How New Leaders Can Inherit a Business Without Losing Trust or Breaking Culture with Keegan Evans

- When you are stepping into a culture that has not been defined by you as the founder of that company, how do you figure out quickly what that culture is necessary and what are the barriers that are preventing transformation? We have an impulse to assert control, assert authority quickly in these kind of situations. The very short answer is simple, but not easy. - Today's guest is Keegan Evans, CEO, executive coach and AI consultant of UTA.

He is also the limited partner at Beyond Earth Ventures, a former Marine Corps combat pilot turned tech leader. Keegan brings decades of experience building leadership, culture, guiding AI transformation, and helping executive teams navigate high stakes change with clarity and trust. We have a human need for certainty, and so building the experience and wisdom to make decisions with imperfect information, knowing that you're going to get it wrong. Sometimes, instead of making one big decision, make a lot of small decisions and learn from every single one of those decisions.

Failure within bounds is essential to learning. How do you when you're doing leadership development, encourage your team to try things and fail when the impulse is, just plow through this and do it right the first time. This can come from a couple of different ways one the baseline. - If you're like most of our listeners, you love the idea of running the show, but you're constantly second guessing yourself if you're ready or the person for the job.

Are you missing a key skill? Are you aware of the things you need to know, like reading a financial statement or financing the operations of a business? We are here to solve that for you. Our new Free Ownership Readiness diagnostic will rank you from 1 to 4 on five foundational pillars of successful business ownership.

It is the ultimate confidence builder that will tell you, yes, it is time to have that conversation or know these are the areas that you might need a little bit more time to develop. If you're interested in taking that assessment, you can find the link for that down in the description below. Welcome to the Art of succession podcast with Barrett Young. Join us as we explore the strategies, stories and insights that shape the journey of leadership, transitions and business success.

No matter where you find yourself along the journey, this is the podcast where you'll find the tools to make it happen. My name is Barrett Young and this is the Art of succession podcast. My guest today is Keegan Evans, a combat tested Marine Corps helicopter pilot. After his service, he started working in tech product management and leadership development.

And then he started a company called UDA, where his pioneering a human centered approach to AI implementation. Keegan. Welcome to the Art of succession. Thank you, Barry, it's wonderful to be here.

Thanks for having me on. Sure thing. Semper fi. I'll get that out of the way from the very beginning.

Absolutely. And I know this is broadcasting later, but happy birthday. We're recording the week of our birthday. That's right.

250 years, United States Marine Corps. So fantastic milestone. And that's, you know, we'll get to what brings you to the artist succession in a minute. But that's what interests me about having veterans on here.

Even though you didn't purchase your company from someone else, like the core tenet of the Art of succession. I had a buddy on Joe Bogdan a year ago, Air Force vet, because I feel like the military positions us for the ability to step into somebody else's role and take over, get spun up really quick on where the mission is at, and you know what the status of our our forces are at. And so I think that that's a beneficial lesson that a lot of leaders in succession, multi-generational businesses could glean.

So that's like my purpose for bringing you on. Besides the fact that you're a fellow marine. And I want to I want to hear all the stories. Um, but I wanted to ask you, like, starting out, what brings you to the art of succession today?

What do you hope that our listeners would gain from our conversation? Well, thanks, Barrett. And first, I want to double down on what you just said about the the the veteran capabilities and the military foundation, I often say. Whether it's in entrepreneurship, whether it's in succession, whether it's in just placement inside established companies and hiring in for veterans, transitioning veterans bring two particularly unique qualities that are pretty universal.

We all have our back, different backgrounds and experiences and personalities and approaches. But first off, veterans bring attention for on the job training that is pretty much unmatched, especially at any age range, because we're trained in our core, our core specialties. But every so much else about what we have to do as marine sailors, soldiers is an airman. I won't leave them out.

Is learned on the on the job and on the way. There's a lot of collateral duties. And so that ability to be technically flexible and an athlete is is really powerful and pretty universal on veterans. The other thing is that we bring a penchant for problem solving.

That is almost unheard of because in our service, problem solving is not called problem solving. It's called mission accomplishment. And that's pretty it's less optional when we put it that way. So thank you for setting that up.

What brings me here today is I really like the conceit of what you're talking about for your audience. There is a special uniqueness in I'm taking on something that was built by someone else. I'm continuing the legacy and also making it my own. One of my the core through lines of my career, whether it was a marine Corps pilot and the aviation safety officer or product manager through a few different tech companies or my own entrepreneurship, is that intentional organizational culture is the key to effectiveness.

And someone who's in your audience, who's coming into an established organizational culture as a new owner, as a new leader, I think has to be clear and intentional and understanding about that. So bringing my experience and my perspective on that to your audience is something that I hope to I hope to get out of this. You mentioned the AI transformation stuff. I can imagine, and that's how I approach AI transformation, not as a tech and tools problem, but as a workforce culture.

Anyone in your audience is going to be more successful thinking about how you can transform your culture to adapt AI and adapt your teams to incorporate it and adopt it. It's the right way for you, not just something off of a book or something off of a website. Yeah, yeah. I mean, I'm certainly looking forward to this conversation.

I'm got my eyes constantly on the horizon where accounting is going with AI. I mean, we're probably one of the top five, if not top three professions at risk of being replaced by AI. But the point that you bring up the a, the human centeredness approach to AI is critical, because we don't want to give up that trusted advisor status that we enjoy as CPAs to just say, well, now the ChatGPT can do everything, so we've got to figure out what that looks like, and it's going to require our entire profession to to shift.

So. But we're getting ahead of ourselves. So as, as as happens. Yeah.

So, um, just give me just a little bit. We talked about your veteran experience a little bit, but give me just brief synopsis. What brings you what brings you to this point? Sure.

So I was active duty from 2002 to 2010, in the Marines I my senior year of college. I was doing ROTC. My senior year was September 11th, and that kind of changed the perspective on on what the future was going to be. I went to flight school, learn to fly, designate as a naval aviator, and then eventually moved out to California to Camp Pendleton and learn to fly that thing that's above me.

The CH 46 I deployed three times to Iraq as a H 46 pilot, flying casualty evacuation and the general umbrella of what we call assault support. I've got over 1000 hours in combat time and moved from being a boot copilot up to one of the senior captains and instructors by the end of my third deployment. And I finished out my time. We were talking about this in pre talk as a series commander leading.

So I had the I had the joy of finishing my active duty time, reloading my Marine Corps motivation by leading some of the absolute best Marines I'd ever met in the Drill Instructor Corps, forming new Marines at San Diego. I transitioned into grad school on the GI Bill down in San Diego, and when I was finishing that up, my dad got sick and I moved up to the Bay area to be closer to him. Got into tech through a veteran's internship program at TiVo, where I learned learned the ropes of product management and tech.

And it was a wonderful learning environment. I didn't know a lot of the terms, but I always had a open conversation to ask people, and every single meeting I was in, I had a Google window open, and if I didn't know something, I just googled it first and then followed on with some very generous engineers. Five years at TiVo and I wanted to move on to other things. Working with international cable companies can be a little bit soul draining at times, but it was wonderful to get the TiVo product in.

I moved on to a startup in San Francisco working on mobility, rideshare, car share with, or looking at autonomous vehicles in the future, and then eventually transitioned out to interviewed, founded my own company to combine that military leadership and culture with the experience in tech. Around the time I'd had my business proposition figured out there, I got a call from a former executive from TiVo who was at Intuit at the time. She was leading a team of 200 engineers, and she said, I'm hiring a chief of staff.

I don't know what the job is, but you're the first person I thought of, which has been kind of the way that I like to be, bring a lot of value to any of the clients or employers. And so I started in a team there working on the QuickBooks Online Payroll team, closely working with the QuickBooks accountants, um, uh, products as well, and learned a lot more about customer driven innovation, design for delight and Intuit's philosophies and the small medium business and the mid-market.

During the pandemic, I took on a role, an internal mobility move, and I worked on the future of work and what the workforce of the future in a hybrid is going to be. And that brought me to, uh, in 2021. We didn't know what hybrid was. We thought it was roughly 2 to 3 days a week, and that's about it.

And everything else was learning. It was a big blue ocean of of that. So being able to be on the forefront of that, uh, of innovating in, uh, what the culture is going to be, what the, what, what even the questions to ask before collecting the data of what was working is going to be and then the execution, bringing the teams on board, uh, through this developed workshops and engagement measures to help bring people along, uh, back into the office in ways that weren't just forcing us back in, but really innovating and like, how can we actually make this different than purely, purely in person a couple days a week and purely virtual a couple other days a week?

How can we be intentional about that? Moved on from, uh, into it in 2023, I think. Yeah, 2023 and then founded or then re-energized into UDA and putting all that together. And so now I have a we offer a suite of an individual executive coaching team coaching.

Uh, and then the AI focus, because I thought in 2021, I thought hybrid work was going to be the generational change in work for our time. But it turns out that that was The Hobbit to AI is Lord of the rings. Um, as as we go. So all of that brings me to today, where we offer a suite of referral only coaching, general coaching, and executive coaching.

And then we're, uh, we have offerings around what we call the UTA methodology for AI adoption. Nice. Awesome. - I didn't even know about the Intuit connection when, uh, when we booked this thing.

So, um. That's interesting. We just. The more we talk, the more we find out we have things in common.

So. Absolutely. I do want to put something to rest, though, because I have I feel like I have to do this, um, with whenever I have a veteran on the show. I think there's this misconception that when you're in the military and especially being an officer, it's like everybody has to adapt to you.

You are in charge. You're the new captain, uh, of the, you know, the company and get on board or get out is. You know, that kind of impression? Um.

Another guess. Like I said, Joe. Uh, 22. Your, uh, - master sergeant in the Air Force.

So very high ranking in the enlisted ranks. And so there's I think that they they have this misconception that there is no adapting as a leader when you're in the military, everybody just needs to salute and say, yes, sir, and and go and do it. So could you put that to rest and maybe share just in your own development? Because going from a boot lieutenant to a captain, eight years of experience, you make a lot of mistakes along the way to where you do assert that too early.

So I just want to hear from you and put that to rest and and share and experience. I love the question. The prompt is excellent because it is a misconception and it is, I think, a disconnect, uh, for a lot of, uh, civilian employers, civilian teams who miss a lot of opportunity because they, they make the misunderstanding of of who we are. Uh, coming out.

Yes. There is a uniform code of Military justice. That is a separate legal structure. Yes, we are legally obligated to follow orders if an officer or any leader has to rely on that.

They have already failed at their job 100% of the time. Organizational culture. What I love about it is it is true, no matter the human circumstance. When I got to TiVo, I learned that a software hardware innovative, pioneering tech company has more in common with the Marine Corps medium helicopter squadron than it does.

Different product management is always trying to push the boundaries, and maybe a little frustrated that software engineering is is running behind. Just like squadron maintenance is always pissed that - their helicopters yeah, operations is pushing too hard not listening to them. It's about human organizations fitting together. And there are the rules and the structures, and there's a lot of there's a lot of wonderful familiarity and 250 years of history and culture that falls back on.

That's very hard to replicate. Not impossible, but very hard to replicate in outside organizations or in civilian organizations. But the fundamental tenets of leadership don't change. And that's actually what I bring forward when I'm working with clients is these leadership frameworks.

Yeah. In fact, I just I talk about a couple of the Marine Corps, know yourself and seek self-improvement as a leadership principle. Like that's that applies to everyone. Easily.

When I talk about AI adoption, one of our core principles is AI as a teammate. And that means that we can think of it as we have generations of great leadership and great high performing team frameworks, so we can fall back on the ones that we know and are familiar with. And I bring forward what we call an aviation crew resource management. Seven critical skills that I distill down to the three most important for these kind of things around assertiveness, situational awareness, and decision making that applies across military aviation, civilian aviation, and in just general teamwork and leadership.

So leadership is always about influence, no matter how much formal authority you actually have. Yeah. So I mean, could you share a story where you screwed this up because, you know, that's that's kind of the thread. - Um, and that's what I like to get from my guest, because a lot of people think, oh, well, you just bought your dad's company, and so you just stepped in and it's like junior is taking over.

And so that kind of same kind of risk of, do you know who my dad is? Do you know what my rank is? That that kind of assertiveness there. How did you learn that?

Because they tried to teach it. I know you officers are taught find that senior enlisted person and, you know, listen to what they say. Don't just assert your college degree over them, but you still make those mistakes and you still are. You have to gain wisdom, not just the knowledge there.

So. Uh, share with us, please. So I, I probably learned I took those early, like, uh, intellectual lessons on perhaps a little too far and being an aviator. So I heard all the stories.

I saw examples of the arrogant officer, second lieutenant who rolls up on a platoon and the the doesn't listen to the gunny, uh, and just and just has it. And I saw those examples. I also had the benefit silver lining benefit. Uh, like I said, my active duty time started in 2002.

Uh, I finished the basic school I was driving to, to med school for flight school, uh, and I was staying at a friend's, uh, room in Lejeune the night the Iraq war kicked off, uh, in 2003, I had so my peers who were infantry officers who were, were had done that, falling in on, uh, units that with the combat experience and then deployed and I joined squadrons. Uh, I joined my squadron in 2005 as they just returned from a deployment where they supported Operation Phantom Fury as casualty evacuation.

They had a period for listeners as the was the very kinetic invasion of, uh, Battle of Fallujah in 2004. So I saw all these lessons, and I really I didn't want to be that lieutenant. I didn't want to be that lieutenant so much that I probably over indexed on, on listening to some junior listed mid-level and junior enlisted who had more experience and perhaps didn't advocate for a didn't understand the difference between my responsibility a lot and so that that can be a another side of that risk end coin.

Now, that did not prevent me from, uh, being a little bit too arrogant with perhaps my peers and other officers because I don't know how good my camera is for your viewers, but the the mug behind me, that's my squadron mug has my callsign. My callsign was britches, as in, too big for my britches. - So you don't get to pick your nicknames. Oh, you don't know you don't.

And the bigger than the the myth of military leadership is just authoritarian and structured and control and inflexible. Uh, the bigger, far bigger myth is pilot call signs are about being cool. We are not Maverick. And, uh, it is all about finding your biggest weakness, your biggest shame, and then making you wear it on your chest for for your career.

Uh, so I think where I showed up, where where the example that you're talking about on coming in succession was less about not looking for those subordinate to me with, uh, with leadership experience and learning from them, but more about something my nose and an arrogance, uh, towards my peers and towards those who were who had more senior positions to me. But, uh, and they have their growing to do too. But I, I early on responded poorly to mid-level leaders on the growth curve, which is how I heard my call sign.

Gotcha. Yeah. I mean, that's there's two good points there. One is, like you said, abdicating that responsibility and deferring to somebody who's been in this career.

They're not the boss. But you're like, well, you've been here for 25 years. I'm not going to tell you what to do and know your job as the leader is to differentiate and distinguish. So I really like that lesson.

But then also, I mean, absolutely that, you know, the boss's son coming into the company, it's like, dad, this is the old way. This is the way things were done when you started the company. I mean, I oh, man, when I went out on my own, I had six years in public accounting and had just been a CPA for about a year and a half. And I'm like looking at the the two firms that I spent time with that are 40, 45 year old firms.

And I'm like, man, they suck at everything that they do. They have no idea where the future is. And I had to learn that lesson the hard way by falling flat on my face, you know, in my first couple years of entrepreneurship. So, yeah, it's it's a good point.

The arrogance is not always directed at those subordinate to you. More often than not, it's like, get out of here with your old school or old school methods. I think you brought that up too, in the tech. Uh, Your move into the civilian sector and, you know, the Marine Corps.

250 years is a great example of this, too. When you are stepping into a culture that is not been defined by you as the founder of that company, how do you figure out quickly, triage quickly. What is that? Culture is necessary.

What in that culture is actually the structure and the framework that makes that a successful business? And what are the gaps? What are the the barriers that are preventing transformation as you're stepping into that role? The very short answer is simple but not easy.

And it's listen, it's listen, listen, listen. Early on there's an we have an impulse to assert control, assert authority quickly in these kind of situations, a fear that we if we don't say something, if we don't have a strong position early on, that is the right one that that will undermine. But so much about leadership is about listening and especially in times of transition, organizational and cultural transition. So we've talked about I haven't I haven't acquired an organization and taken that on yet and growing my own.

But but through my time with TiVo or into it, I've been, uh, I've been a part of or adjacent to, uh, acquisitions and mergers of of cultures. So when I was at TiVo, we were acquired by ROV, and when I was at Intuit, Intuit acquiring companies all the time, but one in particular, when I was at payroll, uh, had acquired t sheets out of Boise, and it was a multi-year integration of those teams and listening and paying attention to the culture and to find out what's important. The TiVo example is one of my is a really stark one.

TiVo is a iconic, uh, brand and company, and the people who work there, there were a lot of people who worked there for since the beginning, which is somewhat unusual in tech companies, uh, for, for that long tenure to go had a, uh, annual holiday called the Blue Moon holiday. Um, because the the first shows that were launched was launched in a blue month was a blue moon. Two full moons in a month. And the the final push with all hands on deck boxing tvOS into boxes to get them out the door in that startup mode was memorialized by this annual Blue Moon holiday, right when Roe V acquired us.

One of the things that showed up in questions in all hands that showed up over and over again was, we're going to keep Blue Moon, right? Because not because, hey, I want to squeak out that one extra day off a year. But that was important. So it's really about listening to what's important.

Similarly t sheets uh, we'd acquired them the the Boise site was a growth site as well, moving into new buildings while I was doing while I was on the workforce of the future team and there was t sheets was a very good, really strong local culture, really iconic workplace and important and people will ask. People will tell you what's important to them. You just have to listen in terms of those those cultural things. So that's the good.

That's the what you want to keep. The other things you're listening for, though, are where are the friction points, what's not working, what's entrenched, what's what's unwilling to be at least flexible and change. And it doesn't always have to mean you find people who are inflexible and just get rid of them. But where can you?

What's the underlying problem? What's the other, what's the underlying unmet need? One of the favorite books that I teach from is Turn the Ship Around as, of course, as I'm saying, and I'm blanking on it. But the submarine command, Navy submarine commander, who was assigned the Santa Fe attack boat, that was, I think, the worst performing boat in the Navy at the time.

And by six months later, by the time the deployment turned it around to the best performance, by instituting a philosophy of a leader leader mentality empowerment throughout. And it started by going in and finding where's the where's that fulcrum point. In that case, it was the Chiefs. Where are those?

Where's that? That management layer, that operational execution management layer. That's not getting what they need from the top or from the bottom. And how do we how do you solve that problem?

I'm an organizational consultant and coach. And so outside help often can help that that objective that can be that extra point of view that you can actually kind of offload some of the responsibility, not not offload the accountability, but offload the perspective to get that extra outside help. Little bit of bad cop, but also just like, hey, it's not just me feeling insecure about me as the leader. They they work through and you find the right people who can come in and and develop trust and help you listen.

Be your extra ears. That's important. There's there's so much more. We can go down there.

But but my monologue timer just went off in my head. No, totally. And that's the hard part. I guess it's to back to that first question of, you know, you are you can't abdicate as the leader and it's deciding, yes, you need to listen, but how do you know who to listen to?

Especially if you have a superior? That's like, we brought you in to change this department. We brought you in to turn the ship around. You're sitting here listening.

You're sitting here stalling. Like, where's instant performance? Kind of kind of turn around. So how do you how do you work through that?

You know, we always had a joke in the barracks. It was like, be wary of the first marine that ever, you know, befriends you when you get to a new duty station because there's a reason they're not hanging out with their other friends. Um, sure. How do you.

The people who say this is a new guy, I want to talk to him, tell him all the problems that I see. How do you, like, discern, um, in that that this is somebody I need to listen to versus this is somebody that's just trying to win brownie points with me. I think you, uh, you actually just you you opened up some enlightenment to me, to some of the problems I've had, uh, in past jobs where I come in and listen to that first person a little too much, especially the one with the who struggle with the wanting to just kind of dump a lot of the problems that, uh, that that marine barracks wisdom as as is often the case, perhaps needing refinement in other cases.

But uh, applies lessons from the Lance-Corporal underground for years. Listening. Here's - this gets back to why executives, leaders, officers, why there is a difference, why the responsibilities and roles are different. It is because it is about decision making.

Ultimately, like the one thing that differentiates executive leadership from other leadership or other roles and organizations is responsible. Accountability cannot abdicate decision making. The hardest part about decision making and where where whether my clients or my people I've worked for or worked with, uh, get stuck is we have a we have a human need for certainty, which we're never going to achieve, uh, full certainty. And so building the experience and wisdom to make decisions with imperfect information, knowing that you're going to get it wrong sometimes and finding the discernment to make instead of making one big decision every so often, make a lot of small decisions and learn from every single one of those decisions.

So you're walking into organization. You've got the friendly person who you don't notice off the bat no one else is talking to or is rolling their eyes when when they're talking, listen to them out. Hear them out because it's important to get all those different perspectives. But don't take everything at face value.

Put it into little buckets. Okay. Oh, hey. That's okay.

Good. I'm noting this. I'm noting I'm noting XYZ. And then have the same conversation with people who aren't coming up to you.

Set those set those intentional conversations up. Have individual conversations. Have skip level conversations. You want to talk to people when their manager is in the room.

You talk to people and managers not in the room. You want to talk to people as a group. You want to talk to people one on one. You want to talk to people informally.

It's on the calendar sessions. You want to walk around leadership by walking around. It's one of the absolute most valuable things I learned leadership. I presence was the specific form that we used as series commanders at.

At the recruit depot. The drill instructors are the ones who run around screaming. And the recruits know that the officers are gods to the drill instructor. So if God is.

Yelling and screaming and the drill instructors are supposed to be more intense than God. That's how abuses happen. That's how mistakes happen. Uh, so the officer is just being the calm presence, the physical manifestation of the regulations is important, but that's also how we are just kind of wandering.

And we blend into the background, which means we can see more stuff as it's happening and never wanted to see an officer when I was in basic training. But but for us in the enlisted side, your senior drill instructor kind of played that role for you too. So those that don't know you have a senior and then you have a bunch of juniors. The seniors, it's not really the good cop, but it's like they're the ones that the father I always thought of as.

Yeah, they're the ones that are consistent. they will listen. If necessary, they will scream. But you don't want to see that you're seeing your screaming.

The juniors are the ones that get everybody, you know, riled up and in order and everything. But if you if that senior raise their voice, it's like, oh, crap. Like, we really screwed up at this point. But more often than not, he would take the juniors into the duty, into the into the die hut, and he would tear them a new one for whatever they weren't doing.

So yeah, it is that, but it's that invisible presence of knowing that you're there, knowing that they're being observed and knowing that there's accountability for the middle ranks, too. It's not just they can just do whatever they want. They're being supervised, too. They have leaders that they're subject to.

The original question was, of course, how do you know what you're hearing and know what you're trusting. And so listening that getting multiple viewpoints and putting it together, the accepting that you're going to have imperfect information. And the other crucial thing is figure out who you can trust, who, not just who you can trust in a binary, but who are your trusted people to help you, help you check your your horizon. Make sure you cross-check your instruments from you know, I'll pull my pilot metaphors in.

Now, if you've got someone that you can bring in to do to do this stuff together. So I'm assuming an acquisition succession scenario. If you have someone that you worked with before in your career that you trust that complements your skill set to to bring in, that's fantastic. If you don't figure out quickly who's going to be on on your your core team and your leadership team, figure out their strengths and gaps as well and how they fit and complement build that team that is both complementary and function and skill, but also personality and approach.

I'm a huge fan of the the Lincoln Team of rivals approach, where putting people together for that, assigning a common goal, a really, truly aligning on that, having different roles, having different personalities that will provide that natural critical thinking and backup support. I do that. My chief of staff is. She's 15 years younger than me, but she we have a relationship where she knows she can call me out in and press me like, hey, I really think we're doing the wrong thing here.

We need to focus. She recognizes my. My impulse is to. Okay, I really want to.

I really want to volunteer and mentor this group. She's like, we need to make money. Let's do. You can volunteer after we book these clients.

These kind of things. So I mentioned earlier the Marine Corps principle, leadership principle, know yourself and seek self-improvement, learning, being and having confidence to engage and recognize what's real, what's not. Putting together that perspective of an organization you're taking on really starts with the humility and grounded confidence in knowing yourself. Talk to me just a little bit.

Shifting from a mission in the Marines to shifting to a mission with a tech product or, you know, something that's not as life threatening. You know, we always say in accounting, we're not doing brain surgery here. Yep. Um, how do you bring over that mission focus, that mission intensity without taking it too far or without, you know, just demoralizing everyone to, you know, everything is on the line.

If this if we don't succeed, there's a lot of different ways to take to bring work in life or death stakes into future work. Um, and whether that's military and combat, whether that's folks who've been, uh, healthcare professionals, uh, EMTs, firefighters, service, any, any sort of or even people who have just had traumatic experiences and have experienced that level of stakes. How we bring that forward control in a couple of different ways, it can show up in when nothing's ever going to be that intense again with a level of judgment, uh, or the way that I prefer to do it is that gives me perspective, that I know that I can handle that kind of thing.

So when I start to feel the neurochemicals getting, uh, getting into fight flight, uh, freeze, I can try to intercept that and ground. Hey, I've handled something like this before. What's going on? So bringing perspective rather than judgment.

I had three combat deployments. I've got 2000 flight hours. When I was in a combat, uh, 700 on night vision goggles. I don't even know the number of casualty evacuation missions, but, um, 15 strike flight air battles.

Uh, which takes a lot of points to get. Um, I think it's 15. I hope I didn't just stolen valor. - It's double digits.

- That's a lot of intense experiences. Life or death stakes. Before I was 30, I felt more exhausted and stressed. After a week at a international broadcasters conference in Amsterdam, my first year as a TiVo full time employee than I did throughout those combat deployments.

Stress. Acute stress. Durable stress is relative to experiences. I deployed to Iraq under a culture, an organization, and a system that deeply prepared me for many, many circumstances.

I went and worked a booth talking to potential clients as a TiVo product manager with about seven months of rapid learning generally, and not having talked to customers much before I'd done that. I'd worked with one client. The fatigue is real and the fatigue changes, and I could have gone down a path of self-judgment. What's what's wrong with me?

I survived Iraq, should I instead be just should? I've stayed in the Marines because that's all I'm good for. Like, that's where I'm good. Or I could acknowledge that this is just different.

This is this is hard stuff because it's new and that that toll, isn't it? So recognizing the difference between I'm wrong and what I'm doing is a learning curve is a is an important part of bringing forward that that kind of experience that you're talking about. Um, you mentioned earlier about making a lot of smaller decisions instead of risking it all on the on the one big decision. Can you talk just a little bit because, you know, again, some of that misperception is failure is not, you know, not an option in the military.

But can you talk about failure within bounds is is essential to learning. You know, I joked I had to fall on my face starting my own company before I started to realize these, you know, 60, 70 year old men knew what they were talking about on my previous firms. How do you when you're doing leadership development or stepping into a team, encourage your team to try things and fail when the impulse is just it would just be faster if we just plow through this and do it right the first time.

There are always things where doing it right the first time is going to feel better, but I what I tell my kids is I got nine year old twins. What I tell my kids is total failure is like the rarest experience in, in or rarest event in all of human experience. It happens. Sure, there's catastrophic failure, but it's as long as we're learning something.

And we have we are aware of the stakes of what we're making a decisions on. Then then it's not a failure. That can be a big level. Projects, uh, that can be.

And the way that you shore up the risk of the unacceptable failures is to make is to learn those things in smaller and smaller increments. This I learned this originally in the military and aviation, in what we call the Ooda loop, orient, observe, decide, and act. This is John Boyd's, uh, Colonel Boyd's theory coming out of the Korean War, Vietnam War in, uh, dogfighting, that is then applied. And so the more and success was not making the success in dogfights pretty high stakes.

There is a there is a total failure option. Uh, there uh, was not Did not come from those who made the the perfect decisions every single time. It's the ones who made more decisions faster. They were faster to get through that Orient.

Observe. Uh. Decide. Act.

Loop. Okay. Act. Now.

Now I've acted. Something's happened. Orient again. And so doing that faster and faster and faster is led to success in dogfights in many other things.

That was reinforced, um, through my tech time, uh, and especially in Intuit's design for Deloitte system. They have an organization, a sub organization called the Innovation Catalyst. They're it's it's not unlike the Marine Corps. Every every Marines, a rifleman, every wanted into it is customer obsessed and familiar with has goes through a full day of training on this design for delight or at least did when I was there.

And that was all about rapid experimentation. Getting something in front of a real customer as fast as possible, even if you're just sketching, like hand drawing it on a piece of paper and saying, okay, here's what I'm imagining the screen looks like. Put your finger where you would push it for for the next thing. Oh, you didn't understand your natural.

You didn't understand where it was. That's not a reflection on you. The customer. Too stupid to know what my what?

Where you're supposed to push it. That's a reflection on. I didn't design this well enough, so I need to learn how to make that more intuitive. Making the faster and faster you can make decisions and get more data and learn to make the next decision with more information is always going to be better outcomes.

That also allows you to make smaller stakes decisions each time. Now you're going to have to make larger decisions periodically, especially as an executive. And this is where I also apply. And I think we got this from Amazon.

But I heard it's all over the place now, the one way door versus two way door framing, understanding what type of decision this is. Is this a decision that can be reversed? Get over yourself, make the decision, learn and get it back. Is this a decision that is a one way door.

And there are significant impacts that that are almost impossible or hard to take back. Yeah. Spend some more time on that. You're still going to have to make a decision with the imperfect information.

But. But that kind of quick qualifier, one way door to a door can help get over the that fear of failure. I know one of the issues that I've observed in my myself and and see it in my team, if I'm always asking questions, if I'm always trying to ask why something is the way it is, and then you layer on multiple small experiments or failures on top of that. Yeah.

How do you prevent yourself from appearing like you're an idiot that doesn't know what they're doing? Sure. How do you how do you convey that this is intentional. And I knew I knew this could fail, you know, how do you work through that?

Because that's I think the fear when we say, don't be afraid to fail, it's like there's going to be some people that need to hear that, and then other people that are just like, yeah, just make it up as you go along. Fake it til you make it kind of thing. And yeah, and you're looking at them like you, you're you are an idiot. How did you get into this position?

Oh, it must be because dad started the company. Yeah, yeah. So how do you. How do you still hold on to.

I'm. I am an officer. Or I am the head of this department. But we are failing.

I am asking questions. Clarity is important. One of the one of the great quotes I got during our future work and navigating through the pandemic was, as leaders, our job was to provide clarity where we can't provide certainty, and so clarity in the case of situations you're talking about, often starts with defining what success and failure looks like. Far too often I see leaders under index on communicating, feeling that oh well, everyone already knows this stuff.

Uh, you know, I'm sure everyone's aligned. If everybody can hear the voices in my head, can't they? Yep, yep. This this can come from a couple of different ways.

One, the baseline, whatever we're focused on, no one else is thinking about it as much as we are. And so I always coach sub teams in large organizations when they have to do executive briefings. Remember that? No.

Even if you talk to that team and had wonderful engagement with those executives a quarter ago, they have forgotten everything and they don't have time to relearn everything. So, so communicate and ground on on the really most important things to make it as easy as possible for them to snap in and lock into what they're talking about. That's kind of bottoms up from top down. Overcommunicate overcommunicate Overcommunicate I can almost guarantee that any leader in your audience is not communicating enough to their people, because the voices in their people's heads are focused on what does this mean for me?

Which means sometimes they're not paying attention to all the words you're saying because they're thinking about what does that first part mean for me? Or I'm worried about this other thing going on. Sometimes they're they've got something else going on in their life and they're just not in the head space. So I like to use the concept of surround sound like just just keep, keep talking and, and meet people in different places or to steal a line from Brad Smith, former CEO of Into It.

Repetition doesn't ruin the prayer. So just saying. Keeping a consistent drumbeat of clarity over and over. Hey, this is what we're trying to do.

There's one other thing I thought, but I think I just lost it. So the question being, how do you not look like an idiot? By asking questions one. Most perceptions of curiosity as weakness are internal, and if we're asking questions that are genuinely about trying to understand what other people's experience are, that's connecting rather than dividing.

In most situations to you got it? You gotta you have to get information somehow and you can set up sneaky ways of doing it. But people who we have a lot more success actually working with people in collaborative ways than putting keyloggers on to to know whether they're being monitored and watched. So it's about setting up the incentives for that.

Yeah. This I want to transition now to the future work and AI workforce development. Because this brings up a point. You know, we we put ChatGPT in the hands of our team two years ago at this point, and just me and my partner were talking about, we were both starting to experiment with it.

And we're just we need to set guidance and get a team plan before we find out. Everybody's using this on their own. It was over a year before they really started leaning into that, and we honestly, we should have trained them on it too rather than just throw it at them. But we you know, it was a year of reassuring them like, this is not your replacement.

This is a tool that we need you to learn how to use for the best of your ability. Before that really started to sink in. And then they started leaning into it and seeing how it could improve, improve their life. I'm interested in the future of work from the from into its perspective, just being in a an impacted profession there.

But I mean AI is can be seen as a threat. It can be seen as a tool. Some employers are like, I could I could lay everybody off because this is going to do everything. Other ones are like, it's going to make us rethink future hires, but we're not getting rid of the people that we have kind of thing.

So, um, just talk to me just a little bit about. Yeah, just your experience and what you see and, and that shift for you from working for other people to getting into this leadership development specifically around AI. Yeah. With what little time we have left now, the AI - could do a whole podcast on that easily, I know.

So yeah, easily. And many have. My starting principle is, uh, and I'm ripping off Reid Hoffman, co-founder of LinkedIn, and a number of others. When AI breaks humanity's way, it it amplifies our humanity, not replaces us.

And that's at a large level. That's at an individual level. That is not to say that there's not going to be a lot of disruption. There already is.

There's going to be more as we navigate this because this is a for a long time I've, I've referred to this again, not originally, but as the Industrial revolution for knowledge work. I heard something recently that I like even better is the Renaissance because whereas the Industrial Revolution was about completely changing a lot of ways, and there's going to be a lot of shift there. The Renaissance was is about unlocking, unlocking and reorienting so much, uh, still rethinking.

So I'm also a fan of the quip, AI is not going to replace your job right now. Uh, for a little while. But a human who's in high will and will can beat you. Um, so I bring that as a baseline philosophy into, uh, how we do our work and how I work with our clients to, to look at what are the ways that we can augment what we do.

I generally think that most, most organizations that are laying people off now, thinking that they're just going to backfill with AI are either rehiring or they're just setting themselves up for failure, or they're using AI as an excuse for something they had to do anyway. But they felt they had to do it like Covid and return to work. Exactly. Yeah.

But looking at the possibility, looking at the potential of of what we can do with this. You said it earlier. You you don't in your profession. You don't want your you don't want to lose the trusted advisor role.

And I'll I'll again double down on that. It's not just that you don't want to lose that. That's your that's the humanity of your role, of your job. It's to bring that in.

Now, with that, I'm going to make an assumption that you want you would love to be able to be the trusted advisor to more people, to bring your expertise and and what you have earned as a trusted person to benefit more people. So what's holding you back from that? And and that's where I start with, with our clients of what what is in the workflows and your tasks that keep you from doing the things that you love. And that's where AI can augment the way that we tackle that is we've got a five stage approach.

We start by identifying the priority pain points. This and this is just the pebble in the shoe. You all are already, it sounds like already well in the way you had ChatGPT. You've given some rough guidelines I'm sure, and you set it up with a general hey, use this as experimentation.

That's a great start. What we do is we focus down. We're seeing, uh, we're seeing in our clients. We're seeing in the in the academic studies.

Successful organizations adopting AI are the ones that focus on specific problems. So the just use AI is fine. But our first principle is AI curiosity. And to enable curiosity there needs to be frameworks.

So we identify on what the right what the right focus is at an organization level, but not in a restrictive way. But hey, we're going to solve it here. But everyone should should feel empowered to experiment and learn on their own and continuously learn from there. We establish those clear guardrails.

We do them across three vectors one. What are your professional, uh, guardrails? What is the identity as accountants or as journalists or I work with political organizations or XYZ, anything, you know, who are we that we would tell anyone coming on board? This is our code of ethics.

This is how we behave. Now. What are our guardrails for AI use within that? The second I apply, uh, a couple of Marines are going to know this all too well.

Or operational risk management frameworks. What are the threats to the organization? How are we going to mitigate those? What categories do they come into?

High, medium or low or severe? Moderate. Minor. And what are the standing guardrails for something that falls into that so that as our team applies this, it starts to experiment with AI starts thinks of a use case that hasn't been done in the team before.

They can make a quick assessment of is this a severe, moderate or minor risk? If it's severe, I know I got to go to Barrett and get permission. If it's if it's minor, I know, hey, I've got I've got kind of hands free to to run on this and checking in. So clear clear usage guidelines.

The third step is building that effective human AI collaboration. And that gets into our second principle is I love that you you've used the word application multiple times here. I've been grinning at this one because it's a great use of the word two. For a year now, my marketing team has told me, you got to you got to change the name of this principle.

And I'm stubborn on this one. Our second principle is amplification without abdication. So - nice. Glad I can help.

Yeah. No, you're you're you're grounding me in on this one. They've given up on fighting me on that one. I'm I'm I'm.

I concede a lot of other areas with this that we've settled on this one. Amplification with that without application is about not never releasing responsibility as the people. Put another way. AI is the copilot, not your autopilot.

Yeah, I see there's a work swap thrown on LinkedIn. You see this in things just thrown over, uh, shifting the executive function responsibility of, okay, I just spit this out of ChatGPT. And now it's my boss's job to figure out what it means. That's not how that's not helpful.

Still be using it to augment yourself. So we figure out how to map. We've defined that specific task or workflow we're going to target. We're going to map across what where is AI going to be used here first and where is it not and what's the human responsibility.

And where's the checkpoints and all that stuff? We do a detailed math of that. Our third and final principle I mentioned earlier is AI is a teammate. And so we we understand and assess and reinforce the team principal like the team operating principles of that are going to be going to help this adoption work.

I said the core three are assertiveness, which is about communicating. And the the definition from Marine Corps Aviation was holding firm to a point of view until reasonably convinced by the facts otherwise. And it's always professional. So it's about communication.

It's about building that's in your communications with your eyes of, hey, that doesn't feel right. Talk. Tell me more about that as well as other points of view. The second is situational awareness, which I also love the original definition of.

It's the degree of accuracy to which our perception of reality maps actual reality, and similarly, understanding what's real and what's what's not, and having and listening to our gut and the. And then the third is decision making, which we've talked a lot about, and finally executing a systematic transformation of all of this. So we're building an intentional roadmap, not one that puts all of their work on stop to implement AI usage, but to integrate it into the work that you already have to do it your CPA.

You're you're about to come up on a pretty busy season. If I remember my, uh, my calendar. Right. Um, you're not going to want to spend January stopping to figure out incorporating AI across the board, but what what's the task or workflow that has sucked year over year and and not that people are angry about or wish they didn't have to do.

But I look for what are people avoiding doing? What are you avoiding? What do you put off uh, day over day and finally do on a Friday when you're exhausted and you just have to do it because you can't put it off any longer? Yeah, that's the area to find the fertile ground for things.

That's, uh, a lot of the ways that I'm thinking about team based and supporting folks, navigating through getting over early resistances and, uh, and problematic uses. You talked about shadow AI ages earlier. It's great that you got ahead of that. Now you have an active resistance or apathy.

It's funny because one of the keys for us was that practical use that I think it was your first or your second principle, or the thing that you have to like, get them to see. For me, it was and we talked about this before we started recording. I'm I'm a game master for role playing games, and I picked up ChatGPT six plus months before ever doing any business use for it because I'm like, I have to come up with bad guys for my players. So good.

Kill. It's so good. Come up with scenarios. And this is 2003 at this point, like first six months of ChatGPT 3 or 4, whichever two I don't even remember.

Yeah, I've lost the numbers. It's been so many models since then. But I joke about that and that, you know, people's eyes glaze over when I talk about that because they don't know about what role playing games are. They don't know.

No. You have no contact. You've got a friendly audience here on this one. Yeah.

But the point is, you've got to find. I had this conversation with my father in law a year ago. He's a master gardener at 70 years old, and he's using AI and his apps for plant identification. He he knows plants, but he doesn't know every single, you know, branch that there is.

You have to find that thing for you that's going to make you pull out AI every single day. And it doesn't have to be like it's going to solve the biggest tax problem that you have. It's play. It's getting comfortable with AI through play, getting into it, knowing how it works.

So it's good at knowing what's bad at. And this is the focus I've taken with, you know, people coming into my profession. I have faced the same fears 20 plus years ago. Is there going to be a future in accounting when everything is QuickBooks online and you know everything's automated?

I use the perspective of the table saw. The table saw completely revolutionizes work. Woodworking because you don't have to hand saw everything you could. You can slap together something really quick with a little garage, foldable table saw, or the people who know woodworking are leaning into the benefits and the capabilities of what that tool now unlocks for them.

And so that's where I encourage my team. I'm like, we're not going to stop being that trusted advisor. Yeah, it's actually going to free you up from the repetitive tasks. I don't want to work with more clients.

I want to work more with the clients that I have. And right now, I'm so distracted by filling out all the Excel files and, you know, all the prep that goes into the actual hour long conversation each month that I live for. Lean into that, know what good tax looks like so that you can recognize bad tax. Know what?

Good journalism. Know what good marketing looks like so that you can recognize the bad. And that encourages us in our professions to to lean into that stuff so that we can differentiate the good from the bad. So Satya Nadella, CEO of Microsoft, on the Dwarfish podcast.

I think it was earlier this year called out, we have to. We have to separate the concept of the knowledge work from the knowledge worker. AI is going to be able to do a lot to most of the knowledge work we do right now. Well, that doesn't replace the knowledge worker.

What? When is what makes our humanity and our effectiveness as a knowledge worker? Being able to read and process an entire email inbox? Or is it something else?

And so to your point, yeah, handling the Excel spreadsheets. That's an excellent, excellent point of view. All right, I know we're I'm we're at an end here. We've gone way too deep into this.

We didn't even get into pricing models. And that's my my profession is not prepared for you know when it's something does take us six hours and now takes us six seconds. Yeah. That's a whole other topic.

I'm sure you guys were all over it into it as well, but, um, so we have to schedule a follow up for that one. Yeah. But, um, before we jump into the lightning round and bring this in for a landing. Keegan, is there anything that we haven't covered that you wanted to add?

Sorry, I just I just authorized my my nine year old to go self get some chips. Um. - Um, I implied this a lot. AI adoption.

There's a reason that it feel like our tummies feel funny when we think about this, and the disruption and the change is going to happen, and it's because the technology and AI is changing faster than we as humans can adapt to change. And we have evolved to understand change in two ways. There's linear change, which is life cycles, growth, education. Generally, if it's linear, it is a good kind of change.

Exponential change is cancer, volcanos, terrorism, those bad stuff. AI is changing at exponential rates, which means we have a natural physiological reaction to that as a bad thing. AI is unique and special in that the solution is within the problem though, because by one, by working together in terms of organizations, just like you've talked about doing with your team, we can address those kind of outsized things together to learning AI. Learning to leverage AI.

It is this wonderful democratic distribution of capability. It can. It can bring in and shore up so many things to allow us to focus on the parts of ourselves that are. That are really about thriving and contributing the most.

I named my company Yoda, based off of the Greek word eudaimonia. Aristotle's interpretation of eudaimonia, which is roughly translated to good life or human thriving, is to achieve. It is to contribute the most to society. And the way we contribute the most of this society is to find that intersection within ourselves, the life's work, to define this of what we're good at, what we have talents at, what we can, natural skills any doing can make money doing, and what we like to do, because it's and it's the intersection of all those things.

And when we find those intersection points, master those towards excellence and continue that. Because we are all unique in this area, the distribution is naturally going to the rising tide is going to lift all boats and society will be bettered. The promise of AI, as I see it, it's going to amplify all the bad parts of humanity too. But the promise of AI is allowing us to really focus on those parts of ourselves that help us achieve individual and collective eudaimonia.

So that's how that's where I'll end it on the philosophy before I jump into lightning around. I'm resisting, uh, unpacking that some more. But we are way past time, so, yeah, we'll have to schedule. I'll come down.

So. - All right. Keegan, are you ready for the lightning round as we wrap this one up? Yep.

Okay. Um, coffee or tea? And how do you like it prepared? Uh, coffee?

Black tea when I'm feeling guilty. All right. Um, pie or cake? And do you have a favorite kind, uh, cake?

Coconut cake or red velvet? Uh, but cherry pie as a nostalgic cake is my dad's favorite. Uh, only periodically, but mostly cake. All right.

Uh, do you have a favorite holiday and why? Uh, Thanksgiving. I have a longstanding. I love the food.

I have memories of family gathering and Friendsgiving. Gathering and orphan Thanksgiving gatherings. That's one of my favorites. Um, do you consider yourself a morning person or a night person?

And do you have a favorite routine? I think I was at 1.1 of one or the others of these, but, uh, I like I said, I'm a single dad of nine year old twins, and I'm tired all the time. - My night person ends at 930.

Yeah. It's. Yeah, yeah. My favorite routine is learning to put my phone on a charger on the other side of my room, so I actually go to sleep, so.

Yeah. Nice. - Um, what's a common belief among entrepreneurs that you would want to challenge? You got to do everything yourself or that there's only one way.

Tying into what I said about eudaimonia. Leadership is about authenticity and decision making. And yes, there's it's not a it's not just about bleeding hard or all over everything about a full self, but you can't just fake it til you make it. You have to have confidence and that has to be.

Sometimes you have to push yourself outside and learn more. But it's yeah, there's not just one way. And that one way is not just emulating Steve Jobs, who I have a great appreciation for. But yeah, don't do that.

But his his solution is not our context that we're working in and our individual. Yeah. Awesome. Um, what is one thing that you would want your successor to remember you for?

My first commanding officer, uh, had a, had a leadership philosophy that has stuck with me throughout everything. And that's everyone's trying to do the right thing. And and that, you know, a marine gets in trouble and is in front of him for an NJPW. First thing he does is reach into his fridge, hand him a Coke and say what happened?

To hear it from their perspective, everyone's trying to do the right thing from their perspective, from their collection of perceptions and whatnot. I would hope that any successor I have, uh, remembers me for always trying to do the right thing. Awesome. Thank you.

Um, where are you finding creativity right now? I'm a single dad, a nine year old twins with a, uh, trying to grow a a consulting and coaching practice. Uh, so it's. I will admit, it's fairly limited, but some of my favorite places for creativity are you and I have role playing games in common when, uh, when I can keep groups consistent.

I've enjoyed writing. It's passive creativity and really continue to expand my fiction reading. In addition to all my other real reading. And I'm guessing there's actually creativity in navigating parenthood.

For sure. I was going to say Minecraft and YouTube videos. Yeah yeah yeah. This stage.

Last question for you before we wrap up, Keegan, what do you have? What do you have coming up in the next year that's got you really excited? I really think that we can bring a lot of good to to a lot of companies, you know, not a lot of companies like your audience, a lot of companies like yours, organizations, uh, that are not big tech, not software tech, who are maybe a little reluctant about adopting AI or as not for me, or that's for the engineers or something like that.

AI is going to augment everyone. There's there's possibility in everything. And over the next year we've got our 30 day kickoff program. We've got durable coaching around AI adoption.

We're going to be doing webinars. We're going to be continuing to find, uh, find events to show up at. And I'm really just looking forward to getting in and helping more people, uh, like, you all take this on and find that competitive advantage and really unlock unlock some greatness. Awesome.

So, uh, Keegan, where can people go and find out more about you and Judah? We're up on LinkedIn. That's a primary source we're always posted on there. Please follow us.

Uh, ayuda. Uh, we got the website Udemy. IO. Uh, that will continue to be updated.

We'll have more there. We also run a Luma calendar on Luma uh, UTA events. Uh, we do local Bay area. We did a series of roundtable events for, for tight knit, uh, networking events.

We're doing all of our webinars are going to be posted there as well. And, you know, I may regret this, but keegan@uta.io uh, emails, uh, I'll do my best to to get you or find me on LinkedIn as well. Okay, good.

Well, Keegan, I appreciate you coming on the Art of succession and just, uh, sharing these principles and and your approach with us. I really appreciate having you on. I really it was a wonderful conversation. Barrett.

Thank you for having me. Absolutely.