The Future of Work Demands a New Playbook for Upskilling
The world of work is being redefined in real time. Technology is accelerating. Roles are evolving. Expectations — from both workers and employers — are higher than ever. In this moment of transformation, traditional training models aren’t just outdated — they’re holding us back.
We don’t need a tweak. We need a new playbook — one built for speed, scale, and people.
The headlines are loud: AI is accelerating. Skills gaps are widening. Talent is walking out the door.Yet, beneath the buzzwords lies a more urgent reality: most organizations aren’t just behind on skills — they’re missing a playbook for how to adapt.
The systems we’ve relied on — outdated training, disconnected tools, one-size-fits-all programs — were built for a different era. Today’s workplace demands something smarter: a new upskilling playbook designed for speed, scale, and staying power.
Why now? Because:
We’ve brought together insights from employers, practitioners, and experts across industries to refresh the UpSkill America playbook so it is both practical and ambitious — designed for the real-world complexity of workforce transformation.
This isn’t a checklist. It’s a strategic guide to help leaders shift from good intentions to lasting impact.
Inside, you’ll find:
Design Anchors That Drive Impact
The foundational elements of successful programs — from shared diagnostics and personalized learning paths to agile implementation, and leadership alignment.
Steps That Bridge Strategy and Action
Guidance on how to move from concept to execution, resource effectively, and adapt even in resource-constrained environments.
Stories, Tools, and Prompts You Can Use
Real-world examples, practical tools, and decision-making frameworks to support design, alignment, and rollout — no matter where you’re starting.
Metrics That Reflect What Matters
Strategies for measuring what actually drives value — internal mobility, retention, business agility — not just participation rates or course completions.
Whether you’re launching a new effort or scaling what already exists, this playbook is designed to help you:
We created this playbook not just to document best practices, but to help organizations design for outcomes, lead with intention, and empower people to thrive in a rapidly changing world of work.
Every organization feels the pressure to act, but the most effective ones don’t rush to solutions. They pause, get clear, and build with intention. That’s what this playbook is here to support.
Whether you’re reimagining what’s possible or just trying to make real progress inside your current constraints, this is a moment to move with focus — not blindly. To design systems that support people and performance — not just respond to disruption. You don’t have to have it all figured out. You just have to start differently.
Open it with a colleague. Choose a section that resonates, and use a tool to jumpstart a stalled conversation– or apply a prompt in your next strategy session. Identify one place where you can start building traction.
Wherever you are in your upskilling journey, this is your moment to move — not perfectly, but intentionally. Don’t wait for ideal conditions; use what’s here to start designing forward.
Because the only way to close the gap between intention and impact is to begin.
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.
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
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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.
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