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Art of Leading

Chris Todd

“You’re Leading In Every Single Interaction Of Every Single Day.”

July 14, 2023

Chris Todd, CEO of UKG, a workplace software company, shares his key leadership insights in this “Art of Leading” interview with Adam Bryant.

Q. What is your playbook for leading?

A. It starts with working with the team to co-create a common vision, and then revisiting it constantly to make sure we are maintaining that vision and telling the broader organization over and over and over the story of where we are headed. Repetition wins the day.

A big part of doing that is telling stories, such as something I may have heard from a customer, so that people can link the vision back to some tangible examples. I’m also a big believer in continuing to communicate our “why” to the employees, and working really hard to make sure we’re crisp on what that “why” is and coming back to it as part of the stories we tell.

Q. Did you always want to be a CEO? 

A. No. I’ve historically been attracted to steep learning curves. I’m curious. I like learning new things. By the time I was 30 years old, I had had a series of different experiences. I’d been a banker. I’d been a consultant. I had gone to law school. I’d been at a startup.

Then once I started to work in enterprise software around the year 2000, I would work in a department, learn a lot about it, and then move onto others. The next thing I knew, I had a pretty broad exposure to the business and how it works, and that has served me well.

Q. What were important early influences for you?

A. I grew up in a small town in Ohio. My mom was a high school math teacher and my dad was the local YMCA director. That job was like being the high school principal or the chief of police, in that he knew absolutely everything that was going on in town.

My dad took that job and his role in the community very seriously. Yes, they provided camps and housing and organized sports for people, but for him, the responsibility in the community went beyond that. He gave meaningful employment to people in town who otherwise were idle and might get into trouble or who were pretty close to unemployable. By providing meaningful work, he made them feel seen and valued. They had an important job to do at the YMCA, whatever their job was, and he made them feel like they had purpose in the community.

Since it was a small town, I knew these people. I would see them at high school football games. I would see them at basketball games. I would see them at local festivals. I saw the impact he had on their lives. They were proud of the roles they had.

Decades later, I saw what he meant to them when they showed up at his retirement party. The impact of providing meaningful work stayed with me, and now I can help do that at scale with 15,000 employees and tens of millions of people who use our products every day.

Q. What was an early leadership lesson for you once you started your career?

A. Early on, I was at a company called Blackbaud. I was a one-person corporate development group, and we bought a company. We spent about $300,000 on this company. It had four employees. I remember I went to lunch in the cafeteria with our CEO at Blackbaud, Bob Sywolski. He sat me down and said, “Well, Chris, you bought it, now you’re going to run it.” I said, “But you didn’t tell me that before we bought it.” He said, “Well, it will be good for you.” I said, “Well, what if it’s not good for me? Will you save my other job for me?” He said, “No. You’re going to hire somebody else to do that job.”

You start to develop some courage based on things that went well.

It was sheer terror. But I got to work. It was exactly what you think a small business unit with four employees would be. We had to build everything. We had to write the marketing materials and hire the first salespeople and build out a customer support function.

I remember very early on going for a walk with my wife after dinner and saying, “I feel like I know what the people on this team need to do, and I don’t have any idea how to get them to do it.” It was just about getting the courage to try things, see how they work, and adjust from there.

You make some mistakes and you stumble, and you get some things right, and you internalize those and move on. You start to develop some courage based on things that went well. By the time I left the company, we had built it into a $100 million business unit. That’s how my leadership journey started: it starts with sheer terror, not knowing how to get anything done. But if you do the work, and are committed to learning and keep a growth mindset, then good things will happen.

Q. What about more recent leadership lessons?

A. Leadership is sometimes a decision and leadership is sometimes a process. That means knowing when to make a quick decision and when to let the process run — because that will help the rest of the organization grow. It’s a subtle balance that you never quite get exactly right and you’re always thinking about.

For example, when is it best to have a five-minute meeting and when is it best to have a one-hour meeting, even if we could have had the decision in five minutes? And how does that help you lead a team? How does that help you build buy-in for where you’re going as a team? I’m constantly calibrating decisions.

Q. When you coach and mentor senior executives, what are the most common themes that come up?

A. One is telling them, “You’re doing great in your job. If that’s what you want to do, that’s enough. If you want to do more, we’re going to have to actively find a new challenge for you and talk about how to set you up for success.”

I also give a lot of feedback on how to give executive presentations. Sometimes people have great ideas and they need help communicating them to get the organization to move in the direction they want. Lastly, in this post-Covid world, I’m also advising our leaders to spend more time in person with their teams. Yes, you should make the most of your time while you’re working at home, but you should also be really purposeful in the time when you’re with other people. I try to help our leaders make sure they get that mix right.

Q. How do you hire? 

A. I think I do it backwards compared with most people. First, I try to go very deep on the technical elements of that job. What do you do? How does it work? What reports do you read? What are the trends? I want to make sure that the person really knows their job.

I also want to see how passionately they talk about the actual work they’re doing. I want to make sure they are not confusing passion for getting the new job with passion for the role itself. The next conversation is around culture and fit. How do you work? How would we work with one another?

Q. What do you think is the hardest part of leadership?

A. Knowing that you always have to be leading. There’s never an off day. You’re leading in every single interaction of every single day. You have to think hard about how you show up and what your leadership shadow is. And if you ever are having an off day, you need to have one or two people in the organization you can go to and say, “I’m having an off day. I need a little bit of cover between now and quitting time.”

This is why we were very intentional when hiring new roles onto my CEO staff during succession planning. I made it very clear to each candidate that the second or third most important role in their job description was that they needed to be a culture carrier for UKG both internally and externally. If you want to be a leader in today’s world, you must embrace the role of culture carrier.

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