How to Launch an Upskilling Strategy with Measurable Results

You’ve seen it, haven’t you?

A top performer leaves. A key role sits open for weeks, maybe months. Teams stretch thinner, deadlines slip, and morale dips just a little lower. You post the job, screen dozens of résumés, and still… no one quite fits. Meanwhile, there are smart, capable people inside your organization who just needed a nudge. A bit of training. A shift in direction. But they didn’t get it because your systems weren’t built for that.

That’s the quiet cost of a broken upskilling strategy. It doesn’t always show up on balance sheets, but it eats away at progress, retention, and momentum.

And yet, we talk about talent all the time. How to attract it, how to retain it, how to build it. That’s why upskilling, reskilling, and skills-based internal mobility have become critical initiatives that HR departments and business leaders are looking at as possible solutions to their current and future challenges.

And these initiatives could have a huge impact. For example, “wide-scale investment in upskilling has the potential to boost global GDP by 5-6.5 trillion USD by 2030”, according to a World Economic Forum report.

So where do we go from here?

With the significance of upskilling in mind, we’ll explore the main skills gaps in work environments, some of the key upskilling initiatives you can implement, and a few successful examples of upskilling programs.

What Do We Actually Mean by “Upskilling”?

The term “upskilling” tends to surface in strategy decks and HR discussions, often with an air of urgency, but without much shared understanding. That’s a problem. Because if we can’t define it clearly, we’re unlikely to implement it meaningfully.

At its core, upskilling is the process of developing an employee’s current capabilities so they can take on more advanced responsibilities within their role or adjacent roles. It builds on existing knowledge rather than replacing it. Think of a support agent learning data tools to contribute to process improvement, or a marketing associate gaining technical fluency to collaborate better with product teams. The role evolves, but so does the person.

How Upskilling Differs From…

To keep things straight, here’s how it compares to its often-confused cousins:

• Reskilling is about preparing someone for an entirely new role, like training a warehouse associate to move into IT support.
• Cross-skilling usually means expanding someone’s abilities across functions, say, helping a sales manager understand basic UX principles.
• Lifelong learning is the broader philosophy, encouraging ongoing growth throughout someone’s career, regardless of title.

All of these matter. But upskilling is the lever that lets companies move quickly, retain internal talent, and stay competitive without constantly chasing external hires. It’s proactive without being disruptive. And when done right, it’s one of the clearest signals you can send that your people matter, not just for what they do now, but for what they’re capable of becoming.

Major Skills Gaps Faced by Organizations

It’s easy to think of upskilling as a benefit, something progressive companies offer when they have the time, budget, and headcount. But that framing misses the point. This isn’t about staying competitive someday; it’s about staying operational now.

Not every skills gap shows up on a performance review or hiring dashboard. Some take shape slowly: missed deadlines, stalled projects, roles left unfilled for too long. Others are more immediate, surfacing when teams can’t adapt to a new platform or respond to fast-moving risks.

The type and level of skills gaps will vary from one company to another. But they definitely exist and the impact is real. A McKinsey survey reveals that 87% of organizations are either already facing this issue or expect to in the next few years.

It’s important to point out that skills gaps and upskilling — the solution — can encompass both soft and hard skills. And the best way to find out how your workforce stacks up is with an in-depth skills gaps analysis. This analysis, together with a mapping of critical roles and current (and future) abilities should be part of any healthy upskilling strategy.

Still, there are certain areas where gaps are more likely to be present, including:

Digital Skills Gaps

Digital fluency isn’t just a tech department concern anymore; it’s become foundational across nearly every role. But the pace of change continues to outstrip internal training capacity. As new tools, platforms, and systems roll out, many employees are left to figure them out on their own or not at all.

The direct result is a decrease in productivity and competitiveness for businesses, especially in industries where employees need specialized digital skills. Another consequence is the increased competition for qualified workers and longer periods of vacancy since the hiring process is hindered by the talent shortage.

Some of the most important digital skills that organizations need to address include but aren’t limited to:

• Artificial Intelligence (AI): Tools powered by artificial intelligence — particularly generative ones — have quickly moved from curiosity to daily utility. But without guidance, teams risk misusing or underusing them. AI still requires human context, quality prompts, and strategic judgment, none of which happen without training.
• Cloud Computing: While it is an essential aspect of remote work, using the cloud to store data and run applications is now common practice for most organizations. And as such, employees need to learn how to use and collaborate across these platforms. Mismanagement of shared resources, data fragmentation, and security risks often stem from simple unfamiliarity.
• Cyber Security: While not as attractive as AI or as fun as Social Media Marketing, there is a growing need for workers to step up their game when it comes to cybersecurity. In a world where fake web pages, emails, and now voices, are becoming more convincing than ever, knowing how to prevent and respond to a scam or a cyberattack is crucial.
• Data Analysis: While initially, you might think this skill is more relevant to people in specialized industries, don’t make a mistake. Data-driven decision-making applies to any team and department, and learning how to gather, sort, and extract insight from data is more important than ever.
• Social Media Marketing: While (almost) everybody has social media accounts, not everybody knows how to make the most out of these platforms to promote their brand, engage customers, or drive growth in sales. Organizations often find that while employees use social media personally, they lack the skill to engage communities or communicate brand values effectively.

Embracing upskilling and addressing digital skills gaps has become a must for businesses that want to remain competitive in the digital age and ensure their workforce functions at its full potential.

Soft Skills Gaps

Another area where organizations are witnessing significant gaps is soft, or as Simon Sinek likes to call them, human skills:

These skills are difficult to automate, difficult to teach, and disproportionately affect team cohesion, leadership potential, and customer experience. When they’re missing, it’s usually obvious. Interpersonal friction increases, trust weakens, and productivity drops without clear cause.

LinkedIn’s research highlights the stakes: 91% of talent professionals consider soft skills crucial to the future of HR and recruiting, and 89% of poor hires are attributed to gaps in these areas.

Here are some of the human skills we recommend including in your upskilling initiatives:

• Empathy: Arguably the foundation for everything else, especially in hybrid or remote work environments where tone, intent, and emotional context often get lost. It’s what allows us to understand colleagues, and their intentions, and to create true and meaningful connections.
• Communication: There’s a reason communication skills show up every time there’s a discussion about soft or work skills in general. They impact almost every interaction, be it with colleagues or clients, and can often make or break career aspirations, especially for those interested in managerial roles.
• Teamwork: In many jobs, the ability to work with others seamlessly is essential. And it’s a skill that can be mastered in time, even by employees who are more introverted or who are used to working on their own.
• Conflict resolution: Tension in teams is natural. Letting it fester isn’t. People need the skills to surface disagreement early, listen fully, and find common ground. Without these abilities, small issues compound into larger cultural problems. That’s why it’s important to know how to identify the root cause of conflicts, listen to different perspectives, and find mutually acceptable solutions.
• Problem-solving: Challenges are a part of work (and life) and knowing how to analyze problems and come up with possible solutions will prove to be valuable in many job roles. Problem-solvers rely on critical thinking and collaboration to find the best solutions to problems at work.

The importance of bridging the soft skills gap is further emphasized by LinkedIn data, which reveals:

What Companies Need in Place Before Launching an Upskilling Strategy

It’s tempting to jump straight to programs; build a course, license a platform, launch a new LMS. But upskilling isn’t something you bolt on. It only sticks when it’s connected to how people already work, how they grow, and how the organization makes decisions.

In other words, if the foundation isn’t right, the strategy won’t hold.

Before introducing any formal learning initiative, there are a few structural pieces that need to be in place. Without them, even the most well-designed programs tend to fade out or lose traction quickly.

1. A Clear, Organization-Specific Purpose

Why are you upskilling in the first place? Because other companies are doing it? Because a vendor promised ROI in six months?

Generic motivation leads to generic outcomes. Upskilling should serve a defined business need, whether that’s internal mobility, cross-functional agility, leadership pipeline development, or reducing reliance on external hiring.

If the goal isn’t clear internally, it certainly won’t be clear to your employees. And when learning feels disconnected from real opportunities, participation drops. Fast.

2. Shared Ownership Across Roles

Too often, learning is siloed; an HR or L&D function that operates on the edge of the business. That structure rarely works. Upskilling has to be co-owned across departments:

• HR and People teams can create frameworks and systems
• Managers can identify relevant skill gaps and apply learning in real time
• Employees can give feedback on what’s working and what’s missing

If no one takes ownership, the program drifts. If only one team owns it, it struggles to scale.

3. Realistic Expectations from Leadership

Leadership support can’t just mean greenlighting a budget. It means understanding what upskilling actually looks like day to day: messy, nonlinear, often quiet. It means accepting that not every outcome will be instant or easily measurable.

When executives expect overnight results or over-prioritize efficiency, learning becomes performative. And when that happens, trust erodes.

Support from the top should include time, psychological space, and public backing, not just talking points.

4. Space in the System for Learning to Happen

People can’t learn in theory. They need room to try, apply, fail, and recalibrate. That means carving out actual time. If workloads don’t shift, deadlines don’t flex, or systems don’t accommodate learning activities, even the most motivated employees will deprioritize it.

This is where structural design matters:

• Can team members shadow other roles without disrupting delivery cycles?
• Are there designated windows for learning sprints or experimental projects?
• Is learning tied to performance conversations or just treated as extra credit?

5. A Feedback Loop That Doesn’t Wait Until It’s Too Late

Whether formal or informal, feedback has to be built into the process. What’s landing? What’s not? What are employees actually using from what they’ve learned?

Surveys, check-ins, and even quick informal chats can tell you far more than completion rates or platform log-ins. The key is to make sure that input is acted on. When learners see their feedback shape future programs, engagement deepens. It becomes a conversation, not a campaign.

How to Upskill Employees: Methods and Tools

Now that we’ve looked at where skill gaps tend to show up and what foundation you need, it’s time to shift to the “how.”

Upskilling isn’t about offering a course and hoping for the best. It requires methods that reflect how people actually learn, through repetition, context, collaboration, and timing. Successful programs often blend formal systems with informal support, mixing digital tools, human connection, and real-life application.

Below are several core upskilling approaches that organizations are using, individually and in combination, to build a more capable, adaptable workforce.

New Learning Ecosystems

Perhaps one of the most interesting approaches to upskilling is the one we’re seeing implemented in Singapore, where institutions of higher learning have started turning into institutions of continual learning.

This is an effort that involves the collaboration of the government, education institutions, and enterprises — all to help people become and remain ready for the job market, both now and in the future.

Through this collaboration, curricula will stay up-to-date and will constantly evolve based on changing business needs and the necessary skills of future employees. Programs and courses will also become flexible, enabling everybody to keep learning, even those who have already entered the job market.

For companies, this signals a shift in mindset:

• Learning must be continuous, not occasional
• Programs should flex with real-world demands
• Employees need access to modular, job-relevant, and time-conscious options

What this looks like inside a company:

• On-demand learning platforms with curated role-based libraries
• Short, skills-based credentials instead of multi-week courses
• Hybrid models blending internal training with external certifications

Tools commonly used:

• LinkedIn Learning, Coursera for Business, Degreed

Coaching

Coaching is an upskilling method that is increasingly being used in the corporate environment. It typically involves regular one-on-one sessions, during which the coach:

• Provides guidance and support
• Asks questions to help the employee identify improvement opportunities
• Offers feedback on progress

One of the stand-out benefits of coaching is that it is tailored to the individual needs of the employee, which allows them to focus on the areas where they need most help. It is also a more personalized and flexible approach when compared to traditional training or learning methods, such as online courses or group workshops.

To be successful, coaches need to help people identify their strengths and weaknesses, set goals, and develop a mutually agreed plan of action to achieve them.

Implementation tips:

• Internal coaches can come from HR, L&D, or team leads
• External coaches may be valuable for specialized roles or senior leadership
• Sessions should be time-bound and structured. Coaching without direction turns into unproductive conversation

Mentoring

Unlike coaching, mentoring is often a longer-term relationship between a more experienced and knowledgeable person (mentor) and a less experienced employee (mentee).

The reason why mentoring can be a hugely successful upskilling method is the fact that it helps workers develop skills that aren’t always easily taught through formal training or learning programs. Or, in other words, employees develop knowledge that wouldn’t otherwise be (easily) available.

The relationship between the mentor and the mentee can focus on specific skills or interests, like project management, or on general guidance, perhaps related to career development or making the right lateral move within the company.

Mentoring also has a positive impact on the company culture, since it creates a stronger sense of community and deep connections built on trust and mutual respect.

Peer-To-Peer Learning

Peer-to-peer learning or learning through collaboration may be one of the simplest and yet most impactful upskilling efforts. It involves employees learning from each other, usually (but not always) within the same team or department.

This can include:

• Informal Q&A channels in Slack or Teams
• Internal “teach-back” presentations after training sessions
• Role-based roundtables or lunch-and-learns
• Paired peer coaching across departments

The beauty of peer-to-peer learning is that while it can be initiated — and thrives with support from — the organization, it works just as well when workers start it out of their own initiative.

It is one of the most cost-effective upskilling methods while still providing a great development experience. That’s because learning from and with peers provides real-world examples and insights from hands-on experiences, which are often more valuable than theoretical (online) courses.

Leadership Development Programs

Unlike the other upskilling methods we’ve explored so far, leadership development programs don’t target all employees, focusing instead on the high-performers with the potential and desire to make vertical moves in their careers. The aim is to help them:

• Become more effective leaders
• Manage teams more efficiently
• Drive business results

During leadership development programs, employees can focus on improving in a variety of areas, including public speaking, strategic thinking, project management, decision-making, etc.

It’s not uncommon for companies to collaborate with third-party providers when offering this type of upskilling. But the advantage of offering them using internal resources is being able to address specific skills (gaps) related to the organization’s goals.

The obvious and most important benefit of leadership development programs is that companies can build a strong pipeline of future leaders. It’s a very effective way of developing a talent pool of high-performing individuals who will be ready to take on leadership roles in the future.

On-the-Job Learning Through Project-Based Sprints

Not all learning needs a formal classroom or a login screen. In fact, some of the most valuable upskilling happens through structured, real-time experience. Examples of on-the-job upskilling methods include:

• Stretch assignments: Projects that push employees beyond their current responsibilities and require them to apply new tools or thinking.
• Learning sprints: Time-boxed initiatives tied to a specific business goal, often involving quick experimentation, iteration, and feedback.
• Team rotations or “innovation pods”: Temporary cross-functional groups focused on a challenge or internal opportunity.

This kind of embedded learning does more than transfer skills. It accelerates decision-making, encourages creative thinking, and breaks down functional silos.

It’s especially useful when:

• You need faster outcomes, without waiting for a formal program to launch
• The employee is curious and self-directed
• Formal training budgets are limited, but there’s internal expertise to tap into

The structure doesn’t have to be complex. What matters is clarity around the scope of the project, the support available during the process, and space for reflection once the work wraps. Done right, these sprints become both a growth experience and a pipeline for internal mobility.

A Practical 90-Day Playbook for HR and People Teams

The idea of launching an upskilling strategy can feel overwhelming, especially when time, budget, and internal alignment are all moving targets. But it doesn’t need to start with a full-scale rollout. The most effective programs often begin with small, focused actions that build momentum and earn trust.

If you’re wondering where to begin, this 90-day framework offers a realistic path forward, designed to help you test, adjust, and learn as you go.

Weeks 1–4: Assess and Align

Before you introduce any new initiative, start by getting a clearer picture of where your teams stand and what they actually need.

What to focus on:

• Run a quick internal skills audit
  Ask team leads: Where are people struggling to keep up? Where are they learning on the fly? Keep it conversational. Don’t over-engineer it at this stage.
• Map critical roles and emerging needs
  Identify functions tied to upcoming priorities (new product launches, system transitions, market shifts). These are natural pressure points and good test areas.
• Check existing resources
  What content, expertise, or access do you already have? Chances are, you’ve got more in place than you think: internal documentation, team experts, past trainings, or external partnerships.

Weeks 5–8: Pilot Something Small but Meaningful

The second month is about action. Choose one area to experiment with, ideally where the need is clear, and the team is engaged.

Ideas for low-lift pilots:

• A peer-to-peer “show-and-share” session on a core tool or workflow
• A short-term learning sprint (2–3 weeks) tied to a specific project goal
• A one-on-one coaching test with a high-potential team member
• A cross-team mentorship match with optional participation

How to make it work:

• Keep expectations clear, and participation voluntary where possible
• Create space for reflection after
• Capture feedback early, even informally, to adjust quickly

Weeks 9–12: Reflect, Refine, Expand

By the third month, the goal isn’t perfection. It’s clarity. What landed? What didn’t? Where is the energy building?

Here’s what to do:

• Collect feedback from participants and managers
  Keep it lightweight: email check-ins, Slack polls, short voice memos. You’re not looking for survey data yet; you’re looking for patterns.
• Look at internal signals
  Did participation increase over time? Did team leads start asking for more? Are people talking about the experience in 1:1s or retros?
• Document learnings
  What would you keep? What would you scrap? Capture these while they’re fresh. They’ll shape your next iteration.
• Present early outcomes to leadership
  Frame it as a progress report, not a final verdict. Share what worked, how teams responded, and what you’re planning to build next.

Final Advice: Don’t Wait for Perfect Conditions

You’ll never have full alignment, unlimited time, or complete certainty. What you can have is intention, curiosity, and a willingness to learn from the process just like your employees.

Start small. Stay honest. Build from what’s real.

How to Track and Improve Your Upskilling Strategy

If you can’t measure it, you can’t improve it. When it comes to upskilling, most companies track the wrong things or stop at surface-level data.

A report that shows “100 people completed training” doesn’t tell you whether anyone actually learned something or used it. And while ROI is often top of mind, proving value isn’t just about cost reduction. It’s about understanding whether your people are becoming more capable, more confident, and more prepared to take on what’s next.

The goal isn’t to track everything. It’s to track what matters: engagement, behavior change, and business impact over time. The best measurement strategies balance hard numbers with lived experience and use both to refine, not just report.

The most effective measurement frameworks combine four types of indicators:

1. Participation and Engagement (Leading Indicators)

These early signals tell you whether people are actually engaging with the learning opportunities available to them.

• Enrollment or opt-in rates for upskilling initiatives
• Attendance or participation in learning sprints, mentoring, or peer sessions
• Resource usage (e.g., time spent in platforms like LinkedIn Learning, Notion, 360Learning)
• Manager or mentor involvement and support

Caution: High participation doesn’t always equal high value, but low engagement often points to deeper issues (misaligned content, unclear relevance, lack of time).

2. Application and Behavior Change

The goal of upskilling isn’t just consumption; it’s translation into better work. Behavior-focused metrics can show whether skills are moving from theory into practice.

• New capabilities observed in performance reviews or project work
• Increases in cross-functional collaboration or expanded role responsibilities
• Manager feedback on skill application post-training
• Peer recognition (formal or informal) related to learned skills

3. Business-Level Impact

These are lagging indicators. They won’t show up immediately but they matter when it comes to long-term strategy and executive buy-in.

• Reduced hiring costs through internal mobility
• Faster onboarding for lateral transitions
• Improved retention in high-turnover roles
• Better customer outcomes tied to trained functions (e.g., faster support resolution, better product feedback)

4. Sentiment and Cultural Signals

Don’t underestimate the power of perception. Employees need to feel that upskilling is supported, valuable, and worth their time. Otherwise, even the best programs fizzle out.

• Pulse surveys on learning satisfaction, usefulness, and accessibility
• Qualitative feedback in 1:1s or team check-ins
• Participation in optional development activities (a sign of voluntary buy-in)
• Requests for additional learning, especially when specific and self-initiated

How to Make Measurement Useful

• Combine data types: Use a blend of hard metrics (participation, retention) and soft indicators (feedback, sentiment). One without the other leads to shallow conclusions.
• Focus on direction, not perfection: Trends matter more than isolated numbers. Are more people engaging? Are they applying what they learn? You’re tracking growth, not chasing a score.
• Share results where they matter: Communicate learning outcomes to leadership, but also to managers and employees. When people see the impact of their efforts, engagement improves organically.
• Adjust quickly, publicly, and often: If something isn’t working, say so. Kill what doesn’t serve your teams. Make improvements visible. It shows responsiveness and builds trust.

Companies With Successful Upskilling Initiatives

To prove that upskilling isn’t just the passing fad in the endless sea of business trends, here are a few attention-worthy examples from companies that have successfully implemented upskilling initiatives:

Capital One

Capital One has adopted a strategy of upskilling and cross-training its employees to tackle a talent shortage in tight labor markets. The company’s approach is focused on “developing the whole person” via a range of programs, including:

• a full-stack development academy
• an internal “tech college”
• leadership development
• other soft-skills training

The Capital One Developer Academy (CODA) is perhaps the most successful program, with over 200 people being hired annually after graduating.

And this approach is paying dividends in more ways than one. For instance, their culture of learning and the “entrepreneurial spirit” has also helped to attract new engineering talent to the firm.

Verizon

One of the largest global mobile network operators, Verizon, provides free online technical and soft skills training (in partnership with Generation USA) to prepare American workers for future tech careers.

Participants have the freedom to choose from various 10- to 15-week programs in fields like cybersecurity, IT support, or web development among others. And the company doubles down on its efforts by supporting participants to continue their education or find employment afterward.

According to Verizon, 70% of program graduates find jobs within 3 months of graduation and they are committed to training 500,000 workers for in-demand tech jobs by 2030.

Walmart

In 2021, Walmart announced that it would pay 100% of college tuition and books for associates through its Live Better U (LBU) education program, removing the previous 1 USD per day fee.

At the time, this meant 1.5 million Walmart and Sam’s Club associates in the US could finally earn college degrees or learn trade skills without the burden of education debt. And so far, the results speak for themselves:

• over 330 million USD in tuition savings since LBU launched
• 66% increase in enrolment since the 1 USD/day fee was removed
• LBU participants are 2 times more likely to be promoted
• LBU participants are 4 times more likely to stay at Walmart

By the end of 2022 alone, over 89,000 associates had already participated in LBU, and more than 15,000 had completed a degree or program. And Walmart continues to honor its initial commitment to invest nearly 1 billion USD in career-driven training and development until 2026.

Final Thoughts About Upskilling

A successful upskilling strategy doesn’t start with a platform or a playbook. It starts with intent. It builds through consistency. And it scales when learning is treated not as an “extra,” but as a core part of how work gets done.

You don’t need to fix everything at once. You need to start where it matters, where skills are missing, where motivation exists, and where even a small shift can unlock new value. When people see that learning leads somewhere — whether it’s more confidence, more opportunity, or more contribution — they engage. Not because they have to. Because it’s worth it.

Frequently Asked Questions About Building an Effective Upskilling Strategy

1. How can we tell if our company is ready to launch an upskilling strategy?

You’re likely ready if you’ve identified recurring skill gaps, stalled team performance, or roles that are hard to fill internally. Readiness isn’t about having a full learning platform. It’s about having leadership buy-in, some organizational space to test, and a clear business case for improving employee capabilities. If managers are open to learning conversations and employees are asking for development opportunities, that’s your signal to start.

2. What’s the difference between upskilling, reskilling, and cross-skilling?

Upskilling helps employees improve in their current roles; like learning new tools, deepening expertise, or expanding responsibilities. Reskilling means training someone to move into a different role entirely, often due to automation or restructuring. Cross-skilling is about gaining skills in other departments or functions to boost flexibility and collaboration. Each strategy supports workforce development in a different way and should be matched to your organization’s specific needs.

3. Should we create our own training content or use third-party learning platforms?

Third-party platforms like Coursera, LinkedIn Learning, or 360Learning are useful for broad or technical topics, especially when speed and scale matter. But internal content, such as peer-led tutorials, process walkthroughs, or custom guides, is often more relevant for company-specific tools and workflows. The most effective upskilling strategies often combine both, using curated external content alongside in-house knowledge.

4. How do we get employees to engage with upskilling programs?

Engagement rises when employees see a real benefit. That means connecting learning to career progression, promotions, or visible project opportunities. It also helps to build learning into the workday, not just offer it as an after-hours activity. Managers play a key role here when they actively support and model learning, employees follow suit. Recognizing participation, sharing success stories, and creating space for learning in team workflows all contribute to higher engagement.

5. What’s the best way to measure the success of an upskilling strategy?

Go beyond course completions. Track whether employees are applying what they’ve learned in their day-to-day roles. Look for improvements in performance, internal promotions, stronger collaboration across teams, and faster project delivery. You can also use engagement surveys, 1:1 feedback, or manager assessments to capture more qualitative signs of progress. Long-term, success shows up in better retention, reduced hiring costs, and more agility when business needs shift.