In tech, you’ve probably heard it a thousand times: upskilling is the key to staying relevant. And it’s true—by 2030, more than 1 billion people will need to learn new skills just to keep up with changing workplace demands. With rapid advancements in AI, cloud computing, and more, skills are evolving faster than ever.
But here’s the kicker: most skills lose half their value in five years. And technical skills? Just two and a half. That’s why continuous learning isn’t a luxury—it’s a necessity. To do your best work, you need to keep adding to your toolkit.
The challenge? It might be carving out time, overcoming doubts about age, or managing costs. But these hurdles are surmountable—especially when you have a supportive employer ready to invest in your growth, financially and otherwise.
Many companies struggle to deliver effective skill-based training due to budget constraints, outdated learning models, and the fear that employees will leave once they’ve gained new skills.
But with the right approach, you can still secure the support you need. Here’s how.
First, identify the right skills.
To get into a stronger position to present your case, consider:
- What skills do you need to get even better at your job?
- How can upskilling benefit your entire team?
- Where is your industry headed and which skills will keep you competitive?
What skills do you need to get even better at your job?
Upskilling isn’t always about preparing for a new role—it’s also about deepening your expertise in your current one. You may already be proficient, but there’s always room to grow through the adoption of transferable skills.
Think about the areas where you can fine-tune your abilities to perform more effectively.
Ask yourself:
- Where in my workflows do I get stuck?
- Which routine tasks could I automate?
- Once automation is in place, where can I redirect my focus to make the biggest impact?
For example, if you’re a project manager, learning advanced data analysis could allow you to assess project risks more effectively and make data-driven decisions.
If you’re a product manager, acquiring skills in UX design could enhance your ability to oversee user-centered product development.
Or if you’re a marketer, gaining knowledge in front-end web development could improve your ability to create optimized landing pages and better collaborate with software engineering teams.
Addressing skills gaps will help you make a case for why upskilling is beneficial—not only for you—but for your entire team and organization.
How can upskilling benefit your entire team?
Collaboration is at the heart of most workplaces, so consider the skills your teammates are working on or could benefit from as well. If your entire team upskills in complementary areas, it can streamline projects and improve your overall productivity.
Consider:
- Do you have one particular teammate with a skill others would benefit from?
- How might upskilling more than one person ensure continuity of business?
- How can a shared learning plan for the team enhance project outcomes and innovation?
By considering how your upskilling benefits the entire company, you can advocate for your own development in the context of building the capacity of your whole department.
Where is your industry going?
Technological advancements, new regulations, and evolving consumer behavior constantly reshape the demand for different skills.
To keep up, focus on these key areas:
- What emerging skills are gaining traction in your industry?
- Which tools or technologies do analysts believe make companies more competitive?
- Which skills will become obsolete in the next five years, and what’s replacing them?
To find answers:
- Explore industry reports and research from credible sources like industry journals, research firms, and professional associations.
- Attend webinars, conferences, and workshops.
- Engage with industry experts through networking events, forums, and social media.
- Analyze job postings to see what skills are increasingly in demand and identify which skills are becoming less relevant.
By aligning your upskilling goals with industry trends, you’ll have a compelling argument that your learning isn’t just about your personal growth—but about driving the company forward.
5 Proven Ways to Get Your Employer to Fund Your Upskilling
Now that you’ve identified the skills you want to develop, aligned to your job and industry needs, the next step is asking your employer for support. This can be a nerve-wracking conversation, but with a strategic approach, you’ll increase your chances of getting a “yes.”
- Find out if HR has a learning stipend.
Many companies already offer learning and development stipends for employees, but these programs may not always be widely publicized. Start by reaching out to HR to inquire if any such programs exist. Knowing what’s available can help shape your request.
- Come to the table with a clear story.
When making the ask, be prepared with a clear explanation of why you want to develop a particular skill and how it will benefit the business. Highlight how your upskilling aligns with current company challenges or future goals.
- Be upfront about the cost and time investment.
Employers appreciate transparency. Provide them with specifics: course duration, fees, and how you plan to manage your workload while completing the course. If applicable, mention any scheduling flexibility the course offers (like our two-evening workshops and part-time short courses).
- Offer to teach your team.
One great way to sweeten the deal is by offering to share what you’ve learned with your colleagues. This could be through a presentation, written report, or team workshop. This makes the investment go further by ensuring that others benefit from your newly acquired skills.
- Frame it as a long-term investment.
Remind your employer that upskilling is a long-term investment in the company’s future. You’re not just asking for money—you’re asking for a partner in your development, which will pay dividends in your performance, the team’s performance, and the company’s bottom line.
Upskill with General Assembly
Increase your chances of securing your employer’s support by promoting a proven program from the nation’s longest-lived tech bootcamps. If you’re ready to take the next step in your career, explore General Assembly’s courses in software engineering, data analytics, data science, UX design, and more—all built to help you gain the hands-on, high-demand skills to thrive in today’s competitive job market.