how do I ask my boss for the money they owe me?

A reader writes:

I am currently interning with a small environmental non-profit. I started the internship in February, at a time when essentially none of my target organizations were hiring, and I was looking for a position where I could gain experience in the field. Throughout the interview process, my contact and other staff members who interviewed me were very honest about the fact that although normally the internship comes with a stipend, it was going to be an unpaid position due to the organization's financial situation. I was offered $50 a month to cover some of my transportation costs getting to and from work, but that was all. I accepted because it IS a great experience with an outstanding small nonprofit, and I was really excited about the opportunity.

The first day of my internship, my contact - the only person with whom I had contact outside of my interview - left to go to the field for a month. That first month, I had trouble getting assignments from the staff, and no one brought up the transportation reimbursement. It wasn't an important issue and I figured the organization needed the money more than I did, so I didn't push the staff about getting the $50. When my contact returned, I reminded her about our agreement to cover transportation, and she agreed to speak with the EVP of our department about getting that money for me. She also helped me find assignments, and my workload has been fine ever since.

As time progressed, it became more apparent to me that because of the high volume of candidates, I was not going to get a job offer from my favorite organizations in the first 8 weeks, like I originally (and naively) believed. So I agreed to extend the length of my internship to 6 months, pending a job offer. That is, I would stay until the end of August unless I got an offer for a full-time job. Again, I spoke with my contact and she promised to speak with the boss about getting my transportation money.

Now it's nearly the end of my internship, and it turns out I need that money; I'm moving into a new apartment and need it to cover some initial expenses. I know that the situation is partially my fault, because I didn't push harder to get the reimbursement in the beginning. Things are complicated by the fact that the EVP has since become the Interim President & CEO until a new CEO is found, and I have been acting partially as his assistant so he is my direct manager. He is (understandably) maniacal about the organization's budget; in all seriousness, last week he told a staff member that she couldn't buy a microphone to talk to our field staff in Africa over Skype, even though it would save the organization thousands of dollars to avoid the telephone charges. At this point, I'm owed $250, but I'm nervous about asking him for a lump sum.

Should I go back to my original contact or should I approach my boss directly? Should I just accept the fact that I'm not going to get that reimbursement?

The contract I signed didn't contain a mention of the transportation money, but I do still have a copy of the email in which that offer was extended.

You need to take this up with them right now, today.

This is not okay. They made a financial agreement with you that they are not honoring.

Go speak with the person who originally made this agreement with you. Say something like this: "We made an agreement at the start of my internship, and I've been counting on that money. It's now at the point where I can't put it off any longer; I need this resolved right away." Insist on having a concrete plan for when that check will be issued.

If she tries to put you off, don't let her. Say something like, "I would feel much more comfortable if we could resolve this right now. We talked about this earlier and it was supposed to get resolved, but then it never did. I really need to resolve this right now."

And by the way, there's no reason it should take longer than next week. If someone brought this to my attention, I'd be mortified and have the check for them that same day. If they put you off or tell you it'll take a month, stand up to them. There's no reason why they should have trouble writing a check for such a small amount of money. Do not let them mess around with this any longer.

If they balk over paying you $250 that they agreed to pay you? In any case, but especially when you've been working for free? Run.

By the way, it's possible that your contact never got official authorization for the offer she made you, and that's why she's dragging her feet now. Doesn't matter. You accepted the offer contingent upon that, and they need to honor it.

Now, go to talk to them right now.