Do you remember the Saturday morning TV "Shazam/Isis Power Hour"? Among the many wonders this show offered was young Billy Batson driving all over the US in a big recreational vehicle with his mentor, Mentor. Despite Mentor's presence, the two of them somehow continually got into difficult situations which prompted Billy to shout "Shazam!" and transform into Captain Marvel in order to save the day. I always think of "Shazam!" when mentoring comes up in conversation, and I can't help but get a momentary image of Mentor behind the wheel of the RV, eyes twinkling, but looking somewhat deranged.
Mentoring is a tricky business, and it is not for the faint of heart. Superficially, it's quite straightforward. You, the wise and senior person, make yourself available to Billy, a person of hidden talents and perhaps flowing brown hair, but nonetheless something of a punk, and give him sage advice in his times of need. He is grateful and respectful. You are modest, but you're still totally the one on the ball.
But what happens in real life?
Uncertainty: One chief difference between you and young Billy is that you've been humbled by any number of situations in the past, and of the two of you, you are the one most likely to suspect that there may not be a good option out there in some difficult situations--it may simply be a choice for the lesser of two evils. Like "if the CEO really thinks that power is the same as knowledge, it doesn't matter how much you empower the team, because he's still going to surprise them with complete changes of direction every four months, and they'll have to start all over again."
Rapid (but inexplicable) Cognition: Your years of experience may give you a tendency to come to quick, shorthand, Gladwell-esqe "blink" type conclusions you can't fully explain to your mentee, like "I think that person is totally evil and probably enjoys inflicting pain but not leaving visible bruises." These instincts could be very good, but if you can't explain them, the more rational of your mentees may not feel you've transferred anything of use to them in your conversation.
The Occasional "Shazam!" Moment: sometimes you just know exactly what is going on for your mentee, and you can explain it to them in a few deft sentences, and leave them with a clear idea of how to move forward. Like "if you want to quickly put together a good plan for implementing test automation in a legacy environment, just look at Mike Cohn's blog on the topic--he explains the whole thing!"
Despite our best efforts, we often cannot help our mentees learning difficult lessons for themselves. Few people can actually learn from the experiences of others. But we keep trying, and become more humble as we go.
It turns out that "mentor" wasn't originally a verb. In Homer's literally epic "The Odyssey," Mentor is the name of the person Odysseus leaves in charge of his young son, Telemachus, when Odysseus goes off to the Trojan Wars. Eventually, Odysseus comes back, and gets young Telemachus to help him wipe out the many suitors who have come to court Penelope, Telemachus's mom. As part of this nuclear family defense plan, it turns out that Telemachus is actually strong enough to wield Odysseus's bow himself, but he tactfully refrains from doing so on his dad's signal, to ensure the appropriate happy ending to the story.
I'm not sure what Mentor was thinking as he observed this bit of byplay, but for me, part of the strength of being someone's advisor is that eventually the tables turn, and sometimes you learn more from your mentee than they learn from you.