Trust, Teamwork and the Road Ahead

Jon Clifton:
[0:08] Kendra Tucker is a prominent leader in the technology and software industry. As the CEO of Truckstop, Kendra oversees one of the leading freight-matching platforms, connecting carriers, brokers, and shippers. With decades of experience scaling tech businesses, she excels in driving growth, innovation, and operational excellence. Forbes describes her as a dynamic leader transforming the logistics and transportation industry. Join me as we dive into Kendra's insights on effective communication, leadership, and the challenges of being a CEO.

Now, you have Communication, Competition, Achiever, Significance and Command. Of those five, are there strengths specifically that you're using in your job every single day?

Kendra Tucker:
[0:53] I use absolutely all of them every single day. I don't even think I could turn it off if I wanted to. I use them all.

Jon Clifton:
[1:01] Is there one, though, that stands out? Or is there one that if you interviewed your team and said, "What are the strengths that really stand out with her?" what would they say?

Kendra Tucker:
[1:09] I think the ones that are most visible to the people around me would be Competition. I think they can see that. We talk a lot about what it means to win in our space, what it means to win for our company. We talk a lot about what it means to win together as a group. So when I think about Competition, it's not just about me winning so much as it's about us as a collective, right, the whole business. What does it mean to win for our customers? So Competition's pretty big. You hear it a lot in my language.

And then I'd say Command. I think with Command, I synonymize Command with courage. And I think that in my role, I have to display a lot of courage to do things that others might not do or that might seem intimidating or challenging to others. I have to demonstrate that a lot, so I think that's visible to my team.

Jon Clifton:
[2:11] So a few years ago, Jim Harter and Frank Newport did a very interesting study where they asked the American public, "What are the leadership attributes that people want in the United States in either a leader in the White House or as a CEO?" And you and I both have Competition in our top five. And one of the things that emerged from that study is that one of the things people want the least is competition. What do you think about that?

Kendra Tucker:
[2:40] Yeah, I think I've been familiar with my strengths for a long time, for decades. Ever since I first took the StrengthsFinder, Competition showed up in my top five. I took it when I was first a teenager. I remember seeing it and not wanting to tell people that I had Competition in my top five. Because I think, you know, socially, it's hard to be around someone who feels super competitive. It feels like you have to have a definite winner and a definite loser, and it feels like you can't build relationships, I guess, with others when you've got Competition.

I think what I've really come to experience, though, especially as I got older and watched the Competition strength really develop, is helping others understand that it's not about me winning versus another person, but it's rather this pursuit of continuously trying to get better and better and better to ultimately be the best. And particularly as I moved from individual contributor roles into leadership roles, helping teams understand that I care most about the collective winning, that's really, I think, helped people be more comfortable with it. And so I understand it. Conceptually, you think as a person, from one person to another, it feels hard to have somebody next to you who you think, "that person's ultra-competitive." But in a leader who's trying to win on behalf of an organization—whatever kind of organization that is—you definitely want a leader, I think, who pushes really hard to win, a.k.a. be the best you could possibly be.

Jon Clifton:
[4:26] Does it change your communication with your colleagues about what you and I draw inspiration from is not losing? Or we get inspiration from the fact on what is the win or what is the objective also with Achiever? But do you feel like you have to moderate that or in any way adapt your communication to get people revved up basically in the same way that you and I are?

Kendra Tucker:
[4:51] Sure, I am. Because I also have Communication in my top five, I constantly think about who's in my audience and which of my messages will hit which parts of my audience. So there are definitely people within my company who will feel lots of energy the way you or I do about winning, and then there's people who won't. And so I will draw from other parts of my person in order to reach that part of my audience to help them hear a different part of the message.

So when I talk about winning at Truckstop, it's not just about winning, but I've actually—we've positioned it as being Truckstop. What it means for us to win is that our customers see us as being their most trusted partner when they're doing business. And so, yes, I'm talking about winning, but for those who don't gain energy the same way from the concept of winning, now I'm talking about something else, which is, we get to build relationships with truckers where they get to trust us more than they trust others. And so it's just defining it differently. So I hit different segments of my audience with a different part of the message.

Jon Clifton:
[6:05] When you're thinking about Competition, do you feel like what drives people with Competition or what drives you is the need to win or the fear of loss?

Kendra Tucker:
[6:16] It's probably a bit of both, honestly. I love the win. I also hate the loss. I hate losing. In fact, I've joked about this in my personal life. I really don't play games I can't win, so I don't go bowling. That's not for me. So it's a bit of both. So that's for me insight, though. When I think about externally and how I communicate it with my teams, it's not about fear so much as it is about the pursuit of success, which is, "Here's what it looks like for us. Let's move forward in that direction." It's not about the fear when I'm thinking about the group of people that I lead.

Jon Clifton:
[7:00] And with Command, you know, it's often said that those with Command confront in order to create clarity. How do you manage that?

Kendra Tucker:
[7:12] You know, that's another one that was in my top five since I was 16. I've got to tell you, having Command when you're 16, you know this, it's difficult. It's really difficult. People have described me as having sharp elbows. In fact, I think at one point when I was younger, I would say, "Other people might appear to you if you were to describe them as a shape, circular. I'm a square. I have sharp edges, so watch out." And that worked for a period of time, until it didn't.

Like I said, crossing over from being an individual contributor at work into being a leader really forced me to reconsider how I approach Command and what I do with it and how to be really intentional with it. So when I think about Command, I think of it as courage, and I have a lot of courage to do things that others might not be as willing to do. So when it comes to making tough decisions, I have a lot of courage to make tough and difficult decisions, weighing all of the inputs, and then leading through that and communicating through that. So the process that I use, even though my Command is present, it's not necessarily always so in your face, like, "I'm telling you, here's what we're going to do," so much as I'm designing a process that helps people get there with me. And by the time we get there together, then we as a collective are going to execute this change that otherwise might have seemed scary. I use it to instigate the change and help others come along with me on the process now versus before, like I said, sharp edges, more of a steamroller approach. Sometimes I still have to do that here and there, but I do it now with intention and purpose versus before it was more spontaneous.

Jon Clifton:
[9:15] When you have the title CEO, how do you know that those audiences are being completely honest with you on that feedback?

Kendra Tucker:
[9:23] Well, let's be clear. They're not always being completely honest with me. I've accepted that. Then there's other things that I do to create constructs. So one of my strengths is obviously courage and being willing to do things that other people perhaps cannot. I don't expect them to have the same level of courage as I do, but I've now created systems that enable them to have that kind of courage.

So one of the constructs that I have with my executive team is we do a pretty structured set of leadership meetings. It has a very specific opening. Then we have an agenda where we do lots of discussion and vigorous debate, which I have set as an expectation that we will vigorously debate. And then we do what we call a team audit at the end. Every single time, we have three questions, always the same. Question number one at the end of a meeting is, "Is there anything unsaid that you have a responsibility to the business to say?" This question is super powerful for the team because, one, we all agreed that it's really important that you say the unsaid thing. And if you hit the end of the meeting and you're sitting in that leadership team meeting and you haven't said your unsaid thing, you've got to say it.

We've established it. And the best thing about it is even the person who's most opposite to me, right, maybe the person with Harmony as number one, will still feel a responsibility to say, "Here's my unsaid thing." And the way we talk about it, this language of "my unsaid thing," gives people license and permission to say things that might be challenging to the CEO. That happens all the time. It is very, very good. So it doesn't catch it all, but it allows for it. It's so much a part of our lexicon that even outside of the meeting, now I hear people saying, "I gotta say my unsaid thing to you," which is this, and so it enables, I guess, it allows for the courage.

Jon Clifton:
[11:41] Do you see your Significance?

Kendra Tucker:
[11:44] I think of that as an impact theme.

Jon Clifton:
[11:47] Meaning?

Kendra Tucker:
[11:48] Meaning. So when I was younger, I really believed that I myself can change the world. I believe that I am capable of having a large, lasting, positive impact on people, things, situations. I see it as impact.

Jon Clifton:
[12:06] And what role would that have been that you had dreamed of when you were young?

Kendra Tucker:
[12:11] You know, when I was younger, I really wanted to be a doctor because I saw the ability to help people heal or recover, to help fix them, would have a lot of impact. And then in the end, it's too much science for me, I think. And then I realized that I could impact people in all kinds of ways. But it took a while when I first figured out that Significance was in my top five. It was another one where I thought, "What am I going to do with this? How will I use this?" And then I came to, "Oh, no, I really care about what my legacy will be," and the best way to describe it is impact.

When I think about the role that I have today and what I do, what we as a business do at Truckstop, I think about it as we as a business have this really large opportunity to impact a really large community that is at the heart of America. Transportation has hundreds of thousands of players in it, particularly on the trucking side of transportation. What we do at Truckstop is we connect freight—so goods that need to be moved, which is everything—with trucks that can actually move it. On the freight side, there are fewer players than you think there might be because there are just, you know, like 10,000 to 20,000 companies that think about freight itself. And then there are hundreds of thousands of trucking companies on the other side, up to anywhere between 400,000 and 600,000 trucking companies.

The thing about these trucking companies is they are typically, 85% of them are single truck owner-operator led. So it's just one dude driving a truck. What we do is we create a virtual marketplace where that one dude is a part of hundreds of thousands of truckers that access our products. So they become not one dude, but now a part of this community and now get access to all of these different kinds of goods that need to be moved that come from name-brand blue-chip companies. And the reason why this is so attractive to me is because of Significance, which is my business gets to level this playing field between the little guy and the big guy. And we help this side of the equation make money every single day. And that is really, that's so attractive to me. I've figured out it's because I care about being able to impact large groups of people, and I now look for opportunities to be able to do that. And this business is one of them. I love what we get to do for regular people every day.

Jon Clifton:
[15:20] If there was a young person that just learned that they have Significance, top five, what advice would you have for them?

Kendra Tucker:
[15:28] I would say look for places where you can be impactful. I mean it as getting involved with organizations, whatever kind of organization it might be, that feeds the need to leave a legacy, to leave a mark on something, and start to get a feel for what those things might be. When I think about where I was as a young person when I had Significance, again, it was like the one I tried to hide from people because I thought, "Oh, it means like I have a big ego or I just care about my own reputation." Instead, I don't think I knew enough to say it really is this drive to just be a positive presence in the world, to show up in a way that I can look back and say, "I did great things with my time here." And so being able to, especially as a young person, try on the organizations that might feed that need, it's something I wish I would have done.

Jon Clifton:
[16:51] One of the research studies that we did was we looked at what the demands of leadership are. And one of the things that emerged was being an effective communicator. So the fact that you are an effective communicator, you lead with Communication, what advice would you have for all executives, all leaders on how to engage in better communication?

Kendra Tucker:
[17:11] Yeah, it's knowing and understanding your audience is where I always start. Sure, we could talk about like PowerPoint techniques and how many words to put on a slide or tactics like that. But I think in order for a leader to show up authentically, they have to show curiosity for whoever it is they might be talking to or trying to convince or sell, persuade, whatever it is. Understanding and being curious about the people in front of you helps you then figure out what message you should take to them to be most effective and most heard.

So I think it's about knowing your audience, the language that they use and how it's different. We get close to their ambitions, their hopes, what they're trying to achieve, and then we work really hard to put that into our language. I don't mean just our own individual language, but almost to instill it in our marketing. So the language that we're using when we go to market and how we design and think about the products that we build, even the scripts that our customer support team uses as they're talking to truckers, is being able to say, use the same words.

One of the things that I did when I first joined Truckstop was I shadowed a bunch of sales calls and a bunch of support calls. I'd come out of the private equity ecosystem, and I'd been at a number of different companies. The way you talk to a trucker customer is totally different than the way you might talk to a customer who's trying to purchase a CRM like a Salesforce, for example. The language has to be so much more casual and colloquial, and you have to understand here's exactly what problem they're looking to solve and then be able to flex and tailor how we speak to them in order for them to get the value out of our product. So we spend a lot of time internally talking about, "Are we speaking their language? Is this how they would say it? How do they feel about it? What did you hear from the last 10 truckers that you talked to?" We get really close to our customers in order to be able to hopefully provide them what they need.

Jon Clifton:
[19:38] There are a lot of companies that are doing remote, they're doing hybrid, some are arguing to come back, but the communication changes. How do you do that in an environment where I think you're more remote and hybrid, is that true? That's right. And if so, how have you adapted your communication in that context?

Kendra Tucker:
[20:00] Yeah, this is one that we continue to work on and experiment with, I think, not just us, but I imagine a large number of leaders around the world. We do a lot of things. When I first became the CEO, which was in 2022, so we were coming out of the pandemic, but at that point, our company was more geographically distributed than we'd ever been. One of the things that I set up to help the parts of the company that hadn't gotten to know me get to know me was every two weeks, I did an "Ask Me Anything" town hall.

So we call it the AMA. When I first started it, I sent out a survey to say, "I'm your new CEO. What would you like to know about me?" And I received 75 questions, of which 80% of them were all about me and my personal life. So I went about answering all 75 questions over the course of weeks of AMA. It probably took me six months to get through.

Jon Clifton:
[21:08] Why were the questions overwhelmingly about you personally, not on strategy, not on culture? Why was that a dominant question?

Kendra Tucker:
[21:18] It's seeking to connect, I think, in the virtual environment. So many of these people had never met me as a human. And part of the reason why I set up the AMA was to try to overcome that, the fact that they hadn't seen me as me. I mean, I think one of the questions was, "How tall are you?" I think they were disappointed by the answer because I am short.

So we had to create connection in a virtual environment, and this was one of the ways. Trying to create constructs like this AMA was really important in 2022. As we went through 2023, we actually turned these AMAs into hybrids. Part of them we would do virtually, and then part of them we would go to cities where we knew we had enough presence, like Denver or Chicago, Phoenix, DC was one of them. So we'd get some people into a room and then still broadcast it for everybody, but trying to balance the in-person and virtual parts of it takes planning and thoughtfulness and lots of trial and error.

So this year, we've got a variety of different communication channels that we're testing. We've kept some portion of the AMAs. We're also now using video, not just video that comes from me or from the leadership, but video that comes now from other employees, partners, we call them at Truckstop, that we then send out to the whole company so that way people get a chance to know each other in different locations even though they might not ever meet in person. So there's a lot of testing on how we create this connection.

Jon Clifton:
[23:11] When you're doing the town halls with your colleagues, what are the hardest questions they ask?

Kendra Tucker:
[23:18] The hardest questions are ones that affect their livelihood, as we've gone through changes. When you're on the front lines and you're not in the corporate center, you feel like things get done to me, and I don't have any control over it. And so the questions that come up a lot, it's phrased differently every time, but it's more like, "Am I going to lose my job?" People get worried about that. And that one's always hard to answer. Sometimes it's like, "Are we going to have layoffs? Or are we going to restructure and then that's going to put me out of work?"

Here's what I say to our employees is we do everything that we can not to impact the livelihood of our employees. And at the same time, we have to make tough and difficult decisions for the business. We try to do everything else before we get to cutting or changing roles. And so the answer is always we prioritize the success of the business. We prioritize trying to keep and engage our employees. But there are no guarantees about what we can or cannot commit to. And we will inevitably go through some kind of change that will happen. It's also helping them just understand that change can feel so scary because it can have these risks to it, but if we don't change, we won't be able to grow and adapt and be this company we know we can be.

So it's always hard to strike that balance. No one really wants to hear, "So you're saying there's a chance I could lose my job?" And the answer is, "Yes, I am saying that." I'm saying there's also a tremendous opportunity for us to be successful as a business, and we want as many people as it makes sense for Truckstop to be a part of that.

Jon Clifton:
[25:24] Now, a lot of times CEOs get charged with the fact that they bring in people on their team that are "mini-mes." Yet you have had an approach where you can actually see strengths rather than judge them on how much they like you because you may see some of their faults or flaws more evidently if it is not necessarily reflected in your own strengths. But how is it that you perceive that kind of diversity of strengths on your team and appreciating them for things that are unique to your own set of strengths?

Kendra Tucker:
[25:57] Yeah, I really think about people as talents on the team, and it goes back to I don't expect any one individual to be well-rounded, but as a team, I expect us to be well-rounded. Diverse and representative of our population. And when I say diverse, I don't mean just gender or race. I really mean diverse in terms of background, experiences, and then diverse in terms of strengths or innate talents and filters.

So, especially when I look at the leadership team that we have today, I think about them as pairs or offsets and counters. I think about my product leader and my technology leader. And those two people, those two roles have to work really well together, but they cannot be the same. They, in fact, have to be like a yin and a yang. It has to have enough points of overlap and intersection, but enough points that are different.

I've got a product leader who I tease her, she's a classically trained software product leader, and she's a bit more risk averse. And in our technology leader, I've got someone who has also a fair amount of software experience, but in scrappier environments and is more risk tolerant. And those two things have to exist on our team in order for us to be really effective.

When I think about who I am on the team relative to my leadership team, I for sure need people on my team who are going to be particularly sensitive to emotional shifts. I know who the people on my team are. Our product leader is exceptionally perceptive when it comes to emotional shifts on the team. So I rely on her, and I have told her I rely on her to channel that information, not just to me, but other parts of our team as well.

Then I've got a chief legal officer who her job, she does way more than just be a lawyer for us. She is exceptionally good at big picture thinking. So things like Futuristic and Strategic are themes that I think would show up for her. She's got that differently than other people on the team. And so when we're having one-on-ones, I do encourage her to share that point of view in our meetings frequently because it is unique and distinctive about who she is.

And then I've got hard-charging people on our team who come with really opinionated points of view and they want to act super quickly. So my people leader, he's got Activator somewhere, and he's ready to go. And that's really good. It's this mix of leaders, bringing them together helps us execute, I think.

Jon Clifton:
[29:13] Being CEO is a hard job. Do you think it was harder to get to be CEO or is it harder to be a CEO?

Kendra Tucker:
[29:23] Harder to be a CEO in that when I became CEO of Truckstop, I really wasn't expecting it. So it was not an active process of me saying, "I'm working to be the CEO of Truckstop." It sort of took me by surprise, honestly. And then I really decided, obviously, to lean into it.

So being a CEO is a job that requires a lot of balancing and at some points can feel like tightrope walking, which sounds perilous. I don't mean it in a way that's perilous. I just mean it is. You said this a number of times, you're threading lots of needles. It's the lines that you are towing are really thin and making sure that you create enough tension so that way you can stay on that line is really important and hard to do. It takes a lot of emotional commitment, it takes a lot of personal investment, it takes a ton of reflection, so much reflection and openness to lots of feedback from different channels. So it is a challenging role, and I will tell you, I really love it.

Jon Clifton:
[30:49] What's the hardest part?

Kendra Tucker:
[30:52] I might not know yet, meaning that there's always different kinds of challenges. It could be that threading the needles and making sure you get it right is the hardest part. But then I say that, I'm like, but I know I'm going to get it wrong. So at points, I'm a normal human. I think what's hard is trying to get as many of the needles right as you can and being okay with, and I will get them wrong, and if I get them wrong, here's the plan for what happens to right that wrong. So maybe that's the hardest part, is being not necessarily okay as if I'm passive about getting something wrong, but knowing that it will happen and being confident that there's a plan to make it better, to work through it.

Jon Clifton:
[31:51] How do you find time to just dedicate to think or to study? And do you reserve time? There was even one time an article, I can't remember if it was HBR, The Economist, but it said that CEOs before a kind of COVID disruption, their time to think was on flights. And so what do you do?

Kendra Tucker:
[32:11] I definitely do lots of thinking on flights. I do love travel for that reason. During COVID in particular, I had gotten into the habit of starting my day really early at 5:30 or so and not checking email, though, in that time. This is really important. I check email on my calendar. It says 8:30 to 9 is a daily calendar and inbox scan. And the 5:30 to 7 slot is my time. So I will schedule time for thinking.

In fact, because I have Achiever, this is where you see it show up as I'm no longer a to-do list person, but rather my Achiever really shows up on my calendar. When you look at my calendar on a seven-day basis, you'll see often a red box on Sundays that's not an actual meeting, but it'll say "priorities for the week." In it, I'm writing, "Here are the things that I need to accomplish for this business this week." And they will range from being the most strategic to the most tactical.

Part of what I'm doing is looking at, "Do my meetings help me accomplish this? Or am I trying to put time to accomplish it?" Where I have to put time to accomplish it often happens before other people get started in a workday. So it's between that 5:30 to 7 a.m. where I'll do a lot of the thinking or strategic work or the research that will help me think about, "How do I lead my team better? How do I communicate and get the communications and messages to cascade throughout the organization? How do I think about what it means to really be the most trusted partner for our customers?" All of that will show up in a red box and then I will find slots across the week.

Jon Clifton:
[34:13] Is there something you read regularly? What's your daily news diet?

Kendra Tucker:
[34:19] My daily news diet is a mix of scanning the Wall Street Journal, an industry publication called FreightWaves, and then I get alerts as they come in from various sources. So I get a newsletter alert from Axios about moves in the VC and P.E. market. I use CNN sends me alerts for all the, I don't know, I feel like it's pop culture news that I'm getting from there. I mean pop culture, not just like Beyonce's new album, but, you know, just from what are, I guess, what are people generally talking about? So I use the alerts, the notifications for those quick hits. But the true news sources are the journal, the FreightWaves industry publication, and then often as I'm getting ready in the morning, I will listen to NPR because I can listen to it and not just have to dedicate time to read.

Jon Clifton:
[35:24] Where do you get your inspiration?

Kendra Tucker:
[35:27] I get it from connecting with people around me, from things like catching up with people like you for lunch, or I've got a network of female CEOs that I catch up with, either past or previous CEOs. I get it, honestly. I know people complain about meetings across their day, but I need the person-to-person connection, and I get inspiration from small wins that my team has across a week, small things that will add up to be big things over the course of time. So it comes from connecting with other people and shared experiences.

Jon Clifton:
[36:12] Kendra, thank you for spending time with me today. But also thank you for being a great friend to Gallup and also for being a great coach because you've given me great advice as well. So thank you.

Kendra Tucker:
[36:24] Well, thank you so much for having me, Jon.

Transcript autogenerated using AI.