Manager charged $718 in hotel expenses on his employee's card in April, he still won't pay them back months later in August: He told me he'd pay me back the next morning as soon as accounting fixed the issue. That was April 27'

Having a friend or family member who borrowed money and won't pay you back is annoying. But what do you do when it's your manager who refuses to pay back money you loaned to him on a business trip?

It's pretty natural to want to be seen as helpful in our workplace environments. I think we hope that our faith will be rewarded, and in the back of our mind, we are a little bit wary of telling an employer "No," as well. 

It's not all that uncommon for one negative thing about you to stick in someone's mind—especially when that someone is your manager. As an employee, the last thing you want is for some comment about how you weren't helpful or "a team player" to come up at the wrong time to the wrong people in some boardroom meeting. And then, to have this begin a narrative about you (and against you) that spirals out of control.

These things do happen, and it can be impossible to claw your way back up that slippery slope once the wrong word has been spoken in the wrong ear.

This is why managers need to be careful about the demand they're placing on an employee, no matter how personal the relationship might be between them and how informal the situation is. The blurring of these boundaries—well, it's going to create some problems. 

A manager asking an employee to cover a business expense is an immediate red flag. And while the power imbalance already puts unfair pressure on the request, here there isn't even a grey area. There's nothing personal about asking them to effectively contribute their own money to the business and it should never be a request. 

Sure, it's often the case that an employee will "spot" the company money on a business trip by spending their own money at the time and asking for reimbursement later. I still think that is a weird practice, but it always exists as an established process.

Having your manager off-hand ask you to cover their hotel costs, however, is not. Putting that employee on the spot and then not repaying the amount immediately, and when you said you would, is a major issue. And it repeatedly puts the employee in the awkward place of having to bring it up… over and over again.

Without a doubt, this employee needs to start looking for new jobs. Fast. And find some other way to get their money in the meantime.