Questions are powerful in all sorts of conversations, including those as a leader. I’ve often been asked for the perfect or even best question for a specific situation. It is a valid request, but the wrong question.

There is rarely one perfect question that will always work.

Let’s start here…

Have you ever been in a conversation with one of your team members (or the whole team), asked what you thought was the perfect question, and got silence or a confused look in response? When that happened, chances are, if you then asked a different version of the question, it went better.

Have you ever had your perfectly crafted question get misunderstood?

And have you ever had the same question work wonderfully?

These examples show us that the question isn’t the problem. The problem is the premise of the best question.

If someone said you could only eat one food, read one book, or have one artist to listen to for the rest of your life, you would have a hard time choosing. Or perhaps you wouldn’t want to choose at all. Similarly, why do we need to choose only one question?

There is no best question. But there are lots of right questions.

Crafting Groups of Questions

Rather than trying to find the one question, do this instead.

  1. Understand your goal for the conversation.
  2. Make a list of possible questions that move in that direction. (Yes, write them down.)
  3. Start with one you like (or better, one that you think will resonate with your team member). But be ready to use others as needed.

Not all your conversations go according to a plan, and you can’t pre-plan for all conversations anyway. That’s OK. Using this approach when you are planning will get you more comfortable and skilled at using versions of questions.

An Example

Let’s say you want ideas from someone about possible solutions to a problem. After you have framed or reviewed the problem, it’s time to ask. You probably have a favorite or go-to question you use, but here are some others to consider or adapt.

  • How do you think we should solve this problem?
  • What are some possible solutions?
  • What options could we try?
  • How does this situation remind you of other problems we solved effectively?
  • What have we already tried?
  • What might get us the quickest results?
  • What ideas have you thought of but haven’t shared yet?

Note that these questions will all get you slightly different answers, but asking for the same general information in a couple of different ways will give you a greater appreciation of their perspective than asking just one.

How to Ask the Questions

Warning: Having a list of questions doesn’t mean you need to use them all!

Remember that you are having a conversation. Questions help you learn things, engage the other person, and build relationships. Asking inquisition-style, rapid-fire questions won’t get you any of those results.

Instead, ask a question and wait for the response. If you get one, great. Perhaps one of your other questions will be the best or helpful follow-up. But if your first question yields silence or confusion, step back and ask another to clarify your inquiry. Be careful not to rely too heavily on what you have deemed your “best question.”  Having several questions will make your conversations more fruitful, comfortable, and effective.

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High Impact Leadership: The #1 Fastest Way to Accelerate Your Organization’s Success

February 22, 2024  1:00pm ET

Kevin Eikenberry is a recognized world expert on leadership development and learning and is the Chief Potential Officer of The Kevin Eikenberry Group ( He has spent nearly 30 years helping organizations across North America, and leaders from around the world, on leadership, learning, teams and teamwork, communication and more.
Twice he has been named by as one of the top 100 Leadership and Management Experts in the World and has been included in many other similar lists.

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