Five Challenges Killing Your Upskilling Programs

Why upskilling can feel like treading water

Most HR and L&D leaders agree that upskilling is no longer optional. Employees expect growth, and business strategy depends on having the right skills in house. Yet, despite good intentions, many organizations see only modest returns from their learning investments.​

Learning and development budgets are shrinking while skills demand grow. Recent data shows average spend per employee dropped nearly 20% year on year to $774. This may still seem sufficient but with less money and higher stakes, training needs to show business impact. With the rise of skills-based organizations, the availability of skills data has increased significantly. However, many organizations still struggle to translate that data into actionable development insights. Without a clear link between skills data and targeted learning interventions, upskilling efforts fail to drive meaningful improvements in performance, retention, and organizational agility.

Challenge 1: Learning that doesn’t match strategy

How many leadership workshops or “communication skills” sessions have been rolled out simply because they’re “good to have,” not because they close a critical capability gap?

The disconnect is clear: strategy may say we need an AI-enabled workforce, but training is generic that doesn’t target those specific skills. When L&D programs aren’t built on actual skills data, they become expensive distractions from the capabilities the business actually needs.

Challenge 2: Development that isn’t personal

Without visibility into their strengths and development areas, it’s hard to tailor learning to individual needs.​ Research shows that 60% of employees say they don’t have a personalized development plan, so when forced to take part in generic programs, uptake and engagement is low, and skills development is minimal.

Challenge 3: Managers without the right tools

L&D teams build great programs, employees complete them, but without manager involvement nothing changes. Managers have the most influence on day‑to‑day skill application but without clear data on team members’ skills and development areas, managers cannot effectively coach, provide targeted support, or create meaningful development plans - ultimately limiting the impact of upskilling initiatives.

Challenge 4: Progress that’s invisible

Course completion rates don’t measure skill growth. A team might finish a project management certification, but can they actually run complex projects any better?​

Most organizations measure activity (hours completed, courses finished), but only 16% effectively measure the business impact. Without clear metrics that enable stakeholders gain an informed view of skills development and capabilities gained, L&D becomes a cost center, not a performance driver, and it becomes harder to prove ROI and secure future investment.

Challenge 5: A culture that doesn’t support learning

Only 35% of employees feel their organization provides effective training and development opportunities. There’s an all too familiar story of an employee trying to implement new ideas or ways of working but then gets pulled back into “how we’ve always done things.”

In the age where AI-readiness will be a key advantage, skills like embracing new ideas and innovation need organizational support and encouragement for both business impact and employee motivation. Learning needs to be built into project assignments, team collaborations, and problem‑solving, not something that happens only in scheduled sessions.​

From insight to impact

Skills insights without action are expensive reports that gather dust. The real opportunity lies in turning those insights into investing in appropriate upskilling programs which provide targeted, personalized development that aligns with business strategy.​

The good news? Organizations that combine data‑driven skills insights with focused development see higher engagement, better retention, and the agility to pivot when markets shift.​ 

Grab the full eBook, The Upskilling Disconnect: Why Insight Alone Isn’t Enough, to see how to overcome these roadblocks with practical steps to turn skills data into a workforce that grows with your business.