Thinking Questions

When team members come to you with a problem, is your first instinct to tell them what to do? Of course it is. Jumping into help is a normal thing. What is the benefit of helping the employee think through what to do vs. telling them what to do? Research shows that advising or telling is effective only 1/13 of the time. What is far more effective is to ask probing questions and encourage your team member to think for themselves.

Next time someone comes to you with a problem, you might set the stage with, “Hmm, you have a good challenge there. Would it be OK for me to ask you some thinking questions to help you plan your actions?”

Here are some thinking questions to use:

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​1. How clear is this issue to you?
2. What do you want to achieve in this situation?
3. What is your best thinking on this so far?
4. What is the root cause of the issue?
5. What do you want to do? What might be holding you back from that?
6. What is your gut instinct about solving this problem?
7. How committed are you to solving this?
8. What resources do you have to solve this?
9. What’s your best first step?
10. What haven’t you thought of?
11. What do we need to do to solve this?
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If your team member is totally stuck after trying several of these questions, here’s what you might say: “Ok, I have some options to consider. Would you be willing to brainstorm ideas with me? Remember with brainstorming, there are no good ideas and no bad ideas. We’re going for volume, not quality. I’ll start with one idea, and let’s see what that inspires in you. Then I’d like to hear an option from you.”

​Offer one possible solution and say, “Ok, it’s your turn to offer up an idea. The crazier the better!” Wait for your team mate to come up with something. Recognize that it is hard to allow silence into a conversation, but if you avoid the urge to jump in with another idea, you will be rewarded with one of their own. When they do, thank them and offer another idea. Rotate in that manner until you have a handful of options, then say, “Of these ideas, which one is the best?”

As the old saying goes, “Give someone a fish, and you feed that person for a day. Teach someone to fish, and you feed that person for a lifetime.” As a leader, your job is to develop your team members to be self-sufficient and think for themselves. If you do that, you’ll be remembered as the best boss ever!