Asking Good Questions

Want to help your mentee? Ask more questions! 

Each time you meet with your mentee, it is important to assess the progress being made toward goals he or she has set. These are some sample questions a mentor might ask:

  • Asking questionsHow are you doing with your job search?
  • What’s going on in your support group?
  • How’s your church group doing?
  • What’s happening with your family?

Before each meeting, think about the most important issues you need to discuss and jot down pertinent questions. The goal of your discussion will be to help your mentee evaluate progress and receive encouragement in difficult areas.

Ask open-ended questions that cause the mentee to think and evaluate his or her thoughts and actions. Then listen carefully and ask deeper questions where you sense the mentee needs additional guidance or support.

An important question to ask those with past addictions is: What recent situations have caused you to think about using again? Help your mentee identify the triggers and some practical ways to manage these times. Pray together and ask God for strength and power to overcome.

When you talk about the mentee’s family, remember that parole conditions may prevent the mentee from contacting certain family members. Encourage your mentee to share some of their pain and frustration – and their joys – in reconnecting with the family. Healing take time, so rejoice in the small steps and don’t get overly focused on the setbacks.

One of the most common struggles newly-released prisoners have is their relationship with their parole officer. Patti Tasa, a former Prison Fellowship field director, recalls a revealing conversation she once had with a newly-released man:

Mentor & menteeDuring a conversation, he said, “I had a beer the other day.” And, I responded, “You know, you need to call your parole officer and report what you did.”

He got really upset and said, “I am going to end up going back to prison.” But I answered, “If you do the right thing, God’s Word says He will honor you, and He doesn’t go back on His Word. But if you hide this secret, you’re just going to end up going deeper and deeper into sin.”

He agreed to call his parole officer right there in the office and left her a message telling her what had happened. The next day, he came back to my office smiling ear to ear, and said, “She called me back and thanked me for being honest.”

What if I had ignored that parole violation? This scenario would have been a lot different, I think, because one cover-up would have led to another. But God used that situation as a very teachable moment about being honest and trusting Him for the outcome.

No matter how good your mentor- mentee relationship is, you may discover some issues are very difficult for your mentee to be open about. Try to be sensitive to where they are emotionally and spiritually. Ask the Holy Spirit to help you hear your mentee’s innermost needs and to give you wisdom to speak.

The right question asked at the right time can inspire a turnaround in a situation and even completely change a person’s life. For more insight, read this book by Dorothy Leeds: The 7 Powers of Questions.


EDITED: Frontlines interview of Patti Tasa, former Prison Fellowship field director