So I was prepared for a long evening of stories about how Doogie Howser* couldn't tie his shoes without supervision. Instead, I heard this. "It turns out this guy is one of the best bosses I've ever had."
The key was that the young man not only understood the potential awkwardness of the situation and defused it with a joke, but he also actively sought advice from my friend at every turn. Turns out the young man was wise about wisdom.
Harvard Business blogger Tammy Erickson checks in on the age issue with the post, On Young Bosses And Older Direct Reports. As the workforce continues to age, she says, expect you will have numerous occasions to work with a younger manager or an older direct report.
To the young boss coming into a situation with older employees, she suggests asking a lot of questions and being respectful of the positive elements of "the way things have been done around here."
For the older staffers, Erickson recommends they determine the way the younger boss likes to communicate and to appreciate the new skills and energy he or she is bringing to the party. Erickson concludes:
In both cases, don't worry about "convincing" the other guy that you have the necessary skills and experience â€" demonstrate that you do.*To save you a trip to Wikipedia, Doogie Howser, MD was a TV show in the early 1990s about a teen-age doctor and his startled patients. It shockingly lasted four seasons.