The difference between "have you considered using X?" and "I tell you to use X", the difference between "can we hit date Y?" And "we must hit date Y so start cutting corners"
Authority as a position is a difficult stick to carry - if you are telling people "my way or the highway more than once of twice a year" you are over doing it.
"I feel uncomfortable with this architecture" or "this will take longer than you hope" are all indicators you are doing it right. Stop hearing those and you should worry.
I think a lot of these cultural questions require you to say over and over what's important, and demonstrate that you really mean it. I always ask people what they think, and when I sense hesitance I work to draw them out. In the end a lot depends on your relationship with the individual; I make sure to spend time getting to know every engineer who joins.
More broadly, one point Marc often makes is, if someone does something you don't like/disagree with, let them know directly. (There are some exceptions to this, and sometimes it's helpful to role-play with a manager to get some practice before doing so, but we work hard to make direct feedback a core part of Stripe.)
I spent a few days in the Stripe office with my team (Hey guys!) and I can tell you with certainty that they have a very strong collaborative team. They actually have a really great culture that they actively try to build (thanks for including us while we were in town!). Fridays are particularly awesome.
Anyway, my point is that I never got the feeling like people say "it's going to be this way, no questions", but also got the feeling that if a superior did say "look, I know you guys feel this way, but we are going in this direction and the deadline is X" that the team would rally behind their leader and support their decision.
Stripe, from what I saw you have done a great job building out your team. Congrats, it's nice to see companies doing it right!
The difference between "have you considered using X?" and "I tell you to use X", the difference between "can we hit date Y?" And "we must hit date Y so start cutting corners"
Authority as a position is a difficult stick to carry - if you are telling people "my way or the highway more than once of twice a year" you are over doing it.
"I feel uncomfortable with this architecture" or "this will take longer than you hope" are all indicators you are doing it right. Stop hearing those and you should worry.