Halloween is here, and everyone where I work really gets into it. We all wear costumes; it’s a lot of fun! This year I’m thinking of dressing up like one of my co-workers (my boss, actually). Her work style wardrobe-wise is very recognizable, and she wears her hair in a pretty unique way too. Both should be easy for me to imitate. I can’t wait to surprise her! She’s great, by the way; I love working for her… – Name withheld
Honestly, I can’t imagine a scenario in which this would be a good idea.
Sure – it’s been said that “imitation is the sincerest form of flattery.” But it’s Halloween, for pumpkin’s sake. What’s she supposed to think when she sees your “costume”? Hey – I noticed you basically wear the same outfit to work every day? Your hairstyle hasn’t changed since the 00’s? Sometimes you scare me??
I understand the inclination, though. One of the odd side-effects of traditional, top-down management practices is that we spend an inordinate amount of time thinking about, observing, and even obsessing over our managers. Given their outsized capacity to affect our daily work routine, not to mention our career trajectory, this is understandable. The hours we’re expected to keep, the projects we’re assigned (or denied), and the promotions and/or raises we may or may not receive – all of these things are in the ghoulish hands of those we report to. So we pay a frightening amount of attention to their mannerisms, idiosyncrasies, and habits. In that way, we might better judge their mood, or get a feeling for whether we’re still in their good graces or not.
The result of all this is, in some respects, we may know more about our managers than they know about themselves. This makes them tempting targets to impersonate.
But pouring all that knowledge into a Halloween costume is bobbing for disaster. Even if she isn’t outright offended—which she has every right to be—at the very least you’re sure to make her feel self-conscious, and not in a good way. Maybe she wears her hair that way to conceal her pointy vampire ears? Or perhaps the other zombies around the office hadn’t noticed she always dresses in black, making her uncomfortable about doing so in the future?
So in my opinion, resist the urge.
You may get a snicker or two out of your colleagues, but that will almost assuredly be at the expense of your relationship with your manager – no matter how easygoing she happens to be. Not much upside, in other words, and the potential for a whole lot of downside. (You know, like staying out just a little too late trick-or-treating, and having the neighborhood bully steal your pillowcase full of candy.)
I would hate to hear you have to work in costume the other 241 days of the year just to disguise yourself from your manager.
 Estimate based on a five-day workweek, with two weeks of vacation and eight paid holidays per year. Does not include any expectation to work weekends, overtime, or the capacity to work remotely.