Upskilling has become quite the buzzword in recent years, and for good reason. As technological advancements, artificial intelligence (AI) and shifting market demands continue to reshape the workplace, companies are under increasing pressure to ensure their workforce remains capable, agile and future-ready. Yet, a recent Gallup study shows that “less than half of employees (47%) strongly agree they have the skills needed to be exceptional at their current job.” Yikes.

Adding to this challenge, only 26% of U.S. employees strongly agree that their organization encourages them to learn new skills. Notably, senior leaders are much more likely to feel supported (43%). But for the folks doing the day-to-day work — managers (25%), project managers (24%), and individual contributors (26%) — that sense of support drops off fast. Ultimately, this means most employees do not feel adequately prepared to do their jobs and may not be encouraged to, or have access to, the upskilling opportunities they need to perform and make an impact.

This gap presents a critical opportunity for learning professionals to provide high-quality upskilling experiences that benefit all employees, regardless of their tenure or level.

Why Does Upskilling Matter?

The skills employees need to be successful in today’s (let alone tomorrow’s) workplace have changed dramatically over the last few years. As the world changes, The World Economic Forum predicts that by 2025 (that’s now!), 50% of employees will need reskilling. At this pace, it’s no wonder that employees feel like they are falling behind.

And the urgency to upskill is only increasing. In fact, 22% of workers fear their jobs will become obsolete because of advances in technology. And those concerns appear justified — 72% of Fortune 500 CHROs expect AI to replace jobs within their organizations in the next three years.

Yet, as illustrated earlier, companies are falling short when it comes to addressing these challenges. To truly future proof our organizations, learning opportunities need to be accessible and effective for everyone. So, how can you make upskilling a company-wide initiative?

Here are three effective strategies to help you upskill your entire team:

3 Effective Strategies to Upskill Your Entire Team

1. Make Learning New Skills Engaging (and Practical) for Learners

Unfortunately, skills training is often viewed as a check-the-box activity by both leadership and participants. Just getting it over with becomes a priority over the quality of those experiences. But upskilling efforts are only as effective as the learning experiences they provide. Kahoot’s 2024 Workplace Culture report found that “nearly half (46%) of workers find corporate training boring, and 37% say it’s delivered in an unengaging way.” Simply offering training programs isn’t enough — those programs must be engaging and practical to ensure employees are motivated to participate and apply what they learn.

So, what makes a learning experience “engaging?”

Relevance
Training must be relevant to employees’ day-to-day work and the business’s priorities. Exercises like case studies, role-plays and simulations that mirror real challenges employees face make skill-building more contextualized and hands-on for learners. Relevant timing of training is also important. Align training with critical moments that matter to ensure it can be immediately applied. If your managers need to improve their performance management capabilities, it will be much more impactful if training is scheduled alongside the performance review season rather than on any old Tuesday.

Collaborative
Many of the top skills workers need to thrive today and in the future are best learned through interaction, not isolation. According to the 2025 Future of Jobs report, outside of technological skills, traditionally “soft skills” like creativity, resilience, agility, leadership and social influence remain among the top 10 skills on the rise. These are people skills that need to be learned through interaction with others to stick. To design effective upskilling experiences, we need to leverage approaches like group discussions, breakout activities and social learning tools. These methods not only help participants build connections but also reinforce concepts through dialogue and collaboration.

Opportunities for Practice
As the saying goes, “practice makes perfect.” And it’s true — research shows that learning by doing is one of the most effective methods for skill retention. Creating opportunities for learners to practice new skills immediately, whether through interactive exercises, projects or other collaborative tasks, is essential for embedding skills in the long run.

2. Build a Culture of Accessible and Continuous Learning (at Scale)

The call to upskill your entire organization may seem daunting. Now more than ever, teams are operating with limited headcount and resources to support learning programs. However, as workplace complexities and skill needs evolve, so do the methods for delivering effective and scalable learning.

Create Blended Learning Solutions
Gone are the days of relying on a singular delivery method for training. Blended learning approaches not only allow for variety, reinforcement and hands-on experiences, but they also help distribute the responsibility of training to both formal and more informal methods. By combining different experiences, like live learning, self-paced resources, AI tools and on-the-job training, L&D teams can create comprehensive strategies that can also scale by distributing the responsibility of development more broadly across the organization, including supervisors and peers.

Build Learning Into the Workflow
With limited time and capacity across all teams, it behooves learning professionals to encourage more baseline learning habits through the integration of training opportunities into daily work. This means providing more than just structured programs and finding ways to embed and connect to learning throughout the employee lifecycle. For instance, connecting learning to career building through individual development planning, or regularly celebrating achievements in skill development by attaching them to organization-wide learning goals.

Encourage Informal Learning Opportunities
Beyond formal training and development, organizations should also promote more informal learning opportunities, such as mentoring, employee resource groups, networking, book clubs or team-building activities. These self-directed learning experiences encourage continuous growth, facilitate knowledge sharing and enhance employee engagement. By fostering an environment where learning can happen more organically, organizations can empower employees to take ownership of their development and build skills in a more flexible, continuous way.

3. Get Leadership Buy-In for Skills Development

L&D teams can’t succeed in isolation. It takes a village to make learning initiatives successful. One of our most critical responsibilities is to help build that village by partnering with leaders, ensuring learning is seen as both a business priority and an employee imperative.

Senior Leadership Support

No upskilling initiative will succeed without senior leadership buy-in. To get leadership on board, we need to understand what’s really important to them by asking questions like, “What is their specific vision for the future?” And “What skills are needed in the team to get there?”

By asking powerful questions and serving as trusted consultants, L&D professionals can position themselves as strategic partners. This collaborative approach enables you to design training programs that clearly align skill-building efforts with organizational objectives, demonstrating that skills development is not just a one-off, check-the-box activity. Instead, it becomes a strategic driver for both employee growth and overall business success.

Leaning into these executive partnerships and demonstrating the value of skills development can help you secure the necessary resources and commitment from leadership to invest in your initiatives. Therefore, demonstrating the impact of your initiatives becomes crucial. It is our responsibility to capture metrics that matter — such as productivity, employee engagement and retention — along with compelling success stories that show the true business impact.

Manager Enablement

Senior leaders are not the only influential leaders on the block. Mid-level managers and front-line supervisors play a critical role in supporting and reinforcing learning across the organization. After all, they are the ones interacting with employees day-to-day, guiding their performance and creating environments where learning can either thrive or falter.

For your upskilling initiatives to be effective, managers need to see how supporting employee growth directly impacts their team performance and improves their leadership effectiveness. But expecting managers to support learning without the right skills themselves is unfair and unrealistic. Many managers are promoted because of their technical expertise, not necessarily because of their ability to coach and develop others. This is why it’s crucial to provide managers with their own training experiences that equip them to be effective coaches, feedback givers and mentors.

It’s also important that we put tools, processes and resources in place that can help them to better embed these practices into their own work, such as 1:1 templates, individual development plans or guidance on how to reward employees for reaching their goals. When managers are empowered to foster growth on their teams, upskilling becomes a shared responsibility across all levels of the organization.

Moving Forward

In today’s workplace, upskilling is no longer optional. The data is clear: Employees at all levels are feeling the pressure to keep up, yet many don’t feel supported in their growth. To future-proof your workforce, upskilling must be embedded into the fabric of your organization, ensuring learning is relevant, engaging and accessible to everyone, not just high-potential employees or senior leaders.

The good news? You don’t need a massive overhaul to begin. Small, intentional steps can make a big impact. Take a moment to assess your current strategy. What’s one way to make skills development more accessible and effective for your team? By focusing on incremental efforts, you can build real momentum that empowers your employees with the skills they need to thrive in today’s — and tomorrow’s — workplace.