Art of Leading
Surround Yourself With People Who Can Embrace Complexity | Jennifer Tejada
February 1, 2024
Jennifer Tejada, CEO of PagerDuty, shared her key leadership insights on how to perform in ambiguity, embrace complexity, and engender trust in this Art of Leading interview with The ExCo Group‘s Adam Bryant.
Q. What is a key value for you as a leader?
A. Integrity is very important to me—being able to stand behind doing what I said I would do. I also want to constantly engender trust through my actions. Nobody is perfect, but trust comes from setting high standards and demonstrating your effort to constantly try and live up to them.
Q. Is there a story behind how that became important to you?
A. When I was growing up, my dad was a hospital administrator. He did turnarounds, and we lived in many different cities. He had a tradition for many holidays of visiting people working the night shift and helping to serve them a meal in the cafeteria. He often brought us kids along. So we would miss a day of school because we stayed up all night with him, wandering around the hospital and maybe serving a midnight Thanksgiving dinner.
I remember a member of the custodial crew came up to talk to him. My dad knew his name and knew his children’s names. The employee shared the challenge he faced in taking care of an elderly patient. It was like a short conversation, but I remember thinking, “That’s what trust looks like.” That stuck with me for a long time, and I think today about how you scale trust into an organization. It takes consistent effort to show people that you’re there to help them move their career and life goals forward and to help the company win.
Q. What were other early influences for you?
A. My siblings and I were expected to give back to the community with our time, talent, and sweat equity. And we all knew that we were going to have to save to put ourselves through college. So, our parents made clear that it was our job to advocate for ourselves in school, to contribute to the community, and to find ways to earn money and support ourselves and the family’s future.
So, I started delivering papers at a young age. I babysat for a local hairdresser. I did the night shift at the local radio station — I was Jenny Tejada from 97 WKHM. I learned a lot about work ethic, and I grew up with a deep sense of responsibility, believing that leadership is an honor and a privilege.
Another big influence was that my father died in a scuba diving accident when he was 49. It’s about knowing that tomorrow is not promised. He was probably at the height of his career at the time. We were lucky that we were close, and we had a lot of conversations about how to have an impact on the world and what was the right direction for me from a career standpoint. I learned that you have to make the most of every moment you have.
Q. Did you always want to be a CEO?
A. I always knew I wanted to lead something. But for a long time, I was in a number two role because the combination of being a young mother and living overseas at the time made being a CEO seem like a very daunting job. But then my CEO at the time sat me down and said, “You’re really doing the job, but you’re not getting the credit. Why aren’t you putting your hand up for the CEO job?” I said, “Knowing that I can delegate the big stuff to you enables me to sleep at night.” He said, “The funny thing is that you’re so responsible, you never do that.”
I realized then that the best job for me was one where I could see everything. What I’m good at is consolidating a lot of data and information, identifying opportunities, articulating and designing a vision, and driving people around it. When I could only see part of the whole picture, I was very frustrated.
I would often ask for more responsibility — not because I wanted a bigger organization, but because I felt like I’d do the job better if I could see what was happening in other parts of the business. I was pushed into the CEO job multiple times before I actually accepted the challenge. Then, once I got into the role, I said, “Oh, this is the place for me.”
Q. What is it about your wiring that makes you able to survive and thrive in this kind of environment?
A. I like breaking down complex problems. I like to consume a lot of information and try to understand what’s at the heart of a problem or opportunity. I get a lot of personal fulfillment from doing that. So that wheelbarrow of Rubik’s cubes showing up at the door is like someone delivering groceries for me ahead of holiday baking.
A lot of leaders are opting out these days because it has been physically, mentally, and emotionally exhausting to work in the last five years. The level of complexity and the layers of stakeholders are proliferating at such a fast pace that it’s hard to keep up. The grind is really about sorting through the complexity — all the unstructured but mission-critical and time-sensitive work constantly coming our way.
You can’t forecast the next social justice issue or geopolitical issue that’s going to land on your doorstep that is going to affect your customers and your employees. You can’t predict the next market trend that may or may disrupt your business or the sentiment that Wall Street may embrace for a reason that’s likely outside of your control.
So, all you can do is anticipate the unexpected and try to be ready for it. You need to be surrounded by people who embrace complexity and embrace problem-solving. Then, you have to nourish your teams because crisis fatigue is real.
Q. How do you hire?
A. One of the things I really look for is hunger. Is this somebody who not only wants to roll up their sleeves but is also a builder and a designer? Because we’re always having to rebuild or adjust or create because the market has changed. Ideally, you want someone who has experience, can grow faster than the company, and is willing to roll up their sleeves.
So, in interviews, I’ll ask questions like, “Describe a time for me when you realized that the business did not have a process or system that it needed, and you had to design it.” I’ve flunked big company executives through that question because they’ve inherited a lot of systems and processes that they can incrementally improve upon, but they’ve never had to break something down and then design a new one from scratch. That design thinking, on top of the willingness to build it, becomes super-important.
Q. What are the most common themes that come up when you’re mentoring executives?
A. One is reminding people that if the members of their teams are successful, then they will be successful. This is particularly relevant for younger leaders who are trying to find a way to take the elevator straight up and figure out how they get the next promotion.
I also try to understand the full picture when I’m mentoring someone. I’ll say, “Tell me what’s going on with your family. Tell me what’s going on with your health.” When a leader gets stuck, it’s not usually unilaterally a business problem. If the whole person is stuck somewhere, that’s impacting their ability to diagnose their own business issues or their own leadership issues.
You have to be thoughtful about how you know what’s going on with the whole person, and there has to be trust. If you only have a transactional relationship, you’ll never know the depth of the layers that are contributing to a problem or the way someone is suddenly showing up differently than they used to.