“We need to upskill our workforce.”

I hear this constantly. But when I dig deeper, organisations often mean something more fundamental: they need to reskill people for entirely different work.

The distinction matters because upskilling and reskilling require different strategies, different investments, and different expectations. Confusing them leads to programs that don’t achieve their goals. The World Economic Forum has been highlighting this distinction in their workforce transition guidance, noting that each requires fundamentally different approaches.

Let me clarify the difference and what each requires.

Defining the Terms

Upskilling means building additional capabilities that enhance someone’s current role. The core work remains the same; the person becomes better at it or gains adjacent skills.

Examples:

• A marketer learning to use AI tools for campaign optimisation
• A project manager developing advanced stakeholder communication skills
• An accountant learning new analytics software
• A salesperson improving negotiation techniques

Reskilling means developing fundamentally new capabilities that enable someone to move to a different role. The core work changes; the person transitions to something substantially different.

Examples:

• A retail worker training to become a data analyst
• A call centre agent developing to become a customer success manager
• An assembly line worker retraining for robotics maintenance
• A journalist transitioning to content strategy

The difference isn’t always sharp—there’s a spectrum between minor upskilling and complete reskilling. But the strategic implications differ significantly.

Why the Distinction Matters

Treating reskilling like upskilling sets people up to fail:

Time requirements differ dramatically. Upskilling might take weeks or months. Reskilling often takes years.

Investment scales differ. Upskilling might cost hundreds or thousands per person. Reskilling can cost tens of thousands.

Success rates differ. Most people can upskill successfully with appropriate support. Reskilling has higher failure rates—not everyone can make fundamental role transitions.

Support requirements differ. Upskilling often works with self-paced resources and occasional coaching. Reskilling typically requires intensive, structured support.

Measurement differs. Upskilling shows impact in improved performance. Reskilling shows impact in successful role transitions.

Strategies designed for upskilling produce disappointing results when applied to reskilling challenges.

When to Upskill

Upskilling is appropriate when:

Roles are evolving but not disappearing. Technology changes how work is done, but the fundamental work remains. People need new tools and techniques within familiar territory.

Skills gaps are moderate. The distance between current and needed capability is bridgeable with reasonable investment.

Time pressure is manageable. There’s runway to develop capability before it’s urgently needed.

The goal is competitive advantage. You want people to be better at what they already do well.

Upskilling strategies:

• On-demand learning resources for self-development
• Short intensive workshops for specific skills
• Coaching and mentoring for applied development
• Project assignments for experiential learning
• Certification programs for validated capability

Most workforce development falls in this category. It’s incremental enhancement of existing capability.

When to Reskill

Reskilling is appropriate when:

Roles are disappearing or transforming fundamentally. The work itself is going away, not just changing. People need entirely new capabilities to remain valuable.

The alternative is workforce exit. Without reskilling, people will leave the organisation—whether voluntarily or through reduction.

Investment makes business sense. The cost of reskilling compares favourably to the cost of turnover plus external hiring.

Individuals are willing and able. Reskilling requires significant effort from participants. Not everyone is suited for fundamental career transition.

Reskilling strategies:

• Structured multi-month programs with clear curricula
• Intensive support including dedicated coaching
• Practical experience through rotations or projects
• Strong partnerships with business units receiving reskilled workers
• Clear pathways from training to new role placement

Reskilling is less common and more demanding. It’s appropriate when business conditions require it, not as a general development approach.

The Assessment Challenge

Determining whether someone can successfully reskill is difficult. Factors that predict success:

Learning agility. People who learn quickly and adapt to new situations reskill more successfully.

Motivation. Intrinsic desire to make the transition matters more than compliance with organisational direction.

Foundational capabilities. Some skills transfer; people with strong foundations in transferable areas have advantages.

Resilience. Reskilling involves struggle and setback. People who persist through difficulty are more likely to succeed.

Support systems. People with strong personal and professional support networks navigate transitions better.

Assessment should be realistic. Not everyone can reskill successfully. Better to identify who’s likely to succeed than to put people through programs they’ll fail.

Organisational Implications

The choice between upskilling and reskilling has organisational implications:

If primarily upskilling:

• Learning infrastructure is more important than structured programs
• Manager capability to support development matters most
• Self-directed resources can do much of the work
• Measurement focuses on performance improvement

If significant reskilling:

• Dedicated programs with substantial resources required
• Career transition support becomes essential
• Partnerships with receiving business units critical
• Measurement focuses on successful transitions

Many organisations need both—upskilling for the majority while reskilling the minority whose roles are fundamentally changing. Resource allocation should reflect this.

The AI Dimension

AI creates both upskilling and reskilling imperatives:

Upskilling for AI: Most knowledge workers need to learn to work effectively with AI tools. This is enhancement of existing roles, not role change. Upskilling strategies are appropriate.

Reskilling because of AI: Some roles will be substantially eliminated by AI. People in those roles need fundamentally new capabilities. Reskilling strategies are required.

The mistake is treating the second category like the first. People whose roles are disappearing don’t just need AI fluency—they need entirely new professional identities.

Getting the Strategy Right

For L&D professionals navigating these decisions:

1. Assess the scope of change. For each affected population, is the work evolving or disappearing? This determines strategy.

2. Be realistic about reskilling. It’s harder, more expensive, and less likely to succeed than upskilling. Don’t oversell it as easy.

3. Match investment to challenge. Light-touch development for upskilling. Intensive support for reskilling.

4. Set appropriate expectations. Upskilling can reach most people. Reskilling will succeed for some, not all.

5. Measure appropriately. Performance improvement for upskilling. Transition success for reskilling.

6. Communicate honestly. Employees deserve to understand what they’re facing and what support is available.

The Human Dimension

Behind strategy and investment are real people facing uncertain futures.

For people upskilling: The message is “your role is valuable, and we’re investing in making you better at it.” This is generally reassuring.

For people reskilling: The message is “your current role is changing fundamentally, and you’ll need to become someone professionally different.” This is challenging to deliver and receive.

Both deserve honesty about what they face and genuine support for navigating it. Strategy without humanity isn’t effective L&D practice.

Summary

Upskilling and reskilling aren’t synonyms. They describe different challenges requiring different approaches:

Dimension	Upskilling	Reskilling
Role change	Enhancement	Transformation
Time frame	Weeks to months	Months to years
Investment	Moderate	Substantial
Success rate	High	Variable
Support needed	Moderate	Intensive
Measurement	Performance improvement	Role transition

Get the categorisation right, and appropriate strategy follows. Get it wrong, and programs underdeliver because they’re designed for a different challenge.

The current environment demands clarity on this distinction. Make sure your workforce development strategy reflects it.