Ethics: My Direct Report and Friend Wants PTO When We’re Understaffed. What Should I Say?

A Reddit member writes: I have an employee who was my friend before I became his boss. We’ve been good friends for more than a decade. At times, we blur the boss/employee/friend line and it makes things difficult. I have to deny his request for PTO around the holidays because others have previously been approved for the time so we won’t have coverage if I approve his and it will look like favoritism. How would you have the conversation with him?

Minda Zetlin responds:

You need to have a tough conversation. Not with your friend, with yourself. It sounds like he didn’t do anything different from any of your other reports. He asked for PTO around the holidays. He just made the request a little too late.

As several who responded to your post have said, your task now is equally straightforward. Tell him the truth. You might have been able to accommodate him if he’d asked earlier, but now that others have time off already scheduled, it’s no longer possible. You won’t have enough people working those days if he goes too. This is no different from the response you’d have given to someone who wasn’t your friend.

Unless you’re withholding pertinent information, it doesn’t sound like your friend was attempting to gain special treatment from you, or do anything other than be a straight-up employee. So based on what you’ve said, it sounds like you’re the one blurring the lines between employee, boss, and friend. He seems to be clear on the difference.

Has he ever requested special treatment?

This is why you need to have a serious talk with yourself before you have the conversation with him. Ask yourself if he has ever requested special treatment from you as an employee. If the answer is no, then ask yourself why you’re having so much trouble managing the boundaries between your work relationship and your friendship. Because it doesn’t sound like there’s a problem on his side.

If he hasn’t requested or expected special treatment up till now, then it sounds like he understands the necessary distinction between your roles at work and your friendship outside work. In that case, there’s no need for a whole discussion about the appearance of favoritism. All you need to say is something like this: “I’m so sorry. I’ve already approved time off for others who asked earlier, so I can’t spare you then. I’m happy to give you time off right after the holidays if you would like.” The fact that you’re both his boss and his friend will only be a problem if you make it into one.

Update:

The Reddit member talked more with the friend, and learned that one of the requested days off was for a doctor’s appointment. So the friend was given that day off only. For the rest, the boss explained that there were too many projects in the works, and too many others taking time off for the friend to do so as well.