In this candid episode, Mike Krupit, Founder and CEO of Trajectify, shares why successful teams suddenly “get dumb” during growth and what you must change to scale past it. If you’re hitting plateaus where results stall and early leaders no longer fit, you won’t want to miss it.
You will discover:
– What it takes to have difficult conversations and stop rescuing instead of coaching your team
– Why growth itself forces people, processes, and expectations to evolve or the team stalls
– How to spot the markers that you’ve outgrown current roles and need new leadership capacity
Episode Transcript
Scott Ritzheimer
Hello, hello, and welcome, welcome once again to the Start, Scale, and Succeed podcast-the only podcast that grows with you through all seven levels of your journey as a founder. I’m your host Scott Ritzheimer, and today we’re going to talk about managers and why it seems that sometimes they stop managing. There’s this story that I tell all the time when I’m teaching, it was actually a client of mine. I was asking him about his team, and I was expecting him to say, you know, this person’s great or that person the other. And he just paused for a moment. He looked up at me and he said, you know, if you had asked me about my team six months ago, I’d have told you I have the best team in the world. But some point in the last six months, we just got dumb. It’s like we’re tripping over our feet. I don’t know what happened, but we can’t seem to get anything right. How is it that great teams stop producing great results, and what can you do about it?
Well, if I had the answer, no, I’m just kidding. We’ve got with us today a gentleman who who has done this a time or two. He knows his way around it. With us today is Mike Croupett, who is founder and CEO of Trajectify, where he helps growth stage technology, manufacturing, and professional services companies to bridge the gap between early success and scalable leadership. With more than 30 years of experience as a CTO, COO, and CEO, Mike has led organizations through rapid growth, IPOs, M&As, and even bankruptcies, giving him rare real-world insight into what actually works when the stakes are so high. Known for his practical and candid approach, he helps founders and CEOs build courage, align their organizations, and unlock momentum from the inside out. Mike, what’s happening? here? How do we just get dumb, and and what can we do about it? So, a lot of founders will find themselves in this place where they’ve been through a season of success, and I think that’s important to articulate. Is this isn’t necessarily like the startup problem, although that’s a very real thing, these are folks who beat the startup problem and are bumping into something else. What is that?
Mike Krupit
Well, Scott, one thing I’ll say first and foremost is people don’t often change, and so if the the outcomes right getting dumb if things aren’t going as well as they used to. Something changed other than the people, and that’s always where I start to my my exploration, where I get curious, where I start to ask questions about what’s different, and and that we can go in a in a dozen different directions because it’s always, it’s often something else. Because one of the things we know about getting through these stages is you you hit some plateau, and then you’ve got to figure out you know what gets me to the next one.
Scott Ritzheimer
So particularly for those that are in that have had the success, but they’re trying to scale, and they find themselves kind of two steps forward, two steps back. They have a year of success and a year of frustration. What what do you find to be the primary drivers of that kind of cycle? What’s changing outside the team for that pattern to hold?
Mike Krupit
Well, often we’re a victim of our own successes. It’s growth, right? So, you know what works for a $1 million company won’t work for a 2 million or two to five or five to 10 to sort of you know grossly estimate them. the The fact is that we have to constantly be evolving our people, making sure we have the right people in the right seats, our processes, our systems, our perspectives, our you know perspectives meaning expectations, accountabilities, outcomes, and so there’s every time we hit a new level, things need to change, right? You know, and the people aren’t going to change, right? So we need we need we need the either the the organization to change and bring the people with it, or we need to change the people.
Scott Ritzheimer
Yeah, what is that? Because it feels like the role is to to like help lead this thing forward. It’s to help me as the CEO and to manage these other people that I don’t have to manage, and so it can feel like a distinction without a difference. What are some of the markers that there is a new level, and and how does that change who we need as the leaders around us?
Mike Krupit
Sure. Well, the markers are often I can characterize them as a feeling of being stuck. Right, I’m not meeting my goals. It’s it’s profits are decreasing. It’s taking more effort to generate the same revenue. I’m losing confidence, right? In a more emotional take on it. I used to I used to be sure how to how to get this these things accomplished and. I don’t know, so so the markers could be financial, they could be emotional, or it could just be that nothing is moving. I’m watching my dashboard, and nothing is moving. And what happens often is our people or our processes just don’t keep up with the business. The business grows, and we’re expected to grow with it. Our systems are expected to scale with it, and something’s, you know, it’s very often that something won’t. And we’ve got to we’ve got to get and do our root cause analysis and go figure out where what is keeping us stuck. What is is creating these elements of of that that I’m of uncertainty?
Scott Ritzheimer
When I’ve coached with founders that are going through this this period, and and they learn what it takes to scale. So it’s not this like I just don’t know how to do it anymore, but they know. Okay, this is what it’s going to take. There seems to be one reason that rises above all the rest that they still decline to do so. And the number one reason that someone who knows at least what direction to go to scale chooses another direction, in my experience, has been their we’ll call it their trusty right hand man or woman. It’s not always their second in command, but it’s some meaningful leader on their team, and they’ve got a personal and professional relationship. They’ve got you know years of sweat equity, you know the blood, sweat, and tears, the shared experience, all of that. But they recognize, like you said, people don’t change, and to in this context, they’re not the same. They’re not the leader that they need moving forward. Yeah. How do you help folks navigate? Like, should you scale anyway? Should you not scale? How do you help folks walk that decision?
Mike Krupit
Yeah. It’s it’s difficult conversations are very hard to get good at. Maybe maybe I’ll say that we never really get good at difficult conversations, but we may get skilled at having them. So that’s a skill I tend to work with, work with founders on is is being comfortable with the uncomfortable elements of what it is that we’re doing. So so often conflict avoidance, we not wanting to have authentic, vulnerable conversations with some of these key players in our organization. People who maybe we feel a commitment to because they’ve been with us since the beginning, or or people or or other things are moving, and it’s like you know what I don’t want to deal with it. It’s too disruptive. I’ve worked with founders who have punted decisions, people decisions for two years because they kept finding other distractions that they thought were more important, and then of course they make the decision about the person two years later and realize, hmm, I should have done this sooner. Everything’s better now, or everything’s easier now, and so it’s it’s it’s a matter of for me building the skill and having difficult in in mastering difficult conversations.
Scott Ritzheimer
Yeah, I was it Marshall Goldsmith is famous for what got you here won’t get you there. There’s also the who version of that. Who got you here won’t get you there. Right. I just had this conversation with a gentleman last week. He’s he’s leading a business. He’s not quite at this point yet, but he could see it coming. You know, and and and through the course of the the content we were sharing together, he he saw like this pattern is playing out, and he asked me, “Well, what can I do so that my my people can make the leap? Like, how can I train them now so that they can evolve with me? I’d be interested to have your take on that. Is that something that’s possible? Is that something that we should do? Can we develop our team all the way through?
Mike Krupit
We all have the capacity to grow, and so if our leadership or our organization invests in growth, we’re all given that chance to grow with the organization. Now, a fast-growing organization might require fast-growing people, and that’s not all of us. I remind a lot of founders as they’re in their evolution towards being a full-fledged call a CEO that they’re responsible to coach their team members, you know. And so, what I find often, I had this conversation with a with a founder a lot recently about rescuing the team. The team is on the verge of making a mistake or isn’t getting it. So I’ll come in, I’ll do it for you, I’ll do it with you. It’s like, why not let them fail? Why not let them learn from that failure, and why not invest in giving them space to grow? Because these rescues are very expensive in your time, but also in in in a sense putting boundaries around their own their growth. So it’s it’s so part of this. To to improve the outcomes, we want to get the founders and the leadership team to think like coaches to bring their organization forward with the with the company as as the company grows.
Scott Ritzheimer
Yeah, sometimes the more heart forward founders have a tendency to do that, maybe better than others, but can they run the risk of trying to get somebody to turn into something that that person doesn’t want to be? Have you seen that happen?
Mike Krupit
Yeah, it happens very frequently. You know, especially in the startup world at the early stages, it is because in the early stages, things are changing so rapidly. The not everyone can grow at the rate that the organization is is needing that additional capability. That doesn’t mean there’s still not room in the organization for them, right? So we’re constantly evaluating accountabilities and positions and and relationships with an organization. So, for example, a an organization I work with who had one of the co-founders doing sales was more of an evangelist. He was an introvert, sat behind the computer, did Zoom calls, loved doing demos. There was a lot of inbound opportunity, but when that inbound opport when when all the low hanging fruit had been picked, so to speak, we needed a different type of salesperson. We brought in someone who was more of a hunter, more outgoing, who definitely broke company culture because they were very extroverted.
You know, the kind person who walks into the office at 8o’clock in the morning and high fives everyone, which which takes a technology company of of a bunch of of reserve people and makes them really uncomfortable and and within a couple months, the new salesperson was out producing the old salesperson, the original, the co-founder, and eventually they both grew together. They they both you know they both grew. But sometimes you introduce something that’s ahead of where you need to be, or ahead of where you thought you where you had planned to be, and and the rest of the organization follows along or provides a complementary role for that for that new individual,
Scott Ritzheimer
That’s so good. So, Mike, there’s this question that I have that I ask him. I guess I’m interested to see what you’d have to say, and the question is this: What would you say is the biggest secret that you wish wasn’t a secret at all? What’s that one thing you wish every founder watching or listening today knew?
Mike Krupit
Invest in relationships before you think you need them, right? And so often we may call that just building rapport. But you know, one day you’re going to have to have a difficult conversation. You have some conflict. You maybe have an ask, a favor to ask, or or problem to solve. It was Teddy Roosevelt who said, “People don’t care what you think until they think that you care. It’s building that relationship with people first gives you the influence when you need to cash in on it.
Scott Ritzheimer
Yeah, so good, so good. Invest in people before you need it, yeah. There’s a whole bunch of different ways I can go with that. However, I want to try and keep this nice and short and sweet for our our audience here. Before I do, though, I got one more question for you, and that is: there’s folks who are going through this right now and would love help, you know, just navigating all of these changes. Where can they connect with you? Where can they find out more about the work that you do?
Mike Krupit
Sure. trajectify.com, t r a j e c t i f y, or or Mike Krupit on LinkedIn. Happy to accept connection requests and direct message me about about where you’re feeling stuck.
Scott Ritzheimer
Brilliant, brilliant, Mike. Thank you so much for being on. Really was a privilege and honor having you here. Great conversation, and for those of you watching and listening, you know your time and attention mean the world to us. I hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care.
Scott Ritzheimer
Hey everyone, Scott Ritzheimer here. Thank you so much for listening to the Start Scale and Succeed podcast. I hope this episode gave you exactly what you need for the level you’re in right now. If you want to discover what level you’re in, take our 10 question Founders Evolution Quiz for free at foundersquiz.com. That’s foundersquiz.com It’ll pinpoint exactly where you are and give you tailored tips to move forward and reach that next level in your journey as a founder. If you got something out of today’s episode, don’t forget to subscribe, rate, or review. It helps us reach more founders like you, and let’s be honest, it means a ton to me, my team, and all our incredible guests. So keep starting, scaling, and succeeding, and. I’ll see you in the next episode.
Contact Mike Krupit
Mike Krupit is the founder and CEO of Trajectify, where he helps growth-stage technology, manufacturing, and professional services companies bridge the gap between early success and scalable leadership. With more than 30 years of experience as a CTO, COO, and CEO, Mike has led organizations through rapid growth, IPOs, M&As, and even bankruptcies—giving him rare, real-world insight into what actually works when the stakes are high. Known for his practical, candid approach, he helps founders and CEOs build courage, align their organizations, and unlock momentum from the inside out.
Want to learn more about Mike Krupit’s work at Trajectify? Check out his website at https://www.trajectify.com/
Connect with Mike through his LinkedIn at https://www.linkedin.com/in/mkrupit/
Check out his YouTube channel at https://www.youtube.com/@MichaelKrupit