The do's and don'ts of employee upskilling: A strategic guide for HR leaders

As the pace of workplace transformation accelerates, upskilling has become a mission-critical investment for organizations aiming to stay competitive. As roles shift and new technologies emerge, HR leaders are under pressure to ensure their workforce is future-ready. However, launching an upskilling program isn't just about offering courses — it's about designing a thoughtful, inclusive, and results-driven initiative.

The stakes are high: Organizations that fail to invest in workforce development risk falling behind in innovation, productivity and talent retention. According to the World Economic Forum, 44% of workers' core skills are expected to change by 2027. This means HR leaders must not only respond to current needs but also anticipate future demands. When thoughtfully designed and aligned with business goals, an upskilling strategy can strengthen organizational resilience and deepen employee commitment.

A 2024 study by Executive Networks and the University of Phoenix found that 74% of HR leaders consider upskilling and reskilling a critical business priority — yet many still struggle with execution. To help you get started, here are the key "Do's" and "Don'ts" to keep in mind when rolling out an employee upskilling program:

Do: Set specific targets for driving utilization to roles with increasing demand
Upskilling should be aligned with business needs, so it's vital to identify roles that are growing in demand — such as data analytics, cybersecurity, or AI operations — and set clear participation and completion goals for those areas. To determine where your company should focus, use labor market analytics and internal skills assessments to identify where the biggest gaps and opportunities lie.

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Do: Offer depth and breadth of offerings
The most effective upskilling programs reach across departments, demographics, and job levels — from the frontline to the c-suite. Accessibility to these opportunities ensures that all employees, regardless of background or current role, have access to a plethora of growth opportunities. Not only does this result in more corporate loyalty, but programs that prioritize accessibility typically result in higher engagement rates. To ensure your program is the best fit for your unique workforce, consider auditing your program as well as partnering with internal employee resource groups to promote equitable participation.

DO: Communicate clearly and often
A common mistake when it comes to upskilling programs is assuming employees will engage with it solely because it exists. Clear, consistent communication is key to driving awareness and participation. In fact, according to Gartner, when engagement initiatives are made more relevant and visible to employees, engagement increases by 49%. Start by developing a multi-channel communication plan that spans email, your employee intranet, webinars, manager toolkits and company meetings or town halls. To build momentum, you should also consider highlighting success stories and career outcomes in a public forum on a regular basis.

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DO: Track progress and stay adaptable
The skills landscape is dynamic, meaning that what's in demand today may change tomorrow. So, you need to regularly track program engagement, completion rates and business impact — and always be ready to pivot. One way to stay on top of these changes is to establish quarterly review cycles with key stakeholders to assess the program's progress and have the opportunity to adjust your offerings based on emerging trends and employee feedback. 

DON'T: Launch a generic, one-size-fits-all program
Generic programs that aren't tailored to your industry or business needs often fail to resonate. Employees want learning opportunities that feel relevant to their individual roles and career aspirations, alongside clear communication around how the opportunities will impact their role and the larger business. Consider offering curated learning paths tailored to specific job types or career stages, alongside personalization tools to recommend specific content based on employee goals.

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DON'T: Be rigid in what you offer
The most successful learning programs are ones that evolve — being too rigid in your offerings can leave your workforce behind as new technologies emerge. Additionally, this should not only extend to the subject matter, but also the type of learning opportunities — while some workers may be interested in pursuing a degree, certifications or certificates might be a better fit for others. Building flexibility into the DNA of your program will allow for more elective learning and encourage employees to suggest new mutually-beneficial topics or tools they want to explore.

Ultimately, upskilling should be viewed as an ongoing journey — one that evolves alongside your workforce and business strategy. By setting clear goals, fostering inclusivity and staying agile, your company can help build programs that not only future-proof their workforce but also boost engagement and retention. As the workforce continues to transform, the organizations that invest in thoughtful, strategic upskilling programs will be the ones that not just survive — but thrive.