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:

- 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

- What it takes to have difficult conversations and stop rescuing instead of coaching your team.

This episode is ideal for for Founders, Owners, and CEOs in stage 4 of The Founder's Evolution. Not sure which stage you're in? Find out for free in less than 10 minutes at https://www.scalearchitects.com/founders/quiz

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

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?

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.

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?

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.

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?

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?

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?

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.

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?

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.

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?

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,

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?

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.

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?

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.

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.

Hey everyone, Scott Ritzer here. Thank you so much for listening

to the Start Scale and Succeed podcast. I hope this episode

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