Jessy James: Welcome to the True Leadership Podcast, where we explore the essence of leadership beyond tactics and performance by sitting down with executives to hear what matters most to them. I'm your host, Jessy James, and today's guest is Sean Patterson. Sean is a technology executive, former US Navy submarine officer, and an AI educator dedicated to helping organizations adopt AI in practical, human-centered ways. With executive leadership experience spanning healthcare, manufacturing, aerospace, and advanced technology, Sean has led operations, technology, and business transformation at the highest levels. Today, through CrossGen AI, he equips leaders and teams across generations to integrate AI into everyday work by focusing on people before technology. His philosophy is pretty simple: AI should amplify human expertise, not replace it, creating organizations that are more capable, more adaptable, and better prepared for the future. Sean, it's an absolute pleasure to have you on the podcast today.
Sean Patterson: Thanks for having
Jessy James: Sean, I'm curious, who was someone from your early life or it might even be an early experience that you had that shaped the kind of leader that you are today?
Sean Patterson: Yeah. there's my my first sort of two. as you mentioned I was was in the Navy and my the first captain that I I worked for as an officer, you know, really I think shaped my view of the empathetic leader. you know, we had some, you know, being underway and at sea and places we shouldn't, you know, that we're not supposed to be, and I was kind of the last frontier of submarines, right? we had some issues that we had to deal with and it was about integrity for s some people and how he handled that I thought was very appropriate. But if you got kind of one on one with him, it broke his heart about how he had to actually hold some people accountable for something that, you know, was more integrity based, right? 'Cause you're you're You're really so you're calling somebody out, right? In a in a very real manner. and it was big enough where we actually have to have this person actually had we had to have the helicopter peek the person off the the submarine at sea, which is not a cheap thing to do. and just that he did the right thing, but also had the human element of the whole situation still there. in a in a in a real empathetic way, right? so I think Th that's really important. and then there was one other leader, and and I thought by the way, if you can always get lucky with your like your f the first person you work for out of out of the gate or with your real with a real job, I think it's it probably sets people's careers up to make or break almost right away, you know. Because you you start off with what good looks like, especially as your bag of tricks is not your bag of leadership just isn't that full full yet, you know, filled at at all. you wanna be filling it with the right kind. the the sustainable kind. and and I do think that first one is is really important. So, you know, as individuals start to, you know, go out in their career, I do think it's important to make sure you're interviewing both ways, right? Navy, I have less choices for sure, but you know, you just getting a job, beware of just the offer to and that you want to get something versus the right kind of thing. It goes both ways. The company has to get the right person and you need that the right company and the right boss, right? and then I had one other individual after I got out of the Navy I h less empathetic leader, but somebody that really understood business and operations and how to get things done. And and he himself was going on a journey of learning how to be increases emotional intelligence. And, you know, I was there kind of along that journey with him and saw the humbleness to for a leader to be able to learn those tools and and absorb them. And that's, you know, something that I took on as well, right? having, you know, personal coaching for some time now for executive coaching and businesses had started paying for that, but I carried it on because I really saw the value in how I adapted and even paying out of pocket sometimes to keep that going. I think that that's really important. So there's there's definitely been two largely influenced people, influential people there. And honestly one more's a person on Amazon. my and it I think it all comes down to emotional intelligence. I mean The people you remember, you're gonna rather n negative thing or the positive things is usually has nothing to do with we ship the product. It has to do with the interactions of people, right? Right. And so my father had passed away right before I got transferred to this individual VP at Amazon. because I'd already been working there, I got moved. the organization got moved. And my father just passed away, was the first time I ever met him, and I remember going to have burgers with him at the top of some hill in Seattle. And the first thing he said to me was, Tell me one of the best stories you remember about your father. That was it. That was the first s like sentence out of this guy's mouth that I've never met before at the highest levels of Amazon. And that's what he asked about. Wow. So Yeah. That's what I remember. Very
Jessy James: And I'm curious, Sean, how did all of these people kind of shape the leader that you are today?
Sean Patterson: well as I mentioned, the get getting humble enough to realize, you know, your own gaps on not the management side of things, right? The leadership side. I think so many people think about management and leadership as one and the same and they're really not at all. you know, the people aspect and coming from an emotional intelligence point of view. I would also say some of the standards they kind of imbued in me in terms of where people can kind of get caught in a trap. For instance, the second person I mentioned that was my first real leader, manager leader out of the military, you know, he told me he's like, never let a vendor pay for your meal. Full stop. I don't care how much the meal is. There was this one story that we we went going with DuPont. DuPont vice president was like four of us. And I remember Hank, you know, always pay for the thing. Now we didn't always pick the wheel of the Where the meals are at, because the vendors always assume they're paying. And then I like swapped out the credit card because I was going to pay. It was like a $2,000 bill. And I came back and told him, I was like, here's the situation. I didn't pick it, you know, and all of a sudden getting hit with like $250 per person kind of thing, which is not something I would have chosen to do. But he was appreciative that I still followed that mantra because then you are not making decisions for the wrong reasons because you're trying to get something out of it as an individual. and to always kind of pay. And so there's all these kind of like tactical little lessons like that, I think, that really drive n maybe not the EQ side, but like the ethics of business, because that all plays to the leadership side. Right. And I think it can be learned by individuals. I think that I've gone through that journey and my best, you know, if you ask aside from leaders, I mentioned, you know, the best partners I've ever had are all HR. Like they're the sounding board that That was the gap I had, and I think it's the gap that the plurality of people in leadership have. They let the business aspect dictate too much of it. It's a f I wouldn't say it's a fine balance. I think you need both full stop. and I don't think there's enough humility in the world to work on those kind of gaps. and it's been proven scientifically that the most successful businesses are EQ forward. Mm-hmm. And the ones that most people want to work for, right? You don't leave jobs, generally speaking, you leave it because you're boss. It's proven time and time again. I think most people can reflect on that and realize that. And I think if I reflect back, all but one time I changed careers or changed jobs was because of a boss. Every time. because that's your day to day at the end of the day, you know? Yeah. Yeah.
Jessy James: Yeah, this this is a nice segue into, you know, I'm curious, what does true leadership mean to you from your experiences, from your lived experience? What does true leadership mean to you?
Sean Patterson: I think people that are invested at some level of investing in in in the people, but the growth and development of those people. where it's not viewed where it's viewed as an investment, not a necessity. Right? A a belief that anyone can learn the tools to grow a business, to grow an organization. I think that true leadership is investing in that because it's the right thing to do to grow the next person under you, right? And in and in some ways, you know, while there's managerial aspects to this part, you know, if you can go on vacation and actually unplug And you should deliberately do this because it's a good litmus test if your organization is not reliant on the leader, which is what that's the goal, right? You shouldn't have to, it should be colleagues all kind of working together. And you come back and nothing's broken. Good for you. Find a new role now. Right? And and and so many people just try to I don't think micromanagement isn't always the right word for this. I think it's some level of Subconscious job protectionism or self-feeding that like people need me and want me per se. and I think true leaders are able to push away from that and realize that you should always be hiring and moving people up that can take your job. If if you're not hiring to fill some gap that you have or your organization has that will eclipse you in that function, then you are if you're not doing that as a leader, then you are on a constant downward trajectory for the rest of the company's life. You will never be better than the day you are today if you are constantly Trying to protect your own ladder. Now, I will caveat that as an AI person that will also say, I do think flatness is coming. you know, it's gonna be a lot more entrepreneurial flair amongst organizations that will be able to survive the next twenty years or so. And if you look back in history, nineteen sixty six, only twelve percent of the companies that existed in nineteen sixty six in the Fortune five hundred ex still exist today. And the average lifetime is now twenty six years. Twenty six years is the average lifespan. it was thirty-two, I think, in in thirty years ago. It's even less now. Look at look at the S P index index in in the mid 90s and look at what it is today and see how many of those top names that you know are no longer existent. And a lot of that is the turnover of leadership and the ability to to have a sustainable ongoing business. And it comes down to tribal knowledge never getting documented, some level of I leadership but kind of all built it together. But did they make a sustainable ongoing process is not reliant on the leader. And that to me, that's the definition of true leadership. Isn't it's about the team and not reliance on me. I may facilitate. And then if you can go on vac vacation and come back, that's your that's your test to see if your facilitation was was right was good or not.
Jessy James: Yeah. Sounds like a dream job as well, right? Can you share about a time when you realized that your way of leading or living no longer met the demands of your work and life and you needed you know you needed to grow and develop in some way.
Sean Patterson: Yeah, I think Playing on this emotional intelligence side of things as well. At Amazon, I think I I struggled because we were scaling our business. We we built Amazon's middle mile team. So the big blue trailers with the smile on the road. I was the executive that built that out. and we started twenty people. There were twenty people on the team when I when I kinda started. And three years later it was fifteen thousand. And you know, we didn't have any trailers and we like eighty seven thousand trailers at the end and Growing and scaling that team was very difficult because we were re-orging like all the time to almost creating some level of pyramid, right? Hierarchical pyramid, because you're going for 20 to 15,000, distributed across about 500 facilities as well, that didn't even exist the three years prior to that. And so I really needed to figure out how to lead my team where there was some level of not everybody would make the next pyramid structure, right? You'd still have that job, but you're, you know, as we're scaling it, we had to. pick the next core team and then the next subset was the next core team because then but somebody was working directly for me a year and a half ago was no longer doing that and there's some level of hurt you know hurt that kind that maybe that person felt and I wasn't I think I was too dismissive of it. even though it was a practical reality. But I think the ways that I approached it at the time weren't empathetic enough, quite frankly. and so, you know, I met with HR partner, and kind of went through that journey of like how do I how do I get this better on the next reorg of the pyramid, which we had to go through again and again and take people on the journey where they where they still felt invested in, but also could appreciate the necessities of what the business needed. And I I think it was more I needed more ability to see it through their eyes.
Jessy James: And I'm just curious, you know, it's not very easy to step into somebody else's shoes and see their world from their perspective. What did that journey take from you or for you know, what did that mean for you?
Sean Patterson: This is my honest answer. I had in high school, I had a a girlfriend that was not very stable and she tried to commit suicide. and I think that killed my real side of EQ, like where you could feel from an you know from an empathy point of view, for a very long time. and I think Eventually I sort of academically started to understand the gaps I had as a leader, you know. It's not to say I was a bad leader, I just think there was a lot of opportunities. And the death of my father was the thing that sort of brought that ability to feel back. And at the same time, 'cause he he passed away pretty quickly, he was diagnosed with pancreatic cancer, so it was November and he passed away just a few months later. And I think one I was able to For lack of better words, feel again, but also some level of appreciation or reminder halfway through my life, or hopefully a third through my life, that everybody has something going on in their life, right? Business is not life. and there's there's always something bigger going on. And and you just then that by the way, that applies everywhere, not just in business when you're out at the grocery store and yelling at people. You never know. what's going on and I think that allowed me to like re feel that again. and so I th you know it took a real event for me to not make it academic. Mm-hmm. but and that was my journey, right? I I think just based on how my brain works, it it was it was kind of academic, for sure. Yeah, but then being able to layer that on later was was important and not something I certainly chose. but it's my journey. Yeah.
Jessy James: Sounded like sounds like an awakening for you.
Sean Patterson: Thinking about
Jessy James: Thinking about your journey over the past few years, what's been the most valuable investments that you've made in yourself for your own growth and development?
Sean Patterson: fr from a pure leadership side, I'm going through a different journey now. I left corporate America, as my quotes, a year and a half ago now to do my own business and now forming my own team. We have eight, well now nine starting next week, employees, including myself. And I get to make my like my team this time. Like, you know, not you know, it's not to say anybody I ever that ever really worked for me was anybody I really didn't get along with or work with, but you know, they're already there. and so you kinda work into it, and then you maybe hire a few other people that you get choices on. in this case I got to go from scratch and understanding truly like I knew like these first hires are the most important. to establish the culture that I want to at least get a common core, like a critical mass of what we believed in, because the next person to come in will either naturally they have to assimilate to that, you know, or they can break it. But as long as you kind of get a core, going through that hiring process has been really critical for me. The other sense of leadership that I don't Think I appreciated a much. I went to Amazon because I love their leadership principles. Okay. I did not want to leave my my job that I had before Amazon. I really didn't. I went kicking and screaming in some ways. but I appreciated their leadership stuff, their leadership stuff principles. and One of them is ownership. and I carried that forward to the other businesses I went to after Amazon. But I'll tell you what, until you're actually bit with your own company, you don't actually feel real ownership. Like it's totally night and day difference of what I used to kind of purport that I was an owner and owner and stuff like that. I think there's some level of introspection that a lot of people can do that they think they own it until really If it breaks it's one hundred percent you and there's nobody else you can blame. so I do think levels of ownership kinda play into that as well as building the team. and so far it's worked out. So but that's that's kind of been something I've been, you know, working on 'cause it's a different it's a different approach. I I it's it's different. but this time it's mine, you know, and I get to form that and But it's it's definitely a different level of intensity, even though it's less intensive. Yeah. Yeah.
Jessy James: And you as you think about this entrepreneurial journey that you're on, what's your vision for your leadership, for your legacy as well, or or you know, and the impact that you want to have in the years ahead?
Sean Patterson: so in some ways I don't want to grow this business too large from a headcount perspective. I think that AI enables us to scale to a much higher revenue per employee than was capable. And I will say that already exists now for what we're able to do. And as educators, first we don't do projects right away. We educate and then we will help you do a project, not the other way around. 'cause you need to learn how to use these tools as individuals yourself. and you know We need To grow and create a culture of entrepreneurialism. So we have a we we wrote a a job description, right? And one of the job descriptions says something along the lines of we set constraints and then operate within them without permission. Like we are not asked. We don't ask like how, if you will. Like we don't ask for that permission. As owners, like I say ownership, but like set the guardrails and allow your employees to fail within that. Right. We want that sense of failure, right? we've we've had one major but not impactful failure that we had for something that we worked with somebody on, and we we learned that lesson and that employee was like heartbroken. for for something that didn't work out. And it's like as long as we're living and and learning from that, that's all that matters. And and with AI, at some level of okay, how do we embed this into the system so that this doesn't happen again? And so I want to make sure that it's okay to fail and that we have an entrepreneurial flair. And we're really just a bunch of entrepreneurs kind of operating together because again, kind of with the use of AI, you can start to bleed into areas that you're not an expert in if you do it safely and and thoughtfully. So that allows us to create just an entrepreneurial culture and and not really have hierarchy. I have somebody that was like my first employee that I'm calling like the lead, which is an allocator of work, but not a sense of hierarchy. I'd I'd rather everybody in the company make the same amount of money. Like we're all on the same journey together. yeah, so so I think that entrepreneurialism is is that's kind of my my hope for that. And and with that comes the ability to be okay to fail and experiment. the agility of learning new things is so important with always has been, but even more so now. it's going it yeah, with AI it's just things are getting faster and faster and faster. it's beyond human capacity to kind of keep up with it at this point in time. and so I I think you just have to have people that in in a in a system where you're you're allowed to move with that, you know, those those guardrails and then just rock and roll from from with inside there. Yeah.
Jessy James: Yeah, I mean and you know, the sense I get is that this business idea is really coming to fruition and you're bringing in a lot of your experience and values to play here, right? And having fun with it. And I'm also curious, what are the ways in which you still need to grow personally and develop in order to sort of really realize this vision?
Sean Patterson: I think it it's in some ways sales, right? As as the the the main as the owner, right? how to tell the story in a accessible manner to our prospective clients without overwhelming them. Right? Cause I I can kind of get on the kick sometimes of like, and and and and and you keep on adding on and you lost the message because you just don't you're you're afraid you didn't get that sound bite in. so we do play by play on this. Like I even have my employee we we did a presentation on Saturday for about sixty veterans. they're they're with us for the next few weeks. transitioning veterans. and I had them watch the video and critique me. And so there's things I need to learn in that process, I think, from from the the sales point of view. and and there's leadership in that, right? Because you're really talking to another leader of an organization to and sometimes tell them, like, I'm coming from a place of you need to invest in your people, and a little bit of poking, you know, the bear and saying, We haven't done technology investment properly forever. you know, like I I like to say c companies have always bought the gym membership and affected everybody expected everyone to get fit just because they bought the membership, right? You buy Salesforce and now you expect everybody to just magically use this and we just don't have the staying powers leadership to see it through, nor does leadership generally understand what those things are. And you wind up using five percent of of the system and and paying for it and nobody likes it and it just it's a you know, not I'm certainly speaking broadly, but like we've had this problem with technology for a very long time. And productivity per person in the United States with technology has not been what has been sold to us. Right. And I think a lot of that isn't that necessarily the technology doesn't work. It's just we're bad at integrating this into non technology and albeit sometimes technology companies. and so trying to get people to see this. Fortunately, they have lots of scars from the past of yeah, this doesn't work. We did it five year ERP. For conversion, that didn't work. That didn't work. And so at some level of reminding them that you can't do it the same way. You have to invest in it. And we won't do business if the CEO is not in the first training cohorts. And that's twelve weeks long. And so you're talking almost twenty four hours of a CEO's time that I'm saying you must do this and by the way you have to do homework between the two of them because you need to show that level of humility to your own workforce before I'm willing to teach everybody in it. And so again in terms of the total thing and doing that sale, I'm also trying to say you need to be a good leader too. Yeah. Yeah.
Jessy James: And and where do you feel most tested right now? Like what challenges are stretching you the most, both in leadership and in life?
Sean Patterson: as my wife likes to tell me, I'm the speed of Sean is not the speed of everybody else. And so like it you know, it you know, going back to kind of the sales process a little bit of like, okay, I had these conversations, it's good, good, good, good. And then, yeah, follow up with us, and you follow up, then you follow up, and you follow up, and you follow up. I know it's a typical sales process. I I was a chief Roven officer for one my companies, but even when you get to yes, sometimes closing it takes another two months and you're like, Why isn't it this simple? So I I think those are challenges of of just adjusting my own expectations for things, you know, but at the same time, you know, now that everything's on me, it's like, you know, we didn't take money from anybody. And so if we're not bringing in that revenue, then it's out of my personal bank account to make payroll, right? We don't anywhere near that at this point in time, which is great. but you know, if I fast forward a year from now, technically on paper it looks like that. It looks like I'm it's a hundred percent out of my own pocket. And so that whole sales process and that gut check of like trying to close it as fast as I think it should move, even when things are progressing, to also seeing this, you know, burn rate, even though it's a positive one, and and you know, the gut wrench like, all right, I need to have the pipeline filled so I ever all the employees that I promised that I could take on then pay their salary, like that that's a thing for two years at the minimum or three years or et cetera. and so I think it's just setting my own expectations, but part of that is learning that sales approach that really connects with people where they're at. And obviously that changes based on the individual I'm talking to. so some level of pre-research that's required for that. but trying to really learn that sales process. because we are at the end of the day, we're trying to tell a company we educate and make informed buyers. Eventually we partner with you to accelerate your AI use. And really what we want to be is your full-time partner. So effectively telling companies hire us as your fractional CTO and we want some sort of bonus share and a fixed you know cost. Like if you say that up front, you'll lose everybody. Like they're like, I don't even know what AI is, and you're telling me so we're we're thinking about how do you you know make an informed process so that's we we're we're trying to be empathetic in some ways of that people just don't know what they don't know. I mean with AI everybody's in the unconscious unknown for the most part. There's many people that think they're not in there, but they are like it's very rare that we come across somebody that knows what they're talking about. And so blending that all together is something that I am constantly working on and even like I said, having my team look back and give their own opinions and being humble enough to hear that hear that feedback. Because we're all in this together.
Jessy James: Yeah, and c you know, and and and and Sean, as you think about sort of growing the business, and also about, you know, improving or working on your sales skills and influencing, you know, CEOs and organizations, what are still the ways that you feel like you still need to grow and develop to meet some of these challenges?
Sean Patterson: You know, I I think we'll go back to the the same thing of like this this notion of expectations that I would expect from my customer and and how I can set my own internal expectations so that I am not making decisions that are not aligned to a longer pace of time that happens, right? I think it's just that's it's a natural something by the way I've always struggled with is sort of like the time of how long I expect things to take is always, you know, always double it kind thing, right? Is that patience you're talking about? What's that?
Jessy James: Is that patience you're talking about?
Sean Patterson: I think patience is right. Yeah. Okay. but like I said, I think it's a little scarier now to hold that level of patience when you see the I gotta fill the pipeline and I'm the only person doing it, right? And so the patience is obviously you can't wear it thin with the actual direct interaction of the customer or the potential client, but it's then do you put more fishing lines in the water and then get overwhelmed if they all kind of come through? 'Cause no quite frankly for w w everybody we get to because it's all mostly good word of mouth. nobody says no. It's just a timing thing. And so now I have all these kind of things pent up and then when do I lean into hiring, knowing that if it doesn't fill, then it's out of my pocket. And so yeah, I think it's some level of of patience for that not to overly react.
Jessy James: So we come to our last question, Sean. and this is more of an invitation. You have this time and space to offer to our listeners whatever it is that is top of the mind and heart for you. Anything at all, take your time, the floor is yours.
Sean Patterson: Yeah, I think at the end of the day, you know, for leadership, it really is just in investing and believing in your team and allowing them to fail. And it being okay to fail as long as we learn from that failure. I think we tried as leaders to curate too much of the experience so that we as leaders don't look bad because our team failed, right? And it's that classical thing of like, if we're successful, it's the team, it's a failure, it's me. Right. I think keeping that That kind of mindset is is is important. And I and I don't think we enable our teams enough, right? I think we we try to give them the answer or what we think is the answer. I think there's also some level of hubers that we think just because what we did worked, that means that we'll work now, right? I mean, I think leadership combined with business has some level of timing and luck associated to it. and you can't like I saw this at Amazon a lot. people leaving and like, I'm gonna go do X, Y, and Z and I got the Amazon, you know, background. I'm talking like V P level stuff. And they fall flat on their face. They tried to apply the Amazon method to these other companies and you just can't impose your will on there. It's like it has to it's the people and the organization all in the moment around these kind of living and breathing principles that that applies. And I think that I think we try to overly Just read a book and apply a method. I think you just need to be hyper aware of adjusting and and and bringing that emotional intelligence to the the conversation and allowing your team to experiment with other ways of doing things, even if that's not what you would do. And not even mentioning that, right? It's only yeah, you gotta do it the guardrail side. Like if it's a guardrail, it's fine. Right. But the rest of it. How else are you gonna learn? By the way, the best way you can learn is learn by doing. We talk about that with AI all the time. but usually if you actually fail, you're probably never gonna make that mistake again. And that that holds more weight than being blocked from doing something that would let you fail. So sometimes graceful graceful failing is is important experience to get. And I think we don't like to do that because falls on our own ego if our team isn't able to accomplish that where I'm like, nope, let's let's do it. And and that sense of ownership people get to be able to grow and experiment when you when you allow them to have that, they people really do flourish. It may be it takes time, you know, but you're really growing and developing somebody that that can be, you know, that can take your job. You know, you should be able to grow and develop somebody to be better than you. And if you do that, you're on the up and up. You will you'll never look back. and even if that person isn't capable of the blocks, if you give them those reins, every time they most people let their wings fly if if they really do feel safe, to be able to do that. And so I I do encourage everybody to kind of think about that. The culture of experimentation and failing. And and again, in the age of AI, you need to do a lot more. and you got so many blockers and organizations for this. You know, inertia, cultural inertia and how do you you know prevent that as a leader and re recognize that you're even a part of the problem is something that it takes time and sometimes an external perspective to kinda call a spade a spade. and so I encourage everybody to kind of just do it on your own and and be self reflective because the rate of change adopt change management is increasing beyond exponentially at this point in time. and not many people I think feel the total storm that is here and it's a storm that anybody can ride out, but it does take investment in people. You know, when we put our money where our mouth is there as a business, you know, we we we will not do as I mentioned, CEO has to be in the first training. And this is just lessons learned. Like you have to it's a top-down messaging, but it's a bottom up build. And we also say you must have every employee go through these trainings. You cannot have the have and the have nots and the invested in and not the invested in. And so we kind of force that for the businesses that we want to do business with. Like you have you have to do that, or just it's just not gonna work out the way that we intend and the way that we understand. these new tools to be applied in an effective manner really do first and foremost start with good leadership. and just unfortunately the world hasn't had enough training for that and we've pulled back on training and all these kind of things, right? And it really does fall on individuals to be curious to watch podcasts like what you have. and some level of investment in yourself in a deliberate manner. and so I I I encourage everybody to kind of think about that and and build your team in a a safe yet accountable environment.
Jessy James: What a fascinating conversation, Sean. I've I've gotten so much out of this conversation and I'm sure that whoever's listening will benefit equally from what you've shared. Thank you so much for coming on the podcast.
Sean Patterson: Thanks.
Sean Patterson: Thanks for having
Jessy James: Sean, I'm curious, who was someone from your early life or it might even be an early experience that you had that shaped the kind of leader that you are today?
Sean Patterson: Yeah. there's my my first sort of two. as you mentioned I was was in the Navy and my the first captain that I I worked for as an officer, you know, really I think shaped my view of the empathetic leader. you know, we had some, you know, being underway and at sea and places we shouldn't, you know, that we're not supposed to be, and I was kind of the last frontier of submarines, right? we had some issues that we had to deal with and it was about integrity for s some people and how he handled that I thought was very appropriate. But if you got kind of one on one with him, it broke his heart about how he had to actually hold some people accountable for something that, you know, was more integrity based, right? 'Cause you're you're You're really so you're calling somebody out, right? In a in a very real manner. and it was big enough where we actually have to have this person actually had we had to have the helicopter peek the person off the the submarine at sea, which is not a cheap thing to do. and just that he did the right thing, but also had the human element of the whole situation still there. in a in a in a real empathetic way, right? so I think Th that's really important. and then there was one other leader, and and I thought by the way, if you can always get lucky with your like your f the first person you work for out of out of the gate or with your real with a real job, I think it's it probably sets people's careers up to make or break almost right away, you know. Because you you start off with what good looks like, especially as your bag of tricks is not your bag of leadership just isn't that full full yet, you know, filled at at all. you wanna be filling it with the right kind. the the sustainable kind. and and I do think that first one is is really important. So, you know, as individuals start to, you know, go out in their career, I do think it's important to make sure you're interviewing both ways, right? Navy, I have less choices for sure, but you know, you just getting a job, beware of just the offer to and that you want to get something versus the right kind of thing. It goes both ways. The company has to get the right person and you need that the right company and the right boss, right? and then I had one other individual after I got out of the Navy I h less empathetic leader, but somebody that really understood business and operations and how to get things done. And and he himself was going on a journey of learning how to be increases emotional intelligence. And, you know, I was there kind of along that journey with him and saw the humbleness to for a leader to be able to learn those tools and and absorb them. And that's, you know, something that I took on as well, right? having, you know, personal coaching for some time now for executive coaching and businesses had started paying for that, but I carried it on because I really saw the value in how I adapted and even paying out of pocket sometimes to keep that going. I think that that's really important. So there's there's definitely been two largely influenced people, influential people there. And honestly one more's a person on Amazon. my and it I think it all comes down to emotional intelligence. I mean The people you remember, you're gonna rather n negative thing or the positive things is usually has nothing to do with we ship the product. It has to do with the interactions of people, right? Right. And so my father had passed away right before I got transferred to this individual VP at Amazon. because I'd already been working there, I got moved. the organization got moved. And my father just passed away, was the first time I ever met him, and I remember going to have burgers with him at the top of some hill in Seattle. And the first thing he said to me was, Tell me one of the best stories you remember about your father. That was it. That was the first s like sentence out of this guy's mouth that I've never met before at the highest levels of Amazon. And that's what he asked about. Wow. So Yeah. That's what I remember. Very
Jessy James: And I'm curious, Sean, how did all of these people kind of shape the leader that you are today?
Sean Patterson: well as I mentioned, the get getting humble enough to realize, you know, your own gaps on not the management side of things, right? The leadership side. I think so many people think about management and leadership as one and the same and they're really not at all. you know, the people aspect and coming from an emotional intelligence point of view. I would also say some of the standards they kind of imbued in me in terms of where people can kind of get caught in a trap. For instance, the second person I mentioned that was my first real leader, manager leader out of the military, you know, he told me he's like, never let a vendor pay for your meal. Full stop. I don't care how much the meal is. There was this one story that we we went going with DuPont. DuPont vice president was like four of us. And I remember Hank, you know, always pay for the thing. Now we didn't always pick the wheel of the Where the meals are at, because the vendors always assume they're paying. And then I like swapped out the credit card because I was going to pay. It was like a $2,000 bill. And I came back and told him, I was like, here's the situation. I didn't pick it, you know, and all of a sudden getting hit with like $250 per person kind of thing, which is not something I would have chosen to do. But he was appreciative that I still followed that mantra because then you are not making decisions for the wrong reasons because you're trying to get something out of it as an individual. and to always kind of pay. And so there's all these kind of like tactical little lessons like that, I think, that really drive n maybe not the EQ side, but like the ethics of business, because that all plays to the leadership side. Right. And I think it can be learned by individuals. I think that I've gone through that journey and my best, you know, if you ask aside from leaders, I mentioned, you know, the best partners I've ever had are all HR. Like they're the sounding board that That was the gap I had, and I think it's the gap that the plurality of people in leadership have. They let the business aspect dictate too much of it. It's a f I wouldn't say it's a fine balance. I think you need both full stop. and I don't think there's enough humility in the world to work on those kind of gaps. and it's been proven scientifically that the most successful businesses are EQ forward. Mm-hmm. And the ones that most people want to work for, right? You don't leave jobs, generally speaking, you leave it because you're boss. It's proven time and time again. I think most people can reflect on that and realize that. And I think if I reflect back, all but one time I changed careers or changed jobs was because of a boss. Every time. because that's your day to day at the end of the day, you know? Yeah. Yeah.
Jessy James: Yeah, this this is a nice segue into, you know, I'm curious, what does true leadership mean to you from your experiences, from your lived experience? What does true leadership mean to you?
Sean Patterson: I think people that are invested at some level of investing in in in the people, but the growth and development of those people. where it's not viewed where it's viewed as an investment, not a necessity. Right? A a belief that anyone can learn the tools to grow a business, to grow an organization. I think that true leadership is investing in that because it's the right thing to do to grow the next person under you, right? And in and in some ways, you know, while there's managerial aspects to this part, you know, if you can go on vacation and actually unplug And you should deliberately do this because it's a good litmus test if your organization is not reliant on the leader, which is what that's the goal, right? You shouldn't have to, it should be colleagues all kind of working together. And you come back and nothing's broken. Good for you. Find a new role now. Right? And and and so many people just try to I don't think micromanagement isn't always the right word for this. I think it's some level of Subconscious job protectionism or self-feeding that like people need me and want me per se. and I think true leaders are able to push away from that and realize that you should always be hiring and moving people up that can take your job. If if you're not hiring to fill some gap that you have or your organization has that will eclipse you in that function, then you are if you're not doing that as a leader, then you are on a constant downward trajectory for the rest of the company's life. You will never be better than the day you are today if you are constantly Trying to protect your own ladder. Now, I will caveat that as an AI person that will also say, I do think flatness is coming. you know, it's gonna be a lot more entrepreneurial flair amongst organizations that will be able to survive the next twenty years or so. And if you look back in history, nineteen sixty six, only twelve percent of the companies that existed in nineteen sixty six in the Fortune five hundred ex still exist today. And the average lifetime is now twenty six years. Twenty six years is the average lifespan. it was thirty-two, I think, in in thirty years ago. It's even less now. Look at look at the S P index index in in the mid 90s and look at what it is today and see how many of those top names that you know are no longer existent. And a lot of that is the turnover of leadership and the ability to to have a sustainable ongoing business. And it comes down to tribal knowledge never getting documented, some level of I leadership but kind of all built it together. But did they make a sustainable ongoing process is not reliant on the leader. And that to me, that's the definition of true leadership. Isn't it's about the team and not reliance on me. I may facilitate. And then if you can go on vac vacation and come back, that's your that's your test to see if your facilitation was was right was good or not.
Jessy James: Yeah. Sounds like a dream job as well, right? Can you share about a time when you realized that your way of leading or living no longer met the demands of your work and life and you needed you know you needed to grow and develop in some way.
Sean Patterson: Yeah, I think Playing on this emotional intelligence side of things as well. At Amazon, I think I I struggled because we were scaling our business. We we built Amazon's middle mile team. So the big blue trailers with the smile on the road. I was the executive that built that out. and we started twenty people. There were twenty people on the team when I when I kinda started. And three years later it was fifteen thousand. And you know, we didn't have any trailers and we like eighty seven thousand trailers at the end and Growing and scaling that team was very difficult because we were re-orging like all the time to almost creating some level of pyramid, right? Hierarchical pyramid, because you're going for 20 to 15,000, distributed across about 500 facilities as well, that didn't even exist the three years prior to that. And so I really needed to figure out how to lead my team where there was some level of not everybody would make the next pyramid structure, right? You'd still have that job, but you're, you know, as we're scaling it, we had to. pick the next core team and then the next subset was the next core team because then but somebody was working directly for me a year and a half ago was no longer doing that and there's some level of hurt you know hurt that kind that maybe that person felt and I wasn't I think I was too dismissive of it. even though it was a practical reality. But I think the ways that I approached it at the time weren't empathetic enough, quite frankly. and so, you know, I met with HR partner, and kind of went through that journey of like how do I how do I get this better on the next reorg of the pyramid, which we had to go through again and again and take people on the journey where they where they still felt invested in, but also could appreciate the necessities of what the business needed. And I I think it was more I needed more ability to see it through their eyes.
Jessy James: And I'm just curious, you know, it's not very easy to step into somebody else's shoes and see their world from their perspective. What did that journey take from you or for you know, what did that mean for you?
Sean Patterson: This is my honest answer. I had in high school, I had a a girlfriend that was not very stable and she tried to commit suicide. and I think that killed my real side of EQ, like where you could feel from an you know from an empathy point of view, for a very long time. and I think Eventually I sort of academically started to understand the gaps I had as a leader, you know. It's not to say I was a bad leader, I just think there was a lot of opportunities. And the death of my father was the thing that sort of brought that ability to feel back. And at the same time, 'cause he he passed away pretty quickly, he was diagnosed with pancreatic cancer, so it was November and he passed away just a few months later. And I think one I was able to For lack of better words, feel again, but also some level of appreciation or reminder halfway through my life, or hopefully a third through my life, that everybody has something going on in their life, right? Business is not life. and there's there's always something bigger going on. And and you just then that by the way, that applies everywhere, not just in business when you're out at the grocery store and yelling at people. You never know. what's going on and I think that allowed me to like re feel that again. and so I th you know it took a real event for me to not make it academic. Mm-hmm. but and that was my journey, right? I I think just based on how my brain works, it it was it was kind of academic, for sure. Yeah, but then being able to layer that on later was was important and not something I certainly chose. but it's my journey. Yeah.
Jessy James: Sounded like sounds like an awakening for you.
Sean Patterson: Thinking about
Jessy James: Thinking about your journey over the past few years, what's been the most valuable investments that you've made in yourself for your own growth and development?
Sean Patterson: fr from a pure leadership side, I'm going through a different journey now. I left corporate America, as my quotes, a year and a half ago now to do my own business and now forming my own team. We have eight, well now nine starting next week, employees, including myself. And I get to make my like my team this time. Like, you know, not you know, it's not to say anybody I ever that ever really worked for me was anybody I really didn't get along with or work with, but you know, they're already there. and so you kinda work into it, and then you maybe hire a few other people that you get choices on. in this case I got to go from scratch and understanding truly like I knew like these first hires are the most important. to establish the culture that I want to at least get a common core, like a critical mass of what we believed in, because the next person to come in will either naturally they have to assimilate to that, you know, or they can break it. But as long as you kind of get a core, going through that hiring process has been really critical for me. The other sense of leadership that I don't Think I appreciated a much. I went to Amazon because I love their leadership principles. Okay. I did not want to leave my my job that I had before Amazon. I really didn't. I went kicking and screaming in some ways. but I appreciated their leadership stuff, their leadership stuff principles. and One of them is ownership. and I carried that forward to the other businesses I went to after Amazon. But I'll tell you what, until you're actually bit with your own company, you don't actually feel real ownership. Like it's totally night and day difference of what I used to kind of purport that I was an owner and owner and stuff like that. I think there's some level of introspection that a lot of people can do that they think they own it until really If it breaks it's one hundred percent you and there's nobody else you can blame. so I do think levels of ownership kinda play into that as well as building the team. and so far it's worked out. So but that's that's kind of been something I've been, you know, working on 'cause it's a different it's a different approach. I I it's it's different. but this time it's mine, you know, and I get to form that and But it's it's definitely a different level of intensity, even though it's less intensive. Yeah. Yeah.
Jessy James: And you as you think about this entrepreneurial journey that you're on, what's your vision for your leadership, for your legacy as well, or or you know, and the impact that you want to have in the years ahead?
Sean Patterson: so in some ways I don't want to grow this business too large from a headcount perspective. I think that AI enables us to scale to a much higher revenue per employee than was capable. And I will say that already exists now for what we're able to do. And as educators, first we don't do projects right away. We educate and then we will help you do a project, not the other way around. 'cause you need to learn how to use these tools as individuals yourself. and you know We need To grow and create a culture of entrepreneurialism. So we have a we we wrote a a job description, right? And one of the job descriptions says something along the lines of we set constraints and then operate within them without permission. Like we are not asked. We don't ask like how, if you will. Like we don't ask for that permission. As owners, like I say ownership, but like set the guardrails and allow your employees to fail within that. Right. We want that sense of failure, right? we've we've had one major but not impactful failure that we had for something that we worked with somebody on, and we we learned that lesson and that employee was like heartbroken. for for something that didn't work out. And it's like as long as we're living and and learning from that, that's all that matters. And and with AI, at some level of okay, how do we embed this into the system so that this doesn't happen again? And so I want to make sure that it's okay to fail and that we have an entrepreneurial flair. And we're really just a bunch of entrepreneurs kind of operating together because again, kind of with the use of AI, you can start to bleed into areas that you're not an expert in if you do it safely and and thoughtfully. So that allows us to create just an entrepreneurial culture and and not really have hierarchy. I have somebody that was like my first employee that I'm calling like the lead, which is an allocator of work, but not a sense of hierarchy. I'd I'd rather everybody in the company make the same amount of money. Like we're all on the same journey together. yeah, so so I think that entrepreneurialism is is that's kind of my my hope for that. And and with that comes the ability to be okay to fail and experiment. the agility of learning new things is so important with always has been, but even more so now. it's going it yeah, with AI it's just things are getting faster and faster and faster. it's beyond human capacity to kind of keep up with it at this point in time. and so I I think you just have to have people that in in a in a system where you're you're allowed to move with that, you know, those those guardrails and then just rock and roll from from with inside there. Yeah.
Jessy James: Yeah, I mean and you know, the sense I get is that this business idea is really coming to fruition and you're bringing in a lot of your experience and values to play here, right? And having fun with it. And I'm also curious, what are the ways in which you still need to grow personally and develop in order to sort of really realize this vision?
Sean Patterson: I think it it's in some ways sales, right? As as the the the main as the owner, right? how to tell the story in a accessible manner to our prospective clients without overwhelming them. Right? Cause I I can kind of get on the kick sometimes of like, and and and and and you keep on adding on and you lost the message because you just don't you're you're afraid you didn't get that sound bite in. so we do play by play on this. Like I even have my employee we we did a presentation on Saturday for about sixty veterans. they're they're with us for the next few weeks. transitioning veterans. and I had them watch the video and critique me. And so there's things I need to learn in that process, I think, from from the the sales point of view. and and there's leadership in that, right? Because you're really talking to another leader of an organization to and sometimes tell them, like, I'm coming from a place of you need to invest in your people, and a little bit of poking, you know, the bear and saying, We haven't done technology investment properly forever. you know, like I I like to say c companies have always bought the gym membership and affected everybody expected everyone to get fit just because they bought the membership, right? You buy Salesforce and now you expect everybody to just magically use this and we just don't have the staying powers leadership to see it through, nor does leadership generally understand what those things are. And you wind up using five percent of of the system and and paying for it and nobody likes it and it just it's a you know, not I'm certainly speaking broadly, but like we've had this problem with technology for a very long time. And productivity per person in the United States with technology has not been what has been sold to us. Right. And I think a lot of that isn't that necessarily the technology doesn't work. It's just we're bad at integrating this into non technology and albeit sometimes technology companies. and so trying to get people to see this. Fortunately, they have lots of scars from the past of yeah, this doesn't work. We did it five year ERP. For conversion, that didn't work. That didn't work. And so at some level of reminding them that you can't do it the same way. You have to invest in it. And we won't do business if the CEO is not in the first training cohorts. And that's twelve weeks long. And so you're talking almost twenty four hours of a CEO's time that I'm saying you must do this and by the way you have to do homework between the two of them because you need to show that level of humility to your own workforce before I'm willing to teach everybody in it. And so again in terms of the total thing and doing that sale, I'm also trying to say you need to be a good leader too. Yeah. Yeah.
Jessy James: And and where do you feel most tested right now? Like what challenges are stretching you the most, both in leadership and in life?
Sean Patterson: as my wife likes to tell me, I'm the speed of Sean is not the speed of everybody else. And so like it you know, it you know, going back to kind of the sales process a little bit of like, okay, I had these conversations, it's good, good, good, good. And then, yeah, follow up with us, and you follow up, then you follow up, and you follow up, and you follow up. I know it's a typical sales process. I I was a chief Roven officer for one my companies, but even when you get to yes, sometimes closing it takes another two months and you're like, Why isn't it this simple? So I I think those are challenges of of just adjusting my own expectations for things, you know, but at the same time, you know, now that everything's on me, it's like, you know, we didn't take money from anybody. And so if we're not bringing in that revenue, then it's out of my personal bank account to make payroll, right? We don't anywhere near that at this point in time, which is great. but you know, if I fast forward a year from now, technically on paper it looks like that. It looks like I'm it's a hundred percent out of my own pocket. And so that whole sales process and that gut check of like trying to close it as fast as I think it should move, even when things are progressing, to also seeing this, you know, burn rate, even though it's a positive one, and and you know, the gut wrench like, all right, I need to have the pipeline filled so I ever all the employees that I promised that I could take on then pay their salary, like that that's a thing for two years at the minimum or three years or et cetera. and so I think it's just setting my own expectations, but part of that is learning that sales approach that really connects with people where they're at. And obviously that changes based on the individual I'm talking to. so some level of pre-research that's required for that. but trying to really learn that sales process. because we are at the end of the day, we're trying to tell a company we educate and make informed buyers. Eventually we partner with you to accelerate your AI use. And really what we want to be is your full-time partner. So effectively telling companies hire us as your fractional CTO and we want some sort of bonus share and a fixed you know cost. Like if you say that up front, you'll lose everybody. Like they're like, I don't even know what AI is, and you're telling me so we're we're thinking about how do you you know make an informed process so that's we we're we're trying to be empathetic in some ways of that people just don't know what they don't know. I mean with AI everybody's in the unconscious unknown for the most part. There's many people that think they're not in there, but they are like it's very rare that we come across somebody that knows what they're talking about. And so blending that all together is something that I am constantly working on and even like I said, having my team look back and give their own opinions and being humble enough to hear that hear that feedback. Because we're all in this together.
Jessy James: Yeah, and c you know, and and and and Sean, as you think about sort of growing the business, and also about, you know, improving or working on your sales skills and influencing, you know, CEOs and organizations, what are still the ways that you feel like you still need to grow and develop to meet some of these challenges?
Sean Patterson: You know, I I think we'll go back to the the same thing of like this this notion of expectations that I would expect from my customer and and how I can set my own internal expectations so that I am not making decisions that are not aligned to a longer pace of time that happens, right? I think it's just that's it's a natural something by the way I've always struggled with is sort of like the time of how long I expect things to take is always, you know, always double it kind thing, right? Is that patience you're talking about? What's that?
Jessy James: Is that patience you're talking about?
Sean Patterson: I think patience is right. Yeah. Okay. but like I said, I think it's a little scarier now to hold that level of patience when you see the I gotta fill the pipeline and I'm the only person doing it, right? And so the patience is obviously you can't wear it thin with the actual direct interaction of the customer or the potential client, but it's then do you put more fishing lines in the water and then get overwhelmed if they all kind of come through? 'Cause no quite frankly for w w everybody we get to because it's all mostly good word of mouth. nobody says no. It's just a timing thing. And so now I have all these kind of things pent up and then when do I lean into hiring, knowing that if it doesn't fill, then it's out of my pocket. And so yeah, I think it's some level of of patience for that not to overly react.
Jessy James: So we come to our last question, Sean. and this is more of an invitation. You have this time and space to offer to our listeners whatever it is that is top of the mind and heart for you. Anything at all, take your time, the floor is yours.
Sean Patterson: Yeah, I think at the end of the day, you know, for leadership, it really is just in investing and believing in your team and allowing them to fail. And it being okay to fail as long as we learn from that failure. I think we tried as leaders to curate too much of the experience so that we as leaders don't look bad because our team failed, right? And it's that classical thing of like, if we're successful, it's the team, it's a failure, it's me. Right. I think keeping that That kind of mindset is is is important. And I and I don't think we enable our teams enough, right? I think we we try to give them the answer or what we think is the answer. I think there's also some level of hubers that we think just because what we did worked, that means that we'll work now, right? I mean, I think leadership combined with business has some level of timing and luck associated to it. and you can't like I saw this at Amazon a lot. people leaving and like, I'm gonna go do X, Y, and Z and I got the Amazon, you know, background. I'm talking like V P level stuff. And they fall flat on their face. They tried to apply the Amazon method to these other companies and you just can't impose your will on there. It's like it has to it's the people and the organization all in the moment around these kind of living and breathing principles that that applies. And I think that I think we try to overly Just read a book and apply a method. I think you just need to be hyper aware of adjusting and and and bringing that emotional intelligence to the the conversation and allowing your team to experiment with other ways of doing things, even if that's not what you would do. And not even mentioning that, right? It's only yeah, you gotta do it the guardrail side. Like if it's a guardrail, it's fine. Right. But the rest of it. How else are you gonna learn? By the way, the best way you can learn is learn by doing. We talk about that with AI all the time. but usually if you actually fail, you're probably never gonna make that mistake again. And that that holds more weight than being blocked from doing something that would let you fail. So sometimes graceful graceful failing is is important experience to get. And I think we don't like to do that because falls on our own ego if our team isn't able to accomplish that where I'm like, nope, let's let's do it. And and that sense of ownership people get to be able to grow and experiment when you when you allow them to have that, they people really do flourish. It may be it takes time, you know, but you're really growing and developing somebody that that can be, you know, that can take your job. You know, you should be able to grow and develop somebody to be better than you. And if you do that, you're on the up and up. You will you'll never look back. and even if that person isn't capable of the blocks, if you give them those reins, every time they most people let their wings fly if if they really do feel safe, to be able to do that. And so I I do encourage everybody to kind of think about that. The culture of experimentation and failing. And and again, in the age of AI, you need to do a lot more. and you got so many blockers and organizations for this. You know, inertia, cultural inertia and how do you you know prevent that as a leader and re recognize that you're even a part of the problem is something that it takes time and sometimes an external perspective to kinda call a spade a spade. and so I encourage everybody to kind of just do it on your own and and be self reflective because the rate of change adopt change management is increasing beyond exponentially at this point in time. and not many people I think feel the total storm that is here and it's a storm that anybody can ride out, but it does take investment in people. You know, when we put our money where our mouth is there as a business, you know, we we we will not do as I mentioned, CEO has to be in the first training. And this is just lessons learned. Like you have to it's a top-down messaging, but it's a bottom up build. And we also say you must have every employee go through these trainings. You cannot have the have and the have nots and the invested in and not the invested in. And so we kind of force that for the businesses that we want to do business with. Like you have you have to do that, or just it's just not gonna work out the way that we intend and the way that we understand. these new tools to be applied in an effective manner really do first and foremost start with good leadership. and just unfortunately the world hasn't had enough training for that and we've pulled back on training and all these kind of things, right? And it really does fall on individuals to be curious to watch podcasts like what you have. and some level of investment in yourself in a deliberate manner. and so I I I encourage everybody to kind of think about that and and build your team in a a safe yet accountable environment.
Jessy James: What a fascinating conversation, Sean. I've I've gotten so much out of this conversation and I'm sure that whoever's listening will benefit equally from what you've shared. Thank you so much for coming on the podcast.
Sean Patterson: Thanks.
