March 31, 2022

Mentoring Essentials: Challenging and Confronting 

Featured image for “Mentoring Essentials: Challenging and Confronting ”

How to Challenge and Confront with Grace

No matter who we are, there are moments in our lives when we are pulled into heavy and challenging topics that sometimes lead to conflict. Well-being mentors tend to face these moments a little more often. It’s part of the joy and difficulty of the job; to get into the deeper areas of life, to sit in the pain with someone, to ask the questions most people in life won’t ask. Ultimately, the deeper a mentor goes, the more they can understand and help a person, but also, just like in life, mentors will inevitably come to a point of confrontation with some of the people they work with and that can lead to conflict or other challenging reactions.  

Whether you are a mentor, a leader in your community, a mentee or simply debating entering the world of Christian mentoring, it’s important to be aware that confrontations may arise… in fact, at times they should. Here are the behaviours Dr. Charles R. Ridley (Chuck), Marcy Bradford, and Dr. Robert E. Logan (Bob) and I have collected that will support a healthy mentor as they gently challenge and confront mentees: 

Behavioural Expressions of Challenging and Confronting:

Discerning when and how to address tough issues needing acknowledgement, embrace, and personal action. 

  • Insists on hard and uncomfortable conversations 
  • Identifies unbiblical behaviours and attitudes 
  • Corrects unbiblical behaviours and attitudes 
  • Clarifies discrepancies in words and deeds 
  • Helps mentees to move past their fears 
  • Urges mentees to focus their energies and efforts 
  • Overcomes mentor’s own discomfort with difficult conversations 
  • Ensures a theologically sound view of God 

I don’t find it naturally easy to challenge and confront others. I dislike difficult conversations. However, I’ve found this to be a helpful attribute. Mentors will see ingrained and deep behaviours that the mentee may not see. I find it pragmatic to tread lightly, and challenge as needed; being rough or shocking can cause a person to become defensive and angry. Instead, silently hold an anchor in your soul that the attitude or unbiblical behaviour needs to change. Ask challenging questions that help the mentee come to a point of understanding the need to change.

Sometimes challenging conversations are less about anger but focus more on fears. I once had a mentee who seemed convinced that he was going to be fired. As we explored the basis of the thought, I learned that he had a previous place of employment where he had been unjustifiably fired. He transferred his previous boss’s behaviour into his new situation. It wasn’t a Biblical behaviour to respond through fear and anxiety. As we unpacked further, we could see that he was loved by God and their boss. Recognising this helped him change his attitude, let go of his previous experience and forgive and move on. He changed the way he acted at work, which ultimately changed the way he was treated. Soon after, he was given a promotion!

Link to profile of Christian leader and well-being quiz? 

Continue reading with these articles…

Recent Posts


  1. Coaching
  2. Emotional Health
  3. Empowering Transformative Action
  4. Flourish
  5. Gauges
  6. Grief
  7. Grief
  8. Healthy Emotional Intelligence
  9. Mentoring Excellence
  10. Professional Supervision
  11. Reduced Risk
  12. Replenish
  13. Resources
  14. Sustainable Life
  15. Thriving Relationships
  16. Uncategorized
  17. Videos
  18. Vital Spirituality
  19. Well-Being
  20. Well-Being Mentoring