User Guides

How to Ask Challenging Questions

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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?”.

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Questioning is a key skill in mentoring.
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Questioning is a key skill in mentoring. By understanding how to ask the right questions, you can unlock your mentee’s thinking and generate valuable insights. 

Closed and open-ended questions
Use both closed and open-ended questions in your mentoring conversations.

1. Closed-ended questions: 

Can be answered by a few words and provide information about facts. Use them when you need clarification or a specific answer. They usually begin with “Who,” “Where,” and “When,” and “How much?”.  


  • “Who was part of the conversation?”
  • “Where did you work previously?”
  • “When did you join the company?”
  • “How much was your quota?”

2. Open-ended  questions: 

Open-ended questions cannot be answered with one word, or a simple “Yes” or “No”. Typically, they require more thought and can lead to deeper thinking and insights. Open-ended questions often begin with “What”, “What if”,“How?” and “Why”. 


  •   “What motivates you?”
  • “What accomplishments are you proud of?”
  • “What if you had an unlimited budget for this project, how would you spend it?”
  •   “How will you go about motivating your team?”.

Asking questions can be stressful for some new mentors. Remember, it’s more important to actively listen than to think about what question to ask next. After fully listening, reflecting back and summarizing, the right question will come to you.