Upskilling and Reskilling Independent Talent: What to Know

By MBO Partners • March 20, 2025

2 MIN

Key points

In the modern business environment where change has become the norm, skill requirements frequently shift.
When demand for new skills arises, upskilling and reskilling current workers can be a cost-effective strategy.
Encouraging your independent contractors to pursue upskilling and reskilling opportunities is a win for both your company and the independent talent.

Today’s evolving job market requires workers to continuously adapt their skills. What many call a “skills shortage” is often just rapidly shifting demands where certain expertise becomes highly sought-after before the workforce can catch up.

The technology sector shows this clearly. Right now, artificial intelligence and machine learning skills are in peak demand, while other times, project management or digital marketing expertise takes priority.

Different Strategies for Upskilling and Reskilling Your Workforce

When facing skill gaps, organizations typically choose between:

Recruiting external talent with the needed qualifications
Investing in upskilling their existing workforce

The first approach often creates expensive turnover cycles. Constant hiring disrupts teams and risks losing valuable institutional knowledge from long-term employees.

The second approach—developing your current workforce’s skills—typically proves more sustainable. It builds workforce capabilities while maintaining stability and preserving company-specific knowledge.

Learn More: Building the Workforce of Tomorrow: Key Skills for the AI Era

Strategically Developing the Skills of Independent Contractors While Staying Compliant

Important note: Independent contractors operate differently than traditional employees and can’t be required to complete training. However, companies can still support their professional growth within legal limits.

For organizations using independent talent, encouraging skill development benefits both sides. To do this effectively:

Conduct Regular Skills Assessments

Evaluate workforce capabilities annually—or more often if needed. Market changes or new strategies might require extra check-ins to stay aligned.

Monitor Industry Trends Proactively

Watch for emerging skill needs and share updates with contractors. While training can’t be mandatory, offering learning resources and incentives keeps your talent pool ready.

Maintain Transparent Communication

Keep open conversations with both contractors and employees about changing needs. The frontline insights of hiring managers can guide better skill-building approaches.

Discover: How to Maximize the Potential of Your Workforce With Contingent Talent

Ultimately, these strategies create a collaborative ecosystem where organizations and independent professionals grow together—turning skill gaps into opportunities for advancement.