Doug Hicken
COO | Chatbooks
Could you share your approach to mentorship, including any advice you have for aspiring executives?
First, is it possible that you are the one person who is right about everything? Okay, then, what are you wrong about? Ask for criticism before giving it.
Second, words matter — they can move mountains, or change the world for better or worse. Martin Luther King and Adolf Hitler are both remembered because they were able to sway people with their words. Aspiring executives need to learn to wield theirs wisely — how you talk to your people shapes how they show up, how they think about themselves and what they believe is possible.
Third, life is short, and most of the decisions you’ll sweat over really don’t matter. What matters is that the team is enjoying the work, learning, growing and rowing in the same direction — and that you’re not so controlling that you steal that from them.
Don’t fall in love with finish lines, either. The euphoria of accomplishment usually gives way to an unexpected emotional void, because the brain thrives on anticipation more than attainment. Fall in love with the build, not the goal.
And finally, you’ll never plow a field by turning it over in your mind.
What does success look like to you?
A question I wrote in a journal years ago has become my scoreboard: “Why is the world glad you exist?” Success is being able to answer that honestly — through how I parent, how I show up at work and how I treat the people in front of me.
Practically, that means emptying the tank every day, building an unwavering foundation of faith and courage in my kids and focusing on becoming the kind of person who could achieve the results I want rather than fixating on the results themselves. At work, it’s growing profitably, making sure the team is genuinely enjoying the build, and making sure we’re all rowing in the same direction. Profits are great, but my people are the purpose.
What leadership philosophy guides your strategic vision and decision-making?
I organize my thinking around three things: FCS.
F — Fewer things done better. Essentialism is the discipline. Every day I ask: What’s the highest-priority thing right now? You can’t do everything, but you can always do the most important thing. In practice, that means small bets on six-week timelines — if you can’t ship it in six weeks, the bet is too big; break it down. It also means empowering anyone in the room to call a time-out when we’ve spent ten minutes on something that won’t move the needle by $500K. Strive to do even the small things well.
C — Communicating the right information to the right people at the right time. Lead with context, not control. Executive time belongs to the things only the executive team can do — not redoing other people’s jobs or telling them what to think. It also means we need to stay in the opportunity space, not the solution space. You can’t get aligned on a solution if the team hasn’t aligned on the customer problem first. When people get to “write their own lottery ticket,” they’re five times more committed than when the answer is handed to them.
S — Speed and quality of decision making. The best teams aren’t the ones with the strongest opinions; they’re the ones that learn fastest. Underneath all of it, place small bets with six-week timelines, farm for dissent and trust that process drives outcomes more than individual heroics do.
