According to Inc, a manager posted on Reddit seeking advice about a difficult personnel situation involving a direct report who is also a close friend of more than ten years. The manager needs to deny this employee’s request for paid time off around the upcoming holidays because other team members have already been approved, leaving the team without adequate coverage. The manager’s primary concern is that approving the request would appear as blatant favoritism. The source argues the employee did nothing wrong, simply making a late request, and that the manager is the one blurring the professional lines, not the friend.
The Real Conversation
Look, the advice to “just tell him the truth” is technically correct. But it’s also kind of naive. Here’s the thing: if this were any other employee, you’d have that five-minute chat, they’d be disappointed, and you’d both move on. The entire reason this is an “ethics” question posted to the internet is because of that decade of friendship. That history doesn’t vanish with a job title. So while you’re rehearsing the “coverage” speech, you’re probably also worrying about awkwardness at your next BBQ or your friend feeling like the promotion changed you. The business answer is simple. The human answer is messy.
Who’s Blurring The Lines?
The source makes a sharp, and probably accurate, point: the employee seems clear on the roles, but the manager isn’t. Think about it. Your friend put in a PTO request like a normal employee. He didn’t text you “hey bro, hook me up for Christmas.” He used the proper channel. You’re the one agonizing over it as if it’s a personal betrayal instead of a routine staffing conflict. That’s the blur. You’re importing the emotional weight of friendship into a standard managerial duty. That’s exhausting for you and, frankly, unfair to him. It sets up a dynamic where he can never be sure if he’s being treated as an employee or a friend, which is a terrible position for any report to be in.
The Harder Talk
Denying the PTO is just the symptom. The disease is the undefined relationship. After you have the straightforward “coverage” conversation—and you must—you probably need a second, more important one. Something like: “I hated saying no to that. It made me realize our friendship makes me second-guess my management decisions, which isn’t good for the team or for us. How do we navigate this going forward?” That’s scary. But it’s the only way to prevent this same anxiety every single time you have to give him feedback, assign a tough project, or, yes, deny a request. You have to build a new, professional layer on top of the friendship for work hours. Otherwise, you’ll keep feeling like you’re choosing between being a good boss and a good friend, when you should be able to be both, just in different ways.
It’s A Process
This won’t be fixed with one chat. You’ll slip up. He might test the boundary. The key is consistent action. Treat his PTO requests, performance reviews, and project assignments with the same detached, procedural fairness you use for everyone else. That’s not being cold. It’s actually the most respectful thing you can do. It proves you see him as a capable professional, not just a friend you’re doing a favor by employing. And in the long run, clear boundaries protect the friendship from the inevitable resentments that sprout when work and personal life get muddled. So yeah, deny the holiday time. But see it as the first step in a much bigger, and more necessary, professional reset.
