Preface: I'm a software engineer at a small-ish company (under 40 people) and I've been there for over 4 years. I was initially hired as QA (I do not have an engineering background) and over the course of 2/3 years, I taught myself (and took night classes) to learn how to code and made the transition. During that process, I figured out that I LOVE DEVELOPMENT. I applied for and got into a graduate program for Comp Sci and it's amazing! I'm learning a lot of theory and I'm becoming a better engineer and problem solver with each class.

Problem: Graduate school is expensive! It's especially expensive when you can't take out student loans or apply for grants unless you're part-time. I really didn't want to sacrifice my work, so I'm only taking one class a semester so neither my education nor my work suffers. At my annual review (early October) I asked my employers about education benefits. (They have both mentioned that they're happy I'm going back to school.) They noted that this hasn't been done in our company before and that we would discuss it further. So I waited... and waited... and it hasn't come up.

I assume this means that they are not willing to offer me any educational benefits and don't want to directly tell me that. The problem is that I would really like to give it one more go before I make a decision about next steps in my professional life.

One of my co-workers suggested putting together a formal proposal for what I would be looking for with education benefits and research what other companies offer, but I'm not really sure how to present that or how that would come across. Or is it better to be less formal and simply ask the question again?

I don't want to come across as pushy, but I'm also really enjoying school. At this point if I were forced to make a decision between taking a less demanding job and continuing my education full/part time or quitting school and continuing at my current job, I would pick the former. I just really hate that option.

So: Any suggestions for a conflict-avoidant people pleaser who wants to ask for financial support for education that will/already is making me a better employee?

  • The country is important here. Depending on that, pushing a little more might be anything, from expected to really impolite.
    – Dirk
    Commented Jan 31, 2018 at 10:55

4 Answers 4


Definitely just ask if you can set up that follow up discussion. The two most likely results of you asking to have the follow up discussion are:

  • they have you schedule the discussion and you finally get to talk it over, and maybe they approve your reimbursement!
  • they say "sorry, we can't do that right now."

Either way, you've gained clarity on the situation. A third option is they never give you a response, which I'd say would be confirmation that they don't want to give you tuition reimbursement.

I've often had brief encounters with my manager or other leaders in my company where we say "that's a good idea, let's discuss it more later". What I've come to realize is that that actually means "why don't you take the initiative and set up a meeting (that you'll run and be prepared for)".

Oftentimes, my manager and I will simply forget about something we talked about, but if he forgot and I remember and schedule something, he's usually impressed at the fact that I followed through. It's a good reputation to have.

So ask.


Any suggestions for a conflict-avoidant people pleaser who wants to ask for financial support for education that will/already is making me a better employee?

Just ask your manager "Is there any way I could be eligible for some level of educational benefits?". Put the ball in your managers hands and see what happens.

This skill, asking for what you want, is critical to learn as you progress in your career. Do not be afraid to ask for something reasonable, which your request seems to be.

I know one thing for certain, if you don't ask you never will receive. So simply ask the question.


At my annual review (early October) I asked my employers about education benefits. (They have both mentioned that they're happy I'm going back to school.) They noted that this hasn't been done in our company before and that we would discuss it further. So I waited... and waited... and it hasn't come up.

Just ask if you can schedule this further discussion. This will tell your employer that you're serious about wanting to progress this, without immediately saying "where's the money".

If they keep putting off the meeting, then that's a good sign that they don't want to think about this and probably won't want to offer financial support. At that point you can either drop it and consider your future education plans or even your future with the company.

If you do get the meeting you have to go in with the aim of asking them for financial support. Go in with hope that you'll get it, but the expectation that you won't - or at least not all of what you want. There's no easy way to do this, so you'll have to practice just saying something along the lines of:

Are you able to offer me any financial support and if so how much?


Careful... you may be barking up the wrong tree.

I advise you to think about it from the employer's perspective. What do they gain by spending money on you for education?

Why should they invest in your advanced degree? training? coursework? You point out that it is expensive. Why do you think your employer won't think it is just as expensive?

My former advisor asked me to entice local companies to sponsor a PhD. I asked my advisor how much it would cost. At the time it was $75,000 / yr with a (x5) year commitment. I don't know any companies that are < 1000 employees that would invest $375,000 without a high probability of a (x10) return.

Work out the math.

At an expense of $75,000 / yr and gross margin of 50%, the company would have to sell $300,000 / yr of product to fund your education (at no profit to them). Can you guarantee this?

Assuming the company is funded by a Venture Capitalist, the numbers are more crazy: a (x10) to (x100) multiplier on any investment. This means the $75,000 / yr investment must turn into $750,000 / yr to $7,500,000 / yr of your education.

Change the numbers as you wish, but the concept is the same.

Now look at the opportunity cost. They hired you and trained you for (x4) years. If they replace you, an average employee is not productive for 12 mos. So, hiring a replacement (that may already have the degree / training you seek) may cost $60,000 to $120,000 in salary. Add the benefits and overhead and you can estimate this as roughly (x2) the salary. So, the cost of firing you and hiring your replacement is roughly $120,000 to $240,000.

Most companies don't do this actual math, they merely intuitively understand the costs and benefits.

The question you need to answer is:

Why should they spend money on your education instead of hiring somebody that already has the education you seek?

If you have a compelling argument, then you can legitimately ask for the education expense. If not, back off and save your own money. Then take time off from work, go to school full time and get the degree / training you seek.

Making the financial argument I made above may be to your advantage. Even if your numbers are off a bit, it'll show somebody that you understand the investment and the gamble.

If I were your manager, I'd send you to (x1) semester at a time to see if you were dedicated. If you got a B+ or better in the class, I'd reimburse you for the courses after you showed me your final grades. I'd only pay for classes that were based upon hard skills (e.g. skills that were directly applicable and likely not theory) and not soft skills (e.g. abstract learning that did not directly affect the creation of products / revenue / profit for the company.

I value loyalty and knowledge of the business. Less experienced (enlightened?) managers do not. Be careful about over stating your value to your company.

  • I think that the point of (increased) employee value with the education may be a good point to talk about if the management doesn't want to give the benefits. However: 1. The current status is that we are actually not sure if the management doesn't want to give the benefits; 2. I would assume most managers would be able to do the math themselves: 4yrs loyal, motivated employee wants to grow. If we don't provide the opportunity, he may be demotivated and possibly leave. Their answer may as well be a good metric of whether this is really a good company to work for. Commented Feb 25, 2018 at 12:12
  • 1
    As a consultant, I've worked with upwards of (x100) companies, most of them small. Most managers don't do the math. In small companies, they are poorly trained and field promoted. Therefore, they rarely think beyond the bottom line of: where is the money going to come from. They don't calculate the return on investment or opportunity costs. They typically assume that employees are completely replaceable, especially those without the right degree for the job they are doing. Commented Feb 25, 2018 at 16:42
  • Thank you for sharing your mileage, this really comes as a surprise to me. As an off-topic, could you please share: Do people working in these companies usually look happy? Are they usually attempt to pursue self-development like OP? Commented Feb 25, 2018 at 16:54
  • Happiness is subjective and existential. Most people that are unhappy have a mismatch between their expectation and the situation; either can change to make you happy. If you learn to be happy in your environment, you can really enjoy your work - do the things you want to do with more effort, more depth, more fun. Do the other things with the minimum expected effort. My personality is that I learn to enjoy everything and find challenges in everything that I do in such a way that others are inspired by the challenges I find. Commented Feb 28, 2018 at 16:00
  • Most small companies don't have time to think deeply. They expect you to learn what you want on your own to become more valuable. I love to teach. I find that if I learn and teach others the entire group becomes more excited and productive. Commented Feb 28, 2018 at 16:02

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