Upskilling & Reskilling Your Team: A Thoughtful Approach to Change

In my years working with small businesses and nonprofits, one truth has become crystal clear. While technology forges its striking path ahead, organizations thrive when their people are equipped to travel on that path. That's why I’m passionate about upskilling and reskilling, not just as buzzwords, but as cornerstones of a resilient, future-ready workforce.

What I Mean by Upskilling and Reskilling

• Upskilling: enhancing your team’s existing strengths.
  This looks like supporting your bookkeeper with professional development opportunities. Maybe enrolling them in a data analytics course. Or being your office manager’s biggest cheerleader as they carve out time to study for a project management certification. It’s focused, purposeful growth that builds confidence and directly improves your operations. When people feel supported in expanding their skills, everyone wins.

• Reskilling: preparing workers for new opportunities in their current roles or for stretch assignments.
  While the very definition of a stretch project takes workers outside their comfort zone, it can morph into a safe space for personal growth. Maybe you notice your receptionist has a gift for storytelling. Perhaps it shows up in the way she recounts her grandson’s escapades with such vivid detail. So, you make the decision to invite her to try her hand at drafting content for the business’s social media. That one invitation might unlock a new skill set, a renewed sense of purpose, or even a future career path. Being a people leader means scoping the potential of your workers. Seeing their potential, nurturing it, and making space for your team to grow in ways they may never have imagined.

Why This Matters (And Why Now)

Every day, I see leaders frustrated by a shortage of talent—or by smart folks ready for change but stuck in the wrong role. In today’s fast-changing environment:

• New tech = new challenges. AI, digital systems, remote collaboration: they demand fresh mindsets and methods.

• Retention depends on growth. When we invest in people, they don’t just stay longer—they feel valued, engaged, and creative.

• Internal mobility saves money. You already know these people and your culture. Why hire externally when you can unlock untapped potential inside?

When we take calm, intentional steps with people at the center, transformation happens. It’s not about filling gaps, it’s about lighting paths. Doing it thoughtfully means a lasting impact.