Questioning leadership

Effective leaders are great at asking questions and there are many articles out there about how to do that. I want to focus on why this matters and how hard it is to do for technically-inclined leaders of knowledge workers. In my experience as a technical leader, the hardest part about asking questions is that you are used to providing answers. Your status as a leader hasn’t altered the fact that people still come to you for all the answers. Your own team might even be doing that. It can feel great to have those answers and share them; unfortunately, this is not scalable and builds dependent thinking when you want independent thinking.

Judge a man by his questions rather than his answers — Voltaire

Here are 3 things you can do this week to combat your tendency to give answers rather than ask questions.

1) Ask questions instead of directing

Leaders need to get to the best answer to the problems they are responsible for solving. It is unlikely that the leader also knows everything to make the best decision alone. You can tell them “your answer” but it is far more likely that the team working the problem has that best answer or knows how to get to it. Your job as the leader is to find a way to get those answers from the team and achieve alignment. You can do this by asking questions (of everyone in the team) and helping guide the team to agreement. This takes more up-front time than telling them what to do, but it should save more time in the long run (since you waste less time doing the wrong thing). Start by reiterating the problem you need to solve, and then asking a question like this:

What is the biggest challenge that keeps us from solving this problem?

Then be quiet and put yourself in listening mode…

2) Ask to understand instead of answering questions

In my experience, asking to understand is fairly natural and easier to do when you don’t think you know the answer, however, it becomes a LOT harder when you “know” where the conversation should be headed. You are probably an expert (or were) in the subject you need to ask questions about and that “curse of knowledge” combined with your belief in your own good decision making makes it difficult to believe you don’t know all the answers. I’ve been there too and I know how hard this is. This is especially challenging in a group conversation or in the middle of a conversation. It’s all too easy to fall back into “answering mode” when you should be staying in “questioning mode”. If you find yourself jumping in to give the answer, stop and ask a question instead. If you cannot think of a question, use this one as a fallback:

Tell me more about (whatever the current topic is)?

3) Ask a question about the last thing they said

Be very careful about asking leading questions. One of the easiest ways to avoid leading people with your questions is to simply ask a question about the last thing the person said.

• You: How can we keep our system from crashing?
• Them: We need more redundancy at the app layer and time to for the team to focus on debugging and stability instead of always building more features to deadlines.
• You (bad reply): We don’t have any more time and customers need these features. In my experience, we just need to… (insert your solution here).
• You (good reply): Help me understand what the focus on debugging and stability looks like compared to what we have been doing.

This technique is a part of active listening. If you are not sure what question to ask, you can always fall back on something like this:

Can you help me understand (insert thing here) compared to (alternative or current state)?

Want a better answer? Then ask a better question.

You’ll become a leader who knows how to solve the hardest problems by asking the best questions. Good luck and keep asking questions until you get to the best answers.