No leader’s got everything figured out

Interview with Kendall Miller, President at Fairwinds
March 14, 2022
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Kendall Miller is a people connector and a people leader. When he’s not juggling his four kids or his dog he does his day job where he works as President of Fairwinds and is on the board of directors at FusionAuth. A background in for profit and non-profit organizations in the US and overseas he delights in a good conversation about moose.

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What’s your advice for people contemplating the transition from an IC to a leadership role?

I think there’s a misconception that the path to a leadership role is to get a CS degree, work in tech, become a senior engineer, and then an engineering manager that makes their way to VP or CTO. While there are people who follow that path, it’s far from the norm. My advice is to not believe there’s a traditional path because almost everyone has gotten to the top through a weird, circuitous route. The easiest way to move up is to get a company to take a chance on you with some small leadership roles. Leadership comes from leading through influence rather than being in a position of power like management. You can lead by influence no matter what role you are in through mentoring people, offering advice, and encouraging them. And if you can recognize the company’s needs/ values and how to get there, that will stand out and people will likely put you in a position of leadership as a result of that. 

What are the keys to influence?

It’s important to have strong opinions about things but also be willing to change your mind when someone convinces you otherwise. You’re not just out for yourself. Being genuinely interested in the good of others and the company is the best way to build influence. The first step to getting people to listen to you is to have an opinion when the time comes, then you interact with others and genuinely care about them while you both work towards meaningful solutions.

What was the biggest risk you’ve taken as a leader?

The risks that I’m most proud of but have also gone the worst for me are almost always people-related. You have to take chances on people and give them opportunities they otherwise wouldn’t get to make mistakes and learn from them. There is no world where you’re not going to fail and you have to be okay with it; sometimes that means firing people and other times making tight lines around performance. At the end of the day, most of my spectacular wins came from taking a chance on a person that turned out to kick ass better than I could have possibly imagined. Other times I took a chance on someone and they burned shit down and we had to clean up their mess, but I’m still proud of the chances I took on all those people. 

What’s your advice for leaders or future leaders?

Let me start with an example. When we had a transition of ownership where I moved from acting CEO to President, we brought in a new CEO who was much more experienced and weathered than me. When he came in, I went to him and said “Hey, what do we do? You’ve done this a million times, right?” He responded something along the lines of “I have done it a million times, so I know that I don’t know what to do. I’m here to figure it out with everyone else.” 

I’m reminded by him that it’s different everywhere; the more experience you have, the more you find that you don’t know exactly how to lead or manage. Nobody, except someone who is widely arrogant, wakes up and thinks “I’ve got this fucking figured out.” You learn how to handle situations as they come so any leader worth their salt will grow more humble over time. In my opinion, the number of leaders who are willing to lead from a place of humility is sadly far and few between, but that’s what makes all the difference.

Tell us about your podcast, Authority Issues. 

The podcast is called Authority Issues, I record with my friend Rachel Perkins who has also been in tech for a long time. The goal of the podcast is to humanize the struggles of leaders who come from a variety of backgrounds, and most of our guests are leaders in engineering. Our guests typically talk about how they got to where they are and the conversations are valuable to me because it’s a reminder that even people I tremendously admire and respect are still just figuring it out. People tend to go through life thinking that those at the top know what they’re doing, but that’s actually not the case at all. So being reminded that even leaders struggle and worry about the same things as everyone else gives listeners a sense of confidence to move forward in their own careers, which is what the podcast aims to do. 

What’s one thing you learned from talking to many leaders through the podcasts?

The thing that stands out most for me is when people talk about their experiences being humbled while transitioning into leadership roles— they mess up, and learn from the experience. A lot of us sit there and watch our managers thinking we could do a better job. When we get the opportunity to move up we try to avoid all the things our managers did that drove us crazy. Sometimes we succeed, but then we end up creating a bunch of new problems from our own personal issues. The beginning of maturity in a leadership role is realizing that the role is hard, then doing the best you can, and acknowledging that there are no easy answers.

Check out the podcast Authority Issues or reach out on LinkedIn as Kendall loves new connections.

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