Updated: October 6, 2025- 14 min read
Skills don’t last forever. What was cutting-edge two years ago might be outdated today and your team feels that shift just as much as you do.
Yes, you should introduce your people to new tools and send them to training sessions. But above all else, you should help them acquire the kind of skills that actually make tomorrow’s work easier, sharper, and more relevant.
In this piece, we’ll walk through how to upskill employees in a way that fits your team, sticks long-term, and keeps your business ready for whatever’s next.
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Why Upskilling Matters More Than Ever
Upskilling is now a strategic priority for many product-led organizations. The main driver is the rapid pace of technological change, which is why it’s crucial to upskill, but also to embrace corporate innovation as well as proven innovation strategies.
Tools and practices that were standard just a few years ago can be outdated today. New technologies like AI agents, automation, and product analytics are reshaping jobs. This means employees need fresh skills to complement or enhance what they already do.
As Prashanthi Ravanavarapu, the Product Executive at PayPal, puts it on The Product Podcast:
Skills are the currency of the future. Invest in skills. In the rapidly evolving world of product management, continuous learning and adaptation are crucial. Focus on developing a structured approach to product leadership that combines technical skills with soft skills.
Hiring new talent for every emerging skill is costly and often unrealistic, especially when the wider labor market faces the same gaps. Instead, building on the skills of your current team keeps the business agile and resilient.
There are clear business benefits:
Stay competitive – Keep employee skills aligned with the latest industry trends.
Boost Agile organization – Teams can adapt quickly to new challenges without relying solely on outside hires.
Increase product innovation – Employees who learn new things are more likely to experiment and bring fresh ideas.
Encourage cross-functional collaboration – Upskilled teams can collaborate more effectively across different areas.
It’s also a powerful driver of engagement and retention. When people see their company investing in their growth, they feel valued and motivated.
According to LinkedIn’s Workplace Learning Report, 8 out of 10 employees say that learning new skills gives them more purpose in their jobs. Companies that create learning opportunities often see a return in loyalty.
Developing an Upskilling Strategy: What's the Best Way?
The best way to upskill is to combine real-world application with structured learning. Employees learn fastest when they can apply new skills immediately on the job, supported by relevant training, feedback, and mentorship.
A good upskilling program starts with a plan. Jumping straight into training without knowing what you need is a quick way to waste time and resources. The aim is to be deliberate. You need to build your approach around your product goals, north star metric, your people’s needs, and the skills you want to see in the future.
Align with business goals to make better upskilling solutions
Figure out what the organization is aiming for in the next few years.
Are you entering new markets, rolling out AI tools, or launching a different product line?
Once you know that, identify the skills your teams will need to get there. Tying your training to actual business priorities keeps the effort focused and relevant.
Identify skill gaps
Take stock of where your team stands today. This could mean running skills assessments, reviewing performance data, or having straightforward conversations with employees about their experience and interests.
Compare the skills you have now with the skills you’ll need in the future. The gaps you find are where your upskilling or reskilling efforts should start.
Personalize and prioritize upskilling in the workplace
Not everyone needs the same training. Decide which skills are most urgent and tailor learning paths to different roles.
For example, product managers may benefit from advanced product analytics or AI training, while customer-facing staff might focus on CRM tools or communication. Customizing the learning makes it more relevant and engaging.
Set clear goals and metrics
Define what success will look like before you start. That could be a certain percentage of the team certified in a new tool, faster delivery times, or higher internal promotion rates.
Clear targets make it easier to track progress and prove the value of your efforts, which also helps when you’re securing budget and resources.
Secure leadership support to unlock upskilling opportunities
Upskilling staff needs time, money, and visible backing from product leaders. When managers make space for learning during work hours, allocate a budget, and take part in training themselves, it sets the tone for the rest of the company.
Without this, even the best training plans struggle to take root.
When your strategy is aligned, personalized, and supported from the top, you’re setting the stage for employee growth that actually moves the business forward.
How to Level Up Your Employees: 8 Strategies that Work
Level up employees by giving them targeted learning opportunities that match both their current roles and future career paths. This can include formal training, mentorship, stretch assignments, and access to tools that help them apply new skills on the job.
1. Build on-the-job learning into real projects
On-the-job learning works because it’s tied to actual deliverables, deadlines, and product team dynamics. It’s skill-building in the same environment where the skills will be used. This makes the learning stick and ensures the time spent training is directly relevant to outcomes, not outputs.
To make this work effectively:
Identify stretch opportunities – Assign employees to projects or responsibilities that are just beyond their current skill set. For example, a mid-level developer might take the lead on integrating a new API, or an associate product manager could run a customer feedback session for the first time.
Set clear, measurable goals – Define what success looks like for the assignment, both in terms of project outcomes and skill development. This keeps expectations aligned and progress trackable.
Pair with experienced mentors – Ensure there’s a senior colleague or subject matter expert available to provide guidance, answer questions, and offer feedback without taking over the work.
Use phased autonomy – Start with more support in early stages, then gradually reduce oversight as the employee grows confident in the new skill.
Incorporate reflection sessions – After key milestones or at project completion, discuss what went well, what was challenging, and how the employee can refine their approach next time.
The value of this method is twofold: the employee develops real, job-ready capability, and the organization benefits from fresh ideas and an expanded talent pool that can take on more complex challenges in the future.
2. Offer self-paced digital learning options
Self-paced digital learning gives employees the flexibility to build skills without waiting for scheduled training sessions.
It’s especially effective in tech and agile organizations where tools, product management frameworks, and best practices change quickly, and people need to learn on demand. The key is to make these resources accessible, relevant, and supported by the organization. Otherwise, they’ll be ignored.
To get the most from this approach:
Curate a focused library – Don’t overwhelm employees with thousands of generic courses. Select platforms like Coursera, LinkedIn Learning, or Pluralsight and pre-approve a set of courses that align with your business priorities and roles.
Create learning paths – Group related courses into role-specific tracks (e.g., “Data Analysis for product managers” or “Secure coding practices for engineers”) so employees know where to start and what to take next.
Allocate protected learning time – Give employees dedicated hours each month to take courses without feeling they’re neglecting core work. This sends a clear signal that learning is part of the job, not an afterthought.
Tie learning to real application – After completing a course, have employees apply at least one concept to their current work or present a takeaway to the team. This reinforces retention and demonstrates ROI.
Track progress and impact – Use platform analytics or internal tracking to see who’s engaging with the material and whether the skills are showing up in project outcomes.
When done well, self-paced learning turns downtime into growth time and helps employees stay ahead of the curve without disrupting team effectiveness.
3. Run focused workshops and hackathons
Workshops and hackathons compress learning into high-intensity, short bursts where employees can gain new skills and apply them immediately.
They’re particularly effective for introducing corporate innovation, testing creative problem-solving, or building rapid prototypes without the constraints of day-to-day work.
For tech and product teams, these formats also encourage collaboration across disciplines.
To get the best results:
Pick a clear, relevant focus – Choose a skill, tool, or challenge directly tied to upcoming business needs, such as learning a new frontend framework before a product redesign.
Set defined outcomes – In a workshop, this could be producing a working demo or completing a set of exercises; in a hackathon, it might be delivering a functional prototype or proof of concept.
Mix skill levels in teams – Pair senior and junior employees so learning happens organically through collaboration.
Bring in expert facilitators – Internal or external experts can guide discussions, troubleshoot, and ensure the sessions stay productive and on track.
Debrief and apply – After the event, have teams present their work, highlight lessons learned, and identify how the solutions or skills can be applied to current projects.
When workshops and hackathons are well-planned, they also strengthen team relationships, spark product innovation, and often produce ideas worth pursuing beyond the event.
4. Implement structured mentorship programs
Mentorship is one of the most effective ways to transfer knowledge and build skills that go beyond what formal training can offer.
Unlike one-off coaching sessions, a structured mentorship program creates an ongoing, goal-oriented relationship where learning is directly tied to real work challenges.
For a mentorship program that actually moves the needle:
Match mentors and mentees intentionally – Pair based on skills, career path, and personality fit, not just job titles.
Set clear goals from the start – Define what the mentee wants to achieve in a 3–6 month period, whether it’s mastering a tool, improving leadership skills, or navigating a new role.
Create a framework for meetings – Weekly or bi-weekly check-ins work well, with each session focused on a specific topic or skill.
Encourage reverse mentoring – Let junior employees teach emerging technologies or trends to senior staff, building a culture of two-way learning.
Track progress – Use short surveys or check-ins to measure skill growth and adjust the mentorship pairing if needed.
When done right, structured mentorship accelerates skill acquisition, improves ownership mindset, and fosters stronger connections across the organization.
5. Use internal mobility as a learning tool
Moving people between roles or departments is one of the fastest ways to build cross-functional skills.
Instead of only hiring externally for new challenges, you can let employees “learn by doing” in a different context while still keeping their institutional knowledge in-house.
To make internal mobility an effective upskilling strategy:
Identify skill gaps and map them to internal talent – Use skills assessments and performance reviews to spot employees who could grow into a role with minimal onboarding.
Offer short-term projects or rotations – A 3–6 month project in another team can expose employees to new tools, processes, and stakeholders without committing to a permanent role change.
Pair with a learning plan – Don’t just throw someone into a new job. Give them access to relevant courses, internal documentation, and a mentor in the new department.
Create a feedback loop – Have senior product managers in both the old and new teams track progress and share observations, ensuring the experience actually builds the intended skills.
Celebrate successful transitions – Publicly recognize employees who’ve grown into new roles, reinforcing the value of internal mobility to the entire organization.
Done strategically, employees see more opportunities for growth without leaving the company.
6. Build structured mentorship programs
Mentorship accelerates upskilling by pairing employees with people who’ve already mastered the skills they need to learn.
Done right, it blends practical guidance, feedback, and career context in a way that’s hard to get from training alone.
For a mentorship program that actually works:
Define clear goals for each pairing – Both mentor and mentee should know exactly what skills or knowledge areas they’re focusing on.
Match based on skills, not just seniority – A mid-level engineer who’s mastered a new framework might be a better mentor for it than a senior product lead who hasn’t used it in years.
Set a structured schedule – Regular, predictable meetings (weekly or bi-weekly) keep the learning consistent and prevent the relationship from fizzling out.
Equip mentors with resources – Give them conversation guides, progress tracking templates, and recommended materials so they can teach effectively.
Encourage reverse mentoring – Let junior employees share fresh perspectives or tech know-how with senior staff, fostering mutual growth.
When mentorship is baked into company culture it becomes a powerful driver of skill development and long-term engagement.
7. Leverage cross-functional projects
Cross-functional learning breaks down silos and exposes employees to the skills, priorities, and workflows of other teams.
In tech and product organizations, this is invaluable. Product managers gain a better grasp of technical constraints, engineers understand market drivers, and product designers see how business metrics shape their work.
The result is sharper decision-making, faster cross-functional collaboration, and more well-rounded professionals.
To implement it effectively:
Identify natural overlaps – Look for projects where different teams already collaborate, such as feature launches or product-led onboarding improvements, and use them as learning opportunities.
Facilitate role shadowing – Let employees spend a day or week observing someone in another function to see tools, processes, and decision-making in action.
Run “skill swap” sessions – Host monthly or quarterly meetups where teams teach each other key concepts or workflows, such as engineers explaining API architecture or designers walking through user research.
Form mixed learning groups – For certain training programs, intentionally group people from different departments so discussions include varied perspectives and problem-solving approaches.
Capture and share insights – After each cross-functional initiative, document what was learned and how it can be applied in future projects, then make it accessible to the wider organization.
By building structured opportunities for people to learn outside their usual lane, you not only upskill individuals but also create teams that can adapt quickly and solve problems.
8. Encourage peer-to-peer learning
Not all upskilling needs to come from formal training or outside experts. Some of the most impactful learning happens when employees teach each other. They share knowledge that’s directly relevant to their team’s product tools, workflows, and challenges.
To make peer-to-peer learning effective:
Run short, focused sessions – 30–45 minutes on a specific topic works better than long, unfocused training.
Rotate presenters – Give different team members a chance to share their expertise. This spreads knowledge and builds confidence.
Make it practical – Encourage presenters to include real examples, demos, or live problem-solving rather than theory alone.
Record and archive sessions – Build an internal library of past talks so knowledge is always accessible.
Reward contributors – Recognize employees who consistently help others level up their skills.
Peer learning keeps knowledge flowing inside the product-led organization and helps build a culture where learning is continuous, collaborative, and part of everyday work.
Try these practices to upskill your employees successfully
Upskilling is an ongoing commitment. Technology will keep evolving, industries will keep shifting, and the skills that make your business competitive today won’t necessarily hold the same weight tomorrow.
The companies that win will be the ones that treat learning as part of the culture, not just an HR initiative. That means embedding it into day-to-day work, rewarding curiosity, and giving people the space and tools to grow.
In the end, upskilling is about building a workforce that’s adaptable, innovative, and ready to take on whatever comes next. If you start now, you won’t just keep up with change. You’ll be the one setting the pace.
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Updated: October 6, 2025
