This post is the third of three in a series: Transform Today, Thrive Tomorrow – the Power of Upskilling.
In the first post we explored why upskilling is more important than ever. Organizations have always needed skilled workers, but now the stakes are higher, and the changes are faster. As roles evolve due to digital transformation and demographic shifts, the need to bridge talent gaps is more important than ever.
In the second post, we explored how to build a smarter, more sustainable upskilling strategy. It starts by clarifying needs unique to your business and talent, then planning for and delivering engaging, hands-on experiences with a variety of learning resources.
In this post, we look at the challenges of managing expectations in the upskilling journey. This is just as critical as the learning itself. For some, there may be an expectation that the additional expertise one acquires would lead to expanded capabilities and a promotion or new role, or that additional compensation or other rewards would be on offer. It can be a good-news story for many, yet for others, there may be resistance to the whole process. Managing post-upskilling expectations, for individuals and their leaders, is essential to realizing the benefits and keeping your people engaged along the way.
For Individuals: Addressing Upskilling Expectations
While upskilling is a business building strategy, the organization is not the only thing changing on this journey! It’s essential to support change at the individual level, from addressing personal concerns and role specific impacts, to offering coaching and guided skills practice, recognize progress, and support ongoing growth.
Let’s look at key strategies that can help manage expectations and engagement in the upskilling journey:
1. Understand Resistance to Change
Not all employees are open to the opportunities that upskilling may offer – there can be numerous reasons for a reluctance to buy-in or to resist change. They can include a fear of the unknown, loss of control, attachment to the status quo, emotional discomfort, a lack of trust in leadership. While the one constant in life and work these days is change, it doesn’t diminish the need for workers to feel psychologically safe in the learning journey, and therefore better able to move through change, if not embrace the upsides.
Consider an example where a customer experience position is shifting from transactional order taking to more expansive customer relationship management, including using technology to track the process. While the organization provides the essential training to adapt to this shift, someone who is currently performing well may fear they won’t be successful with the change. The skill development required around communication, digital literacy, and critical thinking will be aligned with a business goal, and the individual will need to understand that the upskilling will ensure their relevance for long-term career opportunities. Conversations around concerns or fears, if there are any, must be open, frank, and ongoing to ensure the team member successfully navigates the change.
2. Create Opportunities for Immediate Application
Encourage employees to use their new skills right away. Assign them to projects, stretch assignments, or cross-functional teams where they can contribute in meaningful ways. This helps reinforce learning and demonstrates that their growth is valued.
3. Offer Visible and Meaningful Recognition
Acknowledging employees’ newly developed skills—through leadership shoutouts, internal newsletters, or strategic task assignments—can help them feel valued and motivated. At the same time, where appropriate, incentivizing learning with bonuses, raises or other meaningful benefits can go a long way to keeping team members committed and enthusiastically supporting leadership direction.
4. Ensure Transparency in Career Conversations
Be upfront about what upskilling can and cannot guarantee. Have career chats or discussions where employees understand their options—whether that means lateral moves, skill-based leadership roles, or preparation for future opportunities when they arise.
5. Provide Pathways for Career Progression (Even If Not a Promotion)
Depending on your employee groups and their professional development aspirations, the promotion question may be top of mind. Promotions aren’t always the immediate result - or expectation - of upskilling. Skill and talent development need to be framed as a long-term investment rather than a short-term ticket to a new role. Rather than framing it solely as a direct path to a promotion – or a title change - emphasize skill stacking and career progression. Project-based growth, expanded responsibilities, and lateral moves are as powerful (or more so!) when it comes to recognizing skill advancement and high performance.
6. Foster a Culture of Continuous Learning
Make upskilling an ongoing process by offering mentorship, peer learning groups, or access to additional training; if employees see development as a continuous journey, they’ll stay engaged beyond singular training events. Most importantly, they need to see how the organization’s capabilities are increasing or more readily adapting to business demands. Ensuring the business is not just surviving but thriving, will by extension positively impact each and every leader and team member. Many professionals thrive on shared learning and collaboration as an end in itself, the foundation for innovation and long-term career success.
For Leaders: Key Metrics for Measuring Post-Upskilling Success
While much of the conversation here focuses on managing employee expectations—career growth, competency development, promotions, new responsibilities—leaders also need a clear framework for measuring upskilling success. Consider these metrics:
Employee Performance & Application of Skills: Are employees applying new skills effectively in their roles? Has there been an improvement in productivity, quality of work, or problem-solving capabilities?
Business Impact & ROI: Are upskilled employees contributing to key business goals (e.g., revenue growth, customer satisfaction, efficiency gains)? Has the organization reduced its reliance on external hiring by filling roles internally?
Retention & Engagement: Are upskilled employees staying longer in the organization? Has engagement improved (e.g., higher level participation in projects, willingness to take on new challenges)?
Leadership & Career Progression: Have employees moved into leadership roles or taken on expanded responsibilities? Is there a visible talent pipeline forming as a result of upskilling efforts?
Time to Proficiency: How quickly do employees become proficient in new skills after training? Are there measurable reductions in onboarding or ramp-up time for newly acquired skills?
The Takeaways:
Upskilling is a continuous process and for some, a culture shift. Managing expectations ensures long-term success for leaders, team members, and the business. A reality check is also essential. If or when results are less than stellar, or if the learning process is bumpy, it could be due to a lack of strategy to build a strong foundation, lack of patience with the process, and expecting perfection: not every attempt to build skills and develop talent will succeed in the short term. Additionally, in remote learning environments, engagement and connection don’t come as naturally, so it’s important to explore all the ways learning technology can be optimized. A true learning culture embraces experimentation and missteps as part of the growth process.
Encourage leaders to build structures that support skill development while aligning with organizational growth. Narrowing the gap between expectations and reality is success in itself.
Like any change initiative, communication in its various forms (one-on-one, in teams, town-halls, emails and internal newsletters) and frequency (weekly, spontaneously, quarterly updates), is key to building and sustaining momentum. Transparency in career conversations, offering meaningful recognition, and making work the learning lab for skill development will help leaders and their team members reap the many benefits of the upskilling journey.
If you missed either of the first two posts in the series, you can access them as shown below.
