May 4, 2023

Asking tough questions disarmingly builds relational bonds 

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The Tough Questions

One of the reasons that we need mentors in our lives is because we need a person to ask us the hard questions. Many people are too polite or afraid of hurting our feelings to be completely honest about where they see our flaws. And let’s be honest with ourselves; we don’t always want to hear it either. This is why having a safe place where these questions can be asked by someone we trust is so important and essential to building relational bonds between mentor and mentee. 

Even if your mentee knows that your job is to ask the hard questions, they may be reluctant or defensive when it comes down to it. The relationship between mentors and mentees dig deeper than most relationships usually go, leading the mentee into vulnerable and difficult places. So how can you, as a mentor, make this easier for yourself and your mentee? How do you ask the hard questions in the best way? 

My Experience

My own mentor, Keith Farmer, is excellent at asking the tough questions in a way that feels disarming. For example, in helping me recover from burnout, he knew that one of my red flags was reaching for an extra glass after some wine after dinner. (for more flags see Burnout and Beyond).  He knew that asking how I’m going as far as alcohol is concerned, is a good way to gauge where I’m at in other areas of life. If I admit that I did help myself to a third glass he would ask me about what else is going on in life… What is fueling this thirst? Consumption was a symptom of a bigger problem. He helped with fixing the problem and consumption then moderated. While it is a mentor’s job to help their mentee grow, the relationship must feel non-judgemental and compassionate. I know Keith is for me, not against me. 

A good mentor also needs to keep safety in mind. Is anyone being harmed or put in dangerous situations? Mentors have an ethical responsibility to their mentee as well as to themselves and the people around their mentee. While we can still withhold condemnation and judgement, it becomes essential to be serious and direct when asking questions if you sense someone is in danger. 

Here are some things to keep in mind the next time you ask a tough question:

  1. People feel bad about things that aren’t working in their life. They already feel condemned. Adding judgment is only going to make a person become defensive or want to give up. 
  2. The way you phrase your question, the timing of the questions and the tone you use make a huge difference. It should never feel like an attack. 
  3. Check the symptoms. It can be helpful to start with the behaviors you see, and work your way to the root of the problem instead of starting with the main issue immediately. 
  4. Turn it back to them. Ask them what they think the problem is. Often they will ask themselves the hard questions before you need to. 
  5. Read their reaction. Like many aspects of mentoring, knowing when to push and when to back down is essential. Maybe they aren’t ready to answer the questions yet. Maybe they’re ready to tackle an even deeper issue. Shape the path of conversation based on how they respond. 

Reflection Questions: 

  • What is the question you think they want you to ask when you meet next?
  • What questions will lead to transformation? 
  • How am I at asking tough questions? Who can help me see how I could improve?
  • Who is asking me difficult questions in my own life?

Romans 8:1 (New International Version):

8:1 Therefore, there is now no condemnation for those who are in Christ Jesus,

What happens next:

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