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Interested in pursuing an advanced degree or professional certification, but strapped for cash? Shudder at the thought of taking out (even more) loans and being saddled with debt for the foreseeable future? Keep reading.

One of Richard Branson’s nuggets of managerial wisdom is, “Train people well enough so they can leave, treat them well enough so they don’t want to.”

A company’s investment in the training and education of their employees is of paramount importance. Some bosses realize that, and offer generous tuition reimbursement, assistance packages, or educational fellowships. Others need some convincing. In either scenario, if you’re eager to pursue an additional degree or certification, it’s helpful to arm yourself with the knowledge of what’s possible in regard to having work pay for your education. Then you can make a strong case on your way to free, or inexpensive, instruction that’ll stand you in good stead for the rest of your career.

How to convince your boss to invest in your education. via udacity.com

First, get a handle on what kind of programs exist in the workplace. You may not have even realized it was in the realm of possibility for your employer to help foot the bill for advanced education. Good news: plenty do. Some companies partner with a nearby college or university; some offer scholarships as part of their benefits package; some extend financial assistance on a case-by-case basis.

To name a few examples, AT&T provides tuition aid of up to $5,250 annually for full-time employees, reimbursing up to $20,000 for courses leading to an undergraduate degree and $25,000 for courses leading to a graduate degree. Starbucks offers a “College Achievement Plan” for undergraduates who earn a degree through Arizona State University’s online programs. Chevron offers tuition reimbursement for up to 75% of an employee’s education.

Step 1: Do Your Research

OK, so you know that it’s possible, and even common, for companies to help out their employees with managing the cost of higher education. The first step in convincing your boss to manage yours is to research your existing company education-reimbursement programs, the educational opportunities available to you, and the costs and logistics of those opportunities.

Check your employee handbook, intranet, or HR materials to determine if any company policies surrounding tuition reimbursement exist. Also look into whether or not your company qualifies for tax deductions for reimbursing education. If you’re not sure, check with the Accounting or HR department.

When it comes to continuing education, gone are the days of distance learning via correspondence course. Flexible options abound for full-time workers that enable you to balance your workload with a full courseload on your own time, whether you want to take nighttime or weekend classes in a physical classroom or learn from the comfort of your home or a coffee shop. Start by Googling around, asking friends, family, and professional contacts for recommendations, and browsing through online forums about continuing education.

Once you’ve pinpointed the precise program you’re interested in, figure out how much it will cost and what the time commitment will be. Be ready to specify what steps you’ll take to ensure that the commitment won’t affect your work output. Will you forego a lunch hour for the duration of the program? Offer to be on call on Saturdays? Provide your manager with monthly status updates that detail what you’ve been learning, so the bang-for-the-buck is crystal clear?

Step 2: Arm Yourself with Answers

As with any presentation or proposal that’s the jumping-off point for a discussion, think ahead: what questions will your boss or HR representative ask, beyond the basics addressed above like cost and time? It might be helpful to sketch out a script that includes sample dialogue for how you’ll respond to each question. Here are some examples.

Question: What are the short-term benefits for the company paying for your education?

Answer: “To begin with, we’d be establishing a strong mutual investment. It would allow me to demonstrate how serious I am, both about my career and about my role here, and to know how serious you are about setting me up for success. In addition, the enhanced skills I’d gain would serve me well in being able to take on additional assignments and to assume even more of a leadership role on my team and in the company at large.”

Question: What are the long-term benefits for the company paying for your education?

Answer: “This contribution would strengthen my loyalty to the company. I would be grateful not only for the financial investment, but also for this indication of my value. Both of those measures are priceless. I’d also be sharing what I learn with others, which would benefit the company overall.”

Question: What’s the financial payoff for the company? Why is this worth the money?

Answer: “Contributing to my continued education may be cheaper than hiring and training a new employee for the role that I’d be able to fill with the added skills I’d be gaining. It would also enhance the reputation of the company as one that both highly values its employees and generously demonstrates that value. It could attract new talent—even new clients and contracts—which would in turn enhance the bottom line.”

Step 3: Prepare Your Own Questions

Got a green light or at least a “maybe”? Before you sign on any dotted lines, you’ll want to ask your own serious questions. You’ll be protecting yourself, and also come across as thorough and professional.

Question: How exactly will tuition be refunded?

Some companies write a check to the school; some will pay you directly. You’ll want the nuances of the financial arrangement to be clear to all parties.

Question: What academic standards must be met?

In some cases, sub-par grades will cost you your free pass. Make sure you find out what happens if you don’t meet a certain grade point average. And, of course, be ready to demonstrate to your boss how seriously you’ll take your studies and how diligently you’ll work to make the investment worthwhile.

Question: How long must I remain with the company?

Note that some companies that pay for education require employees to sign a loyalty contract. You may, for example, be asked to commit to staying with the company for a certain length of time after you complete your education. Of course, any loyalty contract can be negotiated, and there are different agreements for different types of education. If you break it, it may just mean that you’d have to pay back some or all of the money that your company invested in your education. Make sure to understand and feel comfortable with the terms before you sign a contract.

Question: What happens if I have to stop attending class?

Inquire into what would happen if a family emergency, health problem, or other personal circumstance precluded you from being able to continue your program. Would you need to reimburse your company for the tuition they’ve already covered?

The Bottom Line

Earning a degree, a certificate, or a credential is a great way to bone up on advanced skills in your field or to embark on a new path toward another field. But education can be expensive. One avenue worth exploring is making the case to have your company subsidize your studies.

Convinced they won’t go for it? Too nervous to ask? Use the step-by-step roadmap above and you’ll have a strong footing. Convince yourself first that it’s worth the ask; then you’ll be more confident in convincing your company. You won’t know until you try.