Ask HN: What questions do successful engineering leaders ask themselves?

I'm writing a book about useful frameworks for functional leaders. So, I'm looking for the set of questions that engineers often ask themselves. Some examples might include: "How do I decide between working on new features versus improving stability?" or "When is it better to develop a tool versus using something off the shelf?" Obviously the answers to these questions are all "it depends." If you also have a framework you use to come to an answer, please feel free to share that as well.