How to have a life-changing mentoring conversation

I’ve spent the last three or so years mentoring college-age men in both one-on-one and group settings. One of my initial challenges was figuring out what I should be talking about so I could effectively lead the conversation and make the most of our time together. It doesn’t help that the goals of many mentoring relationships are somewhat vague (learn from the mentor’s mistakes, become a better Christian, etc.)

After my first year as a formal mentor, four essential conversation categories emerged for me. These make up a focused, productive, and ultimately life-changing mentoring conversation. Each of your mentoring sessions should generally include all of these elements (though not always in identical proportions).

1) Relationship building

Relationship building is how I start most of my meetings. This is where you look for opportunities to connect with the person you are mentoring on a personal level. Ask questions about their background if you’re just getting to know them, or about their day or week a little later in the relationship.

Use this time to simply enjoy conversation about topics of mutual interest. If you have the time it’s also great to do something fun and meaningful together. On occasion you may devote your entire session to relationship building. Although it may not seem particularly productive, spending the time up front to simply get to know the person you are mentoring and allowing them to get to know you will lay the foundation for a trusting relationship. Without a certain level of trust, it’s impossible to be an effective mentor.

2) Accountability

Accountability is the tough part of any relationship (and thus, the easiest to let slide), but I promise you will be rewarded as you lean into it. Mentoring relationships usually entail some sort of commitment… Has your mentee followed through?

Ask the tough questions, and don’t let difficult subjects slide by…but remember to practice a lot of grace, mercy, and love as well. Don’t be afraid of awkward silence–embrace it. Sometimes the person you are mentoring will need a few moments to think about how to answer a particularly personal or probing question.

3) Teaching

It’s easy for the teaching step to get lost in the shuffle (especially when you’re having fun relationship building) but a massive part of being a mentor is helping others learn. For them to learn, you have to teach.

Don’t think it needs to be a lecture, though. Never forget the power of teaching through asking leading questions and genuinely listening even as you offer thoughtful feedback. You should always be willing to be vulnerable and share your mistakes, but don’t forget that now isn’t the time for you to be on a soapbox.

4) Prayer

I close every one-on-one with those I mentor with prayer. Few people have someone with whom they can pray with regularly, and I consider it a particular honor to be able to be that person for some of the men I mentor. Make sure to allow plenty of time for this as well (at least 15 minutes). I’ve found that asking someone how you can pray for them can lead to some very honest and very encouraging conversations…sometimes this can be the deepest and most meaningful part of our time together!

How could implementing these four elements improve your own conversations with those you mentor? Did I miss anything? Let me know in the comments!

6 thoughts on “How to have a life-changing mentoring conversation

  1. Great article brother and solid points. I believe that even in our own youth, we are called to mentor to those not too much younger than us. Those that are traveling the path we had to travel 5-10 years ago. We can relate and they appreciate that. I keep up with a few younger men myself and will definitely benefit from this info. Keep up the good work brother!

    1. Absolutely Bryan. Ideally every Christian should be engaged in mentoring relationship on some level, both as a mentor and mentee. Thank you for reading!

  2. Absolutely on target. Can apply broadly for mentoring relationships in business, too! Thanks for the concise nature of presenting a topic with many twists and turns.

  3. Great job Nathan! Appreciated this whole series on mentoring, and love your emphasis on prayer both in establishing the mentoring relationship and in nourishing it. May Father continue to guide you and give you wisdom as you mentor others both formally and informally 🙂

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