Brown & Brown

Heather L. Torres is an accomplished benefits and learning and development professional at Brown & Brown. With a deep passion for education and human development, she specializes in designing and managing comprehensive learning and development programs for the employee benefits business segment. Holding both the Certified Employee Benefit Specialist (CEBS) and Certified Professional in Training Management(CPTM) credentials, Heather is committed to helping organizations optimize their learning and development to empower teammates to achieve their fullest potential.

Upskilling vs. Reskilling: Why Language Matters

Are we upskilling this role or reskilling the person in it?

These terms are often used interchangeably, but they mean different things. And the language we use in learning and development isn’t just word choice; it’s strategy. Words shape expectations. They influence morale, set the tone for development conversations and drive how leaders and teammates engage with growth opportunities.

Upskilling vs. Reskilling

Upskilling

• Expanding or deepening skills within a current role

• Example: Teaching an account manager advanced data analysis for client reporting

Reskilling

• Teaching new skills for a different role or career path

• Example: Retraining an enrollment specialist to become a benefit consultant

Why It Matters

When we use the right language, we create clarity and motivation. Learners understand their path forward. Leaders can set better goals. And everyone stays aligned on the purpose of development efforts.

Consider the emotional tone:

• Upskilling feels like growth; it’s energizing, hopeful and forwardlooking.

• Reskilling can feel heavier, like change is being forced or something is ending.

To a teammate, “reskilling” might signal they’re being replaced. To a leader, it might sound like a high-risk transformation effort. But in many cases, we’re upskilling our teams—adding new capabilities without changing roles.

Messaging Drives Momentum

The way we talk about learning affects how programs are received, marketed and funded. Compare these two phrases:

• “Upskilling our current teammates”

• “Reskilling for career changers”

Both are valid, but one sparks curiosity and confidence, while the other may cause hesitation. When our language feels too heavy, teammates may disengage. Leaders may worry about feasibility. And we risk losing alignment, outcomes and even internal support.

What Can We Do?

• Align your language internally. Ensure HR, leadership and L&D use terms consistently.

• Label programs with intent. “Learn to Lead” vs. “Shift to a New Role” helps signal what teammates can expect.

• Use hopeful language. Focus on opportunity, capability and growth— not just change.

Final Thought

Language is one of our most powerful tools. When we use it well, it helps people see who they’re becoming—and how they’ll get there.