Updated: September 22, 2025- 13 min read
The world of work is changing at breakneck speed. New technologies, methodologies, and market shifts mean that the skills your team used last year might not be enough next year.
The World Economic Forum (1) projects that, between 2025 and 2030, two-fifths (39%) of existing skill sets will be changed or become obsolete. While this “skill instability” has slowed from 44% in 2023 and a pandemic-era peak of 57% in 2020, the pressure is still on. Half of employees have now completed some form of training, reskilling, or upskilling, up from just 41% in 2023.
In this guide, we’ll break down what upskilling vs reskilling means, the challenges of each approach, and why they’re a vital part of your Learning and Development (L&D) strategy.
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What Is Upskilling and Reskilling?
Upskilling means building on someone’s existing skill set to help them perform better in their current role (or advance along the same career path), while reskilling means training someone in new skills to take on a different role or career path. Think of upskilling as “digging deeper” in the same field, and reskilling as “switching lanes” to a new field.
Upskilling and reskilling both involve helping employees learn new skills. Still, they serve different purposes.
“One of my core beliefs is being a student for life. I've been going back to school every year for the last 16 years. Look for certifications, always. This method helps you fill gaps and prepare for the next year, every year. ”
— Vinod Suresh, VP of Product at GoDaddy, on The Product Podcast
Upskilling focuses on expanding existing capabilities
The employee learns more advanced or modern skills relevant to their current job. The goal is often to improve performance in their role or prepare them for a higher role in the same track.
For example, a product marketing specialist might learn advanced product analytics techniques to better measure campaign success. A front-end developer might get trained on a new JavaScript framework to build more innovative user interfaces.
The employee remains on a linear growth path. They become more expert and productive in their domain, and potentially move up to roles like senior product manager or product lead in that area.
Reskilling involves a broader shift to a new set of skills
The person learns a substantially new set of skills to fill a different role than what they do now. Companies use reskilling when a role is becoming obsolete or when an employee’s talents could be applied in a new area of need.
For example, a retail store technician might be trained to become a web developer, switching from managing tech in a store to coding websites. Or in a product-led organization, consider an experienced manual QA tester whose role is being phased out by automation. The company might reskill them to become a software developer or a product analyst, allowing the employee to stay with the company in a new capacity.
Reskilling is a lateral move. The employee transitions into a different career path within the organization, leveraging some transferable knowledge but largely starting fresh with new expertise.
Upskilling vs reskilling comes down to the end goal
Upskilling keeps the employee on a similar trajectory. They are just more skilled and ready for future challenges in that area. Reskilling changes the employee’s trajectory. It moves them into a new role so the company can retain their experience while meeting a different need.
Challenges of Upskilling
Investing in upskilling is critical for keeping your team’s skills current, but it comes with its own set of challenges. Product teams and engineering teams often run lean, so carving out time and resources for upskilling isn’t always easy.
Here are some common challenges of upskilling and pitfalls to watch out for:
Time and productivity trade-off: Upskilling takes time. Time that employees might otherwise spend on their regular projects. Sending a software engineer to a week-long training means their sprint tasks might be delayed. Balancing on-the-job responsibilities with learning is a constant struggle. Many organizations find that a lack of time is the top barrier to upskilling.
Financial and resource costs: Quality product management training programs, courses, or coaching often require investment. Small and mid-sized companies might find it costly to allocate a budget. Beyond direct costs, there’s also the opportunity cost. Leadership needs to be convinced that the long-term gains outweigh these short-term costs.
Choosing relevant skills: In fast-changing industries like tech, there’s a risk that by the time you upskill employees in a particular tool or skill, the industry has moved on. A key challenge is identifying which skills will remain relevant and aligning training with future needs. Product leaders must continually assess industry trends and the company roadmap to pick the right areas for upskilling.
Employee engagement and focus: Not all employees will immediately see the value. If an upskilling program feels like a checkbox exercise or isn’t clearly tied to their career growth, participation may be lukewarm. Busy product teams might deprioritize training if deadlines loom. Overcoming this means communicating the “why”.
Challenges of Reskilling
Reskilling employees can be even more complex than upskilling. You’re asking people to leave their comfort zones and essentially become a beginner in a new domain.
Here are the main challenges of reskilling to consider:
Steep learning curves: Reskilling is a leap into unfamiliar territory. An employee moving from, say, a customer support role into an associate product manager role will have a lot to learn. The learning curve can be steep and lengthy, and not everyone will pick up the new skills at the same pace. This may require extensive training, mentoring, and patience.
Employee resistance and anxiety: Change is hard. Some employees might resist reskilling efforts, especially if they’ve been in their current role for many years. Managing this human side of change is crucial. Clear communication about why the reskilling is happening, how the company will support them, and what growth opportunities it offers can help ease concerns.
Matching people to the right new roles: One big challenge in reskilling is identifying which employees have the aptitude and desire for the target role. Some skills might not transfer well. An excellent product designer might not have the temperament to become a software engineer, and that’s okay. L&D and team leaders need to assess employees’ strengths and career goals.
Resource intensiveness: Reskilling requires even more resources than upskilling. You might be funding a full bootcamp program, a product certification, or even degree courses for someone to gain competency in a new field. This can be expensive and time-consuming. It’s a tough balance of investment vs. payoff that organizations must evaluate.
Despite these challenges, both upskilling and reskilling can pay off greatly if executed well. The next section explores why these approaches are so important to an organization’s strategy and success.
Why Upskilling and Reskilling Should Be Part of Your L&D Strategy
In product-centric companies, continuous learning is what keeps your team and product competitive. Upskilling and reskilling the workforce are critical components of a modern L&D strategy for several pragmatic reasons:
Addressing skill gaps and future-proofing
AI digital transformation and market trends can make today’s hot skill tomorrow’s old news. By proactively upskilling and reskilling employees, organizations close skill gaps and stay ahead of industry changes.
This is especially important in product and engineering teams. There, new programming languages, tools, or market paradigms (like AI product strategy, data privacy, or agile methodologies) emerge frequently.
Rather than scrambling to hire new talent for every new skill need, companies can cultivate those skills internally. A strong upskilling/reskilling program essentially future-proofs your workforce against disruption.
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Improved innovation and productivity
When team members gain new skills, they tend to bring fresh ideas and efficiencies to their work. An engineer who upskills in a new DevOps tool can automate a deployment process that used to take hours. A marketer who learns a new analytics technique can uncover customer insights that drive product improvements.
These gains translate to tangible business outcomes and team effectiveness. Higher productivity, more product innovation, and better-quality output. Companies that invest in learning culture see benefits like increased efficiency and profit, better adaptability, and even improved product quality.
Talent retention and attraction
Offering growth opportunities is good for employees and for business. High performers in tech and product roles want to keep learning. In fact, 70% of U.S. employees say they’d be more likely to go elsewhere if another company offered professional development opportunities (2).
Upskilling and reskilling programs demonstrate that your organization values its people and their growth. This boosts morale and loyalty among current staff and makes your company more attractive to prospective hires.
Cost savings vs. hiring externally
It might seem counterintuitive because training has upfront costs, but developing talent internally can be more cost-effective than recruiting new employees.
When you reskill an existing employee into a new role, you save on the expenses of hiring, onboarding, and the lost productivity while a new hire gets up to speed. That reskilled employee already knows your product, your customers, and your culture.
Various studies and business cases show that companies can reap significant returns on investment from training programs. While not every training yields a dramatic figure, the broader point stands. Effective upskilling/reskilling can deliver ROI through higher productivity and avoiding the larger costs of turnover or long vacancies in critical roles.
Agility and adaptability
Perhaps most importantly, cultivating a workforce that’s used to learning new things makes the entire organization more agile. In product-led companies, strategy can pivot quickly. Maybe there’s a sudden shift to a new platform or a need to respond to a disruptive competitor.
If your team has a culture of continuous learning, they are more ready to adapt. When COVID-19 upended business as usual, organizations that already had strong reskilling programs handled the sudden change better.
In short, embedding upskilling and reskilling into your L&D strategy builds an organization that can navigate change rather than be flattened by it.
Upskilling vs. Reskilling:How to Decide What Your Team Needs
Knowing that both upskilling and reskilling are valuable is one thing. Figuring out which approach to use in a given situation is another.
Should you focus on deepening your team’s current skills? Should you prepare some of them for entirely new roles?
The answer depends on your context. Here are some factors and guidelines to help decide between upskilling and reskilling for your product team or engineering team:
1. Nature of the skill gap or threat
Look at the changes happening in your industry and within your company.
If new technologies are emerging that your team needs to adopt, then upskilling your current team to use these might be the answer. It keeps you on the cutting edge. However, if certain roles are becoming redundant, then reskilling those employees into different roles is the smarter approach.
In practice, you might do both: upskill to stay competitive in new tech, reskill to redeploy people from shrinking areas to growing ones.
2. Workforce demographics and aspirations
Consider the background and career stage of the employees in question. For early-career professionals or those in a growing field, upskilling often makes sense to help them advance in place. They are building depth and might prefer to stay on the same track but at a higher level.
On the other hand, for experienced employees facing a role that might sunset, reskilling can be a lifeline. For example, a veteran operations specialist whose role is affected by new software might want to reskill into an analytics or product support role.
It’s also about personal aspiration. Have conversations with the employees. Some may express a desire to pivot careers (great reskilling candidates), while others love their field and just want to grow (upskilling candidates).
3. Business objectives and strategy
Align with what the company needs to achieve. If your product strategy requires innovation and launching new initiatives, you’ll likely need cutting-edge skills. Perhaps training your team in a new technology (upskill) to drive those projects forward.
If the business goal is to maintain stability or retain talent during a transition, reskilling might be emphasized to avoid layoffs and keep institutional knowledge in-house.
For instance, when a company adopts a new cloud infrastructure, it might reskill its on-premise IT administrators to become cloud engineers. They would meet the goal of transforming infrastructure while supporting employees through the change.
4. Resource availability
Be realistic about your budget and timeline. Upskilling often can be done with a smaller investment and over shorter periods. It builds on what people already know; they can often learn while still contributing to their current role.
Reskilling might require more extensive training. Thus, more budget for training programs or backfilling roles.
If you have limited resources, you might lean toward upskilling first, focusing on critical skill gaps that can be filled relatively quickly. If you have the backing (time, money, executive support) for a larger initiative, reskilling programs can yield high rewards by redeploying talent where you need it most.
5. Urgency of need
How urgent is the need for new skills? If a new competitor or technology is threatening your product mix right now, upskilling current team members might be the fastest way to respond. For example, you can quickly train your developers on a new framework to keep up with market demands.
If the change is more gradual or anticipated, you have time to plan a reskilling program and transition employees into new roles at a manageable pace.
In practice, a product-led organization might use both strategies in parallel. The key is to assess the situation continually. Conduct skill gap analyses and look at where the industry is headed.
Many companies create a skills roadmap as part of their workforce planning. This way, you can proactively decide which roles will need new blood (through reskilling or hiring) and which roles just need deeper expertise (upskilling).
Why Reskilling and Upskilling Is Urgent
Products evolve. So do tools, markets, and expectations. The only way your team stays relevant, without constantly churning through hires, is by learning.
It’s not a trend or a nice-to-have. It’s a core part of building a product team that can respond to change without losing momentum. You don’t need a massive program to start. You just need to pay attention to where the skill gaps are, where the roles are heading, and where your people want to grow.
Done right, upskilling keeps your best people sharp. Reskilling keeps them in the game. And together, they help your product-led organization stay fast, focused, and built to last.
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(1): https://www.weforum.org/publications/the-future-of-jobs-report-2025/digest/
(2): https://www.webmdhealthservices.com/blog/surprising-statistics-about-employee-retention/
Updated: September 22, 2025
