User Guides

How to Ask Challenging Questions

Download as PDF

Asking challenging questions can be helpful to encourage deeper thinking about a situation. However, these questions need to be asked with care and sensitivity.

Sometimes “Why” questions can be seen as judgmental or speculative, for example, “Why did your team react that way?”; however, when used sparingly, they can be effective. Sometimes a “Why” question can be rephrased using a “What” or “How” question. 

Asking questions that are challenging can lead to critical and reflective thinking and may help your mentee generate insights. 

Challenging questions are usually:

  • difficult to answer
  • slightly out of the respondent’s comfort zone 
  • non-judgmental
  • personal to the respondent and specific to the topic
  • push the respondent to think more deeply

Examples include: “What’s unique about your situation?”, “What critical feedback do you most often receive, and do you deserve it?”, “What dream have you given up on?”, and “What are you risking by not stepping out of your comfort zone?”.

Did you find this guide helpful?

Yes
No

Up Next

How to Reflect and Summarize

The ability to reflect on and summarize what your partner has said is part of being an active listener.
step_2,step_3, step_4, step_5, step_6
xyz_mr_mee
0
2 mins

The ability to reflect on and summarize what your partner has said is part of being an active listener and will improve the effectiveness of your session. 


Reflect on what you hear -
Listen to your partner’s words and think deeply about it. Try to understand where they are coming from, what they mean and come up with your own ideas or thoughts on the subject. This shows your partner that you are listening and carefully considering what they have to say.


Observe –
You should also pay attention to non-verbal cues and behavior you see. You may say, “I noticed you looked down when you said that…”, or “It seemed like your voice softened when you mentioned that person. Is there something more you want to say about them?” 


Summarize -
Periodically, summarize what you have heard and check that it’s accurate. Summarizing and checking shows you’ve been listening and understanding what your mentoring partner has said. You may rephrase what they said and ask if it’s what they meant. It also helps you recollect important points they have mentioned or clarify anything that was unclear.

Give a shortened version of what you’ve heard by stating the key facts. Don’t try to interpret or add to it. Use this skill when you feel ideas are getting confusing, or when there seems to be more than one issue on the table.

You may use the Notes tab to summarize and keep track of any ideas or key points discussed during the Session so you have it handy for later. You may also refer to it before your next Session and keep track of your progress.