10 years ago in my mid 20s, I was a product manager at a tech BigCo (not FAANG). Just after starting, I was in a casual in-person meeting with my boss, my boss's boss, and a couple other executives (closer to a meet 'n greet than formal meeting). I don't remember much of what happened in the meeting, but I distinctly remember the feedback my boss gave me shortly after the meeting: "I think it'd help you if you don't ask obvious questions because it makes you look dumb" (I remember it being delivered more compassionately, but that was the essence).

At the time, I was young, insecure, and fraught with imposter syndrome (viewing virtually everyone as smarter than me) so I took it personally. That feedback gave me a visceral "that has got to be the worst feedback ever" reaction.

Fast forward 10 years, I've reached the point where I don't think twice about asking questions in any setting. I'm secure and confident in what I know, understand the vastness of what I don't know, and try to be vulnerable about this truth. I'm no longer worried about looking dumb. Maybe some people still think "well that's a dumb question, he should know that" but I'd rather have this experience, while retaining my adaptability "superpower" of being able to dig to the root of a problem, quickly learn context, and rapidly provide solutions.

I think about that feedback a lot.