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How Leaders Can Build Trust Through Vulnerability and Humor

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About the Episode

What’s the key to becoming a better leader? Dave Gilbertson, Chief Custom Officer at UKG, believes it’s all about building trust. From going on tour with comedian Louie Anderson to helping manage one of the largest SaaS mergers in history, Dave has many incredible experiences to draw on for leadership inspiration. Listen now to learn how he uses vulnerability and humor to bring more empathy, understanding, and trust to the workplace. His unique story and insights may make you rethink what it takes to be a great leader.

Episode Highlights

Meet Our Guest

Dave Gilbertson’s story starts out in the private equity space, but a chance meeting with comedian Louie Anderson changed everything. Dave joined him on tour, learning more about leadership than he ever had in a corporate setting. Now he infuses those leadership lessons as a TedX Speaker and Chief Customer Officer at UKG. His unique perspective on leadership helped him manage one of the largest mergers of all time between Ultimate Software and Kronos, combining more than $2 billion in revenue and nearly 7,000 employees. Yet with all this success, he’s never lost sight of the true core of leadership: serving people.

Episode Transcript

Chris Byers: He ended up deciding to give up a fantastic job in the private equity world, to go out on tour with a comedian and learned more about leadership on the road than in all the years since then. With a chance meeting with Louie Anderson on a plane, Dave Gilbertson entered the standup comedy world, giving him lessons that still fuel his career in business today.

Dave is now the Chief Customer Officer of Ultimate Kronos Group. And while I could list a long history of great successes and accolades, this story comes from his 2018 TED talk called Leading with Laughter. He's spent most of his career blending leadership and humor, and as you can imagine, this is the result of his experience working with those comedians. Yet there's always more to the story.

Well I'm Chris Byers of Formstack and this is Ripple Effect, a show celebrating the positive impact your decisions create. Dave, welcome to the show. We're glad to have you here.

Dave Gilbertson: Thank you, Chris. Absolutely thrilled to be here with you. It's good to talk to you.

Chris Byers: Absolutely. Well, let's jump in. Tell us the story of meeting Louie Anderson.

Dave Gilbertson: This is one of the most random things, like I feel like in school and personally, I always hear about wouldn't it be amazing if just on an airplane I met somebody and you hit it off and it was crazy, or if I got stuck in an airport and then just had to talk to a total stranger for a while, how would that go? This is exactly what this was. Probably a year out of undergrad, was flying back from visiting family to Los Angeles. And I look up and I am sitting right next to Louie Anderson, who was one of the greatest comedians of all time, had been one of my real comedy heroes growing up. And I realized pretty quickly we were delayed by about two hours just sitting on the runway. And so he couldn't go anywhere. And so we were just talking and he was asking me about my family and my career and we just kind of hit it off. And we talked and talked the whole way back to Minneapolis.

Well, finally, he mentioned that he was working on a book at the time called The F Word: How to Survive Your Family and would love some help. And he thought my perspective would be a helpful one. And so after that, I was still kind of working with this private equity firm working in L.A. during the day. And then I go into Beverly Hills, where Louie was living at the time at night. And we work on the book and did that for probably about nine months or so. And through that process, we just got to be really good friends. He was hosting the Family Feud at the time and decided to leave the family feud. It was right about the time this book was coming out. So he was looking for a manager. I knew that my time with the private equity firm is going to come to an end. I get a little bit of time before I was going to go to business school. And so when he asked me to to step in and help him out, I thought this is the perfect time to take a risk like that. And so I did. And so I end up spending about a year or so on the road with Louie. I got to know the funny business really in-depth. It was a really fulfilling process and I felt like I learned so much from Louie. I've always been amazed at how much leadership stand up comedians actually show on stage. So it's been a blessing in my life. And I still look back on the lessons learned with Louie and other stand up comedians as some of the most valuable, and I still try to apply them with my teams today.

Chris Byers: What a fun story. One thing you talk about in your TED talk is I think it was a question maybe you asked him, which is how do you handle two wildly different audiences, walking in the bingo parlor with 10 people, 20 people versus the full concert hall and bring the same energy. Talk a little bit about that and what you learned from it.

Dave Gilbertson: So the show you're talking about was really interesting. So there was a casino on a reservation in New Mexico, really remote, one of the more remote parts of the whole country. So we go to the casino and you never know exactly what you're going to get when you're doing a show at a casino if they're not used to doing comedy. So you never know what the stage is going to look like and the audience set up. And so we came in behind like through a back door, which is normal, not realizing that when you open that back door, you're walking out onto the stage. And so we both walked in and didn't realize. And there's this huge applause because they think Louie came in to start the show like 45 minutes early, when we were actually just coming to get ready for the show. And we look out and we see the bingo board. There's a big bingo board on the stage behind us and there's all these bingo chairs set out where the audience is supposed to be. It was very clear they were maybe thinking a bingo game might break out at any moment. And unfortunately, there's not the entrance you would hope to make as a big name comedian. But fortunately, Louie is so good at rolling with the punches that he just rolled with it. It ended up being a great show. It was a small audience, so it's probably 100 people, but it ended up being a really good show.

And then literally two weeks later, he did a benefit show for Larry King's charity. He had a charity that was dedicated to heart research, and afterwards I went to him and I said, Louie, two weeks ago you were performing in front of 100 people at a bingo hall in New Mexico. Here you've got all kinds of celebrities in the crowd. And the energy you brought was exactly the same. The audience response was exactly the same. How do you do that? And he said, I can't control the size of the audience. I can't control the venue or how prepared the venue is. But I got full control over what happens once they get there. And I thought it was really insightful because I think as business leaders, we often tend to get really distracted by things that are not within our control. And here you've got a situation where he would have had every excuse in the book to have an awful show or to phone it in at that bingo hall in New Mexico. And he didn't, he respected the craft and he very quickly said, you know what, whether I got 100 people or 10,000 people, I'm going to give them the best show that I possibly can. And that's something I tried to do as a leader.

There's always going to be an excuse for what your competitors are doing or for what other decisions that are made in other parts of the business or what your customer expectations are or if they're completely out of whack or unrealistic. There's always going to be an excuse for why you don't deliver a great customer experience or why the business isn't performing as it should. But in reality, if you really think back to the things that are within your control, there's always things we can do better. There's always more we can do for our customers that are fully within our control. And kind of a related note to that, I think a part of it is if you really enjoy that process of working on things that are within your control, your team is going to see it. And I would say back to anyone, any stand up comedian you've seen on stage, if it looks like they're having a good time, I guarantee you're going to have a good time as well.

Chris Byers: The other thing that comes to mind, as I was listening to the classic leadership guy, John Maxwell, talk, and he said something about the moment leaders stop caring about the people around them, that's when things start to go wrong. And what I'm hearing, too, is as long as you care for the people that is your audience, that are the people that you are working with, you're going to put the effort in. You're going to make sure because you know that, yes, one person, maybe it's not 100, maybe it's not 1,000, but there's opportunity to show care for those people. I'm curious how that's played out in your own work life.

Dave Gilbertson: So we are a software company. We do payroll, time and attendance, work management, all things HR software related. And we're a result of a merger between Ultimate Software and Kronos software, which were two larger companies in the software space. We came together just under a year ago. And the one thing that's been really interesting to see is the core element of not just the culture, but the values within those companies is a recognition that our business is HR. So if we're not genuine about how we treat our people and having a core value around the privilege that you have to manage people, then we're not going to live up to an ideal that would result in anybody buying our software. We've got to be genuine and living up to that ideal ourselves and you can absolutely see that play out every day. So I kind of took that as a leader. As I'm building my team, I look at that as a core value in the culture and it absolutely informs how I interact with my team. It serves as a good guiding principle for how I build up my team. It also serves as a guiding principle for those unfortunate times when you've got to let people go. It's a really difficult conversation. But to be on the receiving end of that, as frustrating as that is to know that you've got someone on the other side that genuinely cares for you, that becomes evident very quickly. And I think as leaders, as you talk through that process with your managers and with your team members, they're going to see how you act and react in these situations as well.

Chris Byers: You mentioned bringing compassion into the workplace. And for all of us who've grown up in the work world, we know that's a bit of a dangerous idea. I'd love to hear how you think about that and how you think about appropriately even bringing that into the workplace.

Dave Gilbertson: So I think people have evolved as leaders over the last 30 years. Right. Thirty years ago, there's a reason they call it business. Right? It was very business oriented. All of the goals were based on the right thing for the business or achieving the metrics that have been set out. And there's whole consulting industries that grew up on consulting speak and business speak. And part of how we all saw business leaders growing up was their ability to talk in a very formal, impressive way. I think one of the evolutions in leadership over the last 30 years has been, and in my view, a very positive evolution of leadership, has been this element around being willing to show more of your emotion and building in focusing on emotional intelligence or EQ as much as you focus on IQ. And I think that's been a really positive change in business. A lot of that has led to a recognition that the only way you achieve results is if you've got employees that are really highly engaged. One of the best ways for them to be engaged is to feel like they've got a relationship, they've got trust with you as their manager.

There's a saying that's become popular over the last few years that employees sign on to work with the company and they leave their manager. Right. So most employee attrition is a result of the specific manager that they're working for, whereas most employee attraction and when you're going out and recruiting employees, it's a result of the reputation that the company holds. Transparency in leadership is a trend that is absolutely here to stay. I don't know how you build true transparency into your leadership style if you're not willing to make yourself vulnerable with your employees. There's too many avenues today with social media, with Glassdoor or LinkedIn. There's too many avenues to understand the real story of what's going on with the business. What their leadership team is spouting out there is either not accurate or not consistent with the values that they're actually showing privately. We've seen multiple examples of that over the last couple of years. I feel like that's a trend that's here to stay. Being willing to show that vulnerability and show that EQ is going to have an impact on your team. It's going to make them want to follow you over time. And again, it goes back to being willing to build that relationship one on one with people that builds trust. That trust leads into a vision that's going to allow people to want to follow you. Once you get that, I'll come all the way back and say that's what leads to a ripple effect in the business.

Chris Byers: I think that's a great point, because especially if you're in a growing organization, every time you get bigger, you feel like that much further from yet another person or groups of people in the organization. Andy Stanley, a guy who talks about leadership, he says do for one what you can't do for the many. And I love that, it's the same thing you're talking about. It's OK at times to just pick one person or a small group of people, because if you can do that, it sounds like you can actually have, to your point, a ripple effect and let other people in. I'm curious, have you gotten to see that play out before where you've said, you know what, I don't get to invest in every individual on my team, but I've invested in one or kind of my management team and seen how that ripple effects out to other people?

Dave Gilbertson: Yes, I have. Where I seem to be most effective is when you're starting something new. So a couple of years ago, we were struggling to innovate as quickly as the market was moving. And within our product team, they're keeping up with the market. But there were all these elements of kind of customer friction that were evident throughout the customer experience. And it was a really hard problem to solve, because if you expect the product team to solve customer experience friction points along the way, then they're going to solve the friction points they kind of know about. But they're not going to be real dedicated to it because it'll be five percent of a bunch of people's job as opposed to one hundred percent of one person's job. And so we decided to try something different.

We created a very small or we called the customer experience incubator and the incubator was five people putting a customer experience shine on top of our experience. And we had representation from product management, engineering, professional services, and training. So we felt like we could cover all different aspects of the customer experience. Our role was to use a kind of a hypothesis driven approach, a lean startup method methodology. For those of you that have know the lean startup method, you take a concept, have a hypothesis about how we could solve it, go test it, iterate, test again, once it's solved, then send it off to the functional team that's going to scale it and then do this over and over and over again. So choosing how to introduce that to the organization had some risk to it. And so how we introduced that team was really critical. The leader that we chose to lead that team was really critical. And so I chose a leader who was at a director level. So it's a little bit more senior. She had a lot of experience at a lot of startups over time, and yet she had been within UKG for a few years. So she kind of understood how the bigger company worked. But at the same time, her mindset was all about moving, moving quickly. And at that point we had alignment on the methodology. We had alignment on the types of problemds we wanted to start solving and the way we wanted to solve them, then my role was to step aside, let her push forward as much as possible and really be there as a resource for her to guide any roadblocks that she was coming upon because they were trying to move much more quickly than most of the rest of the organization was used really fundamentally transform the customer experience. We've done it one little bite at a time, but we've done it so consistently that it's a pretty big transformation. I really do feel like that connection point with that director was a big piece of why that's work.

Chris Byers: Well, speaking of that innovation and figuring out ways to introduce new big ideas into a company, one of the most fascinating things that happened last year. I remember reading a LinkedIn post that you put out early last year about the biggest SaaS merger in history. And we were just in the middle of Covid and the pandemic hitting. And my mind is just blown because I'm like, oh, my gosh, I am just trying to stay above water. But doing that in the middle of a pandemic. How did you get that introduced to people and do it successfully?

Dave Gilbertson: We did go in eyes wide open. We recognized right away that these two companies... So Ultimate Software had been a market leader in human capital management software. Kronos had been a market leader in workforce management software, both companies almost exactly the same size. It was a true merger of equals. They both had about a billion and a half in revenues. About sixty five hundred people and very similar values, but realized very quickly that we could not have come at those values more differently. It would be impossible to come at it more differently. It was even down to the technology choices. We chose Microsoft. They chose Google. There were examples like that over and over and over again, across thirteen thousand people. And so to try to do a merger of this size during a pandemic was really challenging and it's still ongoing. I think the expectation is that that's going to take a couple of years or so to work through.

The number one lesson that I've observed at least, is what you miss in not being able to build up a face to face relationship is real. As much as I think we're all looking for indicators that we can do a lot of this by Zoom or by Teams, and we could get a pretty good sense of people. And you can make decisions over a video call and you can, you absolutely can. Day to day, you can. But there is... When you're going into a marriage with somebody, and this merger is effectively a marriage, you have to go into it assuming best intent. And then over time, you build up that trust. The only way really difficult decisions are made, I think, is when there's a level of trust that's been built. And there were certainly pockets where we're able to build that trust, but there were pockets where we were not able to build that trust. And I came away from the experience feeling like this is monumentally harder in the absence of any possibility of getting together in person. If we can just hang out for a little while where we know that everything that's happening is I'm right here and you're right here. There's no multitasking. There's no other people in the mix. It's me and you. And we're just talking about maybe part of it is talking about our business, but we're also just talking about ourselves and our teams and our families and getting to know one another. That's where we're going to find commonality. And I believe that's how you build up trust.

Chris Byers: Yeah. And I can't quite imagine. I'm just picturing the travel budget, which everyone was planning on skyrocketing for about a six month period because everybody was going to be in each other's offices doing dinners. And all of a sudden it's just, nope, not at all. There's another phrase you use in your leadership talk about that idea and you're talking about it right here. Trust plus vision equals leadership. And so I am curious, how have you guys seen trust and vision used to kind of still help drive the companies together?

Dave Gilbertson: So the way I was talking about trust is using an example of the way that comedians build up their act. So little known fact, a lot of comedians go out late on a Tuesday night or Wednesday night, eleven o'clock, midnight, and just test out some new material they're thinking about. They do it to figure out how they can build up this trust with an audience. And the line I use in the TED Talk is one of the least funny comedians I've ever seen was Chris Rock, about eleven o'clock on a Tuesday night in front of 200 people, one of the funniest comedians I've ever seen was Chris Rock, on a Saturday night in front of 2,000 people. He knew exactly the beat that was going to be the laugh line, how long the laugh would be, what was connecting with the audience and the stuff that wasn't connecting throughout. And he built up that trust. You've got to have the vision on stage to carry that through to be able to carry an audience for an extended period of time, but it all starts with trust.

So to take that into the business world, I think over the course of the pandemic type of merger, I have a team that was I think about 36 people. My team today is about 450 people. So it's grown pretty dramatically during that time. So it's absolutely stretched me as a leader to figure out how do I form this trust. And so I knew right away I have got to figure out a way to build trust and I can't do it in person. Previous to the pandemic, I'd be going from office to office to office. I was really big about being in person, forming that relationship in person. And when that was taken away, it was a challenge. I don't know that I fully figured it out, but I can tell you the path I've gone down is I had a one on one through Teams with every single people manager within the first six weeks after taking over. That was really critical to understand who they are, reinforced that I care about them personally and I care about how their teams are doing. They are on my radar. And then, too, it's forced me, I think, just from a leadership standpoint, to clarify what my vision is. And very quickly, after taking over this larger team, like I said, the first thing I did was meet with every one of my people managers. I did that specifically to build trust. And then within a couple of weeks after that, I came out with the kind of our longer term strategy for this particular part of the organization. And it was very clear as I ruled that out, this was built through the conversations I've had with each of you. It was built through virtual off sites that we held with our leadership group, and it was built in conversation with our customers. So we embedded employees voice, leaders voice, and a customers voice into this vision. And I really wanted to marry up that trust and vision as quickly as I could, knowing that it had to be done all virtually.

Chris Byers: I'm curious, how do you use humor itself, both from your past experience and then even thinking today? I mean, one of the things that you're talking about is I think it's so much easier for us to laugh in person. It's harder on Zoom or Teams. And so I'm curious how you incorporated humor into your leadership, but then in particular trying to pull that into those daily video calls.

Dave Gilbertson: It has been way harder during the pandemic to do that virtually. Absolutely. I agree with you there. And so some of the things I've tried to do, so one way that I try to build trust with folks is I've got three little kids ages 10, seven, and two, and there is plenty of humor filled with kids that age. Right. The two that are in school, are all in school from home and working from home. And the third, who is not in school but is potty training. There is a ton of humor that goes into that process. And my shortcomings as a parent and my shortcomings as now a home school teacher have never been more evident. And I'm more than happy to put that on display. So I'm trying to acknowledge that, I'm trying to bring some of that in so that you can see the real person in the real family that is behind this, because I'm fully recognizing my family is what allows me to do what I do professionally. It wouldn't work without their support. And so since I'm inviting you into my dining room anyway, let's just invite you into some of the insanity that goes on behind it. By default there are more times than not when some level of humor is appropriate and helpful, but also recognizing that doesn't mean one hundred percent of the time. And so in some conversations, it's just not appropriate. But if there's a really difficult conversations or if emotions are really high on both sides or on multiple sides, introducing humor in a way that doesn't cut down any one particular person or audience and can be a really effective way at breaking the tension, allowing folks to get away from their emotion and kind of changes your brain chemicals to hopefully open up the conversation as opposed to continuing to shut down through conflict.

Chris Byers: That's great. Well, as we wrap up our conversation just a little bit, I mean, one of the things we're trying to do is really bring fresh perspectives, innovative ideas in terms of leadership and how people recreate the world that they they live in. And I've got a question for you. Would love to hear your advice to our listeners. How can they think about unlocking their genius to create a positive impact?

Dave Gilbertson: One word fail, fail, actively fail. Fail as often and frequently as you possibly can. And it sounds like such wrong advice and such random advice, but I think if you really reflect back on where any of us have had success in their lives or in their careers, you'll notice that breakthrough, that success only comes from some level of failure that that preceded it. There's very few examples of breakthroughs or success coming from a small success that builds into a little bit bigger success and then a little bit bigger and a little bit bigger. You're getting positive reinforcement all along the way. Breakthroughs come from failure. They always do. I think back to the time when I was growing up, and I think this is pretty consistent with most kids. When you're first learning a sport, you know, when you try it out, not really that good at it, but you enjoy it or your friends enjoy it and you practice a little bit more, you get a little bit better, get a little bit better. That early failure was an afterthought. It really didn't matter. Now, fast forward as an adult, and the deeper you get into adulthood, the more successful you get along your career. Typically, the more narrow you get in terms of the things that you try. And that's the thing that I've encouraged people and I've tried in my own life to really break away from, because the more narrow you get, the more self reinforcing you're going to get and the more likely you are to plateau. Whereas if you can go on to a level, you might be very successful in your personal career. But I don't go out on a limb, write a poem, learn a new instrument. I'm not encouraging everyone to get up on stage and see if they can make people laugh at them. There's all kinds of ways you can stretch yourself and embrace the failure that is inevitable when you're first learning something. There is such a level of discomfort that comes from that failure that is so healthy and it's so powerful once you push through it.

Chris Byers: Well, 2020 had we'll call it some failure in it. Plenty of wonderful and good things, but plenty of failure. So maybe as a final word to our audience, how are you thinking about 2020 and taking some of those failures and those down moments and making 2021 kind of a great year?

Dave Gilbertson: It does feel like as hard as it is for all of us that have been cooped up, there are so many positive things out there. I try to keep as much as I can try to keep focused on what are the breakthroughs, the amount of innovation in the health care and pharma space to create a vaccine as quickly as we have is mind boggling, not something that would have been possible even five years ago. The amount of opportunity we have to come together as a culture within the United States and then globally as we come out of the pandemic and as people start getting together again, we've got a unique opportunity to really reset some of the relationships in our lives. And I hope that we all use that time wisely. So trying with myself, my family, to focus on the things that we do have to look forward to rather than dwelling on the past and then the final thing I'll throw in there is we made it through a lot and we made it through a lot together. And as challenging as some of these times have been, and there's no doubt they've been some of the most challenging in the history of our country, there is a lot that we have been able to do together. We have figured out how to collectively work from home across everyone. Our teachers have shown unbelievable innovation in what they've been able to do to completely change their model over the course of a couple months to be able to educate from home. There's so many examples like that of people showing just unbelievable innovation when they're forced to do that, I think does give you some hope for the future. But it will be fascinating to see how many of those innovations really carry forward and make things better. We've had some massive progress in a few areas. Looking forward to seeing that carry through after the pandemic's over.

Chris Byers: Dave, thank you many years ago for taking the risk of going to spend a year of your life with Louie Anderson. I think that those are the beginning of some great stories that sound like not only have they impacted your life, but even just today we get to share to other people.

To learn more about how people are reimagining their world of work, head over to Thank you for joining us today on this episode of Ripple Effect.

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