One of the chapters of my forthcoming book recalls a situation where I received conflicting pieces of life advice within a matter of minutes, all from really successful people. An editor annotated next to that story, "What did you do with all that competing advice? Has your perspective changed?"
It reminded me of my post from September ’04 What Makes a Good Mentor. I realized I left out a key criterion: the best mentors/coaches/advisors give advice to YOU, not to a younger version of themselves. If someone asks me, "What do you think I should do in this situation?" and if I’m not careful, I will respond with what *I* would do in that circumstance, not what I think the questioner should do. This is dangerous, because my strengths, weaknesses, and experiences are different.
A major reason parents use curfews and worry about their adolescent kids is because they are thinking what they did when they were younger, which probably means drinking and having sex. So, they apply a worry that concerns their younger self to their child.
When I talk to people about spending time independently pursuing an education after high school, I often find people thinking about how THEY would spend their time (maybe goofing off) and therefore thinking the idea is nutty.
Finally, I think the *best* advisors can synthesize their experiences to deliver custom, specific advice. The easy way to do this – let’s use an entrepreneurial example – is to say "When I was at company X, we did this". The advisor will then try to draw some connection to the situation at hand to make that experience relevant. For advisors who have a breadth of experiences, this is an unfortunate approach. A better approach is to synthesize the experiences into key lessons and then have a very specific conversation with the advisee about their specific situation.