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

Upskilling Playbook for Employers

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 content is 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 [email protected].

UpSkilling Playbook for Employers

Table of Contents

Explore the Playbook.

Upskilling Playbook for Employers
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

Upskilling Playbook: Overview
Publications

Upskilling Playbook: Overview

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

Upskilling Playbook: Ecosystem
Publications

Upskilling Playbook: Ecosystem

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

Upskilling Playbook: Types of Upskilling
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.

Upskilling Playbook: Program Components
Publications

Upskilling Playbook: Program Components

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

Upskilling Playbook: Metrics
Publications

Upskilling Playbook: Metrics

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

Upskilling Playbook: Implementation
Publications

Upskilling Playbook: Implementation

Effective change management, communication, and stakeholder engagement are essential for overcoming challenges and ensuring long-term success.

Upskilling Playbook: Maturity Levels
Publications

Upskilling Playbook: Maturity Levels

The Upskilling Maturity Model provides a framework for organizations to evaluate their current state and advance toward a fully integrated, strategic approach to workforce development.

Upskilling Playbook: Reference and Citations
Publications

Upskilling Playbook: Reference and Citations

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Publications

DREAM Charter Schools’ Approach to AI for Employees

Close-up photo of hands typing on a laptop keyboard
Publications

Upskilling Playbook: AI, Skill Development, and the Workforce

Leaders must view AI adoption as a development opportunity to redefine how capability is built, focusing on outcomes and consciously reinvesting capacity freed by automation to ensure growth and resilience for both the business and its people.

Upskilling Playbook: Getting Started with Apprenticeship
Publications

Upskilling Playbook: Getting Started with Apprenticeship

This chapter walks organizations through the key decisions and steps required to launch a successful apprenticeship program.

About UpSkill America

UpSkill America, an initiative 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.

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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More from UpSkill America

Room for Growth: A Survey of Upskilling Approaches — 2026 Analysis
Publications

Room for Growth: A Survey of Upskilling Approaches — 2026 Analysis

This publication examines how fragmented skills, credentialing, and workforce data systems limit the potential of skills-based hiring and advancement, and outlines a shared vision for building the interoperable infrastructure needed to create a connected skills ecosystem that benefits workers, employers, educators, and governments.

Employer-Friendly Practices: A Guide for Higher Education
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Employer-Friendly Practices: A Guide for Higher Education

This resource is designed to help colleges and universities become more employer-friendly and build the kind of institutional capacity that sustains and grows partnerships while simultaneously better serving working learners. It offers role-specific guidance for leaders across the institution, a self-assessment spanning five domains of practice, and a process for turning results into action, grounded in the conviction that institution/employer partnerships can become easier without compromising academic missions.

MillerKnoll: Developing Operations Leaders from Within and Beyond — A Case Study in Structured Talent Development
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MillerKnoll: Developing Operations Leaders from Within and Beyond — A Case Study in Structured Talent Development

Bridge, Propel, and Career Academy are built on a practical philosophy: that MillerKnoll has great talent already inside the organization. Finding that talent, developing it, and aligning it to the right opportunities is key to its success. T

A Typology of State-Supported Work-Connected Learning Programs
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A Typology of State-Supported Work-Connected Learning Programs

States invest in work-connected learning through dozens of distinct funding streams, grant programs, and agency initiatives, often developed independently over time by different administrations and agencies pursuing different goals.

The Workforce of the Future Starts with Adult Basic Education
Blog Posts

The Workforce of the Future Starts with Adult Basic Education

To create a future-ready workforce system, we must move beyond outdated credentials and analog processes to one that is skills-first, transparent, data-driven, and aligned with the evolving needs of workers, educators, and employers.

Foundational Skills: Early Insights from Employers and Providers
Publications

Foundational Skills: Early Insights from Employers and Providers

This publication examines how fragmented skills, credentialing, and workforce data systems limit the potential of skills-based hiring and advancement, and outlines a shared vision for building the interoperable infrastructure needed to create a connected skills ecosystem that benefits workers, employers, educators, and governments.

How Tax Policy Can Help Employers Expand Access to Learning
Podcasts Videos

How Tax Policy Can Help Employers Expand Access to Learning

In this interview, Chelsea Miller of Upskill America speaks with Nick Greif of InStride about how employers can design education benefits that are more accessible, strategic, and aligned with workforce goals.

Adult Working Learners Vote With Their Feet: What Employers Are Learning About Foundational Skills
Blog Posts

Adult Working Learners Vote With Their Feet: What Employers Are Learning About Foundational Skills

Putting people at the center of the systems we are building means accepting that career paths are rarely linear. It requires us to build infrastructure that accommodates life transitions, recognizes informal learning, and values a worker’s agency over their own data.