Ask Tough and Deep Questions

Leading well, especially in small startups where things are often up in the air, means being able to ask tough and Deep questions.

Get to the Core

A good engineering leader can figure out if a person really knows their stuff. You don't need to know every little detail about their work, but you need to be able to dig deep. Like how Apple's leaders do, you should ask questions that go three levels deep into your team's work. The goal isn't to micromanage, but to ask hard questions and check out any old assumptions that might be out of date. It's all about trusting but also verifying.

Organized Talks and Finding the Truth

The best bosses use organized talks to get to fair conclusions. Things like "apocalypse meetings" make sure everyone is heard, especially the quiet ones who might not speak up but often have great ideas.

Also, a leader's job involves getting past the usual ways of getting information to find out what's really happening. Think about when TJ Watson Jr. wrote a letter to IBM asking why smaller, more nimble companies were doing better than IBM.

Always Getting Better

A great leader is committed to getting better every day, and they use questions to help make this happen.

As a leader, you should:

  • Figure out when things have changed so much that you need to change the technology you're using.
  • Pick a few areas each quarter to really dive deep into.