TrainACE - IT and Cybersecurity Training Blog

Secret Tips to Get Your Boss to Pay for Training

[fa icon="calendar"] Sep 23, 2019 8:55:00 AM / by Paul Ricketts



You’ve got your eye on a new IT course

Maybe it’s something entry-level like CompTIA A+ or Security+, or perhaps you’re looking to specialize with Certified Ethical Hacking (CEH), Certified Information Systems Security Professional Training and Certification (CISSP) or Project Management Professional (PMP) training.

There’s no question that you’ve got the drive, you’ve done the research, and you know the business benefits. You’re ready.

Except … You’ve got to ask the boss. How do you get them to say yes? More importantly — how do you get them to pay for it?

We’ve got you covered: Here are five tips to help lower your stress and boost your chances when it’s time to ask for training.

Stressed to Impress

Always find yourself on the outside of your manager’s office, trying to convince yourself to knock? Catch yourself thinking, “I’ll ask them later; they look busy,” more often than not? You’re not alone — as noted by CIO, rejection is one of the top seven workplace fears: Nobody wants to hear “no.”

Add in the power gap between you and your direct manager and it’s no surprise you’d rather be doing anything else than summoning all your courage, asking your question and waiting – nervously – for a response.

Here’s how to make asking for training easier — and get your boss to pay for it.

Secret Tip #1: Take the Thanos Approach


It’s all about the endgame. Your boss wants to know how new training will benefit the company — what skills will you learn? Can you earn certification? How does course work translate into line-of-business benefits?

Best bet? Take the Thanos approach. Just like the purple perpetrator of recent movie fame, preparation is key. The antihero didn’t wake up one day, Infinity Stones in hand and lay waste to the galaxy. He did his research through five feature-length films and then went for broke.

Adopting the same approach to asking your boss nets two key benefits: You’re more confident because you go in with a plan and as U.S. News points out, your boss doesn’t have to fill in the blanks.

Secret Tip #2: Become a Con Artist


This isn’t Superman III or Office Space — penny shaving or “salami-slicing” techniques aren’t the ways to pay for your IT training.

But it is worth being a con artist; knowing the potential downsides of training request and offering creative solutions during your pitch. For example, some courses require in-person attendance that would take you out of the office. You could combat this downside by offering to work remotely or helping other staff take on key responsibilities, in turn, diversifying company skillsets.

Secret Tip #3: Channel Your Inner Car Salesman


Used car salesmen have an answer for everything. Window won’t roll down? That’s why it’s priced so low. Not a fan of the color? Paint is an easy fix.

While it’s worth skipping the bad combover and ill-fitting suit, there’s a useful lesson here: Always have a backup plan.

Here’s how it works in practice: Find the course you want to take, then find similar courses that are less expensive, can be completed remotely or don’t run as long. That way, if your boss turns down your first pitch, you’ve got another waiting in the wings.

There’s also an advanced version of this technique: Start with a course you know is out of the time and budget ballpark, then work backward to the one you really want.

Secret Tip #4: Use Small Words


Your boss is (hopefully) intelligent, articulate and empathetic. They’re also under time, budget and resource pressure every. Single. Day.

The best thing you can do to boost your chances and reduce their stress? Keep it simple, use small words, and get to the point. As noted by Fast Company, the quickest way to get people onboard is leading with your “why” statement — it should be clear, concise and uncomplicated.

Try this: “I’d like to take this course at this time. It costs this much, and the company gets these benefits.” It’s not fancy, it’s not clever, and it’s not trying to be. Instead it’s quick, it respects your manager’s time, and it boosts your chance of getting that “yes.”

Secret Tip #5: This Time, It’s Personal


Research shows that emotional investment makes listeners “more likely to align their thinking with ours.”

So how do you give your boss the feels? Be upfront about the personal impact of IT training. Maybe limited skills or knowledge frustrates you at work. Perhaps you’ve got great ideas but need more training to put them into practice. Getting personal makes paying for your courses a plausible outcome.

Making an Ask of Yourself

Asking for paid time and training is hard — budgets are tight, bosses are busy and hearing “no” can ruin your week.

Do yourself a favor and tap our top tips: Think like the mad titan, become considerate, smooth out your sales pitch, shrink your big speech, and make sure you always take things personally.


Need help with funding? Talk to one of our experienced Program Managers about your needs.


Paul Ricketts

Written by Paul Ricketts

Originally from the UK, Paul Ricketts is the Director of Marketing at TrainACE in Greenbelt, MD. Having started out in the field of Geographic Information Systems, Paul has a wealth of experience in a wide variety of industries, focused on tech., graphics and data analysis. Having finally settled in the field of marketing, he has spent the last 8 years fine tuning his skills in the art of communication and persuasion.

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