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.)
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.)