attrition of upper management or anything like that? What do you say? Because certainly that has happened, it will keep happening. Say to those people who this is thrust upon them and they may not necessarily be the best fit or have the real interest or even the skillset.
Walter: That’s really hard. It depends on them. When I look at a coaching relationship, whether I have that conversation with somebody to see if they are coachable, some of the first questions I ask are, “What do you want? How can I help?” Many of them just want out of that engagement, especially in the IT field. They want to go back to the basement with no windows. That’s where they’re comfortable. Some want to break out of their comfort zone, become a phenomenal leader. Some were aspiring that from the beginning. So it’s truly, let’s understand what you want first and then let’s help you achieve that. If you are thrust on that involuntarily, maybe it’s time to leave, maybe it’s time to thrust it on the next guy. Maybe it’s time to take those reins and actually take advantage of the situation. But if it’s not what you want, you got to understand
Charlie: What you want. So if the ultimate goal from coaching, I guess is to the best possible outcome is to have somebody become a great leader, what are the metrics? What are the parameters? How do you define a great leader? Is that a fungible term? Does it mean different things, different people? What makes a great leader and what is a great leader in your view?
Walter: So solely in my view, there’s only one itemization of a great leader, and that’s, can you invoke followers to follow you? Can you lead them? That’s not directing where you tell them to do something that’s not managing, where you’re managing a process that they happen to be involved with. It’s, if you start walking down the road, will people follow you? One of the traits I actually found in my own life—he just retired and I’m sure I’ll send this to him later—retired Colonel Doherty out of the Marine Corps. I sat in his truck for seven months in Ramadi, Iraq, and not once, not a single time did he ever make a decision that was self over team. It was always the team over self every single time at his own detriment. That is a leader.
Charlie: Completely selfless.
Walter: Absolutely. You have to be, the team is the one that carries you. You’re no longer the doer, you’re the enabler of the team.
Charlie: That’s an interesting point, but leadership to me, my definition that I’ve read more recently to prepare for this conversation, leaders help make decisions or make decisions. And you hear leaders or the buck stops here.
Walter: Absolutely.
Charlie: But there are different components to that. There’s strategic. There’s tactical. Does the same person typically make all of those decisions, or should that be separate roles for those types of decisions?
Walter: It depends on the scale of the org. The smaller that you get, the more you’re involved in everything. As the small business owner would know, you’re the jack of all trades door of all things,
Charlie: Chief bottle washer, chief—
Walter: If you’re sitting in a Fortune 500 and you’re involved in both the strategy and tactics, something may be wrong. Strategy, as we all know, it’s the big picture. How do we get to where we’re going? How do we achieve the vision. Tactics is what are the individual tasks to accomplish the strategy? Again, it depends on the org, it depends on the layout of the org. It depends on what technologies you have in place to accomplish the missions.
Charlie: Now, you mentioned that colonel in the Marines and you said how selfless he was, and he was somebody who clearly had an impact on you, it sounds to me. Would you say that he and other people like him perhaps have strong emotional intelligence and are empathetic, empathetic towards their team? They understand the emotions of the relationship. You have a leader and you have a team and you need some empathy, certainly.
Walter: Absolutely.
Charlie: And should that empathy go both ways?
Walter: You can’t expect it though. A great leader generally has great empathy. He understands whatever organization you’re in, the skill of leadership has traits assigned to it. Empathy, EQ fall in there because it’s a people-centric role. You’re assisting an individual. I know on our pre-talk we were talking leaders lead people; managers manage processes, not people. So if the thing that’s fungible and manageable for you is the people, you have to have some level of emotional intelligence to go with it.
Charlie: And that’s industry-agnostic.
Walter: Industry agnostic.
Charlie: IT, healthcare.
Walter: Absolutely.
Charlie: Financials, whatever.
Walter: There’s a reason why absolutely phenomenal CEOs can jump between industries on a whim because the skill of leadership transcends. Its agnostic to any type of business they inspired.
Charlie: Do you think that somebody to have that level of command, and I mean that in the proper context here as a leader, I should say. You said just said that they can jump from one industry to another, but do you think that someone might be a better leader or perhaps better equipped leader if they have industry knowledge? I mean, how easy it is for a leader to jump from one to another without a lot of experience in that one industry? Or does it not seem to make a difference?
Walter: There’s a good book I recommend everybody goes reads. It’s called “Turn the Ship Around.” Essentially, a retired naval captain was assigned to a ship he knew nothing about. The team knew their individualized tasks better than anyone else. So if the team around you knows the subject matter, you can guide them and you’re just enabling them to do the thing. If you’re coming in as a leader on a bad team, it might be time to shake up that team. Maybe that’s why the last leader left because he allowed a bad team to form.
Charlie: An interesting point you got there, but certainly you can’t dismiss the idea of mentorship. I mean, hopefully a leader has the ability to mentor somebody, or am I going off track here? I mean, mentorship to me is somebody with industry knowledge perhaps, or, well, let’s start with that industry knowledge. If I’m mentoring somebody, I’m going to, in my particular case, I want to mentor them how to work better in the industry of it. If I went into healthcare tomorrow, I would be ill-equipped, I think, to mentor somebody in that space.
Walter: Yeah. So let’s pick that a piece a little bit. You as an IT industry leader decided to transition over to healthcare and wanted to mentor over there. I could see you mentoring on leadership. I could see you mentoring on the skills of it. I could see you mentoring those leaders on how it could be utilized in a healthcare environment. But I would also expect you to be mentored on the environment of healthcare because if you don’t understand how it operates, you can’t understand how your skillset applies. I mean, it is all-inclusive. Everybody needs guidance from somewhere. We all can’t be the subject matter experts of everything.
Charlie: Let’s localize this a little more to my orbit. And that’s the IBM community, IBM i community to be more specific. But there are many people who have been, let’s say, developers, perhaps developers for decades. And now they’re promoted and maybe because of just pure circumstances or their desire or as you mentioned earlier, it’s thrust upon them because they were the last man standing or nobody knows the system better than they do, and now they have to manage it, but they may not be able to manage. I have seen some people who’ve been put into that role and have failed because it’s a difficult transition. I mean, in my experience, I’ve seen some people, managers who don’t want to manage, they still want to be, they’re still developers and they can’t break themselves out of that mold. So how do you transition that successfully? Can you do it? I mean, I know you can because I’ve seen it done, but how do you do that?
Walter: It’s a shift in mindset. I mean, you really have to understand and internalize, you are no longer the doer. You’re an enabler, you’re an assister. You provide guidance. You can step in and do something called servant leadership, where they go, I have a problem, can you help me fix it? And you guide them through the fix that’s enabling them to do their job. The best possible thing for you to do is to make the environment so they don’t need you. You’re there to assist in help. They shouldn’t need you.
Charlie: Interesting point.
Walter: Again, we were laughing before this. Every operations, every coach, every therapist, every consultant should strive not to have a job. You should work yourself out of a job.
Charlie: Wow. I mean, sure, yeah. It’s a big world out there. I don’t think that will ever actually happen, but it is a goal, it’s a goal, I guess. Yeah. So let’s keep going then. You did mention 20-year-olds or 50-year-olds or anybody in between. But if you’re working with, if you’re coaching somebody, rather, surely there are some common rules that you’re going to adhere to regardless of who that person is. But certainly I would think if you’re trying to build a leader from someone who is literally in their 20s versus somebody who’s in their fifties, how do those two things compare to each other?
Walter: So just me, myself and my style of coaching, I try to get everybody to a baseline so that’s, can you manage your goals? Do you know what tasks are necessary to reach those goals? And can you budget your time to not only do your daily habits, but budget your time for those tasks for those goals? If you can’t do those three things, it’s a very low probability you’ll ever succeed in an executive role. Most executives that I know are very time-strapped, and they do these things. So for you to step in and just wing it, success is very limited. That’s not being said you can’t succeed on a lower-level leadership role, but I generally like to give ’em that baseline to let them see where the baseline is, and then we start coaching on how to succeed and how to grow from there.
Charlie: So that’s not exclusive to people come fresh out of college either.
Walter: No. If you start fresh out of college, you’ll just be getting 30 years up on the 50-year-old on developing these skill and making them habitual.
Charlie: That’s interesting. So let’s keep talking about being a leader. Surely every leader, every manager, every executive eventually is going to face a setback in their organization, whatever it happens to be, some crisis. And on the scale of these crises, crisis can be very small to very large. Is that something that can be taught or do you have to live through that experience to be better prepared for the next
Walter: Time? Regardless of how you are taught, you’ll never know how you react to a stimuli until the stimuli is applied. You can train an AI model, but you’ll never know what answer it’s going to spit out. Unless you’ve done it a million times, and even then there’s a percent chance it may change. So as you’re going through this, yeah, there’s lots of training out there. Your best results will come with experience. But yeah, somebody to help guide you along the way, whether that’s a coach, a mentor, a leader that you lean on, even your own team, they’re the ones who are going to get you through it. One of the things the military taught us, the team succeeds, the leader fails. So whenever there’s a success, 99.9% of the time, the team gets all the credit. You didn’t do the work. They get the credit. When there’s a serious setback or chaos, you are at fault that you never put the blame on them. You should have led them better. And that’s just the way I was guided growing up.
Charlie: And how do you know, I mean I’ve been in many IT projects, or several IT projects, hopefully not many, but I’ve in IT projects where you’ve had to reverse direction or make a major change in direction. Some of it of your own volition, some of it just external, budgetary perhaps, or people or project scale or whatever, or customers or some combination thereof. How do you properly manage those situations? Because truly that’s going to keep coming up time and time again. And how do you teach that skill to somebody to manage that? Or is that a teachable skill?
Walter: I think it’s a teachable skill. I myself follow something called intent-based leadership, and it’s a conversation with your team. This is our mission vision, this is the end result that I want to happen. Help me help you get there. Again, your team is the one doing it as a leader. So if it’s an IT project, you have some developers, some backend, some front end, some GUI guys, and you’re making this thing, alright, hey, the scope has changed, the client’s expectations have changed, whether budgetary or just stylization, we need to make this change. Let’s have a conversation of how it looks. Help me understand your specialty so I can present it to them so we can make this adjustment. You’re just relying on your team, they’re going to get you through it.
Charlie: And when you’re managing a project, it’s a series to me of short-term wins and also a long-term vision, I think, if I’m saying it correctly. But how do you balance how you find balance in that and how do you teach it to somebody to properly manage short-term? So I guess what I’m really saying is when you come up with a project, you want to grab low-hanging fruit as we always say, or what are the steps, because you have to manage both the short-term wins and also at the same time provide a long-term strategy. How do you instill that in somebody?
Walter: A couple different ways. One, fail absolutely fast. Every failure is a learning tool. You know what you shouldn’t do from that point on. Every win early, celebrate it. Celebrate the small wins, you will raise the morale of your team like nothing else. They will fight that much harder for you. But again, reiterate the strategy, the intent. If your team understands the end goal, they’ll get you there. They’ll get you there in ways you never thought possible. For example, random analogy, we’re going to ride a bike together over there and they go, why don’t we take the car? And you go, I never thought of that. The team will help you. More brains, more power. Throw another GPU on it, let’s try it.
Charlie: Another GPU, that’s great. You mentioned the term to me earlier and it was one that was interesting to me, but I’d like you to expand on it now. You said somebody who is so good at something, they’re really so good that you don’t want them or they can’t go into leadership. And the term you gave me and it stuck with me is unfire-able is unpromotable. Did I say that correctly?
Walter: Absolutely.
Charlie: Alright, so tell me about that. That’s such a great, I want to make sure I want to use that over and over again. I want to get it right. So unfire-able is unpromotable. What does that mean?
Walter: If you’re unfire-able this mean, you are the only one that is capable of doing this thing, and let’s scale this out, best in the world at doing this thing. Only one that can do it. They can’t promote you. They can’t fire you, but they can’t promote you because they need you to do that thing. So it’s a risk-benefit reward. So if you train the people around you, you train the people below you on how to do your thing, you’re developing leadership yourself. You’re benefiting the company at risk of your own job with the intent benefit of you being promoted, you getting more rewards down the line, you becoming the industry expert, you being the best in the world at teaching and guiding that next generation of that thing. But if you pigeonhole yourself as the only one that can do it, they may never be able to get rid of you until they can. So if technology makes a leap over you, you might be the best in the world at DOS until DOS isn’t necessary.
Charlie: It’s funny how you use the word pigeonhole because that’s exactly what you’re doing, is pigeonholing yourself, especially in technology where things are changing at lightning pace and lightning pace. So lightning fast pace I should say. So yeah. So the remedy, to reiterate, is to—
Walter: I had a conversation with another nonprofit executive not so long ago and she said, “I have this issue.” And I said, great, “I’m going to send this individual over to you. They’re going to help you. You’re going to call this person, they’re going to help you in this other way, and you’re going to have this conversation and they’re going to help you.” And knowing I’m a coaching consultant, they’re going to look at me and go, “What do you want out of this? My response is, “Nothing, I want nothing out of this.” They’re like, “Why? You get paid for this?” And I’m like, “Yes, but it’s a benefit to me to have more powerful friends.” That’s it.
Charlie: Okay.
Walter: If you’re training everybody around you to be better, you get better by training them to be better. Everybody wins.
Charlie:
That’s a good philosophy I think to have. I like that.
Walter: Lift everybody up.
Charlie: So what are the basic tenets that somebody you think should have? I mean, maybe, is it possible somebody might come to you either now or in the future and they might talk to you and after some conversation you may say, you know what, I don’t think you have the skillset or the interest or something like that. What are the basic tenets that somebody should really have if they want to go into management and become a leader? And just as a curious side note, we really haven’t spoken about IBM community per se because again, we said these are skills that transcend everything. But what do you say to somebody? What are the basic tenets that you look for? Are there three, any small number or metric that you can quickly determine if somebody is really this type of leadership material,
Walter: Are they narcissistic for one? So if they have a strong self-drive, they’ll want titles and roles, but they won’t have the capacity or empathy for others to lead a team. They will always put themself over team. Never a good fit, that’s chaos waiting to happen. Do you want it? I’ve seen individuals, the running gap in my old job has never become an executive. You’re the first one in last one out. It’s a management role. You really need to have that self-introspection and say, “I want this.” The last thing is leadership doesn’t follow roles. I’m sure everybody listening to this can just think of a friend that can guide everybody around them without a standardized, fixed role, IBM or elsewhere, that if they go, “Hey, we need to do this thing,” everybody will hop on it simply because they have that draw. So you can work on your leadership skills without ever having that fixed role. Minded, some are thrust into that role and have to learn the leadership, but it’s much easier to have the leadership skills and then advance into the role. Your chance of success is significantly higher.
Charlie: Conversely to what you just said, you hear the old expression, people don’t leave companies, they leave people, because there are some people who certainly are just toxic or ill fitted to be in certain management positions. I hear that often: “Sadly, I’m stuck on this job because my boss is a bit of a whatever.”
Walter:
Same thing. I’ve always heard people don’t leave jobs, they leave bosses. You could have a job that is perfectly manageable, but if you have a manager, and I say that definitionally, or leader that is not good at leading, chances are there’s going to be a high attrition or turnover in that role.
Charlie: Well eventually somebody has to—eventually it becomes a pattern. Eventually you have to start looking at the lowest common denominator here. If you see such a high level of attrition, shouldn’t somebody take a step back and say, “Hey, we are losing good people here because of the person in charge”?
Walter: You would think so. And I’ll speak to an example I’m firsthand familiar with. I was speaking with industry leader and entrepreneur in an environment that specializes in minimum wage individuals. He and I are diametrically opposed on leadership. His is, “I will overwork everybody, and the moment they complain I’m going to fire them, and those that don’t complain I’m going to promote.” And that way he got a whole bunch of people that were overworked but grateful for the opportunity. Now you could do that in a very low-skill environment. However, when you get into the technical trades, even the blue-collar trades, they want to be treated with respect, a little bit of autonomy as much as you can give them, and just be treated like decent human beings. He never left that industry. He actually sold for a large sum of money and he got rewarded for it. So he thought that was the only leadership style out there that was profitable. He was never trained otherwise.
Charlie: Interesting. So in technology, but it’s hardly unique to technology, but in technology, very often a CIO for example will manage many teams with all differing technologies, and diverse teams themselves. And that goes to technology and people themselves. Are there any tips or any ideas you can share with us how to manage a very diverse team? Be it technologically different or just culturally different or whatever, just diversity in general. How do you manage that?
Walter: So I’m a big proponent of excellence and basics. If you ever look at a high-performing individual, it’s because they do the very small beginner level things perfectly or flawlessly. That being said, if you’re managing a wide array of individuals, you can only successfully manage, I believe the metric is three to seven. That that’s it. That’s how many you can keep track of. So find three to seven, manage that well and allow the teams that are high performing to stay high performing. Don’t be the micromanager, don’t overbear. Provide guidance and support. Track what you need to track, make sure they’re following intent. And again, your job is not the doer. Your job is the enabler. They’re supposed to come to you to say, “I need help.” So it makes it easy If you premise every conversation like I do, “How can I help?” Makes it simple.
Charlie: Before we start wrapping this up, you mentioned that colonel at the very beginning of our conversation. Are there any other people in industry, whether you know them personally or not, are there any people that you admire who you can point to and say, “That that person truly embodies my philosophy or just does such a great job with their own team”? Is there any one person or one industry perhaps that is better suited for that role or any one person or team manager or anything like that that might jump out at you?
Walter: So I don’t agree with all of his methods. I don’t agree with a lot of his philosophies, but everybody knows him. Everybody loves him or hates him. I’m going to go with Elon Musk, and there’s a reason why. So if you ask him what he wants, he has a singular answer to put people on Mars. There is no second step there. He knows absolutely what he wants and how to get there. He has different strategies that he’s approaching, whether it’s through DOGE and reducing regulation for his spaceships, whether it’s, I think it’s Grok with the X platform, helping generate an AI model to work the spaceships, telemetry and everything else as you get into space, whether it’s his efficiencies within his company. I mean, you let go of 80-percent-ish of old Twitter and there’s no significant decrease in functionality. I mean, the absolute focus and drive to do the thing. And the thing is getting people on Mars. He’s singular-focused, singular intent. And his team, those that remain, are absolutely loyal to that because he shows them a vision and guidance that gets you there. He’s not too proud of himself to admit defeats. I mean, there’s a video of him where he gets called out from a YouTuber. They’re talking about venting gases and he’s like, “I never thought of that.” And then next revision, they did it.
So again, understand where you’re going, be singular-minded in it and help your team and strive along the way. I think that’s a shining example of, whether you agree with them or not, laser-focused, laser-focused.
Charlie: You make a point. Absolutely. You make a point. That’s an interesting point. Thank you for that. Well, I’ll tell you what, Walter, this was great. This was really great. I think a lot of people are going to really benefit from this. And again, we talked so little about IBM per se, or even the tech industry per se. It doesn’t matter. And I’m so glad I brought you in because I think a lot of people could or will benefit from this. And there are people who are moving into management all the time. It doesn’t matter what industry they’re on. And again, your ability communicate what’s necessary is really, it transcends industry, which I love. So that’s really great. Before I officially wrap this up, any final thoughts you want to share with our audience here? Any final thoughts or resources you may want to point out or anything to that end?
Walter: One thing for the audience, I’m going to challenge you and it’s not going to be easy, but I want you to look at everybody in your day-to-day life—your own leaders, your own managers, your peers, your subordinates: Who’s a good leader, who’s not; and then itemize why. Find out if you want to exhibit those traits or not and really examine it, and that gets into that self-introspection. On a more personal note, if they want to hop over to my website, yenkosky.com, happy to talk. Feel free to send me a LinkedIn. Happy to be a resource.
Charlie: Terrific. And based in California.
Walter: I am.
Charlie: Not that that should matter with, thankfully, the technology, back to technology.
Walter: Whole bunch of tech experts: “I need you here in person.”
Charlie: There you go. Walter, always a pleasure. Thank you so much. I’m so glad we got this opportunity to talk and to capture this conversation finally on a podcast. It’s been one that’s been on my mind for quite some time. I’m glad we finally got this done. And that’s on me. But thank you very much. Always a pleasure. And to everybody who is listening, I hope you enjoyed our podcast on guiding the next generation of leaders. What a great tagline and what a great conversation we had. So thank you very much, Walter.
Walter: Happy to help.
Charlie: Great. Everybody, see you next time, and we’ll see you then. Bye now.