Episode 9
Vince Lombardo, Heartland president Creating a defined work culture can help businesses big and small be successful — and enrich lives

Building a business culture can sound expensive and time-consuming. But have you ever considered the cost of not having a value-based culture? Vince Lombardo, president of Heartland, shares why doubling down on culture can make a business of any size more efficient, transparent and give your staff a roadmap of how to operate well.

Vince Lombardo explored many career paths on his way to become president of Heartland. Growing up in a family of entrepreneurs, he learned the grind that many small business owners go through to be successful. From flying planes to making sales, he’s brought genuine curiosity to everything he’s done.

Businesses can have great products, great service and good leaders — but without a value-based work culture, a growing business can quickly fall apart. Culture can be hard to quantify, but not having a defined culture can lead to unintended repercussions: low morale, high turnover, poor service quality and more. Vince has spent the majority of his career investing in leadership competencies and building a unique culture at Heartland.

Learn more about why great work culture should become a priority within your business, and what you can do to ensure that your principles never get lost in the changing hands of time.

Below is an edited transcript of the conversation. In the episode, you’ll hear:

  1. How to receive and extend grace — everyone has blind spots
  2. Why you should use ‘maybe’ to help rewrite your ‘bad first drafts’
  3. Why you should discover your values and live and work by them
  4. Why culture is the ‘most-secret ingredient for success’ in business
  5. Culture is hard to quantify — but the repercussions to your business aren’t
  6. Define your culture to better your business

Chris Allen: Vince, it is really awesome to have you here, but it’s a little weird for a couple of reasons. Number one, we talk a lot, but very rarely do we sit down and have a one-to-one conversation that’s multiple hours long, and about not work.

Vince Lombardo: Or your life.

Chris: You just had to do that.

Vince: You said to be me, so here we are.

Getting a masterclass in entrepreneurship at a young age

Chris: That’s what you should do. Yes. So one of the things that’s really powerful about your story is how long you’ve been a part of the Heartland business, and how little of the story prior to being a part of the Heartland business that we get to talk about. That’s one of the things that I want to unpack with you. A couple of weeks ago, you talked about some of the entrepreneurs that we get to meet being in these roles, and how thankful you were and are about the lessons you’ve learned, knowing the other side of being an independent entrepreneur, versus running a business in a corporate organization.

Vince: Yeah. I grew up in a family of small business owners. My grandpa owned a produce wholesale business, which is back in the day before these big food conglomerates sold all the food to the restaurants. They bought produce from the produce guy, meat from the meat guy. And so we had a produce company that sold to all of the restaurants in St. Louis, and we were a big deal back then, apparently. I was very young at the time, and it went out of business when I was about six or seven, but I have memories of being around that business, being in trucks with my dad, making deliveries, having to go out to check on an alarm that went off at 11 p.m., and sit in the car while he fired an employee, and all the things that happen in life when you’re running a small business.

Vince: And when it went out of business, it was acquired in bankruptcy by another company that was a competitor in town, and then my dad became the leader of that business. And this is back when laptops were really heavy and black-and-white-ish, and Microsoft Excel did like six calculations. But he would come home, and on occasion when he’d be home in the evenings, we would do payroll together, and I’d add up time on punch cards from people in the warehouse and truck drivers, and do the overtime math, and drop it into the Excel formula. And I was 10, 12 years old, but watching that and, at the same time, witnessing the work ethic of a guy running what was a very small business in comparison to what maybe this business is, it’s a lot of the same stuff.

Chris: Wow.

Vince: It just looks different.

Chris: That’s amazing. Yeah, so you were his buddy.

Vince: As best as I could be for a guy that was a workaholic.

Chris: Yeah, OK. Fair enough. What was the most memorable story when you realized that they were providing for an entire household on a small business? What was an early memory of realization of that?

Vince: Yeah, so a couple of years before they went out of business, this is hard to remember, but there was a time that McDonald’s would buy whole potatoes to make French fries. And we had the McDonald’s contract for all of the McDonald’s in the Missouri, Illinois, Arkansas, or Iowa, somewhere Tri-State area. Hundreds and hundreds of cases of potatoes out of our doors, every day, every week, whatever. And then it stopped because McDonald’s changed the way they did things, they started building their own facilities to create the french fry, to freeze it, and all this stuff, and it was a huge blow.

Chris: Wow.

Vince: And I don’t remember that as specifically as, obviously, my parents did, because I was probably four or five years old, but I remember the feeling in the house around that time, like, “How are we going to make it?” But I’ll also tell you that in the next business that my dad went to run, there was a day he came home, and you could just tell something wasn’t right.

Vince: And he had been laid off and let go from a down market and the economy in St. Louis, and the food supply place. He spent three months probably at home looking for a job. And it was just that idea of, “Oh, this isn’t permanent,” and it sounds crazy, but back then, it was normal that you’d break a case of milk, and so you’d bring a gallon of milk home, or lettuce, whatever. So we ate well at home, because all the stuff that was left over and almost bad, we’d bring home. And for those first three months that he didn’t have that job, we were going to the grocery store and buying things I’d never bought in a grocery store before.

Chris: Really?

Vince: Which was a weird experience.

Chris: That is a very weird experience.

Vince: But it’s like, you go to the grocery store, and you’re reminded, “Oh, my dad doesn’t have that job anymore.”

Chris: Yeah. Oh, so it’s a constant reminder.

Vince: Which is interesting.

Chris: Wow, that’s ... I like how you just said that you remember the mood or how it felt at home. That had to be tough, feeling that. But how did you become a pilot and then transition to business? How did the pilot thing happen?

Vince: Well, so being in the restaurant business as a family matter, that’s what I did when I turned 15 and got a worker’s permit. I was a busboy. I became a waiter. I worked in several restaurants in town. I was a pizza delivery guy. I literally had, we counted up one time, somewhere in the 20-somethings jobs between 15 and 19 years old.

Chris: But like food service?

Vince: Yeah, mostly in some sort of service environment. And I was a flower delivery guy. You want to talk about weird? You go from three funerals on a Saturday morning to a wedding on the same day. And just to feel the weight of the air of people’s emotions dropping off flowers at a funeral, and then going to flowers at a wedding...

Chris: Wow.

Vince: ...and then a new baby being born. So you get to be part of these people’s lives and these weird experiences. And then you’re a server at a restaurant at night, and you get these really crappy people who are really upset with you over the wrong tea because their life clearly sucks that that’s something that they’re that upset about.

Finding a career path by exploration and personal values

Vince: So I was always in some sort of a service business. When I was in college — it was a rule in our house, that you’re going to get a four-year degree. That’s just what you’re going to do. I had four years of scholarship money where it was not as expensive for me to go to school, and I needed to graduate. And two years in, I was in the business school. I hated it. I was working way harder than I should to get the grades that were average because I just didn’t love what I was learning. And the school I was at, St. Louis University, had an engineering and aviation college. It didn’t cost any more to be a pilot, and I thought, “I’m going to fly planes. That’s cool. I like speed.”

And so, I switched schools my sophomore year. I did four years of flying in two years and got the aviation management degree with a business certificate. I thought I’d have a career in aviation because it seemed cool. I didn’t think about, which is probably part of why I’ve been fortunate enough to have some of the success I’ve had and the failures I’ve had — sometimes, I don’t think two steps out. So I didn’t think about what the life is like of a pilot. And I finished school in the spring of 2001, and I had a job that was supposed to start Sept. 15 that year. The job went away because of 9/11, and I was forced to spend a month thinking about what I want to do with myself. Because now I’ve got this degree that feels useless, and I talked to a bunch of pilots who were near retirement, and their stories of their lives were really difficult to swallow.

Chris: Yeah, like disconnected...

Vince: Very few still married, multiple marriages, disconnected, gone on holidays...the first 10 years of their kids’ lives. They love what they do, but there was a cost. And that’s not all pilots, so I don’t want to generalize that.

Chris: Yeah, for sure, for sure.

Vince: But it was enough for me to be like...

Chris: It was a theme.

Vince: “I don’t know that I want this for my life.” And so I went back to St. Louis and went back to a restaurant, and ran a restaurant for a year, because that’s what I knew. And the story unfolds from there.

Chris: Yeah, but you have some technical savvy that surprises us. Not throwing a knock at you.

Vince: I don’t know how I should take that.

Chris: I know, because I love the ambiguity. But you have some technical acumen that I think is really interesting. How did the technical ability show up?

Vince: Yeah, look, I was always into some version of tech. In college, I was selling fake IDs from my dorm room from a printer that I engineered to take plastic. And you can come get me for that if some authority needs to do it. It’s been a long time, but-

Chris: We’ll say fake IDs.

Vince: Yeah, Napster was a thing. I had a bunch of songs downloaded. And so I just always enjoyed playing with technology. I was really into technology. But after the year of running a restaurant, I was introduced to somebody who had a small technology company in town that served local businesses’ computer systems. And after meeting him, he told me that I should be a salesperson. I was like, “I think that’s insane. Salespeople are sleazy and horrible, and they do bad things to other people, and...”

Chris: Somebody made an impression on you.

Vince: I had a very bad idea of what a salesperson was.

Chris: Got it, OK

Vince: And was very unclear about the fact that I might have made a good one. So he said, “Hey, you should come work for me and run my sales department,” and that was a sales department of zero, and then one.

Chris: Built it from the ground up.

Vince: So yeah, hired 10, 12 people, spent about 18 months with the business, realized there was a whole lot of other things going on in the business that weren’t really shared with me that I wasn’t OK with. And along the way in that journey, I had met and was engaged to who is now my wife, Nicole. Her brother actually had taken a sales job at Heartland here in Oklahoma City right out of college. And he had a degree in biblical history and was going to be a church pastor. He was making $20,000 or $30,000 a month selling payments, and I thought, “Well, hold on a minute...This might be a thing.”

Chris: That’s an interesting thing, yeah.

Vince: Yeah, so I signed up, and here we are.

Chris: Yeah, I would say ground floor up. So you’ve done ground-floor a couple of times. You went from running sales, being employee number one in a sales department, to being in, largely, the ground floor of Heartland, which eventually went public, got acquired. You’ve stuck with it, right? You’ve stuck with this company.

Vince: Yeah.

Chris: A good friend of ours, Wes, we will not say his last name, one of the things that he says that he loves most about you, he’s worked with you a long time, is that you’re self-taught. All of these sort of things that you know how to do, that cause you to run a $3 billion-plus company, that you’re really largely self-taught. So talk about that. How did you go and get some of the business acumen that you have today? Where did you dig it up? Who did you get it from? Do you have just a sixth sense of observation? How are you self-taught as the president of a company?

Vince: Yeah, it’s a really interesting question. That’s an interesting thing that Wes would share as a perspective.

Chris: When I told him we were having this conversation, it’s exactly what he said.

Vince: As you were talking, I was like, “I can’t wait to hear what Wes said.” That’s not what I thought he was going to say. But here’s what I’d tell you.

Chris: There were worse things said, but we won’t say those.

Vince: So when I was 23 years old, I was at a family wedding of a friend of the family. A guy was there, who was my mom’s high school friend’s brother or whatever. And he walked up to me, and he’s like, “Holy cow,” different word, “Vince Lombardo, I remember you. Do you remember how you used to just ask me every freaking question that you could think of when we would drive to the orthodontist on Saturday mornings together?” And I’m like, “Who is this guy?”

Vince: But every month, he would take me to the orthodontist because it was 30 minutes away, because my mom’s buddy from high school gave us free braces, blah blah blah blah. And I don’t remember being that way, but when I started to think about that and then ask other people: I was this curious kid that just wouldn’t stop asking questions. “Well, why? Well, why? Why? Why? Tell me more about that.” If anybody was willing to answer the question, I was interested in hearing the answer. And I’ve been gifted with a really good memory, so I remember these things when I learn them. My curiosity is what I think has helped me be, as Wes would say, “a self-taught person” because I’m constantly seeking to understand something that I don’t. I feel like knowledge is a gift, and understanding is a deeper one. You need to spend time in things to understand them versus just know them. And so once you ask enough questions to learn enough things, you can choose what you want to go deeper into to get a deeper understanding. I’ve spent a lot of time in my life doing that, and yet I think there’s still so much that I don’t know that I would like to know.

Learning lessons — and how to sell — from entrepreneurs

Chris: I love that. I would say you really, number one, are a good listener. You ask really great questions. They’re super hard sometimes, but the way you synthesize, it’s pretty impactful. And I would say it sounds like it’s just a key part of what makes you great is you’re a lifelong learner. So being in the ground floor as a salesperson, talk about your journey deeper into the sales organization and how you worked your way up.

Vince: Yeah. So, anybody that thinks that a sales job, especially a commission-only, outbound, no-leads, not-a-lot-of-support-type of sales job, is easy hasn’t done it before. I’d start there. There’s a lot of assumptions about how easy this is. I assumed it when my brother-in-law had the job, and was earning all this money, and had a degree in biblical history. I was like, “Well, come on.”

Chris: “He can do it.”

Vince: “I can do it, right?” And then I spent 90 days and didn’t sell a deal.

Chris: Wow.

Vince: And I was looking for other jobs. I was convinced this wasn’t going to work. In that next week, a lot of seeds that I had planted came to bear. And then I got hooked because I witnessed the experience of the thrill of actually having to put that much effort into, say, a 100 opportunities to pull out the two. And that became both annoying and challenging to me — it was annoying because I felt there was so much wasted effort, and I wanted to try to find a better system. We were such a young company then that when you got hired, you’d get a six-inch binder full of paper to read and a motivational CD to listen to in your car because cars back then had CD players in them still. And it was like, “Hey, call us if you need us.”

And the people you’d call were very technical, but they didn’t really understand anything about how to sell. And your local leader was supposed to help you out, and mine was great. She was really good, but she did things her way, and I didn’t really like a lot of those ways. I wanted to try some things out that were different, which was going to cost me money because it was going to take time to fail forward.

And I would say that within a year or so, I realized this had some pretty significant potential for long-term earning potential and a life that had a little bit more opportunity of balance. I could put energy into things I enjoyed, cared about, or loved other than work. And I always wanted something I could work as hard as I wanted to at, but if I wanted to hang it up, I could. The role really appealed to me in that way.

Chris: Yeah. Who at the company that you were like, “OK, I need to model it after this person,” or this is somebody that is pouring into you? What are some coaching moments? What are some influences along the way?

Vince: Yeah, honestly, a lot of the entrepreneurs that I had the privilege of serving as a sales professional taught me a lot. Not just by the way that they maybe thought, or asked questions, or listened. But that curious part of me, I always wanted to build a deeper relationship with the customer, so I could ask more questions so I could learn more. I was really good at connecting those people to other people in town that they might be able to get help from or learn from, or partner with, or whatever.

So much so that, in fact, there was this ... I was really big in the restaurant business, of course, in the way I sold payments. That’s how I made my money because I had contacts, relationships. I knew the industry. I knew what problems I could solve, and a bunch of these local businesses felt they were being overrun by corporate restaurants. This is back in the early 2000s when that was a thing.

And they founded the St. Louis Originals, which was a group of business entrepreneurs that owned restaurants in town that were paying dues to these national, state and other types of associations but didn’t feel like they were getting a lot of local benefit from them. So instead of just killing those memberships, they kept them, but they started their own group. They co-marketed and co-branded about, “Hey, eat local,” and it was before “eat local” became a thing.

And I got to be part of that conversation and help them navigate those waters and think through that, and we created a special program for them. And that was a lesson for me: “Hey, there’s strength in unity, even with competitors.” There’s value in listening to and learning from people who do the same thing you do, but maybe differently, and maybe even are competing for the same dollar of the consumer’s wallet that you are.

Chris: Wow.

Vince: I watched that happen. I watched people who had a knowledge ... people in the business knew that these two guys hated each other. They actually became partners in a business five years later because they started this group. They learned a lot, and they found mutual respect. Watching that stuff unfold, and having a keen eye on the people part of it, was really, really educational for me along the way — and something that I think it’d be a failure of mine not to mention as a learning point.

Extend grace because everyone has blind spots

Vince: I’d say within the business there were lots of people that gave me a lot of grace. There were a few times I probably should have been disciplined, terminated, or demoted for mistakes that I made when I decided to be the cowboy that was going to do it my way. But there’s a couple of moments that stick out. One of them was, that I was in this training, and I had a very low level of awareness of how others were perceiving me. At that stage in our life, we were newly relocated, we had two little kids under three years old, and I was exhausted. I was just trying to make ends meet for my family and working my tail off. And we were at this training, and I was asking a lot of questions.

And at the break, the executive vice president pulled me aside, and he said, “Hey, we haven’t met yet, but I’m your new boss. I’m your boss’s boss, and you just need to shut the F up and listen.” And I said, “What? I’m asking questions.” He goes, “Yeah, just stop.” I was like, “OK, that’s interesting. I thought I was doing the right thing by learning, and I guess I need to stop asking some questions.” And it’s a weird moment because it’s a rude way to handle something, possibly.

Chris: Yeah, for sure.

Vince: But what’s interesting is that was halfway through the day. In the second half of the day, I learned more than the first half of the day.

Chris: Really?

Vince: Because I wasn’t changing the course of what was being taught with all of my questions. I was just receiving the information. And so there’s value sometimes in just listening, and that was a learning moment for me that I’ve looked back to many, many times in my career.

Chris: Well, that’s a positive way to look at a really harsh way of dealing with somebody who’s super curious. It’s like, “Hey, you need to turn your curiosity off for just a moment.” But I do like that. Somehow, you picked up on the fact, at least in hindsight, that you were deviating some of the conversation rather than helping to flow with the design of what needed to get taught.

Vince: Yeah, yeah. And look, there’s been many people along the way that have poured into me in ways that I’m incredibly grateful for. A lot of them are no longer part of the business. They’ve moved on and done other things, great things, with what they learned here and what they did here. And it’s not really worth getting into a bunch of names to mention, but I think I’ve been richly blessed by people who are willing to go the extra mile, to redirect, to course-correct, to interrupt, and help me see what I can’t see. And if anything, I think what I’ve learned along the way is really that: We have to have people around us, no matter what our role is, whether we’re opening a business, we’re running one, big or small, that help us catch all of the blind spots we have. Because we all have them.

Chris: Yeah. Hearing the way that you’re articulating when you described the grace — that people had grace for you — the thing that I think is really powerful is how you have reciprocated that. Where somebody who is down a certain path, right? The way that you have enough patience and enough grace to go, “Hey, here’s some feedback on some changes that need to happen.” And ultimately, the consequences that people would fear for someone being in your position, giving them that type of feedback — the consequences, relational consequences, political consequences — they are not at the same weight somehow, as I’ve experienced in prior lives. Where do you think that comes from? Do you feel like you look back at yourself and you have empathy on who you were and how people had grace for you, and you’re reciprocating that and moving it forward? Or what’s a driver there, why are the consequences lower in many cases, and the grace is abundant?

Vince: Yeah. Without getting into all of the details, because they would take a while, even though they’re great stories, there were a few times in life that I chose to be a participant in something that I probably should have spoken up against. And it had its own set of consequences, each of those times. And in reflection on those, I think after the third one, they were all in a series of like seven or eight years. And after the third one, I made two big commitments to myself. Number one, since I’m in a position of leadership and I have the influence over other people’s lives, I need to be able to look myself in the mirror when the relationship ends and say, “I did everything I possibly could within reason.” Because I need to make that commitment to myself to honor my own values. I don’t want to cut a cord or let a cord get cut or watch someone spiral further into a bad direction because I didn’t have the courage to speak up —and then I’ve got to deal with the consequence of knowing I didn’t honor my values, right?

And then the second piece of that, I think, that the learning came from was, man, if you don’t speak up and you know what needs to be said? Something else is going to happen that probably shouldn’t happen. And so there might be an expense to speaking up. There might be a momentary loss of respect until somebody comes around to recognize it’s really out of care or some anger or some distance, or stomping away or whatever the things are. But I think in this world, if we really care about other people, we’re called to do the thing that’s hardest. And sometimes that means helping them see something they can’t, even in a moment where it’s going to take a lot of courage for that moment to happen.

Use ‘maybe’ to help rewrite your ‘bad first drafts’

Chris: Yeah. Well, that points to a lot of leadership philosophy. So fast forward. You’ve been in sales. The company goes public, in ...

Vince: 2005.

Chris: 2005. Talk about getting acquired and what position you were in, and some of the thinking that you guys had? Those are two really big moments, but was there a shift when the acquisition happened of Heartland and how did you participate in that?

Vince: Yeah. If you go back to going public, I joined the business in 2003. We went public in the fall of 2005. I’d been here two and a half years. And I felt like I missed the boat. I remember the night we went public. We were all together somewhere. And it came on — we didn’t have digital meeting rooms back then. But it came out that like 87 people had become millionaires overnight. And 65 of them were salespeople. And I was like, “Oh my gosh, I joined too late. I missed the boat. Now we’re screwed. We’re public. There’s no chance anymore at the big cash.” And for me, it was very black and white, which is the wrong way to look at things.

But if you go to the acquisition or even when we had our breach in 2009, which was a huge moment. It was the biggest data breach in history at the time, right after the Hannaford breach. It was hundreds of millions of card numbers stolen off of our network. We were the victim too, but nonetheless, it’s not how it looks. And those moments, like a lot of things in life, it feels in the moment like, “Oh my gosh, everything I had pictured or thought was this way is actually now this way.” And you’re looking 180 degrees. When in reality, it might just be five degrees off, and it might be ten degrees in the other direction. And when we fail to recognize that there’s other ways through, we get stuck in whatever our, as Brene Brown calls it, “shitty first draft” might be.

So my shitty first draft was, “We went public, I’m screwed.” When the breaches happened, “Oh my gosh, the stock price is going from $35 to $2.” And I had, at the time, I don’t know, $700, $800,000 in stock. So it was worth nothing for all intents and purposes. And I didn’t see a way through. And so you have these moments of all this weight of like, “Oh my gosh, everything I’ve been planning on happening just got taken away from me by ‘no fault of my own.’ I wasn’t involved. And I’m the victim.” And that thinking puts you in a place to stay in that bad first draft versus thinking about how to possibly get out.

When the acquisition was announced with Global Payments, a lot of people inside of the business had a very negative perception of what was going to happen. The business we knew, that we all felt like we were part of, and this father-like figure that built the company up, that we all respected. What’s going to happen now that he’s going to go? And instead of seeing possibility and perspective, a lot of people just went to like, “We’re screwed. We need to find the new place to go.”

Chris: Wow.

Vince: And there were a few of us in the room, like, “I don’t know, maybe there’s some things about this that are good.” But we had been exposed to some of the things about Heartland that were bad. And back in that world of Heartland from 2003 to 2015, it was well-put-together narratives about what the company was, what the leaders cared about, etc. And most people didn’t really know what was happening in the business. And a few of us, the year before the acquisition, were made aware of that, which made this much more, I think, of a positive moment. But it was so interesting because, in the first two moments of those examples, I sat on the side of the field that was like, “This is bad, doomsday.”

And the third moment, I wasn’t on that side of the field. But I watched hundreds of people I deeply know and care about on that side of the field. And to have the perspective of, “Hold on, it’s not as bad as you think,” was a really interesting learning moment for me about... I have this thing I tell people all the time that I learned in a positive intelligence seminar thing I went through. Stick the word “maybe” at the end of all your sentences that are about things that seem black and white. And all that does is tell your brain “maybe.” “Oh my gosh, I missed the boat, maybe. Oh my gosh, we got acquired, and the world’s going to end, maybe.” And “maybe” forces you to open up possibilities that maybe things will turn out differently than that bad draft has created in your head.

For some reason, as humans, we typically all go to the bad before we recognize what’s possible. And I do the same thing. I haven’t healed myself of this, but that word “maybe” has been a very powerful help along the way.

Chris: Was it easy to put in, to install?

Vince: Once I learned it, yeah. It’s one of those things — I got a whole list of things I wish they would’ve taught you in college, instead of the things they taught you in college.

Chris: What’s one other than the “maybe”?

Vince: That when good people make a bad decision, it doesn’t make them bad people.

Chris: Tag. That is so true. What’s another one? I’m just going to keep asking. This is like three gold nuggets in 20 seconds.

Vince: I think another one is, “You can work yourself literally to death and make less progress than if you find a way to balance what it is you spend your energy and time on.” And that’s this cheesy work-life balance thing. But the truth of the matter is, we all think that putting in more and doing more and having more actually generates more. And the reality is, there’s so many examples out there, that business schools should be teaching that contraction and reducing and focusing in so many parts of your life will actually produce a more fruitful and positive existence for all of us.

Chris: Well, and the “maybe” would help there. Right?

Vince: Huge.

Chris: Yeah. That helps a lot of the decision-making. Because if you have the right mindset, the “maybe” helps you shape the mindset, and if you can do that, you can see the angles.

Vince: Yes.

Discover your values and live and work by them

Chris: Yeah. That’s really good. Something you talked about a couple of minutes ago — you were talking about living in your values. Talk to us a little bit about what living in your values means as it relates specifically to your leadership philosophy.

Vince: That’s a good question. Well, I appreciate the question, and I think the answer about living into your values is the same in other parts of your life too.

Chris: OK.

Vince: First of all, I think that, another thing that should have been taught in college: Figure out what you care about, which I didn’t really do until about five years ago. I would tell you that once you understand what you care about, you’re forced to understand what you care about less. And I didn’t say what you don’t care about. So I’ll give you an example. You go through this list of 300 values, and there’s lots of exercises online and different tools that do this. Brene’s book, “Dare to Lead,” is a great tool for it. A couple other books out there as well, but they have these lists of values, 100, 200, 300 values.

And you start by reducing down to, let’s just say, the 10 that you probably think you care about. Then you got to get down to like two or three, which means you’ve got to get rid of seven things. And by scratching them out, you’re like, “I don’t care about that.” I have a very deep faith. I care a lot about family. Those are not two of my top three values. And I had to admit to myself after a lot of thought and reflection...

Chris: For sure.

Vince: “Holy cow, how is this less important than something else?” But if I’m being honest with myself and what drives my behaviors, my thinking, my action, my motivation, my decisions, that is true. It’s not faith and family above other values. So I think that process in and of itself is a very, it’s a rich blessing on anybody’s life, to get more connected to the person that you are. I also think you probably have to do this multiple times over life because I think we change a little bit over time.

I think when I was 25, my values were probably a little bit different. But my three values are authenticity, contribution and leadership. And in all parts of my life, the first one’s pretty simple. I don’t really enjoy people who are incapable of being authentic, whether at business or in my personal life. I think life’s too short. We have too many demands on our time. We have too many things we want to do. And to spend time with people who aren’t willing to get real with you and won’t let you get real with them, for a guy like me, doesn’t feel good. So I avoid relationships that people can’t get real in.

Contribution to me matters way more than I realized until I had teenagers. You just have to question what exactly they’re contributing to anything. And what I would say about that is, I have this really strong bend towards: We are here to make other people’s lives around us and the world around us a better place. And so we are all called to contribute, with whatever gifts we’ve been given, that we should be contributing to the people in the world around us. And when people are not contributing, I get really, really frustrated. It’s like this baseline expectation of a one-on-one relationship, a group project, where we spend our time and energy. We should be in contribution and service to others. And what an amazing world if we were all thinking about how to serve others all the time. I’d have hundreds of people serving me, and I’d be serving hundreds of people. And leadership is something that’s really near and dear to my heart. Because leadership, when you break it down, is nothing more than influence. And influence is something that we all have the power to possess, on ourselves and other people. From something as simple as the way we send a text message, we influence someone’s thinking. Or the clothes that we buy, or the things we talk about, or all the social media, influence is everywhere. And people don’t associate that with leadership. But the truth is, if you are able to influence how someone else thinks, acts or behaves, you’re leading them.

That moves in all directions. It’s not a single direction. It’s not like a down thing where if you’re above someone on an org chart or you’re their parent, or you’re their elder or their senior or above them in whatever tier — it is literally all around you in 360 degrees. And to not recognize the power of influence and respect the value that influence holds, good or bad. Those three examples — I didn’t share the deep stories of those 10 years of my life, when I learned a lot about the power of not speaking up — my lack of voice was an influence on people. And had I spoken up, I would’ve had a different type of influence on them.

So I feel like we are all called to lead in all parts of our life. So when I think about what that means in business, that means tough conversations, up, down, and around, where you bring your authentic self and require others to bring their authentic selves. We don’t hide behind some fake wall or some shadow we’ve created, and we’re going to get real. Because if we don’t get real, we can’t fix the problem. And that means things might get messier before they get better. They’re already messy, but sometimes you have to be OK with things getting a little bit worse before they get better. And you have to hold onto the “maybe” that they’re going to get better if you choose to step into those kinds of tough conversations. So in work, I think that’s sometimes —I don’t want to say unwelcome — because it’s become a norm in our business. But I think outside of our business, it’s a very unusual thing for people to experience.

Why culture is the ‘most-secret ingredient for success’ in business

Chris: I think you’re right. I experienced how unusual it is — I think something that’s really interesting about what you’re talking about is this is in the fabric of the culture. So if you’re in leadership, you are helping to either modify or redesign an existing culture, and the sort of value-centric thing shows up pretty regularly in this culture. So maybe just share a little about intentionally building culture and how you use values in building teams to shape and reshape cultures.

Vince: Yeah. First of all, this isn’t something I dreamt up or built. This has been written about for a long time by people way smarter than me. And I’ve had the blessing of some leaders who really cared a lot about culture. And I had the blessing of witnessing leaders who professed to care about culture and didn’t act in accordance with the culture they professed to care about.

Chris: You saw them outside of one of your values, which is authenticity.

Vince: Yeah, absolutely. There was an inauthentic connection point there of, “Wait a minute. We say these things, but I’m watching these things. What’s going on there?” And then you have a choice. In that example, in alignment with my values, speak up with influence or don’t and influence. But they’re both influencing. I think what I’ve learned is that when you have a culture defined, and you have a set of expectations of what it means to operate within that culture — and you are required to do the same and held accountable to do the same — there’s nowhere to hide. There’s no reason to hide because you have this, I don’t want to call it a rule book or a playbook, but there’s an understanding of what is expected and why it’s good and produces fruit. If you don’t have that, people don’t know what’s OK and what’s not as an operating mode.

Let’s take a 20-employee company without those cultural definitions — you have 20 people who come from 20 different lives of experience and influence, and their last jobs with different cultures — all trying to find out how they do the thing you’re asking them to do. So as a leader, whether it’s a brand new taco truck or you’ve got 400 locations as a small business entrepreneur, or you’re running the business like mine: If you don’t take seriously the need to define and live and prove the value of culture within your business, you’re missing the most-secret ingredient for success. And I would say this, many, many people who run businesses today, this is not their forte.

And that’s OK. It doesn’t have to be. Acknowledge it and hire your gap. We all have the gap. And if you don’t have the natural gift of defining and living cultural values within a business, or it sounds like hogwash to you? I would tell anybody who hears this: Take my advice and pay somebody to come into your business full time that does that well and can help extrapolate what you want and watch what happens in the first couple of years, because it’ll transform any business.

Chris: So what it sounds like you’re saying is culture, especially designed culture, authentic culture, is a competitive advantage?

Vince: Yeah, absolutely it is. But it’s funny. I don’t even think of that. When we’re engaged in these conversations, and trying to build and continue to strengthen our culture as a business across all of these different operating models, states, people, and roles, it’s naturally a competitive advantage. And I wouldn’t even put that on the table. Because I think that is just something that becomes a side benefit. Because the truth of the matter is that having that culture allows your people to live better lives. And when people are living better lives as employees and teammates of your business, they’re running a better business. And, of course, that’s a competitive advantage.

But I don’t walk around and think, “Now how can our culture become a competitive advantage to these three competitors?” Because I don’t want to spend time thinking about that. I want to make our culture as rich and beautiful and productive as it can be for the people that are here and let the rest take care of themselves.

Chris: Yeah. But one of the things that you’re really calling out is that culture has to have a belief system.

Vince: Yes.

Chris: It’s a common sort of core belief.

Vince: And it has to be held by the people in the most senior roles and embodied by them.

Chris: What is a challenge and maybe a lesson or a secret you learned where you were like: How do we get to the root of what we should believe or what we do believe? And bring that to life in and through culture? It’s a tough question.

Vince: From experience, I would say that when you’re trying to improve or change cultural operating norms within a business, that question shows up most because people are coming at it from different historical perspectives and life experiences. And I think giving space and time to wrestle those out with the people in the room who have done the most listening and understanding and are the most involved in defining and leading through the culture. But creating space for that conversation and not considering it as a loss of productive business time is a really important step that is hard for someone like me to do. Because the five hours we spend deciding what we’re going to do with this cultural thing is five hours that I think we could have been talking about how to advance our products and move down the field, etc.

I care about and love culture as much as anybody I’ve ever met in a job like this. And yet, I still get annoyed by that. And it’s necessary. So, I think that there’s this thing. We talk a lot about rumbling respectfully here. And again, stolen from Brene’s book, “Dare to Lead,” and what the rules are to challenge another person’s behavior or thinking in a way that is respectful, appropriate, and aligned to get to a better outcome. It allows you to come at a problem from two different perspectives and experiences. And you don’t have to agree at the end, but you have to align. And hearing each other out using this toolset, or the system of rumbling respectfully, it’s a big part of our culture here. Not enough people do that and step into it as they should. And I would tell you that when they do, beautiful things come out of it. We typically get to the answer when there’s a conflict about culture and what we should do with culture if we go through the process of rumbling with the right people in the room.

Business culture is hard to quantify — but the repercussions aren’t

Chris: What are the risks that people feel like they face when they know that they need to have a tough conversation? You were talking about having influence, and you’re either influencing by saying something or saying nothing. What are some of the things you’ve seen or heard or maybe go through your mind when you know you need to have a conversation like that?

Vince: Yeah. Well, I think it’s probably an important thing to note that, if you were to take that tip and you were to apply it wholeheartedly across your life without any awareness of the moment or the people involved, that would be a big mistake, and I would call it reckless.

Chris: OK.

Vince: So it’s not just about like, “I’m going to make sure I’m exerting the right influence in the right places.” It’s also like, “At the right time.” And recognizing that for different reasons, it might not be the moment to have the conversation and ensuring that, in fact, maybe you can create that moment to have the conversation — which requires more intention and more desire to have the conversation in the first place.

But I feel like one of the things that people use as an excuse not to is because whatever damage they’re worried about might come from this is greater than the damage they can’t measure that might be happening in the background. So let’s say you’ve got this employee and this thing’s going on, and it’s not going well. They’re a single point of failure, or they’re responsible for this really important thing that’s going on. But there’s just this wasteland around them of people, experiences and bad interactions that are happening. It’s really hard to measure the impact of that behavior. It’s easy to measure that if I just let Susie keep doing what she’s doing? I’m going to get to the finish line of this project, and I won’t have to delay the project. And what we don’t often do is consider what the cost is. Because tangible costs are much easier to us to recognize. I just lost $10. That’s obvious.

Not being able to measure the cost, but knowing it’s big is really, really hard. And so we often go where an objective outcome leads our brain like tangible cost and/or the expense of making the decision. But the expense of not having that conversation with Susie, and the people around Susie that are interacting and losing to her experience and her leadership and falling over because of it? That is something that as a leader you have to be aware of and acknowledge and have the courage to step into.

So choosing the right moment to have the conversation, but not allowing the behavior to perpetuate for an outcome that is more objective or productive for the business. That’s a gutsy thing to do.

Chris: It really is. And Susie thinks in this case that she knows what’s best. She believes her outcome is the right outcome. And you’ve got this wasteland of people and projects in the wake. One of the things that I think is really interesting about the way that I’ve seen you lead is — it comes from observation, curiosity, and experience to recognize the wasteland, right? Because I will tell you, Susie...

Vince: And an environment where people are comfortable sharing that they feel the way Susie’s making them feel.

Chris: So true. You don’t have to pay that price by having that person there if you have the right people and the experience to lead through it.

Vince: Yeah. And it still might cost you a month on your project. Let’s go simpler, and let’s just say you’ve got five locations of a restaurant. One of your managers, they’re just not the right fit. And there’s stuff happening around them. There’s not leakage. There’s not theft. There’s not that severe stuff happening.

Chris: Not just moral stuff or....

Vince: There’s a cultural issue. They’re churning employees. The 20-year bartender everybody comes to sit with has finally quit because she just can’t take this manager anymore. And you are going to have to run the store for two months while you find the replacement.

Well, what are your options? You can wait to have that last conversation, knowing that manager needs to go. You’ve already had the confrontations. The intangible cost is all the employees that they’re impacting, all the patrons who aren’t having good experience because the employees aren’t happy. They’re not producing good food. They’re not serving good food.

Vince: And we all know how sensitive food is. You have two bad experiences; you’re not going back. The cost to your business to sit on that leader is extreme — and yet mostly unknown in exact dollars.

Chris: Hard to quantify.

Vince: Hard to quantify. You could take that exact example to any business, to any model, when you have someone in a position of power who is not operating the way your cultural norms would require them to operate. And it takes guts to choose culture over productivity. And it’s really hard.

Define your company culture to better your business

Chris: I want to talk about the “Heartland Way.” I’d love for you to talk about how it was born and how you’re using it today as something that’s a manifested, very well-articulated way of shaping culture.

Vince: Yeah. Well, I don’t know that it’s as well articulated as people might think because I think it’s still got too much meat on the bone. We’ve got to slim it down. But at the end of the day, this is about defining your culture.

You can have your mission statement. You can have your credo. You can have the vision of where you’re going. But if you don’t give your people the key on how to operate within the map of your business, with people, with relationships, by defining your culture very clearly and readily for them and exemplifying it in the way you lead and reinforcing it regularly with real-life interactions and experiences, it’s not going to take root and change the business for the positive.

And what we learned along the way by trial and error and lots of failing forward is if we talk about something once every couple of months or we stand on a stage in an annual event, and we’re rah-rahing this thing that is supposed to be part of our culture. And maybe we’re doing our best to live it out, but we’re not regularly using it to better the business, to clarify, to define, to create examples. It’s not going to stick.

And when I took over the business, there were a lot of questions that people had. “Hey, we hear these things, but we don’t really know how to live them out in our role. We don’t know what the behavior looks like to be an entrepreneur who respectfully serves an entrepreneur. We need more than that credo to help us.”

And so we went out on a little journey, and we spent three or four months listening a whole lot, talking to a lot of people to understand how they would define things, what they would refer to them as.

We read a lot of books. We hired a couple of consultants. We drew a map out, and we had like 16 or 18 things that we thought were — we call them tenets now because we had to come up with the right word about what they are — but modes of operating, expectations, things in the business that define how we’re going to operate within the business.

We cut it down to 10 and organized some things around them. We created these podcasts and released all this information, articles, and examples. But that was just the introduction. And what we’ve learned along the way is if I stop talking about it, and if the senior team stops talking about it, it just becomes another thing that people occasionally refer back to.

Chris: Yeah. It’s cat posters and eagle posters on the wall.

Vince: And we did a really good job for a year really reinforcing this. And then we were like all leaders, like, “Hey, we told them. They got it. Let’s move to the next thing.” And we’ve learned in the last several months that this is not something that is as deeply rooted in the business as it needs to be, and needs to be talked about more.

What I have found is the most opportune times to talk about is when there’s an example that is somewhat public of a team or a person or a project or a process that is not honoring the culture. And if you define your culture correctly, everything that happens in your business that needs correction can point back to that cultural definition. And almost everything good that comes from your business can point back to that cultural definition. So you have this like thing to lean on of how we’re going to treat people, work together, operate and perform that allows you to always go back to it.

And I would challenge business leaders to consider who might listen to this: If you’ve put the pretty words on the poster or on the website about your values, but you don’t reinforce them, you don’t require people as a standard to honor them within the business, you don’t use real-life examples to celebrate when they show up really well and to call out when they’re missing, then they’re nothing more than pretty words on a page. And that is on us at the top of the business first to embody and change that.

Chris: Well said. One of the things that I think about a lot is your values should shape how you pick people, and your mission should help show you how you pick deals or customers. And one of the things that I would say is really interesting because I look at the tenets as a tool set, right? Because the values are embedded in there. The mission is embedded in there. I’d say those are subtext if you will. But go back to the Susie example. You can’t have the feedback conversation without the definition, right?

Vince: Correct. Or it just feels like you’re speaking another language.

Chris: Or it’s a preference thing. They just don’t like me or whatever. So the intention there has a lot to do with it. And that’s one of the things that I do think we should talk about is one of the tenets is clear expectations and accountability. And this is something that you hammer in, I’d say, a super thoughtful way. I love how you frame up why expectations matter.

Vince: Yeah. And I don’t know if I’ve actually framed it up this way for you. I’ve simplified this recently to try to make it more approachable and really understandable. I don’t even know where I picked this up. It was in a book or a podcast somewhere. Sorry, I can’t credit the original thought leader here. Happiness, I think, in life in general equals reality minus expectations. Forget about work and culture at work for just a minute. Just think about your life and where you’re at, how you’re feeling, your level of joy, happiness, satisfaction, etc.

And if you go to the last time you felt elated, and the last time you felt the opposite, like miserable, it is most often because you’ve created an expectation of that moment, that situation, that story, that experience that didn’t meet reality for a number of reasons.

Maybe because you had a really bad idea of what that was going to be, and you were just off. Maybe because a bunch of crap happened that threw it off. Here’s a great example of this in real life.

So we take our best people, our top sales performers, on these incentive trips every year. The last couple of years it’s been post-COVID, summer travel insanity in the United States, flights canceled, chaos, all the stuff everybody’s experienced in summer travel.

And in years previous, whenever a person on our team who are supposed to be people who honor these values and whatever, whenever their trip would get messed up by something outside of their control, we would have an earful. It’d be this whole thing. They’d all expect everybody to jump to their aid and fix the problems, etc.

We sent an email the week before the trip and reminded people about what it means to give grace and to have patience, and to set your expectations that there are going to be problems. Your luggage might get lost. You might end up a day behind where you’re trying to go.

You might end up stuck next to the bathroom in the back of the airplane next to somebody who smells. Whatever, right? If you set that expectation and it happens, you’re OK with it because you’ve prepared yourself for it.

In the last two trips, we’ve had zero complaints, and we’ve had like ten times the number of issues. And I’m not going to say it’s just because we sent an email, but the reminder of like, “Oh yeah, I should probably not expect this to go perfectly.” It’s a big deal.

And so what we’ve learned is when we can manage our own expectations — and that doesn’t mean always expecting things to suck either, just to be clear — but when we can manage our own expectations, we usually can live lives that feel a lot more at peace or full of joy and less frustration and stress and anxiety and discord and all those sorts of things.

And I think that in having expectations of ourselves and of others and communicating those to ourselves and to others, we put ourselves in a position to be able to measure whether or not that’s happening. And that’s where accountability comes into play.

Because it’s one thing to say, “I’m going to expect this of you,” or, “I expect this of myself.” But if I haven’t told you that, I can’t hold you accountable to it. If you haven’t agreed to it, I can’t hold you accountable to it. And if I haven’t told others what I expect of myself, it’s really hard for me, with my bias and lack of awareness and blind spots, to see when maybe I’m not actually performing to those expectations.

And so, I think there’s a lot of value in accountability. And I think that looks like a lot of different things to a lot of different people. And I don’t think it needs to be prescribed. I do think we all have a better chance at a more filling life if we have managed expectations and people and ourselves to hold us accountable to those expectations.

Chris: That’s amazing. And I think that’s a big part of leadership. You have somebody there who expects that, creates space for it, can set the expectations for themselves and the team, and hold themselves accountable. And leading that way should create the permissions, if you will, or the credits to be able to hold others accountable.

Vince: Yeah. And interesting how that shows up. When we first put all this together and put pen to paper on it and tried to create a program out of it, we were thinking about more of the individual contributor level in the business. They need to have clear expectations so they know whether they’re performing or not because they deserve to have that and accountability to that performance.

What we’ve learned since is it is ten times more valuable and important to make it clear that you have a minimum operating expectation of your leader — that they set clear expectations with their employees so they can hold them accountable.

We had a problem for a while in some departments that they were doing all this accountability holding, but there weren’t clear expectations, or the expectations were changing every two weeks. That’s not a healthy environment for anyone to operate in as a professional.

And so as a business, it takes just as much effort to make sure your leaders know what it looks like to set expectations and hold accountability as it does to create a tenet that gives you permission to do so.

Leadership is influence — and it doesn’t solely go up-down

Chris: Yeah. Well, you talked about rumbling respectfully, which I think is more art than science in many ways. I think what would be really helpful to talk about is this idea of 360 leadership, which is expected of our culture. Everybody’s got a boss, right? And especially if you’re a people leader, you have people that report to you and then you have peers. So I think it’d be really helpful for you to [share] how you think about 360 leadership as it relates to the professional work environment and how you’ve shaped that tenet for us.

Vince: Well, let’s go back to this idea that leadership is influence. We are all leaders in all parts of our life, but we are leaders by name in some part of our life, whether it be at our household or in a a group at church or at school or at work, or with friends.

Every person in the world is expected to lead somewhere, and we all have the power to do it by being someone who recognizes the responsibility of having influence. Once you have that as a core understanding, you can’t look yourself in the mirror and be honest and say, “I’m only going to have tough conversations with people who are below me on the food chain.”

Because that would be what I would call a cognitive dissonance to the agreement or alignment that you have influence ability in all directions. It is my responsibility to speak up and influence above me, around me, diagonally from me in life and at work, and below me without a whole lot of permissionable regard for following an org chart.

I like to describe this with a visual. You’ve got layers of people in an org chart, and in most traditional companies, politics requires you to go up, over and down to have a conversation. At Heartland, that’s the thing that will get you fired almost. That’s ridiculous.

That takes so much time and bureaucracy. Just go talk to the person. Have a conversation. Productivity matters enough that we don’t need to worry about politics and bureaucracy. If you’re choosing to lead in the way of going up and around, you’re choosing to ignore a direct opportunity to influence another person for a better outcome. And to seek to understand their perspective in the process.

So when we think about 360 leadership at the business specifically, we ask all of our people to recognize the responsibility that they have by being a member of our culture with this as one of our tenets. And what that influence comes with the responsibility of recognizing that we’re going to respectfully communicate with people.

We’re going to follow those cultural guidelines, but we’re not going to allow predetermined rules to associate who we influence and who we don’t. And when I think about my best people, the individuals in our organization who have the most, I don’t know, they think the biggest and create the most change, they’re the ones who aren’t worried about my title or your title when they have a conversation. They’re just talking.

They’re explaining what they’re seeing. They’re sharing their perspective, and they recognize this is how they can influence up. And when I see the people struggling the most to achieve what they set out to achieve, it’s usually because they either aren’t trying or they aren’t recognizing that the ways they’re trying aren’t working in influencing around and above them. We get so much more capacity of our own output if we influence around and above than if we influence below. And yet cultural norms require us to think leading is only something you get with a title to push ideas and thought down.

Chris: Wow, that’s powerful. And I think you’re going on three years leading this business. The tenets of the “Heartland Way” show up. And then you have this other side that I’d say is a really great Venn diagram of these leadership competencies coming in, where you want to challenge the leadership that’s maybe over and above or adjacent to — however you want to describe the Heartland Way — is for everybody. And then you got these leadership competencies, and it was like, was that really for just leaders? And it’s like, it actually really is for everybody.

Vince: Yeah. Because we’re all leaders. The leadership competencies are interesting. My wife would tell you I’m way better at acknowledging gaps than complimenting people’s abilities — and she’s right about that. And that’s both a gift and a curse.

But when we looked around the business with the Heartland Way tenets released and communicated, we started to see that there was this other layer of what we needed our leaders to become. And if you take any group of 10 leaders and you put them on a measuring stick, they’re all going to have gaps in some areas. We all do. I’ve got plenty of them.

And so we started to look and study and understand what a lot of the brightest minds in history have said about what good leaders look like from a competency perspective. That is the ability to do or behave or act in a certain way in accordance with somebody who has responsibility in leadership.

And we realized along the way it applies to everybody — because we all have responsibility in leadership. And so those competencies are meant to be not like a report card against which you judge yourself. I mean, they can be. I think people have used it that way over time. But more a map on — if you want to be a really well-rounded leader who influences well — these are the areas that you probably need to aim or seek out competency. It’s funny, but sometimes you don’t realize how you’re feeling until you put a word to it.

Sometimes you don’t realize what gap you have until you put a word to it, and then you can go research and learn about that. So when we created these competencies, we didn’t just come up with a concept.

We put articles, videos, lessons and classes people can take, books they can read, and tests they can take about the level of competency so they can go self-improve in areas that they feel like or have been made aware that they have gaps in their leadership abilities, which again, is all of us.

Invest in culture — and yourself

Chris: Yeah. And the thing that is very clear talking through this, and hopefully it’s clear to everybody listening. It is a significant investment to define the culture, define how you think about leadership, to build the content around it, share it, make it a part of the fabric of how all conversations happen.

And then the thing that I think is really interesting is if you think about those leadership competencies, there’s almost an expectation that we really are leaders somewhere in our life in this pursuit of self-improvement.

The thing that I think is really interesting is the level of investment that you and the company have put out to be able to design this — it may be a reflection of how people should personally invest in themselves and the type of outcomes that are available to them if they do that. And I know that you do a lot of personal development and leadership development — so talk about that and how you’ve made that a core part of your life.

Vince: Yeah. It’s so interesting. I have met so many people who have multiple postgraduate degrees and still haven’t figured out what they want to do, what they care about, how to make the living they want to make, etc., etc.

And I liken that, not because anybody who gets a postgraduate degree is bad. Go for it, heck yeah. There are so many good things in that are really big blessings. And it’s a perfect example of you sign up to receive development, you receive it the way that institution’s going to give it to you, and you hope it’s going to better you.

When in reality, if you think about that modern educational thought, which is: Here’s the prescribed package of information you need to digest for us to certify you as whatever we’re going to certify you as. The level of digestion, understanding and ability of each individual largely relates to their own abilities, experiences, backgrounds and desires.

And you think about that compared to someone who says, “You know what? I want to get better in X and I’m going to go seek getting better in X.” And what we require and talk a lot about in our business is we will give you the map. But we are not going to sit you down in a classroom and teach you the material.

We will coach to a certain standard and help develop your gaps and your competencies to a certain standard, but at the pace and method which you choose to go after it. So to anyone who might hear this, my advice that I learned a long time ago is if you keep asking other people to make you better, you’re probably not going to get better.

Because if you’re not serious about doing a lot of the work on your own? It’s not going to have the same value. There’s a reason why you hear about these top-of-their-field people still having coaches, like a Tom Brady, right? I mean a life-coach-type person.

And those people typically exist to help call you out in the areas where your gaps exist. They don’t exist to give you the solution to the gap. And that’s the beauty of really good coaches. Their job is to ask tough questions to identify opportunities. It is not to solve the problem.

The powerful coaches make you aware of a problem you need to solve and then create a path to solve it yourself. You can go back to the Wes comment about the “self-taught” thing. I think that’s funny. I’ve never labeled myself as that or heard that said about me.

But I was the guy the first seven or eight years I was here that was like, “You need to make me better. You need to invest in me. I want this. I want that.” And I woke up one day and realized no one’s going to do it for me. I just need to go figure it out.

And there’s lots of really good people with lots of good material. There’s great books. There’s good lessons. And if I take seriously me getting better with the right resources and support around me, I’ll actually get better.

And I think that’s something that we all probably need to be a little more serious about. And I’d say it’s OK if you’re in a season where you just don’t want to work on yourself right now because it’s exhausting.

Chris: Yes, it is. Constantly challenging yourself everywhere. I want to talk about lessons and conclusions, things that you’ve learned along the way, right? So think about yourself working, from employee zero as the head of sales of a computer technology company. What would be the first thing that you would say back to that Vince? Knowing what you know.

Vince: Now that’s a good question. Yeah. The best things take time. You think you can do it all really fast, and you probably can’t do any of it to the degree of success that you think you can, if you try to do it all really fast. I would say the most powerful one though — I’d say I learned this five or six years ago from a dear friend and coach in our life here at Heartland. She teaches that the power of words on our own thinking is way more extreme than we realize. And she talks a lot about the words “but” and “and” — and how we use them oftentimes incorrectly. “But” is a statement that takes the second part of what you’re going to say and deletes the first. “And” allows both to exist. “How was your weekend?” “It was really good, but I’m tired.” “It was really good, and I’m tired.” I mean, that’s stupid every Monday conversation at the water cooler. Right? And yet it changes the context of the entire thought and the experience the person’s having.

Chris: It’s so true.

Vince: When you take that into human relationships, and the psychology of human relationships, and you pull “but” out unless you actually mean to use the word “but,” it changes a lot about the possibility and potential of what can happen when two people are trying to work on themselves and each other. And I would say Vince 20 years ago lived in a much more black-and-white objective world where “and” wasn’t really a word that was used a lot in that context. And I think it’s an incredibly powerful word. I would’ve taught myself the equation about happiness because I don’t think I managed my expectations really well the first, I’d say, in my twenties. My first 10 years of my marriage and my professional life. And I’d also say, “Man, make time for fun.” It’s probably good advice for myself at this point too. We are so serious about accomplishing ...

Chris: Progress.

Vince: ... Progress and results that we fail to recognize that when you look back at the last 12 months of your life, at any given moment, what moments had the most joy? They were probably the most unexpected, least planned, with people you care about the most, in a place or a moment where there was very little stress.

Chris: Yeah.

Vince: And that’s not normally while you’re working to produce results.

Chris: Yeah.

Vince: And I think that thing that keeps us going as people is — we want more of that. And we’ve taught ourselves that if we just keep doing the thing, producing the next thing, building the next deal, then more of that will happen. But if you don’t stop and just shut it off every once in a while to let that happen, you usually can’t even recognize when it’s happening. And I wish I would’ve taken more time back then to not be so serious about getting the next thing done.

Chris: Yeah. The couple of things you’ve said, just in this conversation, that have been really powerful: You’ve used the word “and,” the word “but,” and the word “maybe.”

That simplicity really matters. And the thing that I like about what you said a couple of seconds ago about the word “but.” You said, “Hey, when you’re going to say even the weekend thing, ’I had a great weekend, but I’m tired.’” And you talk about how it really deletes that first thing.

Vince: Almost makes the good weekend not worthwhile.

Chris: Yeah.

Vince: Yeah.

Chris: The thing that I think is really interesting about that is something that’s really helped me is this idea of there’s right and there’s wrong. And that’s almost like a — there’s one thing that can exist, not the second. “Maybe” helps both things exist. “And” helps both things exist. And I think that instead of living in a world of right and wrong, I’ve decided to live in a world of what’s wise and what’s foolish.

Vince: That’s a great way to say it.

Chris: Right? And I think it’s really powerful the way that you’ve shaped the words and the using of the word “and” maybe in place of “but,” unless you actually are going to use the word “but.” And the way that you’ve used the word “maybe.” Having both of those exist, I think, probably transformed the way that you think and the way that you look at your life. These lessons that we were just talking about you talking to a younger Vince. Vince who started building teams. OK? Your early ... You’re building teams. What would be a lesson that you’ve learned along the way about early team building, and some things that you wished you had doubled down on, or maybe chosen an alternative path?

Vince: I think defining the mode of operating the rules, the cultural components of any team is the most important thing to do out the gate because it does set a level of expectation of how you’re going to operate. And without it, I think you leave a lot of room for misunderstanding and tension to exist. And tension just completely removes the possibility for success because it’s just constant anxiety and frustration and negativity. And it’s really hard to want to stay in that environment. So I’d say that first and foremost. Secondly, I’d say: Man, everybody’s got something they’re really good at. And don’t put them in a box. I think we oftentimes label people by title, experience, or by results. And we’re like, “Well, they’re only capable of that one thing,” because whatever filter we’ve put on our view of them, or whatever the label is we’ve placed, only lets us see that as their possibility and potential.

And man, I couldn’t tell you how many hundreds of times I’ve seen somebody that we thought was really bad at this thing over here. And when we sought to understand their real capabilities and possibility, we moved them over to a different responsibility and they just set records. And I think that seeking to understand those people on your team and where they’re good, and letting them use those strengths while you’re developing the gaps, allows a team to move much farther, much faster.

And I’d say that the most important thing I’d say of all of it though, would have to be: Give your people permission to push back, change the way you think, lead you, speak back to you, respectfully, both directions, but speak back to you, call you out when you’re full of crap. Because man, nothing’s worse than somebody who’s in a position of given power and puts themself in an isolated tower to not be made aware of how they are operating, or not helping other people feel the way they deserve to feel about their work, and their output, and their life. And unfortunately, in many cases, those leaders, only people who have the experience close enough to really call them out, are the ones they have not given permission to call them out.

Chris: Wow, that’s a mistake.

Vince: And we have to be able as leaders to let the people closest to us, even if they’re quote “below us” in an org, to let the people closest to us to say, “Hey man, I’m going to check you on that. That’s not what we need to be doing.” Or, “What did you mean when you said that? Because it felt like this.” Right? And it takes a lot of courage for people to do that. But if you give permission in an environment, it takes less courage and you’ll get more of it and you’ll get better faster, and you’ll go farther.

Chris: Yeah. But you have two things. Right? You create space for that stuff, but you also have a big personality.

Vince: Sure.

Chris: So if you think, like one of the things that I think is really powerful about that is, every leader has their own sort of dynamic. So you just talked about the ivory tower leader who’s really disconnected. You’re super connected, but you also are really passionate. So how do you think some of the people have been able to, in your life and in your work life, have been able to sort of speak into you? And what are some of the moments of courage, or the moments of speaking up that have really made an impact on you?

Vince: I think it’s really important for people to remember that people in positions of leadership are also human, and they put their pants on one leg at a time. And they have issues, and they have struggles, and they have personal stuff going on in their life, just like all of us do. And to aggrandize those leaders to the degree that you forget those things are real makes them less approachable in your own mind and less real. And therefore, you have more fear in bringing things up.

And so I think it’s really important for us as leaders to acknowledge that we get dehumanized in that way by the nature of the job. And because of that, if we want to invite more feedback and pushback, we need to be more human. We need to show that human side more. We need to be more honest and vulnerable about what’s going on in our life. And what things we’re struggling with, and what things we wish we were better at, and all that sort of stuff. Because the more people feel like you are quote/unquote, “as normal as them,” the less courage it’s going to take them the more often to speak up when you need to hear something.

I think that’s really important for us to take away from conversations like this and remember those things because it’s really easy to forget that. I think I can tell you that I’ve only had a couple of instances where people who hadn’t had the chance to know me as a human still had the courage to speak up and share. And I’d like to say that every time that happens, I respond in a way that invites more sharing, but I’m also human. And sometimes I’m not in the mood to hear that. And I think in those moments, we’ve got to go back, and we’ve got to tie that string.

There’s this old psychology lesson about relationships are about strings being tied and strings being broken. And when you do something that offends, hurts, or damages the other person in the relationship, you’re breaking strings. And when you’re doing something that’s life-giving and fulfilling, and trust is being built, experiences are being had, you’re tying those strings. And the more strings there are that are tied in the relationship, the stronger it is, and the more it can handle some of the tough stuff. Until that last string breaks and the relationship breaks. Right?

And so you think about a moment where somebody who doesn’t know you as the human version of you, they only know you as the boss version, they have the courage to say the thing, and you respond in a way that isn’t in accordance with your values, the cultural operating norms, and the tenets. If you don’t circle back and say, “Hey man, on me, not OK, I shouldn’t have handled it that way. That was not about you. Here’s what was going on.” You immediately set — and by the way, oftentimes you need to do that publicly — because you immediately set a tone “it’s not OK to bring something to me unless you’re close to me.”

And an ivory tower leader, one who has a bunch of people around him and only listens to those people? They all think like him. We have to surround ourselves with people who think differently than us, challenge us, and have the courage to do so. And I’ve been blessed with people coming into my life, both at work and personally, who aren’t like me, but like me, meaning they enjoy me as a person, and I enjoy them as a person. And so we have enough mutual interests and likeness to stay in a relationship, but we think and approach things from very different perspectives. And that forces me to either galvanize my beliefs and feelings about a topic or be changed to a different perspective. And those are really good, healthy things to be happening in our lives.

And the problem is Chris, all of that stuff I just talked about? It takes a lot of time. Because connecting with people takes time. And time’s the thing most precious to all of us, and where we choose to spend it has certain fruitful outcomes or not. And I think that if I could impart any wisdom on the younger version of me, keep taking time when you feel like you don’t have it even, to pour into the connection points, to be more human, to have more connection, to get more feedback, to find and become the best version of you to help other people. And that’s this formula that’s really, really hard because there’s all these things in life that are pulling on us as people. But if we can pause and remember that this moment of connecting is more important than whatever might be going on, it’s going to help all of us be better.

Wrapping up with rapid-fire questions

Chris: That’s such a good statement, man. Well said. Well, it’s really been powerful to hear a lot of things from you that you’ve been able to maybe unpack in a different way. Right? And maybe more of a one-on-one intimate conversation than some of the stuff that we do as groups. Right? So I have some rapid-fire questions for you.

Vince: OK.

Chris: OK? And these are-

Vince: These are the ones you wouldn’t show me?

Chris: These are the ones I wouldn’t show you. Yeah. I was like, no prep.

Vince: Does rapid-fire mean I have to have a rapid answer?

Chris: Hundred percent. I’m going to just rattle them off, and you got to go, “And ...” I know that some of them won’t happen. There’s a couple of them that are going to require longer answers. So don’t feel too constrained. But anyway, so the first question. So you’re a notorious DIYer, OK, around the house. And what’s the home improvement project that you’re most proud of?

Vince: “Notorious” is a good word. I built a shed. I mean, it’s more than a shed. It looks like a little guest house, but it houses a bunch of crap. And I was really proud because it was the only thing I ever constructed from complete scratch. And then the first time it rained, I realized I built it as a low point of elevation, and it gets wet whenever it rains.

Chris: So you’re proud of it?

Vince: I’m proud of it.

Chris: And you’ve feedback for yourself.

Vince: And I have feedback for myself.

Chris: Great.

Vince: I want to tear it down and rebuild it, but it’s like, “Can I really do that if that was the thing I’m so proud of?”

Chris: Oh man. Well it’s ornate and flooded. Got it.

Vince: Yeah.

Chris: Well I know you’re no stranger to the barbecue smoker. What’s the secret to nailing a good brisket?

Vince: Oh, same thing is secret to good relationships. It’s time.

Chris: OK.

Vince: Unfortunately.

Chris: Yeah.

Vince: And brisket’s not my thing because I’ve only done a few of them. But it’s way easier than people make it out to be if you just are willing to let someone else tell you how on a YouTube video or on a website.

Chris: You follow ...

Vince: Yeah.

Chris: Yeah. OK. Well when it comes to food, what’s your kryptonite?

Vince: Man, I’m a big pizza, and burgers, and salad guy.

Chris: OK.

Vince: Mainstream American I’d say. Yeah.

Chris: OK. As a pilot, have you given yourself a call sign? And if not, what would be cool sign for Vince Lombardo?

Vince: Oh, man. No, but I totally should. And man, I don’t know what I would name myself. I more think like what would the air traffic controllers name me? And it’s probably “Loud.”

Chris: Loud Guy 73.

Vince: I have this weird anxiety when I’m flying, that if I’m not really ... Because all these people mumble on these radios. And if I’m not clear, I’m going to die.

Chris: Yeah.

Vince: So I’m slow and clear and loud.

Chris: Yeah.

Vince: And it’s very obvious when they come back that I just surprised them.

Chris: “There’s some loud guy.” All right. Well, you mentioned them earlier, but I do think it’s worth saying it again. What are your three core values?

Vince: Yeah. Authenticity, contribution, and leadership.

Chris: Yeah. That’s good. What would teammates say is your biggest weakness and biggest strength?

Vince: Are we talking like-

Chris: There is a right answer.

Vince: ... my currently or ...

Chris: Yes, yes.

Vince: I’d say my biggest weakness is consistency in where and how I show up. I’d say I’ve become a bit of a swoop and pooper. Which is...

Chris: A corporate seagull?

Vince: Yeah. You pop in, you’re like, “That’s what’s broken,” and then you leave. And so I need to work on that. But being more consistent in how I show up so that the expectations that we mutually create are honored.

Chris: OK. And your strength?

Vince: I mean, I feel like we’ve talked about it a lot, but just being real. I think there’s so much more power to being real than people realize.

Chris: Yeah. I’d say connection too.

Vince: Yeah. Yeah.

Chris: What is your best advice for somebody coming out of college and thinking intrapreneur, corporate, or entrepreneur?

Vince: I would like to talk to them in high school because I would’ve told them to spend the couple years of high school and four years of college where they’re working to try on a lot of different jobs. Because there’s nothing that can paint your feeling about what you want to do like experience. We have this really cool entrepreneur program here, and we just wrapped it up last week. Hearing how many of the entrepreneurs came in with this really clear textbook plan to either validate or devalidate what they want to do in their life. Almost like once they make the decision, they can’t go back, which is funny. But we all thought that when we were 22 too, right?

And a few of them were like, “I took this job because I was sure that I wasn’t going to want to do this in my career. I just needed to be really sure.” It’s like, “What? You spent three months doing something you hate just to prove that you hate it.” Well, I don’t understand.

But there’s a trial and error about that, that I think is pretty impressive. My advice to those people though is: Before you decide to abandon the thing you’ve decided that you don’t like, make sure you’ve given it all the angles of trying that you can. I think we’ve become a culture, especially our younger people, I don’t want to call it a wasteful culture, but one where it’s easy just to back out of the thing and go try something else. And I think it’s really important for people to recognize that when things are hard, it doesn’t mean they’re bad. And I think a lot of our young people back out of something because it gets hard.

And jobs? They’re called work for a reason. Most people don’t feel like they are never at work. Even people who are like, “Oh, it doesn’t feel like work to me.” Yeah. My ass. Some days it probably feels like work. And it will. And it’s OK for things to be hard. It doesn’t mean that they need to be removed from your life, and you hit the eject button. And sticking with something sometimes that’s hard has so much more value to you as an individual pursuing the best version of yourself than exiting stage right to the next thing. That’s not a requirement to stay in a really bad toxic role or business but hard’s OK.

Chris: I like that. One of the things that’s great about one of the Heartland buildings, is every conference room is named after an entrepreneur. And there’s a bunch of these things. What entrepreneur inspires you, and why?

Vince: Oh man. So it’s funny, some of the names when we had the contest to name the entrepreneurs, we got the list back, and I was like, “That’s not an entrepreneur. Why is that person on the list?” And it’s like, “Wait a minute. OK. Yeah, I’m being a little bit too limiting in my thoughts.” But I would say that Olive Ann Beech is probably someone that I’m most impressed with, and that’s not to take away from a lot of other entrepreneurs. But to be a woman in the 1950s and step into a leadership role of an aviation manufacturing company, when there’s only like four in the general aviation space, and to build it into the insane powerhouse that Beechcraft is today is a pretty unbelievable story.

I mean, aviation in and of itself has not traditionally been a female-friendly environment. And I’d say in the last 20 years, that’s started to change. But if I were a woman in aviation, I would still feel like I’m in a man’s field. Not fairly either. I just would. To do it in the ’50s and stay in business. I mean, I imagine a world where she literally wasn’t getting business because she was a woman. And yet still, one of the most successful aviation companies in the history of the world, which is pretty cool.

Chris: It’s powerful. Well, it was really great to be able to sit and go deep on a couple of these topics. Of course, it’s a privilege to sit and do that with you. Appreciate you taking the time. What’s next for Vince Lombardo?

Vince: I mean more of this. You mean like today?

Chris: Lots more of this. Lots more talking.

Vince: Yeah, no. I don’t have some really prescribed plan. I feel like when the right thing that’s next shows itself, I’m going to go do it. And right now I think what’s next is I really want to prove the value of continuing to enforce culture in a huge organization and what it can do. While we continue to try to become this preeminent technology player in the business that we know we have really, really great resources and tools. And to do that with people who are happy and healthy versions of themselves, and really enjoy being part of it, is so much more exciting than just achieving some summit at some point in time. And so I’m heads down in that, and I think that’s ... I’m OK not having some plan.

Chris: It’s good. Well, thanks for coming to the studio.

Vince: Yeah. Thanks for having me, man.

Chris: Absolutely.

Vince: Appreciate it.


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