Tips to Make Sure Your Mentoring Conversation is Actually Helpful

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The following is an excerpt from my forthcoming book, The Deliberate Manager, which premieres on February 16, 2027. It’s technically available for pre-order now, though as of this writing we’re still finalizing the cover art.

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How to Share Your Experience Effectively When Mentoring

Have you ever asked someone for advice and found yourself stuck listening to a 20 minute self-important monologue? Sharing one’s experience is a core part of mentoring conversations, but only if the experience-sharing actually benefits the mentee. Otherwise, it’s just the mentor boosting their own ego.

What makes experience-sharing self-indulgent:

• Telling stories that aren’t clearly relevant to their situation

• Going on at length about your achievements

• Using their question as a springboard to talk about yourself

• Offering your experience as the only valid path

• Failing to check whether your guidance actually applies to their context

On the other hand, what makes experience-sharing effective:

Connect your story to their situation. Don’t offer experiences at random. The experiences you share must directly address something the mentee is facing. The more clearly you can draw the line between your past and their present, the more useful the story becomes. As a good rule of thumb: If you can’t immediately explain in one quick sentence how your experience connects to theirs, you should probably skip the story.