Updated:

January 20, 2026

How to build an award-winning upskilling program

Take your upskilling strategy from good to great.

The best L&D strategies start with listening—to data, insights, and people.

The best upskilling strategies don’t start with spreadsheets—they start with conversations. With your data. With your people. With your business goals. When 75% of organizations say aligning learning with business goals is their top priority, it’s clear: Your upskilling program is so much more than retention. It’s how to make your workforce resilient by building the skills of the future.

This webinar is for professionals who want to build a skills training program that’s fast, effective, and built to last. You’ll learn how to ask the right questions, align with the goals of your organization, and design an upskilling strategy and learning program with the end in mind—measurable impact and behavior change.

Even if you don’t have all the data, you’ll leave with the insights to get started. And often, those insights come from asking the right people the right questions.

10 key takeaways: How to build an award-winning upskilling program

  1. Upskilling is a strategic imperative. Upskilling has evolved from a nice-to-have initiative into a core business strategy. It’s the engine behind stronger performance, higher retention, and faster innovation. Companies that treat upskilling as a strategic priority position themselves to thrive in a rapidly changing market.
  2. Clear definitions matter. Upskilling, reskilling, skilling, development—these aren’t just buzzwords. Each plays a unique role in shaping workforce capability. Knowing the difference helps you design programs that meet both immediate and long-term business needs.
  3. The biggest challenges in upskilling. Skill gaps are widening, roles are shifting, and resources are tight. Organizations often struggle to identify what skills matter most and how to deliver learning that sticks.
  4. AI is transforming learning. Artificial intelligence is rewriting the rules of workforce development. From personalized learning paths to real-time skill gap analysis, AI-driven tools make scalable, adaptive upskilling possible.
  5. Organizational buy-in is critical. Upskilling isn’t an HR-only project. It requires executive sponsorship and alignment across departments to create a culture where learning drives business outcomes.
  6. Learners must drive their own growth. Employees want control over their career trajectory. Personalized learning paths and manager support empower them to take ownership and stay engaged.
  7. Technology foundations for success. Modern LMS platforms are the backbone of effective upskilling. They enable AI-powered personalization, competency mapping, and access to rich content libraries—all critical for speed and scale.
  8. The business impact of upskilling. Upskilling pays off. It boosts retention, accelerates productivity, and fuels innovation—all of which translate into measurable business growth.
  9. Continuous measurement is essential. Tracking progress isn’t optional. Organizations that measure learning outcomes and link them to business metrics can prove ROI and refine strategies over time.
  10. Future-proofing with flexibility. Roles evolve, and so should learning paths. Regular assessments, adaptive content, and visual roadmaps keep skills relevant and employees engaged for the long haul.

Who should watch this webinar?

This session is tailor-made for professionals who want to know more about how upskill employees:

Questions and discussions


Behind every award-winning upskilling program is a series of smart (sometimes tough, always important) questions. These are the conversations that shape strategy, unlock buy-in, and turn good intentions into measurable impact. Here are some of the questions that spark discussion in this upskilling webinar:

What you’ll learn

The most effective upskilling programs share a few key ingredients: clear alignment with strategic business objectives, a sharp eye on emerging skills, the right mix of learning modalities, technology that scales, and strong leadership advocacy to champion the journey.  

In this on-demand webinar, you’ll explore:

Why it’s time to rethink skills training

Take the first step

Organizations that fail to develop workforce capabilities face higher turnover costs, reduced innovation, and stalled strategic execution due to skill shortages. If you’re looking to improve your learning program, here are a couple of places to start today:

Want to try Absorb for yourself?

Get demo