Upskilling Playbook for Employers

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.

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.

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 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 upskillamerica.org and on LinkedIn.

UpSkilling Playbook for Employers

Table of Contents

Explore the Playbook.

Publications

Upskilling Playbook for Employers

This playbook is a strategic guide for organizations to build, scale, and integrate skills-based workforce development initiatives that drive business performance and career growth

May 19, 2025

Publications

Upskilling Playbook: Overview

This playbook provides guidance for people leaders, business executives, and decision-makers to design and implement effective upskilling strategies.

May 19, 2025

Publications

Upskilling Playbook: Ecosystem

Developing a 21st century workforce requires an intentional ecosystem approach that connects talent development to business priorities.

May 19, 2025

Publications

Upskilling Playbook: Types of Upskilling

Upskilling is not one-size-fits-all. Organizations must strategically select the right types to align with business and employee growth.

May 19, 2025

Publications

Upskilling Playbook: Program Components

Designing effective upskilling programs requires a holistic approach that considers various interconnected components.

May 29, 2025

Publications

Upskilling Playbook: Metrics

Measuring the impact of upskilling is crucial for demonstrating its value and driving continuous improvement.

June 5, 2025

Publications

Upskilling Playbook: Implementation

Measuring the impact of upskilling is crucial for demonstrating its value and driving continuous improvement.

June 12, 2025

Publications

Upskilling Playbook: Maturity Levels

Measuring the impact of upskilling is crucial for demonstrating its value and driving continuous improvement.

June 18, 2025