The key to great mentorship conversations is to encourage your mentee to challenge everything. If they are rooting their decisions and actions in well-researched reality, then they will become more confident. However, if they’re acting based on assumptions or ego, sometimes all it takes is one direct question to break that thought pattern.

Below are some helpful questions to use as a cheat sheet to get them thinking.

When they’re overwhelmed

• Have you checked in with your big picture plan lately?

• What individual tasks are you doing each day? What would happen if you simply didn’t do each one?

• What additional support or information could make this easier?

When they’re making poor decisions

• What reasons do you have for doing this?

• What result are you hoping for or expecting when you do this?

• What factors have you considered when making this decision?

• What additional factors should you consider?

• What alternative options have you considered?

When they’re not thinking objectively

• Do you really believe what you just said?

• What makes you say that?

• How do you know that?

• Is there any other way to interpret this situation?

When they’re stuck on a problem

• What options do you have?

• If you had no limitations, what would you change about the situation?

• What is in your power to change?

• Have you handled a problem like this before? What did you do then?

• What assets do you have for handling this situation?

• What action could you take, today, to make this a little better?

• When this is all over, what do you hope you’ll have learned?

When they’re getting distracted

• How does this align with your main goals?

• How could you use this situation to move further toward your main goals?

Questions to Avoid

• Why? These questions typically intellectual and mask all of the facts and motivations that go into a situation. Ask specific questions about those facts and motivations instead.

• Multiple Choice Questions. These are based in assumption, limit their responses, and don’t encourage examining the situation for themselves.

• Yes/No Questions. These can sometimes have a place in very rhetorical and positive way to such as, “Do you believe that you are a skilled person?” or “Do you really believe that everyone hates you?“ In other situations, though, they risk removing any need for them to examine themselves.

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