How to Convince Your Boss to Pay for Your Upskilling

If you're looking to enhance your skills in AI, Cyber Security, Cloud Computing, or any other area, and you are currently employed, then you should 100% get your employer to cover the cost of training. It’s a huge win for you and them (low cost + high ROI).

We’ll give you some arguments and a template you can use to make it happen.

But the #1 thing when making an ask like this is to make them see why it’s such a huge benefit for them. Even if they don’t care about you, they definitely care about themselves. So use that to your advantage.

This template is just a guide. You know your boss and company best. If you think your boss will respond better via a face to face conversation then use the same concepts in a conversation with them instead of an email.

Here’s a training request email you can send to your boss

Subject: Request: Upskilling to support the team

Hi (Manager’s name),

I’ve been exploring ways to be more effective in my role and support the team long-term.

I’ve already started learning (insert skill: AI, automation, coding, cloud, etc.) in my own time, and I’ve used it to (insert example: automate a manual task, build a report, reduce a bottleneck, etc.).

It’s been a small investment of time, but it’s already shown how valuable these skills could be. I’d love to continue, but to really grow and focus on the right areas, I was wondering if the company would be open to covering the cost of formal training.

The platform I’ve been using is called Zero To Mastery. It’s practical, up-to-date, and designed for real-world application.

The cost is super reasonable - $1,299 for lifetime access or just $299 for a year to see how it goes.

Also, it’s my understanding that the cost is tax deductible as well!

I’d continue learning outside of work hours, and the focus would be on applying what I learn directly to my current role (give an example that fits).

I know training can feel like a risk, but I’m not looking to leave. I’m looking to grow here at (company) and hoping you’d be open to supporting me in making that happen

I really appreciate your consideration.

Best,

(Your name)

Why this training request email works (and how it answers objections before they even come up)

Most people think convincing a boss means hard selling. But great pitches work by removing uncertainty and showing value (for them). This email does both, without sounding desperate or salesy - as long as you do a few other things we recommend also.

Let’s break it down and where it removes these objections.

“I’ve already started learning...”

This line does a lot of heavy lifting and makes you immediately stand out, because it shows you’re proactive and self-motivated. That helps overcome the “what if they never follow through?” worry because you’ve already started!

And I know you’re probably thinking:

“Hang on, I’m trying to convince my boss to help me upskill and cover the costs - so why should I start off by paying for this myself?”

I’m not suggesting you pay for it. I’m suggesting you start learning before you pitch them, so that it shows initiative. Almost all the courses here at ZTM have free previews with the first 3-5 hours available to start learning.

Watch those and follow along so you already have a head start and stand out. Better still, use them to help your boss see the benefit of what you’re learning. This leads me to my next point.

“I’ve used it to get X result...”

If you want to get anyone to do something, you need to make it all about them and how they benefit. Saying ‘you’ll upskill’ isn’t something your boss honestly cares about. But showing how those skills save them or make them money is definitely something your boss cares about and makes them look good.

This is another reason why I recommend you start learning before you pitch - because then you can come to them with an example of how these new skills are already helping deliver tangible value.

For example

There’s probably something in your current job that could be more efficient right? Maybe adding data to a sheet or something.

It might only take an hour each week, but what if you could automate it so it takes just 2 clicks? Either from learning some Python scripting, or learning how to add prompt engineering into your current stack?

That’s 52 hours a year saved, which is over a week of work! Now imagine how many other people at your business this could also save time?

If you can share how you did something like this in your pitch they’ll see the immediate value.

We actually had a student do this recently. They brought it to their boss, helped them implement it with others in the company, and were instantly promoted into the tech department and they covered the cost of all their training.

Do this and your boss will immediately see the benefit.

“I was wondering if the company would be open to covering the cost...”

This keeps things low-pressure while still making the ask clear. You’re not demanding support. You’re proposing a conversation. That makes it easy for your boss to say yes, or at least not say no outright.

“The cost is super reasonable...”

By showing you’ve done your homework and that the numbers are small, it removes budget concerns. Add in the fact that it’s tax-deductible, and it’s now a business expense, not just a favor.

By also putting the bigger lifetime cost number first, the $299 for a year seems like basically nothing. Once they commit to that, you now have a full year to show why they should continue paying for your ZTM membership.

“I’d continue learning outside of work hours...”

This helps to show your boss that this won’t impact your current responsibilities. It’s all upside.

And if I’m honest, once they see the impact, they may start offering you time on the clock to learn more anyway. (Especially if you already provided value in some way like I mentioned before).

“I’m not looking to leave — I’m looking to grow here”

This line tackles the biggest fear most managers have: “What if we pay for this and then they leave?”

By clearly stating that you want to grow at the company, you shift the conversation from risk to retention. You’re not just asking for training; you’re offering to stick around and apply it internally.

And if you’ve already started building and proving value (like we covered above), it becomes a no-brainer. They can invest in someone who knows the company and has already shown initiative, or lose you and start from scratch.

“Happy to show what I’ve already done...”

This is your ace. You’re not just talking, you’re showing. Whether it’s a mini project, a small automation, or even just a cleaned-up workflow, this gives them something concrete to react to.

It builds trust, lowers risk, and creates momentum. Once they see how even a bit of learning has helped, they can clearly picture how much more you’ll do with their support.

FAQs: What if your boss still has questions?

The goal of the email is to start a conversation.

If your boss wants more info about the platform, here’s everything you need to answer confidently

Why Zero To Mastery and not another platform?

ZTM courses are built by experienced professionals who work in the industry.

They cut out all the garbage that other courses might cover, and instead focus on the most important skills and trending tools. (Our teachers work in the industry. The courses they make are designed to give the skills of their ideal employee).

This way you’re not only on top of your game, but you’re able to deal with whatever is needed.

We also have a private community of over 500,000 working tech professionals who each help each other to succeed, answering questions and providing feedback.

Who else uses ZTM?

Our students work at companies like Google, Amazon, Shopify, Nvidia, and more, in a wide variety of tech roles. You can see some of our testimonials from real students here.

Is ZTM just for web developers?

No, ZTM has an extensive course catalog in:

Machine Learning
Generative AI (including Prompt Engineering)
Cybersecurity and Ethical Hacking
Cloud and DevOps
Full-stack Web Development
Software Engineering
Data Science, Data Analytics, and Data Analysis
And more

Basically, if it’s a skill that helps tech-driven teams move faster or smarter, we probably teach it or will be adding it into your membership soon.

Is ZTM just for beginners?

Nope! Although we have some of the best beginner bootcamp courses, we also have many intermediate and advanced courses as well.

Are these courses something that you will actually use?

ZTM isn’t just “watch and forget” content. Every course is structured, project-based, and aligned to clear roadmaps, so you’re learning in a way that builds toward real change.

You build as you go, getting hands on experience with projects at all levels. The people who take our courses often end up helping to train other staff!

Can we check out any of the training first?

Each course has the first few lessons open to free preview. You don’t need to sign up or anything, just go to any course, go to the curriculum section, and then click any lecture that says PREVIEW.

That way you (or your boss) can jump in, see what it’s like, and get hands-on with real projects right away.

As mentioned earlier, we also have many crash courses posted for free on our YouTube channel which are taken directly from our courses. Just remember that YouTube videos can’t be updated so the most up-to-date version of all lectures/courses can only be found on our website.

That said, they’re still super useful, you can learn a lot from them, and definitely get a sense of the quality of our teaching from them

What makes these courses better than a free YouTube video?

All of our courses are continually being updated, unlike most platforms. You always have the most up to date content, whereas many YouTube videos are out of date.

Don’t get me wrong, they’re great and you can learn from them for free, but it’s unlikely you’re getting the most up-to-date information (which is important in the tech field) and most YouTube videos don’t go beyond the beginner basics.

So you can learn the basics for free but need access to the full courses to learn the more advanced methods to do this at a fully professional level.

Not only that, but the community and teacher support you get by joining Zero To Mastery (which you don’t get with YouTube) means you’ll be far more likely to finish the training and learn those new skills.