In today’s healthcare landscape, the pressure to reskill and upskill your workforce has never been greater. Between the rapid rise of AI, persistent staffing shortage, and record levels of frontline burnout, healthcare leaders are urgently seeking ways to future-proof their organizations. However, in the rush to transform, many are missing a critical truth: reskilling isn’t just a technology or training challenge – it’s a people challenge.
To often, reskilling strategies focus narrowly on filling roles or adopting new tools, without addressing the human factors that determine whether those efforts succeed. The result? Programs that look good on paper but fail to engage the very people they’re meant to empower.
The U.S. healthcare workforce is projected to face 1.9 million job openings each year through 2033, underscoring the urgency of addressing systemic shortages across the industry. Meanwhile, more than 70% of frontline employees – including many across healthcare – have actively pursued advancement opportunities, often outside their current organizations, due to limited career growth and support. These numbers aren’t just alarming – they’re a call to action.
To truly move the needle, healthcare leaders must rethink how they’re approaching reskilling – not as a checkbox, but a strategic people-first investments. Here are four common missteps organizations make – and how to fix them:
Mistake: Treating Reskilling as a One-Time Initiative
Fix: Build a Culture of Continuous Learning
The simple truth is that healthcare is evolving too quickly for static training models. Thus, leaders need to shift from episodic learning to a culture where growth is ongoing, supported, and celebrated. This means embedding learning into the flow of work, offering flexible, just-in-time training, and recognizing learning achievements as career milestones—not just side projects.
Mistake: Overlooking Emotional and Financial Barriers
Fix: Remove Friction with People-First Benefits
Fear of failure, fear of debt, and fear of the unknown can be powerful blockers. That’s why leading organizations are investing in education benefits that eliminate these barriers. Take Renown Health, for example. In partnership with EdAssist by Bright Horizons, Renown has built a program that supports employees at every stage of their learning journey—with student loan repayment, tuition and certification reimbursement, and equal access for part-time, per diem, and full-time staff.
The results speak for themselves:
- 89% retention among employees using the education benefits
- $863,000 in student loan debt paid down for 643 employees
- 203 new participants in the past year alone
One standout story is Laci, who joined Renown in 2014. Through the program, she earned her associate’s, bachelor’s, and master’s degrees—ultimately advancing into a key quality role within Renown’s Medical Group. Her journey is a powerful reminder that when you invest in people, they invest back.
Mistake: Focusing Only on Clinical Roles
Fix: Reskill Across the Entire Ecosystem
While clinical roles are vital, healthcare transformation requires upskilling across the board—from IT and data analytics to patient services and operations. AI is reshaping every corner of the industry, and organizations that limit reskilling to frontline roles risk leaving major talent gaps unaddressed.
Career pathways should be mapped not just for nurses and techs, but for administrative staff, call center agents, and beyond. When every employee sees a future in your organization, engagement and retention rise across the board.
Mistake: Failing to Show the “Why”
Fix: Make Career Pathways Visible (and Personal)
Before embarking on an education journey, employees want to know: Where will this lead me? Without a clear answer, even the best reskilling programs can fall flat. That’s why personalized career pathways—complete with transparent timelines, role progression maps, and access to career coaches—are essential. When employees can see the destination, they’re far more likely to start the journey.
Healthcare’s future depends on a workforce that’s not just trained – but truly transformed. That transformation starts with empathy, equity and a commitment to helping every employee realize their potential. The organizations that get this right won’t just fill roles, but will build resilient, future-ready cultures where people stay, grow and thrive. In healthcare, reskilling can’t be just about technology – it needs to be about trust.
Diane Bartoli
Diane Bartoli is the SVP of EdAdvisory Services at Bright Horizons and a member of the Bright Horizons Executive Committee, overseeing branded offerings EdAssist and College Coach – which leverages a range of offerings, including tuition reimbursement, student loan repayment, financial college advising and more to help employers combat employee attrition and fill critical labor gaps, while enabling employees to realize their fullest potential. Prior to joining Bright Horizons, Diane held executive roles at athenahealth as the GM of epocrates, Amazon as the Director and GM of Amazon Education leading the K-12 and Higher Education business at Kindle, and Elsevier as the SVP and GM for the Clinical Reference and Workflow business, including clinical and education solutions.
