326: Leadership Shifts: Embracing Change in Business with Mike Krupit

The leadership style that got you promoted can quietly become the thing that holds you back. When you move from building great work to leading people, the rules change fast, especially for technical founders and high-performing individual contributors who suddenly wake up running a business instead of writing code.

We sit down with Mike Krupit, a serial entrepreneur and executive coach who has lived the journey from software engineer to CTO, COO, and CEO across eight startups. Together, we break down why humans are not deterministic, why “best performer” promotions often fail, and why not everyone should be pushed into people management. We also dig into smarter organizational design: building roles around real strengths and creating dual career ladders so experts can grow without becoming reluctant managers.

Then we tackle the pressure cooker topic leaders cannot avoid: AI disruption. Mike shares how to lead through uncertainty when technology moves faster than people can grow, why overcommunication beats silence, and how to run real two-way dialogue that addresses fear without pretending you have perfect answers. We close with a practical lens for situational leadership: knowing when to go into founder mode, when to step back into trust mode, and how to let teams learn through safe mistakes that build ownership.

If you’re focused on leadership development, change management, founder to CEO growth, or navigating AI at work, you’ll leave with clear questions to ask and moves to try this week. Subscribe, share this with a leader who needs it, and leave a review so more people can find the show.

🌐 Connect with Mike:
• Website: https://www.trajectify.com/
• LinkedIn: https://www.linkedin.com/in/mkrupit/
• Instagram: https://www.instagram.com/mkrupit/

Transcript

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Mick Spiers: 0:01

Have you ever wondered whether the leadership style that made you successful in the past is the very thing holding you back today? Have you ever promoted someone into leadership because they were your best technical performer, only to discover that great individual contributors don't automatically become great leaders. And have you ever struggled to know when to step in and help your team, when to step back and let them learn? If those questions resonate with you, then this episode is for you. Today, I'm joined by Mike Krupit. Mike has spent decades helping leaders and organizations navigate growth, transformation, and complexity through his work as an executive coach, advisor, entrepreneur, and leadership thinker. He's seen firsthand how leadership must evolve as organizations evolve. So, if you're leading a team, growing a business, preparing for your next leadership role, or simply trying to become a more adaptable leader. I think you're going to get a lot out of this conversation. Hey everyone, and welcome back to The Leadership Project. I'm greatly honored today to be joined by Mike Krupit. Mike is a serial entrepreneur who's led organizations from the C-suite through all kinds of phases of organizational growth and decline. And you wouldn't, you know, believe the different kind of stages that an organization can go through, the growth, the IPOs, M and A, even through to bankruptcy. And leadership needs to subtly shift through all of those different phases, so what we're going to be talking to with Mike today is those shifts that are needed to be made by leaders based on the situation that your organization faces. And the second part we're also going to be talking about how leadership is learned through those experiences, not through theory, not in a classroom, not through reading a book. It's learned through practice and paying attention and seeing what's working for you around you. So I'm dying to get into both of these elements. So, without any further ado, Mike, I'd love it if you'd say hello to the audience and give us a flavor of that very rich background of yours, and what inspires you to do the work you do today with Trajectify, helping organizations go through these different phases, particularly with startups and founders.

Mike Krupit: 2:36

Great. Well, thank you for having me, Mick. I'm really excited, looking forward to this, to this conversation, you know, I myself developed my sense of leadership over twenty five years and eight startups. I started out as a software engineer in Silicon Valley and evolved to CTO, and then COO, and then CEO, and had the chance in my second, the second half of my career, to run as CEO a number of companies. And which ultimately, after the eighth startup, and I said no more, I had the what do I want to be when I grow up conversation, and decided to start a practice that was initially coaching and has since evolved into advisory services, helping other entrepreneurs on the same journey, the founders often technical founders. But the founders becoming CEOs and taking what some of what I've learned in the approach of how to get there and what success might look like and using that to help others.

Mick Spiers: 3:37

It really could, Mike, that's quite interesting. So you yourself being on the tools as a software engineer, you're an example of what I'm about to talk about. I have this vision around founders that they often accidentally fall into leadership. They've got this innovative idea that's going to, they've got this vision that they're going to change the world through some technology that they want to develop, and then they turned around one day and realized that they're running a business and they're leading team. So they started off as probably someone that was quite technical, and all of a sudden they've landed landed in managerial and leadership roles. Was that your experience as well?

Mike Krupit: 4:16

Yes. In fact, too extreme, I was way better with computers and math than I was with people, so I got a degree in mathematics and ended up working in the defense industry. Literally as a rocket scientist, as you know, doing satellite command and control and, and I had a great boss who saw that I had potential to do more, and basically told me, "Get out of the defense industry, Mike. You're working on a 20 year project, you're going to be miserable. I've been here for 20 years, I can't get out. Get out while you can." That was basically the conversation he had with me over lunch. Best boss ever, because I ended up at a Silicon Valley startup right from there. And again, my role as an engineer, better with computers. I was with people, and so it's we fall in love with a technology, we fall in love with a product or a service, but once it becomes a business, it ultimately is all about people, and that's sort of where the interesting part of the journey takes place.

Mick Spiers: 5:18

There's two interesting things that pop into my mind listening to you there Mike. One is a belief that I have as well, and that happens with any leaders first transitioning into leadership, whether they're a founder or whether they're in a large multinational, you know, whatever the case may be. They discover early days that leadership is more challenging than their craft that I'm going to use accounting just for a moment, just to mix it up a little bit. That when they were dealing with their spreadsheet, their spreadsheet always did what they thought it was going to do, and they would problem solve with it, and it was challenging from a technical point of view. But it was also somewhat predictable and repeatable, whereas human beings are not human beings are not repeatable, they're not predictable, and what works for one human being doesn't work for another human being, but what's worse still, Mike is what works for that one human being doesn't work for the same human being three months from now.

Mike Krupit: 6:20

That's why so many, so many of us stumble when we go for that, you know, managing systems to managing people, is that, you know, as we say in math and computer science, right? It is the algorithms are deterministic, you program them to happen, and it happens the same way every time. I wish it was as simple as that. I spent plenty of a sleepless night fixing bugs, because my algorithms weren't always great. But the very first management opportunity I had was at a Silicon Valley startup. My boss, who was the founder, had 40 direct reports in engineering, and he came to me one day and said "Mike, you're my only engineer who I think has people skills. Would you be willing to lead a department? Because I think I need to tier this organization." So I said, sure. And I had been at the company, probably two years at the time. I was a five-star engineer. I, my five out of five, my performance appraisals were great, you know, engineer versus machine. I was always winning, and all of a sudden, now I've got a team of eight, and my next performance review I'll never forget was a three, and I was mortified because that wasn't how I defined myself. I made every mistake in the book, I didn't have a lot of training, I didn't have a great mentor, I didn't have a coach, I was kind of on my own, but man, I made, I was a terrible manager. Maybe three was three was generous on my review, but you know that was a rude awakening, and is like, and to me a challenge, though I've always, I love a challenge, people is a challenge, or a lot harder than computers is a challenge, but it's a challenge I spent the next 20 years working on.

Mick Spiers: 8:08

Yeah, really good examples, Mike. And I love the word that you use, deterministic. So that's, that's a big takeaway from me today is that you know machines are deterministic, your software program is deterministic, with the same exactly same inputs, you're going to get the same output. If you're an engineer, the laws of physics don't change overnight, they do what you think they're going to do. If you're a chemist, the laws of chemistry don't change, but humans, they're not deterministic, they're erratic and they're irrational. I'm going to just call it how it is, and I'm going to share a little secret of mine, which is late in my career, the reason why I studied psychology, which probably seemed like a really weird twist for a lot of people, considering the career it had as an engineer who wanted to make rational sense of the world. The only journey for me was psychology was to try to make rational sense of an irrational world, because I saw this irrational behavior from a sea of 300 human beings doing completely different non-deterministic things. It was doing my heading Mike, so I had to work out, well, what is this? What is this?

Mike Krupit: 9:21

Well, one of the things I've learned the way, along the way, and we could talk about it a little bit more later, is there is so much to learn that I've just decided I'm going to ask more questions and assume that I never. I rarely have the answer, and maybe that's, that's a lot what psychology, you know, degree gave you was that that ability to ask the right questions.

Mick Spiers: 9:40

Curiosity is the cure here if because, if you, if you keep on showing up to work, just beating your head against the wall and going, why, why is this keep happening to me? Yeah, it's it's going to end in tears. All right, so I've got one more question around this topic for you. so your manager at the time out of 40 engineers goes, oh, that Mike guy, he's the only one that's got any human skills. Here we're going to promote him. Ask you a blank question, do you think everyone should become a leader?

Mike Krupit: 10:12

No, not at all. And I think that that's a mistake that a lot of organizations make, especially larger organizations where your only path, or the best path for growth, is through the management, the ranks of management. We aren't all managers. We shouldn't all be managers. We can't all learn to be good managers, and even, even some good managers don't make good leaders, and some good leaders don't make good managers. There's a whole series of strengths that we develop in our mid 20s as our frontal lobe, our frontal frontal cortex are developing that ultimately are what you've got to work with for the rest of your adult life until you get old and they start to decline. We don't really create a lot of strengths, we have to use the strengths that we have, and we can pick up skills, we can pick up knowledge, and so we're not all wired. Like, for example, had I not shown improvement in management, had I not learned from my first job and taken that to my second job, I would have gone back and just become a principal systems architect, or a, you know, some, or started some sort of, you know, algorithms company, where I didn't have to lead people. So clearly I had strengths that I could tap into to develop the skills of managing people, but not all of us have that, or not all of us have the commitment, because it was a journey made a lot of mistakes along the way. You got to be okay with yourself first and foremost, the permission to make mistakes. And so, if I let that first experience discourage me, I probably wouldn't have been a great manager in the long run, and I may have not stuck with it.

Mick Spiers: 12:00

Yeah, really, really good Mike. So, this is exactly why I was asking the question, and there's two parts of it. The first one is the tendency would have been easy for that manager to go, and I'm not saying that you weren't the best software engineer, by the way, but to just go, okay, who is our best software engineer? Right, congratulations, you're now the team leader, and that's the trap that many fall into, and what happens there is that if that person isn't geared up for it from a human skills point of view, or doesn't even want to do it, what you end up is I'm going to call it a triple whammy, you end up with a leader who's no longer enjoying their work anymore, they're going home frustrated. They used to love coding, and now they're dealing with human beings, and they, they're getting frustrated and going, "I hate my job now." So, you end up with a leader who doesn't enjoy it. You end up with a leader who isn't good at leadership, and guess what? You've lost your best software engineer. Your best software engineer is no longer coding; they're spending all their time in people discussions.

Mike Krupit: 13:05

Yeah, which is why you know being curious and being present is really important as a leader, because you need to identify when those situations might exist. You need to, you need to be aware that that's a risk that you're taking, and and have a plan around that. And I don't know if my boss did or not, and I do, I do appreciate the fact that he asked me. He didn't assume he asked me, and I remember he processes information very quickly, and so I remember always being intimidated by him a little bit, and so I asked him if I could think about it overnight, I didn't answer him right away, and so I knew that I had to sleep on it for me to process the opportunity and, and you know, look, and 20 years later in my career, when I was offered my first CEO job, actually was probably more like 12 years later. I was offered my first CEO job, I did think about it, I didn't answer right away. It's like, is this something I really want? Because I never set out to be the CEO, because I know how difficult that job is, and is that something I want? And so, being given the option, right, working in an environment where people are curious and offer you opportunities, but don't mandate a certain path, is always a great thing, and, and I always encourage leaders to build that within their own organizations as well, but is not to mandate a path, but is to allow people to evolve as they're able to and want to grow.

Mick Spiers: 14:35

So that's the second element, don't mandate a path, that's what I was picking up as well, and I have worked with one company that did this particularly well, Mike, but if you end up with a situation where the only way for your people to get promoted to get extra pay, all of these things is a managerial path, and that's very limiting for your technical experts, right? So, so we need a Y model where. Where they can have a decision point somewhere, and it doesn't have to be too early in their career, but somewhere in the career they can decide, no, I'm going to be an expert, and I'm going to be the master of my craft, and I'm going to go, I'm going to turn left here, and another person is going to go, no, I think I'm cut out for this managerial leadership thing, I'm going to turn right, and I'm going to go off the other fork. Now, the one I'm going to give you an example of, give a credit to a company I used to work for on staff. We had a guy that won the Nobel Prize for physics in 2007. He had exactly zero people reporting to him. I don't think he even liked people, to be honest, but he won the Nobel Prize for physics, and he was getting paid more than the CEO. I can tell you, because he had, he had patents, he had all kinds of things. The structure was set up for him to have a beautiful career that had zero people leadership, and he was happy. We were happy. You need those alternate paths. How does that sit with you?

Mike Krupit: 16:02

It doesn't. It's often we like to suggest that we build organization around the people instead of wedge people into an organization. If you've gotten good at identifying the right talent, the right people to put into the right seats, there shouldn't be a prescriptive methodology for evolving organization, it should really evolve. It should grow around the people who you have, who you've invested in, who have demonstrated their abilities to you, and that is a mistake. Sometimes we think, you know,"Oh, well, I need a, I need a CTO and a CIO and a COO, and here's what my organization should look like." Here's where this, you know, where the customer support department should report into, and ultimately that may not be the right evolution based upon the people who you've invested in, the people who you are, who are the catalysts for how your organization evolves. So, you should, you should build it around them.

Mick Spiers: 17:03

Yeah, yeah, really good. And I've got to say, this is another limiting belief that if we were on this interview right now, Mike, and we had a third person here, and they were an HR expert. I can tell you the usual way of organizational design is to start with an org chart, is to start with what does the business need, and then start fitting the right people into the boxes, but I think that's a limiting belief. We go, well, hang on a second, we've got this unique one over here who's sort of like a CTO, but he's also got these other skills. Well, map a role around that person's strengths, and then complement them with other people with different strengths, and who does the org structure from every company in the world need to look the same, of course it doesn't. Of course, and now I'm going to, I'm going to pivot now to one of the topics that we said that, that structure and who we need around the table might be different at different phases of the organization, so, so one of the things we teased in, in the intro, Mike was to talk about this. You know, you've been through organizations of rapid growth, you've been through IPOs, you've been through M and A's, you've even been through bankruptcies. How does all of that shift, the leadership shifts, but also everything we've just been talking about with the with the organization and the talents that you have. How does that change depending on situations?

Mike Krupit: 18:29

It ups the ante, doesn't it? And which is why I was afraid to take that first CEO job myself, because we talked about the evolution of the organization and building around people, but the needs of the business are also changing during that same time, and so it feels like a constant complicated equation to say here's where people are going, here's where organization is going. How do I best keep them aligned? And by the time you get it aligned, something's already outdated, and we need to realign it, and so it is organization is a very like living, breathing dynamic sort of part of your strategy, and it's not easy, right? It's not easy, because sometimes we need to nudge people in a direction because of particular businesses going a certain way. I'm dealing a lot of that with a lot of that right now through AI disruptions in organizations, so let's take a simple example. Customer Service Department, we know that customer service will be one of the first departments that are disrupted by AI, because Tier One, first, the first tier of customer service is a good candidate for AI to successfully accomplish to successfully fulfill those roles. And then what happens to our customer service organization as AI starts to take over, to take it over, and so I've got some companies I'm working with who, and you hear this in the news as well, where. Where people are being asked to train AI, knowing that the AI may take their job. Now, what do we do? And so I had this conversation just this morning with one of the customer service leaders that I was working, that I've been working with, and you know, we've got to figure out how to shift his team to be the master of the tool, as opposed to the victim of the tool. We can preserve the jobs, if we re-skill, if we retool, if we repurpose, create new roles that these people can evolve into. So, again, he says, "I've got, you know, 18 people now, not all of them are going to be as malleable, not all of them going to be flexible to move into some of these roles." And so it's almost as if we see a revolution coming in how that department will have to run, and 18 different equations that need to be solved in some, or at least an equation with 18 variables that needs to be solved in real time to ensure that we don't have to do a downsizing, we don't have to let half of the department go, but we create role the right opportunities for the right people.

Mick Spiers: 21:13

Yeah, yeah, this is going to be a huge challenge in, in the coming year. I'm not going to say it's the coming decade, it's the coming year, it's on, it's on us very fast. Mike, one of the things I'm looking at when I look at this, and there's lots of people using this term, but I'm catching on to it as well, is the idea that AI means augmented intelligence, not artificial intelligence. And that if we use AI in the right way, it does become an extension of that human, not a replacement of that human. It becomes the productivity core, but that human is still needed and still the person that's going to drive this. But to do that, the leadership challenge there is to get that person to come on the journey, because their very identity is at risk here. Mike, let's use the customer service. They're the CS champion. They're the best person in the room at customer service, and all of a sudden they're getting asked to do it differently, and they've been doing it the same way for 10 years, 15 years. This is a huge journey to convince people

Mike Krupit: 22:19

It is, and it's a scary journey, because they to come along. believe, especially if they're reading the, you know, if they're paying attention to the media that, that at any moment they could lose their job. And they would have trouble finding a new one, and so there's a bunch of, is the fear as well, right, there's resistance, there's fear, and a lot of that comes from uncertainty. But here's the thing, so like you think about a customer service organization that may have first tier, second tier, third tier, a very typical, a very typical model AI can take 90% of the first tier cases that may create more second tier jobs, or may create, you know, we'll certainly reduce the number of first tier jobs we have. Well, what if somebody is at the first tier are not ready to take the second tier, right? What if they don't have the skills or the strengths even to be able to be successful in second tier? Right, their people skills were really good at answering the phone, but AI is answering the phone now. Their technical skills wasn't so, weren't so strong, isn't so strong, so that they can't do second tier, what can they do? Right, that's a question that we need to start asking. If AI can do this part of your job, and that's 90% of the time you spend, I can fire nine out of my 10 employees, but if I don't want to do that, how do I make sure that I have all this other work? Right? When you talk about augmented intelligence is, if AI can do a big part of my job, is there enough left over for me to do? And the answer is yes, almost always yes. If we can mold the people into the roles, evolve the people into the roles that we need filled at that point.

Mick Spiers: 24:02

It's going to be a challenge for sure. And just listening to what you're saying there, I think if we take the right intentional steps, we do get to - we're coming back to organizational design now, but we've got this new player in the on the table called AI that is now going to be part of that organizational design. But how do we make the most of the humans and the AI to create this augmented experience is going to be the design element. The journey element is the one that's worrying me more, which is like, if you, if you read things like the World Economic Forum still says today that AI will create more jobs than it takes away, that's number one. Number two, you'll read things that say things like 65% of people that are graduating high school this year will end up doing a job in their career that doesn't even exist today, and I can recognize that, because I can tell you, when I graduated school, I didn't dream of. Becoming a Prompt Engineer, it didn't exist, so, so there's an element of truthiness to this, you know, making up terms as I go along here, but it doesn't help if you stand up in front of your team at a town hall today and you say, "You know, no, we're going to work with AI, not against AI, we're going to work with AI, and AI is not going to come in to take your job, we're going to work with it and design around it." If they wake up the next morning, and in Australia, I'll give you an example. Some large bank says 700 people laid off because of AI, that doesn't bloody help. So, how do we? What advice do you have here, Mike? How do we get people to come on that journey with us?

Mike Krupit: 25:39

And just to add one note to that journey, and I agree with all that. It will create more jobs, will create the jobs that these people can fill, right? That's, that's sort of their fear. That's where the potential disconnect is. And yes, the next generation will fill those jobs, but what about the current generation? The current people who are in that role right now, those are the ones who were talking about the one thing I've said a lot lately, is there is no such thing as over communication. The one on one time we spend that managers spend with their team members, the amount of transparency and authenticity we have in our communication, the frequency of those communications have never has never been more important. Problem is that a lot of leaders and a lot of managers, because things are moving so fast, don't even know what they're facing, that they tend to communicate less, that they tend to retreat. I don't have the answers, so I don't, I don't want to make anyone afraid. One of them recently wanted to tell his team, you'll learn AI, and that'll look good on your resume, and of course, the minute the minute your leader talks about your resume, now you're thinking about the your job. Thankfully, you know his team advised him not to say it that way, and he did it, but he's not wrong about that framing, is that that's a good skill to have. But what about the people sitting in the organization saying I'm not ready for AI, or I don't think I'm going to be good at it, or I don't have an interest in it. That's not what I do. And the other, the other challenge in parallel that parallels all of this is, which is making this situation around AI so difficult, is that AI is moving more quickly than people grow, and so the most resilient, the most malleable people are half a step ahead of it, and the rest of the people are struggling to catch up and feeling like they're getting further and further behind, because humans develop more slowly than technology.

Mick Spiers: 27:39

Yeah, that's going to be a huge part of the challenge. I'll tell you what my takeaway is from what you're saying, and this is our call to action to everyone listening. If you don't know the answers, doesn't mean that you shouldn't communicate, like listen to what Mike said, over communicate, and I'm going to extrapolate here a little bit, Mike. Including saying it's okay that you don't know all the answers, and don't stand up in in front of a group and pretend that you know what the what the world would look like five years from now. Because none of us know, so just say "Yeah, actually we don't know, let's have a dialog about it, and a dialog, by the way, is two way, have a conversation with the teams, hear their ideas, hear what they're thinking, have a conversation about what their fears are, so you don't just avoid it." How does that sit with you? A two-way dialog.

Mike Krupit: 28:27

Yes, so you know, while in your quiet time as a leader, you're trying to figure out how this affects your roadmap and where you might be headed. The time you spend with your team needs to be in curiosity, right? Again, like we said earlier, asking questions, allowing them to ask you questions, acknowledging emotions, right. This is where empathy is really important, and where especially those technical people like myself really struggle with empathy, right. That was the part that I had to start to practice teaching empathy to someone who wasn't naturally good with their emotions, and probably wasn't, wasn't good at recognizing other people's emotions, is very challenging, and so it's a time where you need to be curious and you need to be empathetic.

Mick Spiers: 29:19

Yeah, okay, all right, excellent. So, curiosity, empathy, two-way dialog, don't ignore it, over communicate, don't under communicate. Really good. All right, Mike, I want to want to come back to one other part of this leadership shift that we need to make. It say AI was a great example of when an organization is going through massive change. Got a question for you about the different things around the stages of an organization, whether it's rapid growth, M and A, or decline. You're in a declining market that is decreasing, not increasing. The question I have for you at the CEO level. Do you need the CEO to shift in their mindset during different phases, or do you need a different CEO? Right, so do you need a different CEO for a rapid growth company versus a declining company, or do you need the same CEO with different mindset?

Mike Krupit: 30:16

That's a great question, and one that I would have to answer. It depends, and in part because there's so many variables. I founded my practice with the presumption that every founder can become a really good CEO, but of course in practice that doesn't always work out to be the case. They may lose interest. I have one founder I work with who just says, "I just like starting stuff, and 10 years into this, and $10 million it's like I don't have interest in this." And you know, my challenge was, could I get them engaged, re-engaged in their business, or do they have to think about a succession plan? Thankfully, they did get re-engaged in their business, and they're all gung-ho. I've been talking recently a lot about what we call in Silicon Valley founder mode, where, where the CEO gets to the point where they've done a lot of delegatio. But now find the need to do a deep dive to handle one particular area or situation where it's not going as well as we'd like, and how to, how to go into founder mode and be able to pull yourself out of it. I do have a handful of CEOs who I'm working with, who get into founder mode and have trouble extracting themselves from it. So that's why it depends, really. It depends on the wiring of the CEO and the experiencing the experience level of the CEO, but more often than not, I think the CEO can, if they are conscientious about it, maybe that's the qualifier here. If they maintain presence and are conscientious about how they look at the challenge at hand, rapid growth, rapid deceleration, big market changes. If they are willing to look at it as an issue that needs resolution and not panic and overreact, and they have the time to respond to it with that conscientiousness, then they're more than like they're more than likely to succeed.

Mick Spiers: 32:19

Yeah, really good. What's bouncing around in my head as I listen to you, Mike is deep in situational leadership, but I'm going to go a step further and say very intentional decisions as to what what will serve the team and the organization well today, is it founder mode or is it step back and empower and trust mode, and there's going to be situations where, oh, this needs my attention, as the founder, this needs my attention. I'm going to lean in, I'm going to help them fix this problem, but then I'm going to parachute back out again and go back to helicopter view. Because if I, if I go in there and stay in there, I become the bottleneck, I become the throttle that is going to choke the growth of this business, so I can't stay in founder mode, but I, there's going to be times where that's needed to making an intentional decision. What does the team need from me today, right?

Mike Krupit: 33:14

And to put boundaries around your interventions, right? To know, and I often say, "Well, let's write them down, like put them on a piece of paper, literally, so that you can see it all the time and understand what your boundaries are, and how you deal with a particular situation. And each time reassess your boundaries for each, for each, each situation." The other thing I think is that we have too many leaders out there who are always striving for perfection, and who don't leave enough room for mistakes, and so I think back, for example, to one of my organizations was merging with another organization, two public companies, and I was CTO at the time, and I was asked to become CTO of the combined company merge the two teams, merge all of our products, and, oh, by the way, could you do it in eight weeks? Because we want to make a big announcement about, about it, because we're both public companies, and I don't think I've ever done anything that challenging in my career. Merging teams is hard enough, but merging databases, merging products and not having any downtime in the course of it, right? You know, a real CTO challenge. So, anyhow, I create this big initiative. I've got the right people in the right seats, some of them I've worked with before, some of them are new to me, and one of them comes to me, presents their plan, and I question the plan. Right, I said, you know, and I'm not quite sure when we launch this new combined entity that this is that you've accounted for this situation, and they say, "Yes, we have, and here's all our data." I didn't believe them, but you know what, I shut up on the day we launch the system crashes within a couple of. Hours as usage picked up, we crash. All hands on deck, they manage the crisis really well. They eventually come back and say, yeah, it was this one thing, it happened to be bandwidth, internet bandwidth. It was this one thing, which was the thing that I was concerned about previously. And so, anyhow, they fix, they come to me, they say, "Here's what it is, here's the plan." And it's taken care of, and you know, within five later, five hours later, we were all fine. Could have we tanked the company? Right, how big of a mistake was that? My judgment was that it wasn't going to tank the company, and if it was an issue, let it be an issue, because me intervening would have been bad leadership, right? Me intervening would have said one, I don't trust you, or I'm smarter than you, or they would have agreed to do it and not learned anything. If I was, what if I was wrong, we would have learned anything other than they hated me, right? Because for overriding them, and so I let it happen at the end of the day that that leader is sitting on the door to the back parking lot, and I'm ready to leave, and he says, "Mike, I just want to thank you for letting me learn that the hard way, for letting me make that mistake, for you know" he says. If any of you just basically validated that the decision I made to let it happen, even though it could have been disastrous and wasn't, was an investment in people and team and a really big evolutionary moment for the organization, and so my long story quick point, right? You also have to be okay with mistakes.

Mick Spiers: 36:44

Yeah, very good. I definitely wanted to talk about this learning through failure, because you know that's what the world of startups is all about. But it's also happens in other industries and big companies too. The words that rang in my head was when you said, is this going to tank the company? I'll share some of my own philosophy here, and wish I had a better way of articulating this, because it sounds really horrible sometimes when I say it myself. I have a saying that sometimes you need to let people scrape their knees, but you don't let them get hit by a bus, right? So, you're asking the question, is this going to tank the company? That question right there. So, you, you are going to intervene if you think this is terminal, but if you think it's going to be okay, let's let them try this, and let's be curious and see what happens. Let them scrape their knees. They're always going to learn from that. They're not going to learn from Mike intervening and saying, I'm going to use a parenting example. "Don't touch the stove. Don't touch the stove. It's hot." Sorry to say this, and I hate even saying it myself, because I'm a father too. The kid doesn't learn not to touch the hot stove until one day that he touches the hot stove.

Mike Krupit: 38:05

Well, and I was two years old when I burned my arm on the hot stove, but I questioned everything as a young child. I questioned everything. My father had a fish tank with a razor blade to clean the algae off the inside of the tank, and don't touch the razor blade, it's sharp, and of course I nearly sliced the tip of my finger off, and so for me that was just part of my personality. But I also bring that to the leadership too, right? You know, and every moment of my life where I've had either a big curiosity or a big fear, one of the questions I've, I've been trained to ask myself, as or, and I use it in the coaching that some of the coaching that I do is, what's the worst thing that can happen? Because often, right, when we have this limiting belief, as you said earlier, but the limiting belief of fear, that you know, when we have a limiting belief that turns out to be fear, we need to sort of understand that the fear is just the emotion, but what are the facts, and we often think that we over exaggerate what the worst thing is.

Mick Spiers: 39:08

Yeah, really good. Okay. All right, so let's now come back to the leadership journey. We've had elements of this going along from your experience. What are some of the biggest mistakes that you've made as a leader, and how did you learn and adapt?

Mike Krupit: 39:24

The biggest mistake that I made as a leader is really that those moments where I think I know more than someone else. Now I have a habit of surrounding myself with people who know their jobs better than I do. But, but I remember, I remember one, one situation where some employees came to HR and complained about something that the company was doing. It was a, it was a picnic, but it was how we framed the picnic. They said that that's offensive. I was like, how is it offensive? Well, you know, these, these picnics have a history in in. Society that that is discriminatory or racist, and it's like, no, it's not. And I Googled it, and it's like, no, it's they're wrong, that's folklore, that's urban legend, that's not true. And so I went to HR, and I said, you know what, show them these articles, they're miscategorizing it, our event is fine. And HR says to me, I had a really good VP of HR, is that the battle you want to pick? Do you want to make people feel that you're right and they're wrong? Right perception is reality, right? This is one of those moments that that bites you in the butt. It's like, okay, you're right, and we changed the event, we restructured the event so it didn't offend anyone. And in today's day and age of a lot of discussions around, right, how much do we cater to all the different perspectives in the in the culture of our organization. For me, I almost made the mistake of trying to prove someone wrong because I knew I was right, when in fact the best thing to do was to say not a big deal, that's okay, we'll move. I hear you, we're going to change it, we're going to move on. And that was great advice, because my natural inclination would have been to pick a, pick a fight, pick a debate, and so that, that was that was a very big moment in my leadership journey, and my, you know, as I was trying to get good at being empathy, was to put myself in someone else's shoes and say, what is their perspective? How do they feel about it, and what is a more suitable response on my end?

Mick Spiers: 41:35

Really good, Mike. It reminds me of one of my favorite sayings, which is, Do you want to be always right, or do you want to be married? You can't be, but you can't be both. And in this perspectives, you're both probably right. You're probably right that it was no big deal, and but for them it was a big deal, for them was a big deal, and they were catastrophizing it potentially. But now that you've truly heard them, they'll feel seen, they'll feel heard, they'll feel valued. That's a relationship builder. If you had a gone in an attack, you know, no, you're wrong, and here's why you're wrong, that would have been a relationship destroyer, right? So, yeah, really good examples. Okay. All right, Mike, this has been a wonderful conversation. I want to summarize a few of the things that we're talking about here, and that is that leadership is dynamic, that's the key takeaway here, depending on the situation, depending on the growth that the organization is going through, the change that is important upon it, whether it's. You know, growth, M and A, the introduction of AI, we're always in a, in a changing world, and our leadership needs to shift with that change, and it needs to be dynamic to the situation that the organization and our people are facing. Some of the key things that Mike taught us here is that to over communicate in these times, where people might have fear, their fear of loss is always going to be greater than their appreciation of any gain. So, you need to address this and over communicate, including when you don't know the answers, and having the humility to say,"Actually, I don't know, let's have a chat about it, and making it a two-way dialog, so this is a huge element of it. Then asking yourself some of the questions around, is this going to be terminal to the company, yes or no, and deciding on a few things here. When am I going to lean in to founder mode? When am I going to step back and empower and trust my team to get on with it, that's a decision, but it's an intentional decision. It's not an accidental decision, it's an intentional decision." Going further with that is even allowing your team to scrape their knees. Sometimes, if you can see them about to do something that you don't think is going to work, are you going to intervene or are you going to let them scrape their knees and learn from it, or are you going to get curious yourself and go. I don't think this will work, but I'm going to stay curious, because you never know, and making sure that you remain open-minded when they try something new, so that you can have this healthy relationship with failure, because it's failures is our greatest teacher, and you never know what might come from this experience that the team is going to go through, and then finally, is that leadership is a journey. Leadership is the journey, but it's a journey that only works if you're paying attention and you're working out well what is working. Human beings are non-deterministic, it's not like your software program, they're going to behave seemingly erratically and irrationally, but if you're paying attention, you can subtly work your leadership through the journey to work out what is working and what is not working. The bad news for you is what is working today might not work six months from now, so it's a continual journey. Me, you never ever ever finish leadership. You're learning every day, but if you're paying attention, you can get better at it. All right, Mike. Thank you so much. I'm going to take us now to our rapid round. These are the same four questions we ask all of our guests. So, first of all, What's the one thing you know now, Mike Krupit, that you wish you knew when you're 20.

Mike Krupit: 45:24

I think it'll be actually something that I just alluded to about always being right, but I was, I was wired as a perfectionist as a young child, and so being right was really important. Being complete was really important, and so it held me back a lot of my career in my life, and you know, and got me the reputation as always someone who has to debate something, and I wish earlier in my life somebody had taught me the Pareto Principle, right, the 80/20 rule, right? If I can get 80% of the outcomes from 20% of the inputs, wow, well, maybe I don't need to be perfect, sounds pretty efficient to me. So I wished I had realized that perfectionism and the need to be complete and the need to be right over before it became an obstacle.

Mick Spiers: 46:15

Yeah, really good one, Mike. I'd love it. All right, what's your favorite book?

Mike Krupit: 46:19

I have so many, and so recently I've been sending people to Brene Brown's "Dare to Lead." I think we're, you know, we talk about communication, vulnerability, right? Not always being right, right? Vulnerability is a big element of that book. How vulnerability is courage, and so that's one of my favorite books right now.

Mick Spiers: 46:40

Yeah, really good. The humility and vulnerability in that have a think about that in the AI age. Lean into it, lean into it. Actually, none of us know, none of us know what this business looks like five years from now. Let's have a chat about it. Yeah, really good. Okay, what's your favorite quote?

Mike Krupit: 46:56

I would say Teddy Roosevelt, and I'm gonna, I'm gonna probably butcher his quote, misquote it, right, but people don't care what you think until they think that you care.

Mick Spiers: 47:05

Yeah, yeah, really good. Yeah, really good. Mike, okay. And finally, there's going to be people listening to this that need help, that they could be founders that are struggling with the transition from founder to all of a sudden I'm a CEO, or whatever the case may be. How to, how do people find you if they'd like to know more?

Mike Krupit: 47:26

Happy to take connection requests on LinkedIn, Mike Krupet or mike@tradectify.com T R A J E C T I F Y.

Mick Spiers: 47:35

All right, brilliant, Mike. Thank you so much for sharing your time with us today, the gift of your time, but also the gift of your experience and your wisdom. You've given us a lot to think about in a very rapidly changing world, and how we need to shift our leadership as we move forward. Thank you so much.

Mike Krupit: 47:54

Great, thank you for the opportunity, Mick. And I have to say that you summarizing my conversation was much better than AI would have done.

Mick Spiers: 48:02

Oh, thank you, sir.

Mike Krupit: 48:05

Thank you, Mick.

Mick Spiers: 48:08

What a fantastic conversation with Mike Krupit. There were so many insights in this discussion, but a few really stood out for me. First, leadership is contextual. There is no universal playbook that works in every situation. The best leaders adapt to the stage of the organization, the needs of the people, and the realities of the environment around them. Second, not everyone needs to become a people leader. One of the biggest mistakes organizations make is assuming that career progression must lead to people management. Sometimes the greatest contributions come from deep expertise rather than leading others. Third, leaders need to know when to step in and when to step back. I know this is something I've struggled with in my career, knowing the difference between those two. The metaphor of allowing people to scrape their knees but not get hit by a bus beautifully captures the balance between support and growth. And finally, leadership is an ongoing evolution, the leader you need to be tomorrow may be very different from the leader who brought you success yesterday. So, let me leave you with a few questions to reflect on. Where might your current leadership style be limiting your future effectiveness? Are you holding on too tightly to decisions that your team could own, and where could you create more space for people to learn, grow, and develop? This week, I encourage you to identify one area where you can deliberately step back and create greater ownership. For someone on your team, you might be surprised by what they are capable of when given the opportunity. Thank you for joining us today on The Leadership Project. Next week, we're shifting our focus from adaptive leadership to something equally important, caring leadership. My guest will be Graeme Cowan, founding director of "Are You Okay Day" and author of "Great Leaders Care." You've been listening to The Leadership Project. If today sparked an insight, don't keep it to yourself, share it with one other person who would benefit from listening to the show, a huge thank you to Gerald Calibo for his tireless work editing every episode, and to my amazing wife Sei, who does all the heavy lifting in the background to make this show possible. None of this happens without them. Around here, we believe leadership is a practice, not a position, that people should feel seen, heard, valued, and that they matter. That the best leaders trade ego for empathy, certainty for curiosity, and control for trust. If that resonates with you, please subscribe on YouTube and on your favorite podcast app. And if you want more, follow me on LinkedIn and explore our archives for conversations that move you from knowing to doing. Until next time, lead with curiosity, courage, and care.