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Beg Your Boss for a Tuition Assistance Program

Tuition Reimbursement Equals Cash Back


Thanks to online learning, you don’t need to leave your job or change work shifts to earn a degree. But even going to college online presents that age-old challenge: how to pay for it.

Employers want to pay for your classes—or at least career advice websites are constantly telling you this. But the realities of persuading your boss to pony up for a tuition assistance program for an online degree can be sticky.

Lots of mega-corporations offer tuition assistance programs for college among their smorgasbord of benefits. Yet, even big firms can have stingy track records when it comes to actually paying out.

Smaller companies may have modest tuition assistance plans, or none at all, but that doesn’t mean it’s out of the question to ask.

Below, we’ve compiled five tips to help you beg your boss for college cash if you have no formal tuition assistance program (TAP). These tips are perfect if you work for a small company or if your company has no formal reimbursement program.

1.) Lobby For Tuition Assistance 

“The well-prepared negotiator has not only thought through what they need or want, but what the other side needs,” says Terri R. Kurtzberg, author of The Essentials of Job Negotiations Strategies, and associate professor of management and global business at Rutgers University.

Let this be your mantra. What courses or path of study would your boss be most inclined to support? How does your academic plan coalesce with your work path? If employer tuition reimbursement for college degree classes is your goal, make sure the courses you want to take have a clear connection to your job and/or the company’s goals.

Be prepared to point out to your boss how what you learn in any college class will help boost the company’s bottom line as opposed to your personal resume. (If not, be ready to pony up your own tuition, at least in part.)

2.) Think Like Your Employer

When it comes to your boss, Kurtzberg says to consider: “What are some of the constraints they are probably feeling? What are some of the reasons why this might be making them nervous, and how can I solve this problem for them?”

Don’t stop there. Let this thinking guide the dialogue you have, and take initiative.

“When you actually get into the situation, ask those questions out loud: ‘What are your concerns about my going back to college or taking this course?'” she says.

Your boss may worry that college means you’re hoping to leave the job. Or switch departments. Or that you will not be available for big work projects.

“See if you can pick them apart and come to acceptable solutions, instead of just reselling the pitch to them,” says Kutzberg.

If your job has no tuition assistance program and your boss is the decision-maker, Kurtzberg says this might be a very positive thing.

“The silver lining of dealing with a small company like that it is, you have the opportunity to shape the policy going forward.”

One thing you might say to convince your boss? “Having this policy may help you in the bigger picture. It may help you in recruiting employees, because it’s appealing to other people in the market,” she says.

Watch out though, you don’t want to stumble when it comes to the next point.

3.) Be Honest About Your Needs

Though you want to effectively “sell” your case, Kurtzberg warns against going overboard.

“Be balanced about it,” she says. While returning to college is potentially a benefit for the boss, “You can’t try to sell an idea like this as if it’s really just for them. That comes across as disingenuous,” says Kurtzberg.

“There’s a bit of diplomacy that’s needed in this. You have to balance it with ‘this is good for this company and I want to help everybody.’ But don’t disown that this important for you,” she advises.

4.) Align Your Expectations With Your Employer

Plan your academic needs with your boss if you want a tuition assistance program that covers not just work training but degree classes. And make sure the game plan works for both parties.

“As much as possible—if you can all align your expectations, the better,” suggests Kurtzberg.

“If the expectation from your boss is ‘Yes, you’re leaving at 4 o’clock to go to class, and that’s it,’ but then your books come out twice a day,” they might not be happy, she notes.

“If you feel that’s a natural part of it, and you can lay it out as part of the proposal, do, but as, ‘I’m also hoping for this and that.’”

Avoid laying on any extra surprises, basically.

Lulls in the work day and lunch hours are perfect for getting online schoolwork done in some offices, but does your boss approve of that?

Will you need days off for taking tests at a site location? Kurtzberg suggests negotiating schedule needs when discussing the approval of employer tuition assistance plans.

“If I were doing this, I would approach it as, ‘Could we talk about maybe one floating day off and one concrete day off right before exams,’” she says, “but building into the conversation that the whole schedule should be revisited over time.”

5.) Keep the Conversation Open

If all goes well, you’ll complete several courses—maybe even a full degree—with employer tuition assistance paying for your classes. However, each semester will bring different needs and may require some re-negotiation with your employer.

“You won’t know exactly what you need until you’re in the middle of it,” warns Kurtzberg.

As long as an open and frank discussion exists between you and your boss, you should be able to establish the groundwork with your employer by stating what you might need during frenzied finals in a worst-case scenario.

“The idea that it’s better to ask for forgiveness than permission really doesn’t apply here. You really want to make sure everybody is on board with what’s going to happen,” says Kurtzberg.


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Jess Wisloski


Jess Wisloski is a journalist and videographer based in Vermont, and former editor of Yahoo NYC. Since 2001, she has written for various publications, including the Village Voice, the New York Times, the Villager, the Brooklyn Papers and various metro weeklies. She is a journalism graduate of NYU.