Build your upskilling strategy: How to tie learning to business growth

How do you define skills in your team? Or at the organization level?

When you boil it down, it’s what people need to do their jobs better. Then, that understanding needs to be simple and shared.

What we’re saying is, don't get stuck on the term “skills.” It’s really about the work that needs to get done. To help people do real work, and to solve real business challenges.

Take Excel, for example. For many of us, the most useful features remained a mystery until a colleague showed us a trick or two. Those quick learning moments save time and frustration, but they often happen by chance. So, the question becomes: how can you identify which skills save hours of time? What infrastructure can you build for employees to have those learning breakthroughs? By training employees on hyper-relevant, current skills that directly support business goals.

Upskilling does exactly that. It helps existing employees grow and deepen their capabilities without needing to hit pause or bring in entirely new talent. Instead of stagnating, employees become more agile, confident, and ready to meet the moment.

That’s not just good for morale. It’s good for business. Upskilling drives:

Stronger engagement and retention: 48% of employees would switch jobs for better skills training
Higher productivity and business agility: Disengaged employees cost the global economy $8.8 trillion in lost productivity
A shrinking skills gap: By 2030, 39% of core skills will be different

These numbers make a strong case for investing in upskilling. But despite the clear benefits, many L&D teams are still facing major roadblocks. According to the Inside the state of upskilling report, the top two challenges are limited people or budget, and finding the right technology or tools.

With limited budgets, lean teams, and systems that don’t scale, even well-intentioned efforts can stall. Knowing isn’t the hard part. It’s the execution that’s holding you back.

Bridging that gap starts now. Upskilling prevents falling behind and keeps your workforce resilient to change. This gives your organization an edge in workforce enablement.

Here’s how to plan, make moves, and win with your upskilling strategy.

More benefits of upskilling

An upskilling strategy isn’t just about learning new things; it’s about how you solve key business problems while helping your people grow.

Check out what’s possible:

Increased employee engagement and retention: Companies that prioritize learning see 30-50% higher employee engagement levels.
Customer loyalty: Higher employee engagement and retention are strongly correlated to higher customer service, improving customer loyalty by 25%.
Improved agility and performance in your organization: Companies that invest in skills are 3x more likely to adapt to changes in the market, and disengaged employees cost 18% of their salary in lost productivity.
Cut down on the skills gap: Executives estimate that 49% of the skills that exist in their workforce today won’t be relevant in the next two years.
Talent development: 74% of employees feel they aren’t reaching their full potential due to a lack of development opportunities.

Another benefit? Upskilling can scale with you. When Trojan Storage wanted to streamline onboarding, they also saw the opportunity to build a foundation for long-term employee growth.

With Absorb LMS and Absorb Create AI, they upskilled new hires faster, equipped teams for new markets, and empowered employees to keep learning. All while saving time and over $20,000 in HR costs.

Want to see how upskilling can work at scale? Download the full case study to see how Trojan Storage used Absorb to boost skills, speed, and performance across the board.

3 strategies to implement upskilling

The best upskilling strategy is one that meets your quarterly and annual business outcomes. Thankfully, upskilling can be as simple or complex as you need. What helps is to break it up into three practical tracks: role-based upskilling, reskilling, and cross-skilling.

Each type serves a different need, so let’s get into the details.

Role-based upskilling

For improving employees' current skills

Your people are great, now it’s time to help them thrive in their role. When someone struggles with Excel formulas or leading client calls, it’s not a talent issue; it’s a training one. Role-based upskilling ensures employees build the practical skills they need to succeed right where they are.

Role-based upskilling is good for:

Sales reps needing better CRM, negotiation, or product knowledge skills
Customer service agents improving communication, empathy, or de-escalation techniques
Project managers enhancing tools proficiency (e.g., Jira, Asana), budgeting, or leadership skills
Marketing specialists updating SEO, analytics, or campaign planning skills
IT support staff needing continuous updates on new tools or systems

Reskilling

For training in new, in-demand skills

Your business priorities are shifting, and so are the skills you need. When roles become obsolete or new technologies emerge, reskilling helps you transition existing talent into high-value areas. It’s a proactive strategy to stay competitive without letting great people go.

Reskilling is good for:

Operations staff transitioning to data analytics or automation oversight
Administrative assistants moving into project coordination or HR functions
Manufacturing workers retraining for tech-enabled or robotics-based roles
Retail employees pivoting to eCommerce, logistics, or digital sales
Customer support reps transitioning into customer success or onboarding roles

Cross-skilling

For cross-functional literacy and collaboration

When teams only know their own corner of the business, collaboration suffers. Cross-skilling builds broader literacy across functions, helping employees understand how their work connects to the bigger picture. It’s the key to stronger teamwork, agility, and leadership readiness.

Cross-skilling is good for:

Product managers learning basic UX, sales strategy, or data analysis
HR professionals gaining insights into business operations or financial metrics
Engineers or developers learning to communicate with non-technical teams or work with sales/marketing
Team leads expanding leadership, compliance, or cross-departmental communication skills
Customer-facing roles developing a stronger grasp of internal processes or technical product details

Each of these strategies is powerful on its own. But together, they create a resilient, high-performing workforce that grows your business. You might start with role-based upskilling to improve today’s performance, then shift to reskilling when business priorities change.

Think of this trio as a growth portfolio. Use them with business outcomes in mind, and you’ll build agility, engagement, and a culture of learning to help you thrive with AI, automation, and constant change.

The upskilling strategy makeover: 4 challenges and how to fix them

Each challenge below represents a common roadblock to upskilling. For every challenge, we’ve included a planning touchpoint, or a stage in your L&D lifecycle where you can proactively identify and solve an upskilling challenge before it slows you down.

1. People don’t know what’s available or why it matters.

You might have a solid skills program, but if employees don’t know why it exists or how it connects to their actual job, they’re unlikely to engage. Sometimes, it’s a visibility issue. Other times? The skills offered aren’t all that relevant to their roles or priorities.

Solution: Make it easy to find and understand what to learn, how to learn it, and when to learn it. Personalized training paths give employees the flexibility to learn at their own pace. And managers? They stay in the loop without micromanaging.

Planning touchpoint: Kick off with a skills gap or role-based needs analysis so you’re solving for the right things. Follow that up with new learning initiatives and check-ins to keep awareness high.

Results:

Stronger program adoption
Better skill alignment with real work
Clear improvements in employee performance and retention

What to try: Intelligent AI training paths, mentoring, social learning dashboard

2. Only certain people get development opportunities.

Too often, training is something you get chosen for. Managers might offer learning to top performers, but that leaves others behind. It can lead to frustration, favoritism, and missed potential.

Solution: Make learning accessible for everyone. With Absorb, employees can choose their own path through self-paced learning and self-assessments. Managers can still support development, but the process becomes more inclusive.

Planning touchpoint: Add skill assessments into onboarding or development conversations, and encourage employees to set learning goals during reviews or check-ins.

Results:

Build a culture of continuous learning
Reduce the workload on managers
Expand opportunities for promotions or internal mobility

What to try: Expanded course library, self-assessments, gamification

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3. Skills aren’t keeping up with KPIs.

Longtime employees often have deep knowledge. But if their skills don’t evolve with the market, they risk becoming overwhelmed or falling behind. Hiring new people to fill gaps is expensive. And ignoring the gaps means more inability to reach your KPIs. What follows? Burnout and underperformance.

Many organizations focus on early development. We found 44% offer upskilling from day one as part of onboarding. However, fewer than 10% provide training when new business needs arise. That’s often when teams need support the most, and the absence of timely learning can hold performance back.

Solution: Reskilling programs help your current employees take on new challenges without starting from scratch. Absorb helps you deliver just-in-time learning that builds confidence and improves outcomes.

Planning touchpoint: Use performance data and role forecasts to spot where skills aren’t keeping up. Build learning plans that close those gaps in a focused, manageable way.

Results:

Protect your existing talent
Improve productivity
Stay agile in periods of change
Reduce hiring and onboarding costs

What to try: HCM integration, skills tracking, pre-built courses

4. It’s too much to manage on your own.

One minute you’re creating customer courses, then tracking participation. And what about updating materials? It’s a lot to take on. When looking to scale, L&D teams are quickly buried in logistics, especially if programs live in different systems with different owners. Before you know it, no one’s sure where to go or what to take.

Solution: Centralize and automate wherever you can. Fortunately, Absorb makes it simple to scale learning across teams without complexity. Reporting, content delivery, and progress tracking are all built in.

Planning touchpoint: Do a quick audit. Find out what platforms are used, who owns what, and where things break down. Use that to streamline your upskilling ecosystem and cut out the noise.

Results:

Save time on manual admin
Reduce duplication and inconsistencies
Give learners a smoother front-end experience

What to try: Smart administration, automate reporting to stakeholders, custom courses with AI-builder

Who, when, and how: Let’s build a business case for upskilling

Getting a solid business case for upskilling starts with one thing: clear ownership. When no one’s really in charge, plans lose steam, budgets become stagnant, and the impact gets overlooked.

Our data shows that responsibility is split pretty evenly.

That sounds good on paper, but in reality? It often just causes confusion and slows things down.

Skills need a clear owner, and that owner should be the business. The business knows what skills matter most to compete, and learning teams bring the expertise to build them. Together, that’s where the magic happens.

Numbers alone won’t move the needle. But when you can tell leaders, “Three people on your team have skills that will soon be obsolete,” now that gets their attention. If your organization isn’t making confident decisions around hiring and development yet, it’s time to change that.

This guide will help you frame (and time) your pitch so you can show leadership exactly what’s at stake.

1. Department planning meetings

These meetings are functional planning sessions (ex. sales kickoff planning, ops roadmap reviews) focused on tactical execution for the next quarter or year. Shape the conversation around upskilling to influence decisions among department leaders, ops managers, and enablement teams.