Reskilling for the Future: Supporting Employees Through New Ways of Working

Based on my research with employees across large organizations, I’ve observed the profound impact that changes like automation, AI, and new ways of working have on day-to-day roles. These changes bring opportunity but also uncertainty. For employees, the challenge lies in adapting to unfamiliar tools, processes, and expectations. For organizations, the challenge is creating the right support structures to ensure that these transitions lead to growth—not disengagement.

Through interviews, design sprints, and feedback from employees navigating disruption, I’ve identified key insights for how organizations can better support their teams during times of change.

Rapid change isn’t on the horizon—it’s here. Reskilling and upskilling are the keys to thriving in this new era.

1. Transparent Communication: Laying the Groundwork for Trust

Transparency is the foundation of trust. Employees need more than just announcements about impending changes; they need ongoing dialogue about what these shifts mean for their roles and futures. But transparency isn’t enough on its own. Wherever possible, organizations should co-create the path forward with employees, inviting them into conversations about how changes will be implemented.

By involving employees in this process, organizations can gain valuable buy-in, foster a sense of shared ownership, and ensure that the plans reflect on-the-ground realities. This collaboration not only reduces fear but also builds a more engaged workforce ready to adapt.

2. Addressing the Learning Curve: Formalizing Reskilling, Upskilling, and On-the-Job Learning

Change often comes with steep learning curves. Employees frequently report feeling overwhelmed by the need to acquire new skills while balancing their current workloads. To alleviate this pressure, organizations should develop formal reskilling and upskilling programs that not only give employees dedicated time to learn but also provide opportunities to apply these new skills directly to their roles.

Formal programs, such as secondments, cross-functional projects, or role rotations, offer employees the chance to immerse themselves in new learning without the distraction of their usual responsibilities. These structured opportunities allow employees to test and refine their skills in real-world contexts, building both confidence and competence.

At the same time, organizations should ensure that employees can continue learning while fulfilling their day-to-day duties. On-the-job learning initiatives, like mentorships, peer collaborations, and microlearning modules, can be integrated into daily tasks. This approach enables employees to balance learning with practical application, making the learning process feel more manageable and relevant to their work.

By engaging current employees in both formal learning programs and on-the-job opportunities, organizations can not only retain institutional knowledge but also accelerate transformation initiatives. Empowering employees with the tools and time to apply their skills ensures that new knowledge is effectively put into practice, benefiting both the individual and the organization.

The business case is clear: organizations that invest in reskilling see improved retention, enhanced innovation, and greater alignment between workforce capabilities and strategic goals.

3. Helping Employees See Themselves in the Future

Adapting to new ways of working requires employees to reimagine their roles. This can be daunting, especially if they struggle to see how their existing skills translate. Organizations must help employees envision their potential in the new landscape.

This starts with redesigning job descriptions to focus on transferable skills and potential rather than just technical expertise. Offering opportunities to "test drive" new roles or shadow others can also make transitions feel less risky. Coaching and mentorship are critical here, providing the encouragement employees need to view themselves as capable contributors to the future state.

4. Building Psychological Safety

Psychological safety is essential for employees to fully engage with change, but it doesn’t happen overnight. Before reaching Challenger Safety—the ability to take risks and challenge the status quo—teams must first feel a sense of Learner Safety (the confidence to admit gaps in knowledge) and Contributor Safety (the assurance that their contributions are valued). Inclusive environments are critical to achieving these foundational stages.

 Transformation isn’t just about implementing new technologies or processes; it’s about creating environments where employees feel safe enough to take the risks required for change. Without psychological safety, employees may hesitate to experiment, propose ideas, or adopt new ways of working. Leaders play a pivotal role in setting this tone by modelling vulnerability, acknowledging mistakes, and celebrating diverse perspectives.

By building these layers of safety, organizations create the conditions for innovation and adaptability—both of which are essential for successful transformation.

The Four Stages of Psychological Safety. Adapted from Timothy Clarke.

5. Aligning Skills and Mindsets with Transformation Goals

Organizational, product, and service transformations often demand more than new technologies—they require shifts in both skills and mindsets. Yet too often, organizations push forward ambitious initiatives without addressing these foundational needs.

Formal reskilling and upskilling programs can bridge this gap by:

• Equipping employees with the technical skills required to implement new processes or tools.

• Fostering adaptive mindsets that embrace continuous learning and change.

• Retaining institutional knowledge while driving innovation, ensuring that transformation efforts are sustainable.

When organizations align skills and mindsets with strategic goals, they unlock not only their employees’ potential but also their ability to drive meaningful change.

The Opportunity Ahead: Transforming Together

The future of work demands adaptability, resilience, and collaboration. By prioritizing transparent communication, co-creation, formal learning opportunities, and inclusive cultures, organizations can turn disruption into a catalyst for growth.

As leaders, it’s our responsibility to ensure that employees feel not just prepared but empowered to navigate the challenges ahead. The question isn’t whether change will come—it’s whether we’ll rise to meet it together.

Call to Action

What is your organization doing to prepare for new ways of working? How are you supporting your employees in building the skills and mindsets needed to thrive? Share your insights in the comments below.