March 14, 2024

Four Questions to Make Difficult Conversations Easier

Featured image for “Four Questions to Make Difficult Conversations Easier”

Challenging and Confronting others is a difficult skill set that all mentors or supervisors need to have. Even our easiest and most pleasant mentees and supervisees will occasionally need to be challenged and pushed to grow. Some of the people we work with will need us to address many tough issues; confrontation may be a regular part of sessions. Either way, being able to acknowledge and embrace difficult issues within this relationship, and to take personal action, is key to successful transformation. This is exactly what we will be looking at over the next few weeks. This is an opportunity to self-reflect: how do you handle challenging your mentees? How do you prefer to confront supervisees? Are difficult conversations something you feel comfortable with? How do you go about correcting unhealthy behaviours? 

Hard Conversations

Today, we begin this series by exploring hard conversations. No one, not even professional mentors or supervisors, enjoys a hard and uncomfortable conversation. Still, unfortunately, this is a task we must take on when the situation requires some tough truths. There is a reason these conversations are hard; we are not uncaring people, and we never wish to make this difficult. It is because we care about our mentees that it is difficult to tell them things they might not want to hear. People come to us because they need help to grow into their best selves, and this can only be done through honesty. 

However, the necessity of hard conversations doesn’t make us naturally skilled at engaging in them. So here are a few questions to help you conduct these uncomfortable moments: 

Is this a necessary discussion?

Especially within workplace mentoring or supervising, there is a fine line drawn between what is acceptable to talk about and what isn’t. It usually comes down to relevancy to the work. Surprisingly, this often does relate to personal lives. For example, talking about issues within a marriage may pertain to work if the issues are impacting their focus or interaction with others. A private conversation between a professional supervisor and an employee can lead to healing that could positively affect the work done and the overall atmosphere of the workplace.

Is this the right time?

There are times when it is productive to bring up tough conversations and when it will be counter-productive. Sometimes, issues can be too painful to handle in vulnerable moments, and you could break their trust by failing to be aware of their needs. If this is the case, take note and find the right time to bring it up. Also, remember that hard conversations often take time. It’s okay if it takes months to find the right time, as long as you are building to that conversation and looking for the opportunity. 

Are there boundaries in place? 

Take some time to return to the original contract that you both set up. Were there any subjects that are off the table or inappropriate for your particular setting? Or does your mentee need a reminder that they wanted to speak openly about their life? If there is not a clearly set contract, then these boundaries should be discussed before any difficult conversations take place. You need to ensure they agree to hear your advice about the particular subject before offering any. 

When do I need to push a direct conversation?

Usually, a mentor/supervisor allows their mentee/supervisee to take the reins in the sessions. We want to respect their journey and be sensitive to their needs. They lead, and we follow. However, there are rare moments where we will need to be very direct and make a conversation happen because either your mentee or those around him are at risk. For example, your mentee might be a manager, and you have come to see that they are burning out their team, and you are concerned that permanent damage could be done. You must bring this to light as soon as it becomes clear to you. 

Reflection Questions for Your Mentee/Supervisee:

  • Who can help you with this? 
  • Has God looked after you in the past? 
  • Will he look after you in the future?
  • Do you want to be captive to this, or is there something God could tell you about what is next?

What’s next for you?

Reflect on your growth as a professional mentor and supervisor  Are you ready to grasp the essentials? Register for the upcoming Supervision/Mentoring Essentials Cohort  

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