In today’s dynamic workplace, standing still is not an option. As technologies, business needs, and workforce expectations shift, tools and processes evolve too. At UpSkill America, we know that a well-crafted playbook — a guide to how programs can operate, collaborate, and deliver outcomes — is essential not only for maintaining operational excellence but for advancing a future where both employers and workers thrive.

The current playbook UpSkill America put out in 2017 has served us well, providing a strong foundation for decision-making and execution. But like any successful upskilling initiative, a good playbook requires regular reflection and iteration. This moment in the United States presents an opportunity to reexamine how we work, ensuring that our practices are current, effective, and aligned with our broader mission: to create meaningful opportunities for America’s workers and strengthen the organizations they power.

The Role of a Playbook: More Than Just a Manual

A playbook is far more than a static document. It is a living expression of how an organization transforms goals into action. For upskilling leaders, a playbook serves as both a map and a method: outlining how to design learner-centered pathways to integrating best practices in implementation, evaluation, and continuous improvement.

Our hope is that this playbook supports leaders at any phase of their skilling journey — not just by providing best practices and tools, but by helping teams make sense of complexity, align on what matters most, and design with intention. It lays out what we believe are key processes, best practices, and important stakeholder considerations. Much like the organizations you serve, we recognize that clarity, alignment, and adaptability are critical to driving both business performance and individual advancement.

Why Refresh Now?

The world of work has changed — and the way we design, lead, and sustain upskilling programs must change with it. This isn’t just a refresh. It’s a deliberate shift toward smarter systems, stronger leadership, and more meaningful outcomes for workers and employers alike.

Reflecting Evolving Practices:
The way we work — and the systems that support it — have changed dramatically. Our workflows, tools, and engagement strategies must reflect today’s realities to remain effective. This refresh ensures the playbook stays responsive and relevant.

Enabling Leadership:
An updated playbook empowers leaders with the clarity, context, and tools they need to lead well — not just to follow process, but to shape strategy and support people in meaningful ways.

Promoting Consistency and Excellence:
Shared frameworks help teams navigate complexity and stay grounded in what matters. A strong playbook supports consistency, learning, and excellence — without stifling adaptability or innovation.

Moving Forward Together

At UpSkill America, we believe that the most successful initiatives are built through collaboration. As we provide this new playbook, we’re inviting voices from across industries to help shape a resource that reflects real-world expertise, shared insights, and bold aspirations for the future of work.

We are grateful to all the organizations that provided case studies and supported our work in this space. The first three chapters of the reimagined Upskilling Playbook will launch next week, on May 20. These will be released on our website along with short video content designed to help summarize key insights as a complement to the playbook.

We welcome your feedback and insights as this is released, you can reach out to us at [email protected]

About the Authors

Chelsea Miller is the associate director of UpSkill America, an initiative of the Aspen Institute Economic Opportunities Program.

Before joining the Institute in September 2024, Chelsea spent five years helping develop and lead the largest employer education benefit program in the US, Live Better U. Leading communications, policy, and portfolio strategy Chelsea made sure access to education was a reason Walmart made the Forbes Change the World list every year since 2018.

Chris Huyck Trout is a builder of what’s never been done before — a strategic innovator passionate about helping organizations figure out what’s possible, achieve it, and then reach beyond it. As a Senior Advisor and Consultant with the Aspen Institute’s Upskill America Initiative, Chris brings more than 35 years of leadership experience across workforce development, organizational transformation, and leadership strategy.

At the Walt Disney Company, Chris led the enterprise-wide Learning and Development function, reimagining leadership development across all levels — from first-time leaders to the C-suite — and creating impactful experiences that drove measurable growth. He also led the creation and launch of Disney Aspire, helping to reshape corporate education at scale and unlock opportunity for thousands of employees while strengthening business performance.

Chris’ work sits at the intersection of workforce transformation, leadership development, and organizational impact — grounded in relentless curiosity, bold action, and a commitment to shaping better futures. Through his firm, Donlon Insights, he partners with organizations ready to rethink leadership and workforce strategies to strengthen business outcomes, advance individual growth, and build thriving communities.

He holds a master’s in education from Boston University and completed the Advanced Program in Organization Development and Human Resources at Columbia University. In life and work, Chris is fueled by creativity, exploration, and a love of learning from experience.

Learn More

UpSkill America supports employers and workforce organizations to expand and improve high-quality educational and career advancement opportunities for America’s front-line workers. We seek to create a movement of employers, civic organizations, workforce intermediaries, and policymakers working collaboratively to implement education, training, and development strategies that result in better jobs and opportunities for front-line workers, more competitive businesses, and stronger communities. Follow us at www.upskillamerica.org and
linkedin.com/company/aspeneop

The Economic Opportunities Program advances strategies, policies, and ideas to help low- and moderate-income people thrive in a changing economy. Follow us on social media and join our mailing list to stay up-to-date on publications, blog posts, events, and other announcements.