This is the second in a three-part series, Transform Today, Thrive Tomorrow: The Power of Upskilling. In the first post, we looked at why upskilling is more important than ever.

In this post we explore the essentials for building a smarter strategy.

Too often, organizations treat upskilling like a quick fix—just roll out a few training sessions, and problem solved, right? Not quite. The reality is, simply offering courses doesn’t guarantee growth. Upskilling isn’t just about learning new skills; it’s about managing change. When done right, it helps individuals and organizations navigate workplace shifts with confidence, ensuring that learning isn’t just an event but a driver of long-term adaptability and career success.

Here’s how to move beyond common pitfalls and create a smarter, more sustainable upskilling strategy.

Clarify the Need

It may seem obvious, but having a clear idea of your organization or team’s upskilling needs is the foundation for success. It makes for easier communication, buy-in, delivery, and achieving desired results. Here are some guiding principles:

1. Start with Business Strategy.  What are your company’s goals for the next year, 18 months, three years? What skills will be critical to achieving them? Are there gaps between current capabilities and future needs?

2. Identify Pain Points & Bottlenecks. Where are teams struggling to meet performance expectations? What inefficiencies could be improved with better skills?  Don’t treat symptoms—diagnose underlying problems. Poor performance isn’t always a skills issue, and training isn’t a cure without proper diagnostics.

3. Listen to Employees & Managers. What skills do employees feel they lack to do their jobs better? What do managers say about skill gaps on their teams? Are there emerging roles or competencies becoming more essential?  Upskilling needs a tailored approach, not a one-size-fits-all mindset. 

4. Use Data & Performance Metrics. Look at key performance indicators, productivity trends, and customer feedback. Are there recurring issues that some next-level skills could help resolve?

5. Prioritize Future-Proofing Skills.  Invest in adaptable skills like digital literacy, problem-solving, and leadership. Ensure employees can grow with the company rather than become obsolete.

6. Balance Technical & Soft Skills. Don’t just focus on hard skills—communication, collaboration, and critical thinking are just as vital. Consider how effective your current efforts are to train and develop your team members.

What Makes Upskilling Work:

Upskilling isn’t “learn first, then work.” It’s work-learn-work. To get it right, we need engaging, hands-on experiences and a commitment to fostering a culture of continuous learning. Here are the components that make for a well-rounded, engaging upskilling experience:

Varied Learning Opportunities. Online platforms, in-person training, and external expertise all play a role. Diversify your approach to match diverse learning needs, ensuring the methods used contribute to learning outcomes.

Blended Experiences, Feedback, and Learning. The integration of experiences, feedback, and formal learning is the gold standard for skill-building and makes for a development accelerator.  Soft skills like communication, adaptability, and emotional intelligence, are best developed through experiential learning and feedback-rich environments.

Technology-Enabled Learning. Consider the online learning platforms and digital resources that can be made available for self-directed learning and on-the-job skill development.

Social and Collaborative Learning. Consider formalizing more cross functional learning, peer-to-peer mentoring, coaching, and establishing communities of practice as effective ways to enhance skills and knowledge.

Build the Fundamentals:

•    Sell it Well: To fully engage team members in active participation, think about the “what’s in it for me” mindset that they will have; employees need to see how upskilling aligns their career growth and the company’s goals. What knowledge, insight or skill-set will it provide them with, and how will the learning improve their work life or advance their career? Or allow them to solve problems more efficiently, complete projects to a higher standard and help them find a greater level of success in their work? Communicate this thoughtfully, or risk lack of buy-in or disengagement with the whole endeavor. A lack of or poor communication can make it all feel irrelevant or punitive.

•    Make Microlearning Key. Short, energized learning sessions of even 30 to 60 minutes can benefit the level of learning more profoundly than all-day sessions, though those are still important for certain kinds of professional development and skill-building. Some distance from newly acquired information allows our subconscious to process it and acts as a “finisher” solidifying it inside newly created pathways in our brain. This allows learning to be better applied to a variety of situations.

•    Change the Learning Environment. Research shows that our brains create new associations with learning content when we are exposed to it in different situations.  We are more likely to recall information that we have retained in more than one environment.  For example, varying the settings from virtual to in-person, and in-person in different physical settings can give it a different feel.

•    Follow up and Accountability. The key to gaining a robust understanding of a new skill or concept is to apply it in a real-life situation. Following up individually and at team meetings to see what’s worked and where they may be struggling, encourages sharing of learning experiences, and demonstrates that you and your organization are committed to successful outcomes.  When it comes to soft-skills training, the value of some individual follow-on coaching by an internal or external coach, can make all the difference in helping even the most motivated learner take their skills to the next level.

Where To Improve

Incentivize Learning:

Recognize and reward employees who invest time and energy in their own development and skill-building. Incentives can include bonuses, promotions, public recognition, or career advancement opportunities tied to skill growth. These incentives should be part of the overall upskilling strategy, and we’ll take a deeper dive into this in the next post on managing expectations.  

Continuous Improvement through Feedback Loops:

Create structured mechanisms such as coaching, peer reviews, or project-based assessments to reinforce learning, and help to embed it in the daily work experience. Continuous improvement should be encouraged, making skill development an ongoing, adaptive process rather than a one-time event. Are you creating a culture where learning is celebrated and aligned with broader goals? 

Align with Organizational Goals:

Skills should serve a purpose. Without alignment, even the best training won’t drive meaningful change. Motivation for learning and development is sustained when development opportunities align the business with individual aspirations. Clear communication about how learning initiatives connect to business strategy and industry demands is essential.

Patience with the Process:

Skill-building takes time, particularly for critical thinking, analytical skills, and conflict management. Technical skills may be quicker to learn, but developing well-rounded professionals requires sustained effort. Skill-building requires practice and application, yet many organizations treat it as a checkbox activity.

The Takeaway

Upskilling is about more than productivity—it’s about creating talented teams ready to meet the challenges of tomorrow. But success doesn’t come from simply offering training. It requires thoughtful strategy, ongoing feedback, and a commitment to supporting employees as they grow.

Take the first step today. Consider conducting a diagnostic review of your upskilling strategy to identify gaps and opportunities. A smarter approach to upskilling doesn’t just improve skills—it transforms your organization and your business.

Check back for the third post in this series: After the Skill Upgrade: Managing Expectations in the Upskilling Journey. Or send a note here to be notified when the post comes available.

Learn more about Talent Development and the roadmap for building a skills-first organization. The Align. Grow. Prosper. Course shows the way.