Asking Great Questions is a Superpower

Mon, Sep 12, 2022 4-minute read

I’m sure this situation has happened to you: you’re in a meeting with a group of people and it seems like no progress is being made on how to proceed until someone asks a really great question and everyone goes silent. That is the power of asking a great question. A great question gets at the underlying assumptions and aligns multiple perspectives on the problem. It’s also a great tool for effective leadership. I wrote this post to reflect and consider how I can ask better questions because it’s a skill that can be developed. Before we get into the how, let’s start with the benefits first.

There are many benefits to asking Great Questions

  1. It brings focus. By asking a great question, it aligns our various perspectives on the core problem and helps make the discussion more focused. It illuminates the terrain in a way that adds clarity and re-focuses the discussion.

  2. It brings underlying assumptions to the forefront. Is our discussion and debate based on a shaky assumption? A great question can be used to cut through uncertainty and reveal the foundation of our discussion. The question creates an opportunity for a knowledge export to speak into the risks and give everybody a better understand of the options.

  3. It’s a great way for people with less experienced in an area learn from those who have a lot of experience. When experts ask great questions it’s an opportunity for others to learn not just what’s important but how the knowledge expert thinks about the problem.

  4. You gain influence by synthesizing the discussion into a key question that is extremely relevant, but has not be asked. In this way you thoughtfully listen to the conversation and when the time is right, show your influence by asking the question that need to be asked and pointing out what’s missing from the conversation.

  5. For leaders, it’s a great way to be humble and show you don’t know it all by asking great questions. Leaders that make mistakes and don’t know the right answer are more relatable. Never mind, it’s always good keep on learning no matter how much influence you have.

  6. It’s creative. Thinking about the problem latterly or taking inspiration from another industry or area of life and asking if that could apply (when it does make sense) shows your not afraid to voice crazy ideas. Even if the idea or question gets everybody thinking, but is discarded in the end, doesn’t mean it wasn’t worth it. It’s healthy to share crazy ideas because they could spark someone else to have an insight that solves the problem in a better way.

How to ask Great Questions

  1. What assumptions are being made? Consider what everybody is talking around and assuming it’s true, or not being brave enough to challenge. If there’s a reasonable chance it could be wrong, bring it into the open and challenge it.

  2. Dig deep into your experiences, even thoughts from an orthogonal domain or industry, what solution do they use and could you ask a question to see if the problems are similar enough?

  3. Simply ask more questions is a great way to learn. Yes it is a bit rough at first, so start with your friends, but being more inquisitive and asking more questions is a great way to practice and develop the skill into what makes a question great.

  4. Before an important discussion or meeting, visualize multiple ways the conversation could go and see if you can gain some insight on your own. If the conversation goes in a different direction than the one where you had the insight, share it to improve the quality of the conversation.

  5. Review the question in your mind and ensure the question you ask is clarly stated. Asking a clearly thought out question that doesn’t require any extra explanation brings alignment and often silence as everyone thinks it through.

  6. Ensure the question is open ended without any bias. Your question will be received more naturally and it will make people think of various solutions instead of pushing them to what you want to hear.

Asking great questions is a superpower. What do you need to do to continue to develop this ability?