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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Sample Agenda for a Regular Mentoring Meeting

This structured agenda is based on MentorCloud’s “best practices”.
1 min

This structured agenda is based on MentorCloud’s “best practices” learned from working with many companies across the globe. It will help your mentoring meetings be productive and successful.

The recommended time is 60 minutes. 

1. Feedback And Update (10 minutes)

  • Reminder on the importance of confidentiality and respect.
  • Update on what has happened since the last meeting. Refer to Notes from last meeting.
  • Feedback from the mentee and mentor on their progress regarding Tasks, Goals and  the action plan.

2. Discussion (40 minutes)

  • Discussion points to be presented by the mentee.
  • Questions asked by mentors to clarify the issues or challenges.
  • Guided discussion on how to address challenges. 
  • Options to address challenges going forward.
  • Mentor can share experience or advice if the mentee requests it.

3. Close (10 minutes)

  • New action plan for mentees.
  • Update Goals, Tasks and add any new Notes
  • New action points for mentors.
  • Preparation for the next meeting: venue, date and time?

When you create a Session, there is an option for your to write down an Agenda. It is best to plan ahead and have a few points of discussion written down for the next meeting.