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How can I get my boss to give me time/money to upskill in tech?

March 26, 2023

If you work in tech, it’s likely someone has told you that you should always be upskilling. Mattias Andersson shares how you can convince your boss to give you upskilling opportunities.

Comic about upskilling

You’ve decided you want to upskill, and you’ve chosen what you want to learn. But there’s one big barrier: convincing your employer to help you upskill. Sure, a lot of employers have company values like “Continuous learning”, but when it comes time to put that to action, the hand-wringing starts.

“We don’t have the budget this quarter.” “Can you explain how this benefits us?” “I don’t think we have the time right now.”

In fact, 18% of tech employees said they lack support from their employer when they’ve tried to upskill, according to Pluralsight’s State of Upskilling 2023. The same amount said they were afraid to use work time to learn due to fear of being laid off. And with big layoffs happening in tech this year, who can blame them? Others are just too busy (42%) — and this could also be seen as employers not prioritizing your learning time.


You could, of course, just take no for an answer. That’s easier, right? But it’d also be sabotaging your career in the long run. Upskilling in tech keeps you relevant, and while your employer might not care if you can get your next job, raise, or promotion, you certainly do. And with the rise of AI tools like ChatGPT really rocking the boat, it’s all the more important for tech professionals to keep ahead of the curve.

So, the million dollar question: How do you convince your employer to give you what you need — whether that’s time or money — to upskill?

1. Phrasing it like you’re checking out a technology to help the business (because you are!)

“Let’s set aside some time to investigate a technology, to understand it better and maybe see if it’s worth investing more into or not.”

This is such a great line for a number of reasons. First, an investigation of a technology is fundamentally learning it, but it’s structured in a way that creates opportunities for business value. You’re not asking for personal upskilling, but showing you’re being proactive in trying to improve the business!

It’s also being upfront that the business value is going to be a dice roll. Maybe this technology will pay off, and return on the investment, but maybe it won’t. You’re not promising anything, but you do see the potential for value.

For more frugal employers, that uncertainty might make them hesitant to invest, so that’s where the next line comes in…

2. Say you’ll share your newfound knowledge with the team

“I can do a presentation to the team about this technology about the benefits and drawbacks, and how it can be used.”

There are a few reasons why this appeals to employers. Firstly, you’re removing ambiguity about the technology. No longer will staff be spending time wondering “would we be better off if we used this tech?” Someone who understands their business situation has checked it out and made sure, which also makes staff more confident in the business and how forward-thinking they are.

Secondly —and this is probably the bigger draw — they get to help upskill a whole team for the cost of having one employee do the focused training. Not only that, it creates a leadership opportunity for you, which also makes any manager look good.

Comic about upskilling

Remember, if your manager thinks you're learning it to indulge your hobbies, be prepared for them to say no!

3. Pointing out that you’re getting rid of a single point of failure

“This other person knows this technology, but I’d really like to learn it, too, so we can broaden the skillset of the team and ensure continuity of business.”

‘Continuity of business’ is one of those risk management phrases that makes any manager’s ears perk up. After all, the opposite of continuity of business is that the business doesn’t continue, and that is decidedly very not good. 

Some employees are single points of failure in the business, and this is known as the ‘Bus Factor’. Unsplash’s co-founder Luke Chesser wrote a great article on how to test this, and how it can impact developers in particular.

Putting something under the umbrella of ‘helping continuity of business’ also helps managers justify upskilling expenses to their higher-ups.

4. Ask to lead projects where upskilling is part and parcel

“I’d like to have the opportunity to learn and grow, so I want to take on more learning opportunities. Can you look for opportunities for me to be put on a project to stretch me out a bit?”

Again, there’s a few dimensions to this one. You’re not asking to take time specifically for learning, but rather to work on a future project that helps the business while you learn. 

It also communicates in a straightforward way that you’re chomping at the bit and looking to challenge yourself, which makes your manager aware they need to do a little bit more to keep you engaged. 

5. Tell them what learning opportunities you need, and why

“I know we do seminars, but I need time to do hands-on learning in this tool, so our team is well-trained in using it.”

Research shows there’s a big difference between what HR and tech managers think are effective learning options, and what tech professionals actually need. Many organizations provide mentoring programs, reading materials, and instructor-based learning…

Learning options orgs provide

… However, research shows most tech pros actually respond better to hands-on labs and sandboxes.  And a significant number also prefer on-demand video courses!

Most effective tech learning options

Communicating to management that, as the expert, you need something more will help challenge their assumptions that they’re doing enough. This doesn’t just help you out, but also every other technologist in your organization.

Of course, there are situations where none of the above options will work, so there’s always the final option…

6. The Nuclear Approach: When all else fails…

“I recognise that I am responsible for moving my tech career forward, and if I can’t get those opportunities  here, then it forces me to have to look somewhere else. I’d love to have opportunities here, though, so how can we work together to do that?”

This really is the last resort, and only for when you really intend to follow through if you don’t get opportunities to grow. Even then, though, ultimatums are a double-edged sword, and could trigger a forced departure, anyway. And even if you stay, this also makes you look brusque, which may well end up biting you in the long term.

Most people are less secure in their work situation than this conversation would require, so this option isbest suited for those who are very confident in their current business value.

Pro tip: Try to see things from the other person’s priorities

In all situations, the person you are dealing with is not only thinking about you. They understandably have to be thinking about themselves and how they will justify their decisions to the people they answer to. And even if you’re negotiating with the business owner, they still need to justify to themselves why they make each decision. 

It’s reckless to ignore the fact that the people you’re interacting with have different constraints, motivations, and valuations than you do for these situations. To demonstrate this point, here’s some data from Pluralsight’s State of Upskilling report 2023 on what HR managers see as reasons they can’t help tech pros upskill:

HR barriers upskilling

And here’s what tech team executives commonly have as their reasons for turning technologists down:

Tech team exec barriers upskilling

Remember that for managers, it’s often cheaper to upskill you than lose you

Savvy managers realize that if someone leaves, that often causes a large retraining cost and significant efficiency hit. Furthermore, they usually have to hire a replacement at a higher salary than the departing employee. So while managers may see upskilling as a loss of efficiency, losing you as an employee may be even more damaging. 

Of course, the key word here is savvy manager, since not every manager is this conscientious. There’s also a bit of chicken-playing involved — “Will they actually quit, or will they just keep pushing me for upskilling but letting me ignore it?” Knowing this, it can be tempting to make an ultimatum to force their hand, but peaceful negotiation is usually your better (and safer) option.

Conclusion: If your organization won’t let you upskill, consider other options

In the end, if you find that your employer simply won't support you upskilling, at all, and you don’t have the bandwidth and willingness to do it in your off-hours, then it might be time to look for greener pastures. If your employer won’t invest in you, then that’s not a great environment for your personal growth. Don’t feel bad about it, either — 47% of tech professionals consider leaving their job to grow their responsibilities and skill sets

If you do end up seeking other employment, though, make sure to ask questions about upskilling opportunities during the interview process, like:

  • Does the company have a budget or program for employee training and development?

  • How often do employees receive opportunities for professional development or upskilling?

  • How does the company stay current with the latest industry trends and technologies?

  • Are there any opportunities for employees to attend industry conferences or events to network and learn from others in the field?

  • How does the company support employees in achieving their career goals and aspirations?

  • Are there any specific skills or certifications that the company encourages or supports employees to obtain?

Remember, don’t give up on upskilling yourself! The person who cares most about your skill set is you, so make sure you’ve always got your eye on the next way to be awesome, whether it’s that next certificate, learning about a new tool, perhaps another programming language, or figuring out how you can use ChatGPT 6.0 to take over the world.  Okay, maybe not that last one.  Leave that one to me. 😉