Asking Your Boss for Training and Upskilling
It’s not uncommon to feel like you're stagnating at your place of work. When you’re always taking on the same responsibilities with little change in workflow, it’s understandable that you feel desperate to advance. The hard part is knowing where to start.
One of the most effective ways to stay relevant at work is through training and upskilling, but asking your boss for training feels intimidating. You may worry it sounds demanding, unnecessary, or like you’re planning to leave. But in today’s job market, learning new skills is no longer optional. It’s one of the best ways to protect your career and open doors to better opportunities.
If you’re thinking about asking your boss for training, this guide will help you understand why it matters, when to bring it up, and how to do it with confidence.
Why Upskilling Matters for Your Career
Jobs are rapidly changing with the adoption of new technology, new regulations, and shifting business needs. Often, the skills that got you hired become obsolete, making you feel suddenly unqualified and unprepared.
This is where upskilling comes in. Upskilling helps you keep pace instead of scrambling to catch up later. Learning new skills can protect your job during change, help you advance quicker, and allow you to be more effective in your day-to-day work.
Building these skills while you’re employed is very important. It enables you to be a better asset to your team, with more opportunities to advance in your career. Waiting to retrain and upskill until you’re in between jobs leaves you in an awkward spot. Your knowledge and experience should match where you want to be, not keep you in the same place.
It’s not just beneficial to you, it’s also beneficial to your employer.
In summary, upskilling helps you:
- Stay relevant in your role
- Take on new responsibilities with confidence
- Improve job security
- Improve confidence and independence
- Qualify for promotions or new roles
- Prepare for career changes before you’re forced into them
When Is the Right Time to Ask for Training or Upskilling?
The right time to ask for training and upskilling is when growth is already part of the conversation, such as during a performance review or goal-setting meeting. Finishing a successful project is another good moment to ask.
Truly, the best time is whenever you feel you need it, but being mindful of when you ask can improve your chances of getting a positive response.
On the opposite side, you should probably avoid asking your boss about training and upskilling during high-stress periods. Think major deadlines, busy seasons, layoffs, or budget cuts. At times like these, your boss is more likely to reject your request for more formal training and upskilling.
Before Asking Your Boss About Training and Upskilling
A good way to make your boss more willing to invest in training and upskilling is with proper preparation. Having a plan already set out takes a lot of the pressure off of your boss’ shoulders. Additionally, it demonstrates professionalism, mindfulness, and a respect for your boss’ time.
Here’s how you should prepare before asking your boss about training and upskilling:
Decide What Specific Skills You Want to Improve
Be specific about what areas you want to improve in and why. If it’s difficult to narrow it down, try to take note of times where you feel undertrained during day-to-day work. Another way is to come back to your overall career goals and assess what is keeping you from achieving them — whether it be leadership skills, client communications, or even something foundational like language skills.
You can help your boss understand why you feel you need these skills, and how you want it to impact your job performance. Managers are more open when training supports productivity, accuracy, or long-term planning.
Find a Suitable Career Training Provider in Your Area
Finding a provider ahead of time saves your boss from having to canvas for one instead. You're saving them a lot of time by offering a clear, ready-to-use option.
Pathways is a career training provider that offers practical, flexible upskilling programs for working individuals in Kitchener and Guelph. Pathways offers one-on-one support to help you identify where you want your career to go—and the steps to get there.
Our programs are designed around real workplaces, not theory. We work across industries and focus on building transferable skills that support both your current role and future opportunities.
Whether you’re looking to strengthen your role, prepare for change, or build long-term stability, having a plan matters — let us help you build one that makes you excited to learn.
Book a Consultation with Pathways today!
How to Ask Your Boss for Training and Upskilling
- Start by explaining what you enjoy about your role and where you want to grow. Then explain how training would help you contribute more effectively. Focus on results.
- Show you’ve done your research and explain your plan. This shows that you are able to take initiative and responsibility for your own growth.
- Be open to compromise. Your manager may suggest a different program, timing, or format than you had in mind.
Will Asking for More Training and Upskilling Upset My Boss?
No, it shouldn’t upset your boss that you’re asking for more training and upskilling. They expect employees to want to grow and, if anything, having the drive to become more skilled and capable is a good quality. Any boss should want their employee to constantly advance, improve, and bring more value to the organization.
Concerns usually come from how the request is framed. If training sounds like a complaint or a backup plan to leave, it can raise questions. If it sounds like preparation and commitment, it should be seen as something positive.
Even if the answer is “not right now,” the conversation still matters. It puts development on the radar and opens the door for future opportunities.
FAQ: Asking Your Boss for Training and Upskilling
Will my boss think I’m planning to leave?
Your boss shouldn’t think you’re planning to leave because you’re asking about upskilling. When training is tied to your current role or future company needs, it signals loyalty rather than exit planning.
It is important to pay attention to your company culture. Many companies prioritize continuous growth, and are open to outsourcing external training providers. Others may be more willing to be involved, and want to personally mentor you instead.
How to Avoid It
Be willing to compromise if they have another plan in mind for your skill development. Unnecessary pushback may end up giving the impression that you’re planning to leave, even if you don’t intend to.
Additionally, suggesting skill development that doesn’t relate to your industry will definitely be confusing for your boss.
What if my company doesn’t have a training budget?
If your company doesn’t have the budget for training and upskilling, ask what alternatives exist or when the conversation can be revisited.
At Pathways, our flexible training programs allow us to be open about offering options that fit smaller budgets or part-time schedules. This can make the program into something more continuous and long-term, rather than intensive, immediate training.
Should I ask my boss about training and upskilling in person or by email?
Generally a conversation is best, but it can be worthwhile to follow up with a short email to summarize what was discussed and next steps.
Overall, it really depends on your company culture and how you typically communicate with your boss.
Is it okay to ask for training early in my role?
Yes, as long as the training supports your performance. Early learning can prevent mistakes and build confidence faster.
