Question: I have recently been placed under the supervision of a young man at least 30 years my junior. Before he was made my supervisor, we shared a casual and relaxed rapport. He sent me an email asking if he could do anything to help get a new employee set up in the office. I jokingly replied that he wasn't paying attention and that I had already taken care of the matter. He immediately called me on the phone and admonished me to "watch [my] tone." I replied with a meek "Yes, sir."
Later, I explained in person that since he was aware of my role in the office and I thought we had a relaxed rapport, I was being facetious with him while letting him know I was on top of things. He explained that he thought my email was disrespectful to him and he didn't see it as a joke, nor would he have made a comment like that to anyone in an email. I said that in the future I will be more careful how I address him.
I was taken aback. I reached out to some of my respected advisors, most of whom responded that he is taking the matter way too seriously. In hindsight, maybe his fur was ruffled because I hit upon some truth about his attention to things around him. We managed to smooth things over. But now I feel like I need to reel in what I thought was an open, friendly casualness between us and let him act out being my boss. How out of line was I?
Answer: When I imagine a 20- or 30-something telling someone 30 years his senior to "watch your tone," it brings to mind my toddler scolding my 19-year-old cat.
It's not that younger managers aren't entitled to respect and deference. But demanding that subordinates Respect Your Authori-tah is counterproductive at any age. At most, it wins you fear — to your face, anyway.
At any rate, it doesn't sound as though you and your boss have the necessary foundation of trust and respect to support the casual banter you enjoyed as peers. Even though you may have intended to send him a winking "It's all taken care of," what he heard was, "Chill, Sparky, I'm on it." (Murphy's Law of Work Email: Any joke that can be misinterpreted will be. Karla's Corollary: So don't hit "Reply" or pick up the phone until you've cooled off.)
Maybe, as you said, he's self-conscious and thus touchy about any suggestion that he's not on top of things. Or maybe he senses that you see him as "act[ing] out" the boss role, rather than being the boss.
For now, stay friendly, stifle the sass and see how he grows into his role. Maybe someday "You watch your tone!" will become an in-joke you two share at a farewell party.
Karla Miller writes an advice column for the Washington Post on navigating the modern workplace.