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
- 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?”.