Why does my boss keep asking me to tidy my immaculate desk?

The person I work under suggested to me that I need to tidy my desk. I was surprised because I like to keep my work area neat. To humour them, I moved some things around and put a few items in the drawer. But my boss suggested it again. I took everything except my laptop off my desk. Yet again, my boss said I needed to tidy my desk.

This is a person I don’t want to upset or embarrass, but I’m starting to feel like asking what the hell they’re on about. Before I do that, is there another angle I have to think about?

It could be good-natured but inept, a genuine attempt to have some fun at your expense by playing a prank nobody else gets or finds funny.Credit: John Shakespeare

This sounds to me – not for the first time in Work Therapy history, I might add – like part of the plot from a Simpsons episode. Namely, the one where Mr Burns recruits a bunch of Major League Baseball ring-ins for the nuclear power plant’s softball side.

One of those players, a New York Yankees first baseman by the name of Don Mattingly is told by Mr Burns during training to “get rid of those sideburns”. He doesn’t have any and seems mystified. Mr Burns demands that he shave them again later in the episode.

Mattingly is again perplexed but returns towards the end of the episode having shaved a horizontal line across his scalp, from temple to temple. Mr Burns screams at him, telling him his failure to comply is the last straw. He sacks him from the team.

Could it be that your manager is a doddering, billionaire whose 100-year-old brain isn’t processing language like it once did? Probably not, but if you just yelled: “Yes! How did you know?” There’s your answer: your boss doesn’t know what a desk is. No need to read on.

Off the team: Don Mattingly is berated by Mr Burns over his 'sideburns'. Credit: The Simpsons

Seriously though, I do think that this kind of bizarre Simpsonian misunderstanding, and the utter befuddlement it creates, is much more common than some of us would like to admit.

Just like in the Simpsons episode, I don’t think the blame lies with you. In fact, you, like Mattingly, have gone above and beyond to comply with what seems like an evermore absurd demand.

You asked if you should be looking at this from another angle. Well, the only other way I think you could approach it is less generously: even if your desk was messy, does it really matter? Unless it’s so disgusting that it’s attracting ants or emitting a foul stench, what’s the big deal? Why is this worth anyone’s time?

As for what’s going on here, my guess is that your boss has made a mistake and is just doubling down on it. They may have someone else’s desk mixed up with yours. They may have you mixed up with another employee. Or they may be using “tidy your desk” as some kind of buzzwordy metaphor or euphemism, and incorrectly assuming you are familiar with it.

It could be good-natured but inept, a genuine attempt to have some fun at your expense by playing a prank nobody else gets or finds funny.

I get that you don’t want to offend this person – a remarkable proportion of Work Therapy questions imply the need to protect the feelings of some thin-skinned dolt in a position of power – and I think you can mention this without going straight to “what the hell are you on about?”

I get the strong sense from your longer email that these managerial directions are happening well away from your work area. Might there be a chance at some stage during the week to bring your pristine desk to your boss’s attention – not just verbally, but as part of an exhibition of sorts?

To avoid any chance of wounding their ego, you could make sure it comes across as a show of pride on your part rather than an attempt to prove them mistaken.

If you do that and the requests keep coming, I wonder if this might be a misguided attempt at teasing. It could be good-natured but inept, a genuine attempt to have some fun at your expense by playing a prank nobody else gets or finds funny. Or (less likely, I admit) it could be a little bit nastier: a practical joke that everyone, except you, is in on.

If this latter possibility is the case, what you’re facing isn’t like The Simpsons episode at all, but something more like the movie The Truman Show. By tidying your desk to a state of stark minimalism, you’re playing right into the prankster’s hands – providing them with perverse entertainment.

It’s a slightly creepy concept, and I think if you suspected it at all, you’d be well within your rights to turn your workstation into a proverbial bomb site and see whether the whole weird game finally comes to an end.

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