5 Proven Steps to Convince Your Employer to Pay for Your Career Advancement Training

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Staying up to speed in your industry and getting ahead in your career means keeping up with technology and continually refining and learning new skills. Some of this can be accomplished on the job, but there’s a lot more to be gained outside the office that will help you advance and get a different perspective. If you want to overcome hurdles in your career and take it to the next level, tackle the challenges head on and convince your employer to pick up the tab.

Do Some of These Obstacles Sound Familiar?

  • I’m challenged with negotiating better payment terms and lower minimums from my vendors so we’re not over extending our budget.
  • I’m fighting with Adobe Illustrator and can’t seem to efficiently translate my ideas from paper onto the computer.
  • I’m frustrated with the current factories we’re using, they’re always cutting corners and missing delivery dates.

Like most of us, you’re faced with challenges in the workplace, and learning how to overcome them could help you achieve your career advancement goals.

Do You Want to Get Ahead?

  • If I could get more lenient terms and lower MOQs from factories, it would allow me to expand our assortment and appeal to a broader market.
  • If I could become proficient in Illustrator, it’d give me the opportunity to design on the fly and have my voice as a designer be heard.
  • If I could find better factories to fulfill our orders, production would come in on time and meet spec.

Accomplishing these goals will add powerful bullet points to your resume, and additional training or continued education can help you get there. Plenty of resources are available to deliver the education you need – think beyond the traditional route of night classes at colleges or vocational schools, especially if you’re not located near a major city. You may find a one day seminar or conference happening nearby that’s offering valuable content, or online training such as video courses, e-books or webinars that offer the skills you need to learn.

Whether you’ve got cash in the bank to pay for this yourself or not, it’s worth asking your employer to foot the bill. Even if they say no, they’ll notice and admire your ambition to further your skills and that in itself is considered a win.

Follow the five step process below to convince your employer to pay for your career advancement.

1. Identify the Skills You Want to Learn

If it’s not immediately obvious what skills you want or need to get ahead, there are a couple of easy ways to brainstorm:

  • What knowledge do people in positions above you have that you’re lacking?
  • What challenges have you faced recently and how could you be better equipped to manage those?
  • What are some projects your friends in the industry are working on that you want the opportunity to be part of?

2. Find a Local or Online Resource to Learn the Skills

Do research to discover the best material that’s accessible to you and relevant to your job:

  • Scour popular blogs that focus on your desired skill – they often list many quality resources or events. Sign up for their email list so you can watch for upcoming opportunities if nothing’s currently available.
  • Ask people in the industry what events or courses they’ve heard about – this could even be your coworkers or boss.
  • Find someone who already has the knowledge you’re trying to gain and ask them how they learned – they’ll be happy to share their information.

3. Define How the Skills Will Make You Better at Your Job and How This Benefits Your Employer

This may be obvious to you, but it will be your most powerful tool in convincing your employer to pay, so be specific:

  • Negotiating better payment terms would allow the company to pay for goods after sales revenue has been generated and getting lower minimums from our vendors would decrease closeouts and leftover inventory.
  • Becoming a more savvy designer in Illustrator would allow me to more quickly create design iterations for sales presentations and edit tech sketches faster for the factory to ensure production is not delayed.
  • Finding better factory sources to fulfill our orders will provide us with more leverage to get better pricing, minimums and quality product. We’ll be able to diversify and won’t rely solely on our current sources, many of which have been missing delivery dates.

4. Explain How the Training Will Not Affect Your Ability to Do Your Job

One of your employer’s biggest concerns may be how this education may interfere with your job – especially if it means missing a day or more of work. Proactively explain how you will make up for time lost. You’ll want to address this even if the schedule doesn’t conflict with business hours, so your boss doesn’t have to ask.

  • The course meets every Thursday from 3-6pm for 6 weeks, and I’m prepared to make those hours up by staying late a couple days each week or skipping a few lunch breaks to ensure I don’t fall behind on my responsibilities.
  • The two day seminar will have me out of the office on Thursday and Friday, but I’ll make that time up by working overtime the week before and after, or coming in for two Saturdays to stay on top of my workload.
  • The webinar meets after business hours, so it won’t interfere with my ability to do my job.

5. Write a Short Proposal and Present It to Your Boss

Take all the information you’ve collected above, prepare a simple proposal and initiate a quick informal meeting. Say something like:

“I’ve got a quick question I wanted to run by you, when can I grab 5 minutes to discuss it with you?”

Make sure you’re ready to talk right then with your proposal already printed in case she responds with:

“I’ve got a few minutes right now, what can I help you with?”

Do whatever it takes to have this conversation in person; requests like this are much easier to deny via email or other digital forms of communication.

Use This Template and Fill in the Blanks

Use the below script, customizing everything in [brackets] with the data you’ve gathered and editing words where appropriate, or use it as a guideline and write your own proposal.

Dear [Sarah],

I’ve done a lot of research on [becoming more proficient with Illustrator], and I found a great [online course] that would [teach me many valuable skills].

Becoming a [more savvy designer in Illustrator] would allow me to [more quickly create design iterations for sales presentations] and [edit tech sketches faster for the factory to ensure production is not delayed].

The [course] costs [$197] and [meets every Tuesday from 5-7pm for 6 weeks]. I realize this interferes with my work schedule, so I’m prepared to [stay an hour late on Mondays and arrive an hour early on Tuesdays] so that I don’t fall behind on my responsibilities.

As I’ve outlined above, the knowledge gained would allow me to perform my job more effeciently and benefit both the company and me. Because this has a directly positive impact on the company, I am requesting the reasonable expense related to gaining these skills to be compensated.

Thank you for considering my proposal,

Dealing with Denial

If your request gets denied, kindly ask why“Can you let me know the reason the proposal was not accepted?”

Depending on the answer, you can feel out the situation and negotiate accordingly:

  • “The skills aren’t sufficiently relevant to your job.” Ask what areas your boss would like to see you improve in, and with that answer, begin the process again.
  • “The cost of the training is too high.” Ask if the company would be willing to cover a portion of it, or ask what budget is available and try to find a solution in that price range.
  • “The conflict with your work schedule is not acceptable.” Push gently on this one, and remind your boss that you will make up the missed time after hours or on the weekends, reassuring that you won’t get behind on your workload. Alternatively, if that doesn’t work and you’re passionate about the training you’ve found, offer to take vacation time for a portion or all of it.

Reaping the Rewards

Gaining new skills and knowledge that allow you to do your job better can bring huge rewards. It may be a promotion within your company and a salary increase or may create powerful bullet points to add to your resume and help you land your next job. Going the extra mile to thoroughly do the research and follow the proposal guidelines above will drastically increase the odds of convincing your employer to pay for the training. Not only may it save you a couple hundred bucks immediately, you’ll reap the rewards in the long term with promotions, salary increases, and new job opportunities.

Be Ethical and Don’t Abuse the System

If you’ve got your eye on a job with a new company but are missing a key skill, don’t use your current employer to pay for the training only to resign shortly after. It’s simply unethical and will catch up to you sooner or later.


Heidi’s eye for design and expert Illustrator skills carried her from an associate level designer to partner at a fashion design firm in less than 4 years. She has a proven track record of teaching fashionistas industry best practices for using Illustrator so they can beat out the competition and land their dream job.  As an educator and advocate for designers, she helps them more effectively use modern design tools as a natural extension of their creativity.

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