I’m Friends With My Boss, and It’s Costing Me Money
What happens when friends get in the way of benefits.
DEAR PETTY CASH,
My boss, who is also a good friend — don’t ask, our relationship crosses all kinds of boundaries that cannot be changed now —always “forgets” to pay my expenses. I know it’s because we are friends, and he is just taking advantage of that, but it’s so awkward to have to ask. I don’t even need the money back, but I do know paying it back is the right thing to do. How should I approach the situation in a way that tows the delicate line between friendship and boss/employee, and get my expenses paid?
I HAVE A CLOSE FRIEND who started at her current company when it was in its infancy. She quickly made friends with everyone on her team. They went to each other’s houses, goofed around at work, and talked shit about the boss together. But then, as the company grew, so did my friend’s position. After three years, she’s still working with some of the friends she made at the beginning — only now, she’s their boss. Sometimes they ignore her directives. Sometimes she’s flippant with them, forgetting that she has to speak to them as employees and not friends. And sometimes, they’re rude to her about feedback; the type of rude that’s relatively normal for a friend who is annoyed at another friend, but the kind that an employee should never be to a boss.
Needless to say, her relationships with her friendployees can get pretty dicey, and it’s not surprising. A close friendship between an employee and a boss is probably one of the most tenuous relationships to navigate. Friendships typically work best when there is an equal balance of power between two people. When one of those people’s job description is “tell the other person what to do,” that balance of power is thrown off.
There’s something specific to your situation that strikes me as particularly concerning, prefaced by two little words: “Don’t ask.” You say that your relationship “crosses all kinds of boundaries,” and the implication here is that you’ve perhaps blurred one too many lines with your good buddy in the corner office. There’s no way for me to know what that might mean, exactly, but in any event I encourage your to, uh, stop crossing those boundaries, whatever they might be. Being friends with your boss is complicated enough without fill-in-the-blank inappropriate behavior.
For now, let’s pretend your boss is simply a friend who gets weird when it’s time to approve your expenses. That in and of itself is concerning, and says just as much about your friendship as it does about his management skills. Think about it: theoretically wouldn’t you be more eager to pay out your friends fairly, and make sure they have what they need? And besides: A responsible, professional boss should care about keeping the books clean regardless of his or her relationship to employees. The fact that he’s not on that wavelength indicates that he’s taking advantage of the situation.
“If he positions himself as a good friend (as you say), you can be direct with him in a fun yet assertive manner that doesn’t damage the dysfunctional rapport you seem to have built,” Dr. Gurner explains. “For example, saying something like, ‘Hey, I think I submitted my expenses a month ago, how about you help a sister out here. When can I expect to see those reimbursed?’ As casual as the approach I recommend is, it’s only because you asked to tow this line between boss and friendship, but let’s be clear: This is serious business.”
Asking him a direct question in a positive, friendly tone is the clearest first step here — that puts him in a position to have to answer you, right then and there, and speak to you as a “friend” who ostensibly cares about your financial well-being You could also try sitting down with him one-on-one and having a more serious conversation. As his employee, speak bluntly about how his sheer disregard for paying out your expenses makes you feel. Be honest, but respectful, and ask him why.
And, if he ignores your requests and concern, Dr. Gurner says it’s time you blow off the normal chain of command and take matters in your own hands.
“Check with accounting or the department processing reimbursements,” Dr. Gurner advises. “Push the process along yourself, even if it’s not a common communication chain.”
It might feel wrong to go over your boss’s head and try to get repaid without his signoff, but the fact of the matter is that if your company promises reimbursement for expenses, but yours aren’t being paid, it’s theft. As close as you are with your boss, you don’t work for him for the sake of the friendship. Additionally, you’re not asking him to pay you back out of pocket; you’re simply asking for his approval so the company can reimburse you for what you’re owed. Your friendship with him shouldn’t impact this transaction in any way.
“Asking for reimbursement isn’t about needing the money,” Dr. Gurner says. “It’s about your employer literally keeping money that should be yours.”
And let’s go back to the boundaries you say you’ve crossed with him in the past, and the reasons you may have found yourself in this situation in the first place. If you want to stay in your current job, perhaps it’s time to reconsider whether or not you can actually be friends with your boss. Clearly, something about your dynamic needs to shift. Even though you say it ‘cannot be changed,’ it can — just like any other friendship, you can distance yourself when and how you need to, even if it means turning down anything social with him outside of the parameters of the office.
Of course, you taking this type of action may result in your dynamic shifting. Even if you get over the fear of making it weird between you and your boss and confront him about this, his reaction could fall anywhere on the spectrum from “totally understanding and apologetic” to “cagey and uncomfortable” to “utterly dismissive.”
Let’s hope he chooses the former, but if not, it’s on you to reexamine how you approach your relationship, both inside and outside the office. At work, perhaps it’s time for you to stop throwing down your card for company expenses. After hours, maybe it’s time to think long and hard about what a “friend” like that — that is, one who ignores your very professional request to be paid on time and in full, in a context that should be totally independent of how you function as friends — actually adds to your life. There's a reason they say don't shit where you eat. But if you must, at least make sure the boss picks up the tab.