112: The Founder’s Dilemma: Grow or Let Go w/ Mike Krupit

Most companies don’t have a culture problem — they have a comfort problem.

In this episode, Sean sits down with Mike Krupit — former CTO, COO, and CEO turned leadership advisor and founder of Trajectify — to unpack what really happens when companies scale.

They dive into the uncomfortable transitions founders must make, why delegation is emotional (not tactical), how to manage up, and what CEOs should actually spend their time doing. Mike also breaks down why culture must evolve and how high-growth companies avoid stagnation by embracing discomfort.

If you’re leading a growing organization — or becoming the leader your company needs next — this conversation is for you.

⏱️ Chapters

00:00 – Comfort vs. Culture
Why most companies misdiagnose their real growth problem.

03:00 – From Individual Contributor to Leader
The mindset shift that derails new managers.

07:00 – Managing Up & Owning Your One-on-Ones
How to take control of your growth at any level.

12:00 – Leading in a Remote World
Overcommunication, systems, and preserving humanity.

16:30 – Founder Mode vs. CEO Mode
Why scaling requires letting go — emotionally and strategically.

19:30 – The CEO’s Four Real Jobs
Visionary, fiduciary, talent architect, and external voice.

25:00 – Evolving Culture Through Discomfort
Why hiring people “like us” limits growth.

30:00 – Vision vs. Mission
Why your mission should change more often than your vision.

33:00 – The Quadrant That’s Killing Leaders
Escaping urgency and investing in long-term growth.

🔗 Connect with Mike Krupit

🌐 Trajectify: https://www.trajectify.com

🔗 LinkedIn: https://www.linkedin.com/in/mkrupit/

🔗 No Limit Leadership

🌐 Website: https://www.nolimitleadership.com

 🎙️ Podcast: https://www.nolimitleadership.com/podcast

No Limit Leadership is the go-to podcast for growth-minded executives, middle managers, and team leaders who want more than surface-level leadership advice. Hosted by executive coach and former Special Forces commander Sean Patton, this show dives deep into modern leadership, self-leadership, and the real-world strategies that build high-performing teams. Whether you're focused on leadership development, building a coaching culture, improving leadership communication, or strengthening team accountability, each episode equips you with actionable insights to unlock leadership potential across your organization. From designing onboarding systems that retain talent to asking better questions that drive clarity and impact, No Limit Leadership helps you lead yourself first so you can lead others better. If you're ready to create a culture of ownership, resilience, and results, this leadership podcast is for you.

Transcript

Sean Patton (00:00)
Most companies don't have a culture problem. They have a comfort problem. Today, Mike Crouppen joins me to talk about growth, delegation, and why scaling a company requires you to get uncomfortable long before your business does. Enjoy.

Sean Patton (00:31)
Welcome to the No Limit Leadership Podcast. I am your host, Sean Patton, and I am honored to be joined by Mike Curpit today. He is a former startup operator turned trusted advisor to founders and CEOs. Having served as a CTO, COO, and CEO across multiple high growth companies, Mike now helps leaders navigate the hard transitions that come with scale, from delegation and culture to becoming the leader their organization needs with his company, Trajectify. Mike, thanks for being on today.

Mike Krupit (00:57)
Great, thanks for having me, Sean.

Sean Patton (00:58)
Really excited. You grew through so many different leadership roles. How did this whole thing start with you to go from startup founder in these high growth companies and then move up into the C-suite? What was that journey like?

Mike Krupit (01:12)
Well, you know, thankfully, it, I wasn't obvious, it wasn't obvious to me that it was happening. Otherwise, I probably would have been too scared. I started my career as an engineer. Because to someone like myself, like a lot of other founders, computers are a lot more comfortable than people, they're more predictable. And, you know, but little by little, as I went from, you know,

growth stage company to growth stage company, began to have more management leadership accountabilities, learned the hard way, what, what might not work. eventually found some good coaching and good training and had some good bosses and great mentors and, went from CTO to COO to CEO almost seamlessly. Like it was like I was getting my MBA while I was in the trenches because these companies were, some of them were doubling every, every six months. ⁓

So it afforded me a lot of opportunities and I didn't have a lot of time to think about it. Now there was a moment where like I almost backed out. I remember that first time that my manager came to me and said, he was actually a co-founder of a Silicon Valley startup. And he said, Mike, you're my only engineer with people skills. I need you to step up into a management role. He had 40 direct reports. He wasn't that great of a manager himself.

Sean Patton (02:19)
Yeah,

holy crap.

Mike Krupit (02:21)
He offered me no training, no coaching. He wasn't a great mentor. And I came in as a manager and I made every mistake in the book. went from a five-star engineer to a three-star manager. you know, when you're wired as I was, when I was younger, to be a perfectionist, you know, three out of five is scary. But thankfully, you know, things move so quickly throughout my career. And before I knew it,

I had mastered the organization as opposed to the quick wins of mastering the computers.

Sean Patton (02:52)
That is, you know, whether an engineer or in sales or whatever, you move from that sort of like individual contributor, technical role, and that first leap into, right now you have to work by, with, and through others is such a, it's such a transition in terms of mindset, skillset, framework, measures of success. You you mentioned that you kind of made all the mistakes that you could learn from them.

Mike Krupit (02:59)
Mm-hmm.

Sean Patton (03:16)
You know, whether it your examples or maybe from other companies you've worked with, what are the keys? Well, let's start with the mistakes. What are some of mistakes that those leaders who are put in that position make that transition? Like, where do they go wrong if they go

Mike Krupit (03:29)
I think one of the biggest ones is an expectation that we can get quick wins. Right? So, you know, as an engineer, you write some code, you fix a bug. As a salesperson, you find a deal, you close a deal. You get that immediate gratification. You go home and you say, job well done. And I remember, I remember

When I was a new manager, I went home to my wife after work one day and said, she asked how the day was. It's like, I spent my entire day in meetings. What a waste. She's like, isn't that your job now? And that was a, that was an important aha moment. Cause yeah, I was investing in people and processing systems, of course. But, but you know, it was an organization in the systems that support organization and it doesn't move as quickly as when you're an individual contributor.

So you've got to reset your expectations to say, this is not for today, this is for tomorrow or next month or next year.

Sean Patton (04:25)
Yeah, what I'm hearing is that there's a bit of having some faith in the relationship, building the trust, the communication and the strength that that pays out in dividends over time. And I could see how that could be a struggle for if you're someone who hasn't, you've never seen that play out. To have faith in the beginning of process could be very difficult.

Mike Krupit (04:45)
Well, and especially, especially in the startups that I was in, That the, you know, my managers, my leaders didn't invest time in me in part because they were also in the trenches, perhaps we were small organizations and it wasn't until things got bigger and they brought in professional, know, seasoned leaders that I got to see what one was like. And so one of the biggest things I do in my own coaching is encourage the regular investment in one-on-ones.

a lot of managers don't see, you know, they either use the one on one as a status check, how things going? How's this? How's this? They check things off the to do list or the, or the in process, the in progress list, but they're not making investments in the people they're not in their team. They're not soliciting their feedback. They're not offering continuous feedback. When, when a problem arises, they haven't been leading up to that. I mean, they haven't been sharing the fact that they see a problem brewing.

They don't establish rapport with their team. So just dedicating enough time to do one-on-ones with your team on a regular basis, on a bi-weekly or even a weekly basis, is something that a lot of leaders...

take a while to appreciate the value in doing that.

Sean Patton (05:53)
Couldn't agree more. Do you have, whether it's a strict or sort of loose framework that you like to use for those regular one-to-ones?

Mike Krupit (06:00)
there are are whole bunch of different ways to do it. And I typically put the onus on the employee. And so a lot of times when I'm coaching a team, the you know, when the employee says, Oh, my boss canceled our 101. It's just like, well, they just put it back on the calendar. Well, it's not my meeting. Well, yes, it is your meeting. And, and so I encourage either through shared docs or share or a a

a performance management system, or even just in the email, like the calendar invites, keep a running agenda. If you're gonna meet once a week or every other week as is common, to just throw what's on your mind into that ⁓ document, into that appointment. And make sure that you're prepared to talk about them, but the leader should always let the employee set the agenda, should hold the employee accountable to set the agenda.

and is there in service to the employee. So for me, it's, you know, the simplest system is just to have a shared repository where we're tracking the things we're talking about or the things that we want to talk about.

Sean Patton (07:03)
I'm interested in your take. thing I've heard, I actually heard this from another leader that I, I like the approach. I'm interested in your take. One, one to ones was, uh, with let's call it like very junior leader or junior employees, right? Uh, tenure, whatever that might be with those his take was. I, the leader sort of like, said that I had a little more control. said that here's what we're going to talk about. Here's why that sort of thing.

And then as you work with more senior folks that like completely flips to where he's like, you know, if I'm talking to a VP, it's like, you're putting the calendar on my meeting. You're telling me you're setting me the agenda before it all that like, was a bit of a flip on like seniority. Have you seen that play out well or not?

Mike Krupit (07:47)
Yes, but also not consistently. So for example, right, somebody may be because of their strengths or their personality or because of their experience level, may not be comfortable to take ownership of a one-on-one. And so their leader might show them examples of how it's done and coach them or coax them into doing so. But I also think it depends, there's some generational differences. Like, you today we're finding younger employees in the workforce today.

are a lot more outspoken about, you know, where they want to go and what they want to be and how they want to get there. And so I think when when I was young, talking, you know, telling my boss what I wanted was considered precocious. And today, it's kind of almost the standard. And and so there is a shift going on in the market in the employment, the workforce today that

Sean Patton (08:29)
Hmm.

Mike Krupit (08:38)
doesn't necessarily mean juniors won't be good at it.

Sean Patton (08:41)
I love that. And I love you mentioned a few times, it sounded to me like leading up, like people in the organization, like you're, you know, I love that concept of it's leadership isn't a position or a title, right? It's like a way of being, right? It's how you show up. So how do you lead? So what I'm hearing from you is as you are a leader in an organization, because, you know, like to say everybody, everybody's got a boss, right? The CEO reports to shareholders or stakeholders, like somebody, everybody reports to somebody, you're accountable to someone.

And so I'm hearing from you is in order to develop maybe as a leader yourself, do that by leading up and taking charge of that type of growth, asking for what you want, that sort of

Mike Krupit (09:11)
Mm-hmm.

Exactly. And our practice, we call it managing up. And that's a common term that that that we coach people on and, that I was even though I was facilitating a conversation with a bunch of big corporate executives, right, so big corporations, you know, so even even VPs and, you know, managing partners at big corporations are still not not quite at the top. And they were they were trying to share some challenges and help one another. And eventually they all realized

man, what we're trying to do here is figure out how to manage up. And because because, you know, a bunch of people there in that in that session had had problems with their bosses, even, you know, even, you know, chief, you know, chief level officers at major corporations. And so managing up is a skill that we need to learn early in our career and practice it.

Sean Patton (10:01)
If you're going to advise someone on putting that managing up into practice, what would be the first couple of things you would tell them?

Mike Krupit (10:07)
Well, the first thing I always suggest is take ownership of the one on one, make sure it's on the calendar and make sure that you're running it. The second thing is the willingness to be authentic or vulnerable. And so, you know, the kind of if you see something, say something that, you know, that we see now in the subways and in large cities, you know, post 911, the fact is that we

lot of employees don't feel comfortable, or may not feel safe in, in being authentic. Right? They may, they may throw a peer under the bus, hey, so and so keeps doing this. But I'm really talking about the organization, your relationship with your manager, the manager's decisions, the organization's direction, to share what you think and you know, and learn how to do it in a constructive way. And

I didn't, I was a precocious young manager. And I remember once I got that three star performance review writing, and I still have it today, I don't know why I saved it because it's on a piece of paper, writing a three page rebuttal to my mediocre performance review. And how that must have been perceived then. And now, you know, there are better ways

And I was in a safe environment, I didn't get fired for expressing my opinions. that is a leader's job is to provide a safe environment where people feel like they can say what they want to make mistakes and, and, you know, show up as themselves. But the so but but it's that willingness to be vulnerable and to make yourself vulnerable and be authentic with your manager.

Sean Patton (11:30)
And that's, yeah, that is so important and it could be so, so difficult, but I know for, for me, what I found is as a young leader, even in the military and things worse, I, natural tendency was to be transactional with my relationships. And, and I think I justified it being in the military, like, wait, I'm an officer. I've got to keep this like level. And I do think there's right, there's a level that there's a leadership.

appropriate relationship to have. But I think I erred on the side of like, well, don't not investing too much in the relationship, like getting too involved. And as I matured as a leader, I started recognizing how I feel like there was so much maybe lost opportunity in developing and cultivating that relationship by being vulnerable and offering them a space to do the same.

Mike Krupit (12:16)
And you would you would know, you know, way better than I would. But you know, the military is not necessarily the kind of environment where you practice these kind of things that that, you know, processes and, you know, systems and processes and, and, know, rule and order is is, you know, has a critical purpose. And it used to be I caught myself doing this the other day used to be that we often use, you know, military analogies in running our businesses.

And I used one the other day and I caught myself and said, you know what, this one's not appropriate anymore. I can't, I can't say it this way because it doesn't apply. there's really been a big shift and, the pandemic, accelerated it or exacerbated it, ⁓ with all of this distributed and remote remote work that's happening today, where we have a different relationship with our managers and we have a different relationship with our employers.

Sean Patton (12:49)
Mmm.

But when you describe that as that shift or COVID, I've seen that too. What have you seen be effective to keep culture intact, to develop people, to lead in those distributed remote environments?

Mike Krupit (13:24)
Yeah. So first and foremost, over communication. Nobody's figuring things out by osmosis. They're not having hallway conversations or overhearing something in the conference room. I remember early in my career, I'd bump into my boss in the hallway and he'd say, you know, come into this meeting with me, I want you to hear this. And he'd like drag me along places and we lose those opportunities. So we have to be

much more deliberate and much more frequent in our communications. And sometimes multi-channel, like say the same thing in a Slack channel, but also post a video about it, also email about it, say it again in a meeting. People may not hear you at the time, you know, it may get lost in, the large number of large amount of communication we need now, it could get lost in the noise. So important things need to get repeated in multiple channels. The second thing are systems of predictability.

like to understand goals and accountabilities and track progress. We sometimes did things informally, especially in the days of open office spaces, open workplaces, where we'd all be sitting in the same bullpen or floor together. we'd roll our chairs around once in the morning to do a stand-up meeting or an all-hands meeting.

We chat for 15 minutes and everyone would have their marching orders and then we'd all roll around at our desks, but we'd still hear what's going on and be able to collaborate spontaneously. And you would know who was succeeding and who wasn't succeeding. And today it's not so obvious in this day of distributed systems. And so we have to be a little bit more specific about it with systems and processes so that people know what the goals are and that we're able to communicate process and demonstrate progress.

And then then finally I think there's a.

try to think of the best word, the word that comes to mind is humanity. Right. So when you're with someone in person, we can go out to lunch together, we could build rapport, we can treat them as people. When you're in a Slack channel, or a teams channel, or a zoom meeting, or on email, we forget that they're people. And so what how how can we make sure that that interpersonal relationships that

you know, exist that that those are often the ties that bonds people together, that creates not only effective workforces, but but helps with retention. And and so how do we not make your relationship with the company or with your manager transactional is, I guess, to use that word, right? How do we ensure that that ⁓

that people know each other and people like each other and people build those bonds together in this new world in which we work.

Sean Patton (16:00)
Yeah, think that's a great, that's two call outs of kind of creating communication and like, agree, over communication and simplified and predictable community, all those things. And then you're right. how do you create those relationships and culture? And what came to mind as we talk about that is with your expertise in high growth companies. So it's one thing to do that in a sort of a static environment. But now as we start to expand and grow in multiples,

Almost new challenges arise. So when a founder or one of the first partners in a small firm is starting to grow it, so now you just sort of floated into leadership of an expanding company. When you see that, how do we tackle that problem? What unique challenges are there?

Mike Krupit (16:28)
Mm.

Yeah, there's a lot of layers to that. And I've been talking about that a lot recently, because some of my clients have gone into what they call founder mode. So they grew to business to 5 million, 10 million, and things are going well until they're not. And then they do a deep dive, they say, hey, we need to go in and do a deep dive in a particular area of the company go back into founder mode, in part, because maybe they made some wrong hires in part because maybe their market has changed or the economy, what have you.

And so they feel like they've got to go back and be more hands on more micromanaging. And and sometimes they have trouble pulling themselves out now. So So the first thing is really, you hear talked about a lot as delegation, right? It's trouble, you know, when you start a business, when you're at a business in the early days, and you're forced to wear many hats, and have your hands in every piece of the company, to realize that you've gotten to a certain point.

where you shouldn't be doing all the work where, you know, and how to delegate and how to delegate well. there's a lot written and a lot spoken about delegation and those of us who struggle with it, see the struggle and work very hard at it. But that's really only one immediate layer to it. the other layer is, as I spoke to earlier, understanding the value of your time and the time that you put into people versus the time that you put into

your own deep work. And to realize that the gratification that you get the reward that you get for seeing a job well done doesn't happen tomorrow. It happens in this the end of the quarter or the end of the year. And so there's a lot of a lot of emotional shifts, I'll call them that have to happen. And the founder needs to be resilient enough to do that.

So that when they do go back into founder mode, they can pull themselves out of it because they see the value. So one of the things that I've done, and I forget where I learned this, learned this a while ago, but I saw this ideal job description for a CEO and it was four accountabilities. First, chief visionary, you create and share the vision. Second is fiduciary accountability, make sure that the company is financially and legally sustainable. The third is putting the right people in the right seats, making sure you got the right team on you.

And the fourth is the outside face and voice of the company. Right? So you are, you know, whether it's investors or customers or the press, right? Or your peers, your marketplace, you are the face and voice of the company. And anything else that's not on that list is someone else's job. Now, mind you, when you start the company, everything in the company is your job. So it's that transition to being say that I am only uniquely positioned

to do these few things and everything else needs to have people and processes and systems in place.

Sean Patton (19:19)
I love that. you find, I found this with several, several clients, sort of a belief around, yeah, of course we need to invest in and develop our middle managers or, you know, our rising leaders, but then it's like, they hit some sort of VP level strategic senior leader threshold. And then it's

I guess they got it now. No more development needed, no more investment needed in those folks. They're my peer, they've got it. And then I've seen that turn into issues down the road. Is that something you see in companies as they scale as well?

Mike Krupit (19:51)
⁓ yes. And then, you know, it's easy to detect because people stop growing. Even the people at the very top. I've got 35 years of experience in some of these markets and positions and I still need development. I constantly find new mistakes to make. Try not to repeat past mistakes. So I know I need help and I need development. So as someone who

doesn't have a boss who's telling me where to or an organization that's telling me where to find it. It's up to me to go say, I know I need it. So whether it's coaching and mentoring or training or just supportive one-on-ones everyone in the organization, including the CEO, including the board of directors needs outside in on emotional perspectives, needs, needs support, needs insight, needs to be challenged to grow as well. We have to challenge ourselves to grow.

and the organizations that we're in need to challenge us to grow, which is why performance development plans are a big part of what I challenge leaders to provide is to make sure with each person in the organization, including the VPs, including all the C levels to say, well, here's the skills I want to strengthen or where I'd like to be in a year from now or five years from now.

Sean Patton (21:01)
And as you watch these founders scale and get to this space, I think I remember you talked about this before about, you know, there's some founders who then can grow into that CEO role and there's some who, whether it's a capability, willingness, whatever, it's better to step aside. You mentioned like bringing in the companies you were a part of, like bringing in professional management. What is that decision process like?

Mike Krupit (21:22)
Well, first and foremost, it's a very emotional decision process, right? Because you start a company, and now this is your baby. It's also a self-awareness challenge in that.

being able to say I'm not the right fit for something. So first and foremost, to know what the fit should be and know that what your strengths are, right? So there's multiple levels of awareness. So know what the right answer is, know what your capabilities are, and then be able to acknowledge and accept that it's not you. In the work that I do, nine times out of 10, investing in that founder can get them there. It takes time.

right, doesn't happen overnight. But a lot of them can get there and they make a lot of mistakes along the way. And hopefully they have a, you know, enough resiliency, resilience in their organization that they're able to survive that. certainly if they're surrounded by investors, advisors, or coaches, or mentors, that someone will prevent them from falling off the cliff. But I'd like to see them try. So often, the the awareness comes from having tried and failed multiple times.

⁓ And that's sort of the realization that says, all right, well, maybe it's not me. But I will tell you, you know, so at nine times out of 10, it is them. And that 10 % of the time where it's not them, I will say that nine out of 10 times the person they picked to succeed them doesn't work out. So in my my support for them to help them grow, and then my preparation of

you know, for them to potentially hand off the business, it's, it's to get the business to a point where it can be handed off. So one of the one of the ways where I see that done successfully is to perhaps use an interim executive. So bring on an interim CEO or interim COO, and look from the outside, look, look from have someone from the inside out, work in the organization to build it up to the point where, where the baton potentially could be handed off.

to the next in charge, which may or may not be that interim exact.

Sean Patton (23:12)
Yeah, with your company, Trajectify, you do fractional C-suite work. Is that the type of work that you do to step in and help transition that?

Mike Krupit (23:18)
Mm A little bit. Yeah, we do some of that. Yeah.

Yeah, we do a lot of organizational development, working with leadership teams on their on their organization and their strategy and the alignment of those. And then sometimes when we see a company needs a little bit more intensive care, we might suggest place place one of our coaches in as an interim executive to do what I say coaching from the inside out.

Like, let's show them how it's done. So like in a product oriented company, in a product company, often the founder is the visionary for the product. And that's the last piece that they're willing to delegate to give up. So we'll take an interim chief product officer, put them in the company, have them work with the founder who's the CEO at the time, and give them a sense of what it's like to have a very senior product organization.

So we can wean the founder from it, train the rest of the organization to work with a product organization as opposed to the founder, and then build the systems that provide product management so that we can then eventually replace ourself with someone in-house or a hire that they make to run the product organization. So we kind of wean them off of, we build the systems to support, to make the new

⁓ the new team successful, we come in and do it by coaching from the inside out.

Sean Patton (24:36)
I can see how that approach would be effective. mentioned like having someone sort of senior in there and like you said, so like wean them off of the thing that they're clinging to most highly. There's probably a lot of great lessons for people in similar situations out there. You know, one of the phrases that you said that I would love to expand on a bit is that, most companies don't have a culture problem, they have a comfort.

Mike Krupit (25:02)
Mmm.

Sean Patton (25:02)
Can you tell me about that?

Mike Krupit (25:03)
Yeah, well, it's human nature, to seek comfort. We got to a place and we are comfortable with where that is. And yet the challenge with an organization is it is constantly evolving. Every new hire you bring in, every growth, new level of growth you achieve, your culture evolves.

And to say that this is where we started and this is what makes us a company and to firmly define it stops it from evolving. And a classic story I tell is that at an organization where one of the co-founders was their head of sales. Now, in my perspective in getting to know them, they were more of an evangelist, right? There was a lot of inbound interest in the company. It was a very niche market. And this person

would very complacently get on zoom calls with them, show them how amazing the product was, and then, you know, use email to close the transaction. They were not selling, they were just order processing in my assessment. And so I said, you know what, but but there's a big part of the market that's untapped who hasn't clicked on the buy now button that triggers this guy into action. And so

⁓ who's selling and they weren't selling and so I said, you know, let's let's bring in a salesperson. So you know, we were interviewing salespeople and finally there's one person who they really, they really seek and do the job. And this person is, is, is, is loud and personable and you know, comes into the office walk around greeting everyone shaking hands and says, so at the end, I asked them, you know, like, is this somebody

know, tell me, you know, debrief on the interviews. And everyone said, well, we really think he can do the job, but we wouldn't want to have a beer with him after work. And I said, Hmm. So you're saying but he's not like you he's different. He's, you're, you're stuck on a culture because you're only hiring people like yourself. And they eventually hired him. And within two months, he was outselling the existing salespeople. And

I will say that he irritated everyone in the company. So culturally, it was a big shift. You know, they said, he's on the phone all day. It's like, yeah, that's his job. ⁓ so it's an example of how they were comfortable, they try to stay comfortable. And that could have killed the company, because they didn't allow the culture to evolve.

Sean Patton (27:04)
Yeah

Mike Krupit (27:19)
So we don't have a culture. Culture, to me, is a living, breathing thing that's created by a number of things, your value system, the people you hire, and your style of leadership.

Sean Patton (27:31)
So it's fair to say that.

culture, like, cause you want to stay on your value. I maybe I'm making an assumption here. You want to stay on your values. You have company values. stand for something, right? You don't want to be this, this brand that just is a logo that doesn't actually stand for anything. But it sounds to me that like culture inside the company, need to adjust and change based on what the outcomes you want from the company. Like, so you're letting sort of vision direct and what culture should happen. Is what you're thinking?

Mike Krupit (27:58)
Yeah, we, we, there are strengths that we know that we need to have on our team in order to achieve the outcomes we want. There are values that we know that our company holds, and we want to only hire people who adhere to those values. And, together, those will determine what the culture ends up being.

right? we will end up with an organization of people who look like us who sound like us who work like us. And and that's not going to help us meet our outcomes because we're you know, we're only as good as the strengths that we have on our team, we need to hire complementary strengths. If I am somebody who's always urgent, and a lot of entrepreneurs are

Are there people who are patient on the team? do I have the, will my culture allow me to work with someone who's patient? Because it better, because I need both of those strengths on my team.

Sean Patton (28:46)
Hmm. How do you do the, what's the assessment look like when you realize we've sort of outgrown this homogeneous culture we've created and we need to, level that up, but that may need means we may need to relook vision or maybe need to look like what we're trying to achieve. Like what's the bigger purpose here that we're in service to? what is, what does a process look like to even make that assessment? Where does it just.

happen when you realize like, you know, growth is slow and we're getting overwhelmed or we've got blind spots because we're all thinking the same way.

Mike Krupit (29:16)
So I like to differentiate between the vision and the mission. And that's not a common, that is a very common framing for it. You know, the vision is why you started the company. You know, what, why, why did we build this? Why do we exist? That almost never changes. Companies sometimes stick with their vision for decades. If not, you know, three, four decades, I know some companies have stuck with their vision. They evolve very slowly. Our mission.

changes very frequently, right? Because how we work towards that vision, we have to iterate through. I used to say when I started my career, three years, three to five year mission, right? Today, I don't know, sometimes I feel like we change our mission every quarter because things around us are changing so rapidly. Like AI is disrupting so much that you probably can't sit on a three year mission. But if we know that point on the horizon, that vision that where we want to

sail towards, how do we craft a path there? And that's what I'll call our mission. And the mission is certainly something that changes frequently because we're constantly getting feedback on it.

Sean Patton (30:16)
That makes total sense. What in terms of that outward, you know, talk about the CEO, like one of his jobs is that visionary looking out into the world and deciding how we're going to play with, play with all that. How is that feedback loop? what I, you know, I think so many companies do that very well. think companies very struggle with, that sometimes that feedback comes from different places in the organization that maybe there, or maybe feedbacks are wrong where maybe it's.

data or observation or thoughts that something's a little, you know, we're missing an opportunity or this thing's going to change. But the structure of putting, let's just say feedback or vision or communication down and then having a system to actually feed it back up based on what responses we're getting from the system. How does that function inside these high growing organizations?

Mike Krupit (31:04)
I definitely encourage organizations to revisit their vision every year. Or maybe now every quarter now that I think a year feels like it's too much. So when you're doing that planning that quarterly planning of that annually planning, you take out your vision, you say, this is why we're here. And then you've got to see if that resonates, right? Does does that make sense anymore? Are the people you're hiring, you know, now versus the people you hired five years ago?

Do they get the vision? Do they understand that? Can they recite it? And does the vision lead in these planning cycles? Does the vision lead us to create to craft these missions that move us forward to get us the outcomes that we set the goals that we want to meet? And then so if any of those are answered, no, like they're not right, we're not meeting the outcomes or the goals are no longer make sense. Or we were having trouble crafting a mission or our people don't understand our vision.

Maybe that's at that point you take that step back and said, we'll have things around us change so much that why we exist needs to evolve.

Sean Patton (32:05)
And when you are trying to, I'm going switch back to individual leadership a bit. So we talk about organization leadership and you talk about the importance of continual growth and development as a leader, as I see, use leader of self, of family, of community, of business all around and, and, and do that.

Where do you, I guess I see a spectrum. see some people I feel like are just like on this like personal development, you know, like IV drip, just like the newest greatest thing all the time, but not kind of kind of spinning your wheels and almost, maybe not getting somewhere in the longterm as much. then, I see people who, your point, like, maybe I do the job and that's, you know, I'm going to learn by osmosis, right? I'm gonna learn by just doing this thing. We'll give you the next thing. And then there's somewhere in the middle. And so when you work with.

leaders or you step in, like how do you help them frame where to prioritize and how to carve out time and energy to their own personal development.

Mike Krupit (33:01)
So the.

Decades later, I'm still a fan of Stephen Covey's time management quadrants or the Eisenhower quadrants, right? And so

like it because of its simplicity, right, that we're measuring two factors, importance and urgency. And that most of the errors that leaders make is in how they're allocating their time, what's important, you know, deciding what's important, because urgency is often masked as importance for them. And and so for me, I'll sit there and look at their calendar with them and say, how much quadrant one, right?

time you spending important and urgent versus how much quadrant two important but not urgent are you spending? Are you spending so much time fighting fires in quadrant one that you're not making investments in quadrant two because quadrant two is I want to see you there 60 70 % of the time. And and so sometimes it's just giving them that language for them to be able to say here's how I'm investing in me or my organization or my my business versus

you know, here's just me spinning my wheels, making sure important stuff doesn't catch fire. And and so it is a understanding. I try to shift them into at least the discipline of spending more time on themselves on their team on their business. You know, look, it's if you want to get more fit, eat healthy and go to the gym.

And does it matter which program you follow at the gym or which program you subscribe to for your dietary habits? The fact that you're spending time thinking about it and working on it is sometimes all you need is just that awareness and that discipline to go do it. Right. So if I go to the gym five times a week, doesn't matter what I do, really doesn't matter what I do at the gym, just the fact that I'm going is going to make me healthier than if I

chose not to go or if I, yeah, chose not to go.

Sean Patton (34:42)
Yeah. No, it's funny. I remember, um, my first business, was in, was a gym and I was in a gym and fitness business for a while. And one of the first things you learn about with like personal training plans is just by getting people to track their food for seven days, everyone loses like 5%. It's like, it's like, just, just the awareness of like, the discipline of like, I'm actually going to pay attention to what I put in my mouth. Like just that creates a meat, that awareness creates immediate results.

Mike Krupit (35:07)
Right,

or it creates accountability, even if it's only accountability between yourself or yourself and your coach or your trainer, right? I don't wanna write donut down, so I'm not gonna eat it.

Sean Patton (35:16)
Exactly. Now I, I love that. And I love the use of the, Eisenhower matrix or urgent import matrix. I was just having a conversation with a client with that recently. It's in my book too. just sort of a classic way to think about it. When you see leaders, in these organizations, you mentioned Quadrant One, urgent and important, putting out fires. And, uh, my interpretation of that is happens for two reasons, unforeseen emergencies, which is life and.

procrastination, letting things get there. Quadrant two being important, not urgent. So that's you mentioned developing yourself, developing people in your organization, working on the business, know, growing in large capacity, investing in relationships. And then quadrant three, being urgent, not important. And that is the one where I, almost it gets fuzzy. Even if people ask me like, what are some examples? I'm like, I try to like email, I try to like list things out, but I do feel like

Mike Krupit (35:41)
Mm-hmm.

Sean Patton (36:08)
It's so easy to get sucked into it. And it's almost like, know it when I see it, but like, where do you see leaders go wrong with quadrant three and getting stuck in doing work that seems seems important because it's urgent, but it's really not.

Mike Krupit (36:18)
Right, those are the leaders who value themselves by how busy they are. And who will allocate two hours a morning to go through emails and to write, you know, or spend all night or all weekend writing a 40 page PowerPoint presentation to try to communicate something. The fact is that that quadrant is

maybe self-importance, maybe that's a ⁓ way to label that. But here's an observation lately. That quadrant is being disrupted by AI.

I had a client the other day asked me, I spend all day talking to Claude, is that okay?

What he's having Claude do is all the things he would have been doing in quadrant one, quadrant three, rather, right? All the stuff that seems urgent, but not important that might've distracted him. He's having Claude take care of. So I think quadrant three starts to the urge to stay in quadrant three starts to diminish when we let AI help us, right? Back in my days, when I made my first CEO job,

I had a full-time MBA assistant.

they worried about all the Quadrant 3 stuff for me, made sure my calendar was optimized, made sure my filing system was optimized, made sure my email, I only saw the important ones. That's Quadrant 3 stuff, right? And so, know, highly effective executives don't spend time in it or delegate it, but AI is now displacing it. So I think there'll be, I think, you know, especially, you know, smaller organizations and their founders,

are so enthralled by AI that I'm optimistic that AI is gonna get them out of Quadrant 3.

Sean Patton (37:53)
and hopefully not push them back up into the fires of Quadrant One, but push them into, maybe I can expand this into some spaces, I think.

Mike Krupit (38:02)
Well, if they're working with me, I'm going to try to hold them accountable to that.

Sean Patton (38:05)
Yeah,

exactly. You and me both, brother. We're on this battle together. Mike, this has been awesome. Thanks so much for your time today and the work that you're doing. We'll have all of your links in the show notes with Trajectify and all of that. But if someone wants to try to reach out and get a hold of you or find out what you're putting out, where's the best place for them to go?

Mike Krupit (38:16)
Appreciate it.

Yeah, I first I mean, you can just Google my name Mike croupet K R U P I T or or you can reach me at Mike at trajectory T R A J E C T I F Y calm. I still even though I have AI in my inbox, I still see all the emails personally.

Sean Patton (38:36)
Awesome. Well, thanks so much for your time, brother. I appreciate it.

Mike Krupit (38:38)
Great. I enjoyed the conversation, Sean. Thanks for the time.