When you're leading a team of five or 10 people, feedback is pretty easy. It's not even really "feedback”: you’re just talking. You may have hired everyone yourself. You might sit near them (or at least sit near them virtually). Maybe you have lunch with them regularly. You know their kids' names, their coffee preferences, and what they're reading. So when someone has a concern about the direction you're taking things, they just... tell you.

You trust them. They trust you. It's just friends talking. You know where they're coming from.

At twenty people, things begin to shift a little. You’re probably starting to build up a second layer of leadership and there are multiple teams under you, but you're still fairly close to everyone. The relationships are there, they just may be a bit weaker than before. When someone has a pointed question about your strategy, you probably mostly know their story, their perspective, and what motivates them. The context is fuzzy, but it’s still there.