Interesting.

Honestly, I'm the guy who would just "roll with it" and eat whatever was brought to me because I honestly can't bring the energy to arguing with the waiter.

But having hired people and other professionals, I almost always hire the person who would assert themselves and demand the right thing be done.

Why?

Well, I recognize that I don't like to be "that guy". So I hire people who can do it for me. It has always worked out quite well in the past, where I've been able to form a team of people who work well together, but can be assertive to external groups. (And I, of course, only need to get out of their way.)