Aspen is a place for leaders to lift their sights above the possessions which possess them. To confront their own nature as human beings, to regain control over their own humanity by becoming more self-aware, more self-correcting, and hence more self-fulfilling.

Walter P. Paepcke, Aspen Institute Co-Founder
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Upskilling Playbook for Employers

May 19, 2025
UpSkill America, and Economic Opportunities Program

About This Playbook

UpSkill America’s Upskilling Playbook is a strategic guide for organizations to build, scale, and integrate skills-based workforce development initiatives that drive business performance and career growth.

Despite rapid economic and technological shifts making upskilling a business imperative, many efforts struggle to gain traction and become embedded in business strategy.This playbook cuts through the noise while preserving the depth needed to drive real change — integrating corporate best practices, academic research, and practical application. It helps organizations amplify the impact of existing initiatives or launch new efforts with clarity and measurable results. It provides a practical framework for navigating challenges, capitalizing on opportunities, and implementing upskilling at scale. Covering key areas such as workforce ecosystem development, program design, measurement strategies, and leadership alignment, it delivers actionable insights for HR professionals, business leaders, and decision-makers.

When organizations fully embed upskilling into their talent and business strategy, they create sustainable talent pipelines, improve retention, and future-proof their workforce against industry shifts and technological advancements. Click below to read more, and join our mailing list to be notified when new chapters are released.

The first edition of UpSkill America’s Upskilling Playbook launched in 2017. If you are trying to access content from the original playbook, please email us at eop.program@aspeninstitute.org.

About UpSkill America

UpSkill America, part of the Economic Opportunities Program, supports employers and workforce organizations to expand and improve high-quality educational and career advancement opportunities for America’s front-line workers. Connect with us on LinkedIn and learn more at upskillamerica.org.

About the Economic Opportunities Program

The Aspen Institute Economic Opportunities Program advances strategies, policies, and ideas to help low- and moderate-income people thrive in a changing economy.

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