I also learned that my best tactic was to reconceive my bewilderment as curiosity, and give free rein to it. I asked a lot of “why” and “what if” questions, forsaking the “what” and “how” questions on which most senior leaders focus. I didn’t know any better. Being in a tech company was new for this old fart. My beginner’s mind helped us see our blind spots a little better, as it was free of expert habits. We think of “why” and “what if” as little kid questions, but they don’t have to be. In fact, in my experience it can be easier for older people to admit how much we still don’t know. Paradoxically, this curiosity keeps us feeling young. Management theorist Peter Drucker was famously curious. He lived to age 95, and one of the ways he thrived later in life was by diving deeply into a new subject that intrigued him, from Japanese flower arranging to medieval war strategy.
Although some older folks in the tech world feel they have to hide their age, I think doing that is a missed opportunity. Being open helped me succeed in tech; I’ve spent a lifetime being curious about people and things, which, I guess, means I’m well-read and well connected. I’m not sure there’s anyone in Airbnb who’s been asked to chat by a more diverse collection of employees. I always did my best to respond with an enthusiastic yes to these invitations. And I’m grateful. Because if I were to plot all of those conversations across the various islands (or departments) of the company, you’d see a rich web of relationships and knowledge. This served me even more as a strategic advisor to the founders, since I had a real sense of the pulse of the company and its various teams.