What's the most non-awkward way to ask your boss for the money he owes you?

Next time you see him (and don’t go into his office SOLELY to talk about the money. Bring it up LAST among other topics) play dumb and open with “Did you ever give me the money for the platters?” He’ll either respond with yes or no. To either one you reply “No. You didn’t”.

Mention him in person, very casually, while you are talking about something else. Be specific about it, make some sort of plan, don’t be as nonchalant as you were in your gchat conversation but don’t be demanding either. I would acknowledge that he likely forgot it and that is why you are bringing it up if the conversation was tense, but if it was smooth I would likely just get down to the business of compensation. A possible example… maybe at the end of the conversation, “Oh, one last thing, about those food platters from Event X…” This could be enough of a hook for him to offer compensation and possibly an apology, to which you could include “Oh it’s no problem, I just figured you’re so busy and I would remind you about it.” Above all, remember, It’s not personal, it’s business.

Oh, a last thought, doing it in person is best because it will get an immediate resolution of the situation. Doing it by email or text stands the chance of the person not being there or shutting off their computer without seeing it, etc.

Next time you see him say “I’ve got that money I owe you”. He’ll say” I didn’t know you owed me money. Then you say, “Oh yeah. You owe me money.”

“Oh Hey, I just remembered. I was cleaning out my wallet this weekend and found the receipt for those platters I bought for Donna’s wedding party a couple of months ago. The total came to $28.50.”
Don’t let your boss think you are a push over.

Does your company have reimbursement forms? If so, fill one out and put it in his box. He probably just needs a reminder.

If not, just casually say that you know he has a lot going on and has probably forgotten about it, but you still haven’t gotten the money for the platters you bought a couple of months ago. Give a specific time for him to give it to you. Tell him not to worry about it today; next week when he comes into the office will be fine.

If you’re not comfortable talking to him, send him an email. I still don’t think he’s trying to get out of it; I think he probably forgot.

Interesting ideas.

@SirBailey: I’m not sure playing dumb is the best tactic. I have a better relationship with my boss than that.

@dynamicduo: This sounds pretty reasonable. Before asking the question, I was leaning toward asking on Gchat prior to a meeting. This is because we typically Gchat about the topics we need to discuss before our weekly meetings so that both of us will bring all of the necessary documentation. I was considering asking him toward the end of our Gchat conversation prior to our meeting next week. This way, he would have the money for me when I came to his office. (If I asked during the meeting, he might not have cash on him.) What do you think about that idea? I could go with the same concept and ask him at the end of our Gchat conversation, after we had discussed the other topics to be discussed. Since we’d be in the middle of the conversation, I wouldn’t be risking him not being at the computer. And he’s not the type to dodge something like this.

@Russell_D_SpacePoet: ...I assume this was not a serious suggestion!

@Lupin: This seems reasonable as well. What mode of communication would you suggest?

@Supacase: Yes, we have reimbursement forms, but only when it’s the company’s money. This was an event that my boss threw out of his own pocket, so the reimbursement forms would not apply.

“Yo boss, check it out. I need the benjamins that you’re holding back from me. The lack of funds are putting a cramp in my groove not to mention my lifestyle. Get with the program and cut me a check, you dig?”

I’d use your normal mode of communication with him. Open door, GChat, lunch conversation.

i’m with @Bluefreedom here.

Ask if they have some sort of check request form he wants you to fill out for the reimbursement.

I like the “came across the receipt” idea, it should be spoken in person, and you don’t have to pretend to talk about something else first.

Be matter of fact about it. Try to avoid any talk like “you been saying this for 2 months” or anything that could come off as aggressive.

Make sure you have the receipt and be upfront about it. “I didn’t mind covering for the food, but I do need to be reimbursed for the expense. I apologize for not clearing it before now, I forgot about it.”

This clears both of you of the forgetting (I know you didn’t, but if you are nervous about approaching it, that is one way to deal with it) – he’ll probably respond with an “Oh, I forgot about it, too!”

It’s not really a bid deal; however, if you are uncomfortable in these situations, try to avoid them in the future. Asking to be reimbursed for your money shouldn’t be something you are afraid of doing. Believe it or not, someone could not that you were too timid to approach money that was owed to you. Believe me, some bosses watch every detail.

Good luck.

@icepebbles Depends on your personality if you can pull it off. For me with my boss I would. You’d be amazed how a little levity can ease situations.

say; ‘excuse me, but I believe my paycheck is due sir’

I have a similar situation going on now. When he’s out of his office, I’m going to go in and extract the $85 invoice he owes me from the pile of crap on his desk and place it in his chair. He’s about 70 and thinks his forgetfulness is funny. Frankly, it’s wearing thin.