KNOW YOUR EMPLOYER

Before approaching your boss, it is of paramount importance to understand the state of your company.  Are economic times lean?  Is a massive reorganization underway?  These could be hindrances or they could help you structure a solid case.  The key is to have an idea of what is happening internally at the organization and use it to strengthen your argument.

A great way for your organization to stay with the pack or excel in an industry is to staff an educated workforce.  If you can specifically spell out ways your degree will help the organization, you will have laid the groundwork of your case.  Be as specific as possible.

Also, is an advanced degree or certificate officially required or encouraged for the position you have your eye on?  While it is true that the greater your education, the greater the number of doors you create for yourself, some positions simply do not call for it.  Make sure the work and expense are necessary.  Look for trends in people's education who currently or have previously held the position(s) you are interested in.  Glean information by asking your co-workers or approaching the individual about their academic past in a friendly way.
 
KNOW YOURSELF

You also need to be clear on what you want to study and why.  Cause let's be honest, improving your company's talent poll is a secondary goal at best.  Raising your stock as a potential job candidate, and as a person, is first.

Make sure you choose a subject that you have genuine interest in and can help you get ahead - or transition into something you want to do.

It's important to be honest with yourself on how long you plan to stay with the organization you are pitching.  Many employers will have you sign an agreement stating that you will stay employed with them for X number of years. Should you leave early, you will likely be responsible for a portion (or all) of the money the company spent on your education.

If you already have one foot out the door, the last thing you need is added pressure to stay in a bad marriage,  As with most career moves, you need to know yourself before you make a move.  

KNOW THE SCHOOL

While online degrees have certainly become more mainstream, they are certainly not on par with their brick and mortar counterparts. Adult learning facilities can play a key role such as Benchmark Learning, who offers Remote Learning, eLearning, Personal Mentoring and Mentored Learning modalities in addition to instructor led. 

There's a good chance you'll have to "defend" the school to your employer, especially if it's one without a physical building.

This is the real world.

Your goal is to be as prepared as possible and make the strongest case you can.  How long has the school been in business?  How many students do they have?  Do they have any affiliation with nationally-recognized organizations?  These are the types of queries you should be able to answers to all question-askers.

KNOW YOUR BOSS'S CONCERNS

As I mentioned earlier, your primary purpose in continuing your education is self-improvement.  Any boss worth his or her salt will recognize this.  Your job is to disarm them as best as possible, assuring them that this will likely be the last stop on your career train.

Since I'm a tremendous fan of truth and honesty, I think it's OK to be upfront that this endeavor is about you AND the company (not necessarily in that order).  Anything else is ridiculously transparent.

There's another hurdle.  It's something that's on your boss's mind constantly: money.  You are going to have to justify that the money the organization spends on your classes will come back to them two-fold.  Get some projected numbers to back up your claims.

KNOW YOUR POSITION

You'll have a much better chance of getting your tuition approved if the education relates directly to your current job.  If it's not an exact match, you better be able to explain how it fits into your career track - and more importantly - the company's goals.

If you want to take classes that clearly fit within a department other than your own, you need to be able to explain why it's worth their time to cough up the cash.

KNOW YOUR FINANCES

Every company has a different policy when it comes to who will initially pay for your classes.  Years back, I made the case to take a specialized course.  The company agreed to pay.  The only catch was that I had to pay and they would reimburse me 6 - 8 weeks after the course was completed.  At the time I simply didn't have the expendable cash.  I also didn't want to put the expense on a credit card and be stuck with several months of interest.  Be sure you have an idea of what you're willing and capable of doing from a financial standpoint before you make your pitch.

WAYS TO LOBBY FOR EDUCATION

• Outline how the training will benefit the company in your current role (and where you may end up). At the very least, this will put your ambitions within the organization on the table.
• Reinforce your commitment to the employer. Share examples of how this increased training will help you stay on top of the latest trends.
• Show how the competition has employees with this level of education and how it offers a reimbursement benefit. In this day and age—when you can find anyone on the Web—getting this information is not as difficult as it sounds.
• Have your paperwork in order, and do your research on the program so you are ready to answer any and all questions. Make it easy for your employer to say "Yes," difficult to say "No."
• If you get the runaround or are rejected, ask when you can broach the subject again. Show that you are committed and that you won't simply go away. (So many bosses I've run across just want to "send you away" as quickly as possible.)
• Don't circumvent your boss, but do have conversations with HR and upper management about your desire to further your education. These can be casual in nature and could lay the groundwork for when your boss approaches them on your behalf.

Especially with recruiters and talent managers becoming ever more mindful of a perceived talent shortage. Developing internal talent streams is an important topic.

That said, the questions listed in Know the School are only the beginning, and not the most crucial.

1. Is the school accredited? If so, by what organization? In the U.S. regional accreditation is king, nothing else matters. As mentioned above, accreditation/affiliation/approval by a national professional organization is also good, but apply on program-by-program.

2. What is the rigor of the program? What is the quality of the curriculum? If a school is not going to work you and push you, it is not worth your time and will not add any real value to you as an employee or job candidate. There is a very real difference between convenient and easy.

3. What student services are offered, who provides them, and how are they delivered? Prospective students should look for schools that are helpful and supportive beyond enrollment. Possibly ones that help define and build your career?

4. If online, what is the platform and delivery model? Here is where you want ease-of-use, plus access to tools that suit and support your learning style. Also know the difference between synchronous and asynchronous.

5. You want good instructors, well trained (especially in online teaching models and practices).

Continuing education is great and necessary. Mistakes can be very costly in time and money, so go in as well-informed as possible.

Reference: http://www.jobacle.com/blog/2008/1/30/get-your-employer-to-pay-for-an-online-degree.html
Reference: http://www.usnews.com/money/blogs/outside-voices-careers/2009/01/05/how-to-get-your-company-to-pay-for-college