Mentoring Is A Conversation, Not A Speech

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Think about your mentors, and any mentees that you might have had. There are many many reasons why the relationship might be (or have been) effective, but one common denominator is that, in the effective ones, both sides gained from the relationship.
But first, a digression. Think about your relationship with your loved ones — especially friends that you’ve had for a long long time. Y’all are different people than when you met — you’ve grown, changed, and moved on from those salad days. Many experiences large and small have shaped you into the person you are, and even more will shape you into the person you will be.
And the same applies to your friends too! It is this personal evolution that has made the relationship last this long — the experiences that each of you have been through creates new vistas to explore, new fields to experience, and new things to learn.
To be an effective mentor, you need to find our what you can learn from, or about, your mentees. Find something about what they do or know (“you teach Pilates on the side?”) that you can come up to speed on. You’ll be surprised at how much there is that you don’t know. Or rather, hopefully you already know that there is an infinitude of stuff you don’t know .
Mind you, This isn’t just about updating your priors, or adjusting any advice that you might give to fit the situation — it’s about the mentee too! When you listen to (and learn from!) them,
• you give them the mental space to accept help, by getting past any insecurity, defensiveness, pride, etc.
• you help create an environment where they feel comfortable in just venting (sometimes that’s all that’s needed!)
• you also create enough room for (constructive!) criticism without barriers going up automatically
If this sounds familiar, it should — this is, pretty much, exactly the same type of relationship that you have with your friends, no? So yeah, your relationship with your mentee (and/or mentor!) should be the same — a path that you both walk and are both enriched from.

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