Reskilling and Upskilling: Turning FOBO into Confidence
Imagine two departments in the same company. One receives generic compliance training once a year. The other takes part in quarterly “skill sprints” blending technical workshops, peer coaching, and project-based learning. A year later, one team is stagnant and hesitant. The other is agile, optimistic, and ready for what’s next. Which team would you rather lead?
That scenario illustrates why reskilling and upskilling—giving employees new skills to grow in their current role or different ones to move into a new role—matter now more than ever. And yet, many leaders are still hesitating, feeling like they lack the knowledge or time to make it a priority.
In my consulting work, I’ve seen the consequences when companies fail to invest: mid-career employees under-recognized and under-developed, subject matter experts undercompensated, and a looming mass exodus of knowledge as retirements accelerate.
As I shared recently with a client, skill-building doesn’t have to be a liability; it can be a catalyst. When supported, employees across generations gain confidence, embrace new tools, and re-engage with purpose. And with the rise of remote work, intentional reskilling and upskilling help measure and maintain performance even when people aren’t in the office.
I see organizations thriving when they intentionally build both hard and soft skills. The leaders of the future aren’t just technically adept; they can inspire, empathize, and connect with people.
As technology, particularly AI, reshapes workplaces, many employees feel the “fear of being obsolete,” or FOBO. And it’s not just younger workers. Mid-career professionals and those in legacy roles, your knowledge experts, often report the highest levels of concern, wondering if their expertise is outdated or transferable.
The Anxiety is Real
Their worries are not groundless. A Gallup and Workhuman survey found that while 93% of leaders say they are integrating AI into their organizations, only 13% of employees feel they understand these plans. And nearly three-quarters of workers say they aren’t getting the upskilling they need to keep up.
A McKinsey survey found the need for upskilling is the top obstacle to occupational change, with an accompanying article delving into how upskilling “could enable a more flexible, adaptive, and fit-for-the-future” workforce. This is especially important as the cycle of obsolescence accelerates, with some technical skills now becoming outdated in as little as 2–3 years. No wonder employees worry about having the right skills and feel the pressure to keep up!
The risk to your organization is disengagement, resistance to new systems, or even quiet quitting. The opportunity, however, is far greater: building confidence, capability, and loyalty by helping employees learn and grow.
Why Reskilling Matters for Employers
Investing in continuous learning isn’t just nice to have: It’s a strategic imperative. Reskilling and upskilling:
- Boost retention: Employees who see clear development paths are more likely to stay. This is critical at a time when baby boomers are retiring and taking decades of expertise with them.
- Close skills gaps: Whether it’s digital literacy, AI adoption, or leadership competencies like emotional intelligence (EQ), today’s gaps can quickly become tomorrow’s vulnerabilities.
- Strengthen employer brand: Organizations with a reputation for investing in people attract talent. They signal that employees are not only valued but also prepared for the future.
Where to Begin
Leaders often ask me how to start integrating reskilling and upskilling into their organizations. Regardless of their sector or company size, my answer is always the same: start with your culture. Here’s how.
- Foster a culture of continuous learning. Encourage curiosity, experimentation, and the ability to say, “I don’t know how to do this…yet.” Learning should feel safe and supported, not like a productivity drain.
- Personalize development. Training isn’t one-size-fits-all. Some employees thrive on micro-learning embedded into daily work; others prefer workshops or self-paced online learning. Variety matters.
- Start with HR basics. Accurate job descriptions and clear performance expectations are foundational. From there, competency matrices and tools, such as skills passports or platforms like SkyHive, can map pathways to advancement.
- Leverage technology wisely. AI can take on the heavy lifting of analyzing roles and recommending development paths. Whatever tools you use, remember: they should complement, not replace, human conversations about growth and goals.
- Recognize and reward learning. Celebrate employees who sharpen their skills, ask tough questions, or adapt to change. Recognition reinforces behavior and embeds learning into the culture.
The Leadership Imperative
Upskilling initiatives cannot be side projects. They must be championed by leadership and embedded in your values, mission, and everyday practice. That includes:
- Regular, constructive feedback rather than waiting for annual reviews, so employees get real-time feedback to sharpen their pencils, and feel challenged on an ongoing basis.
- Clear communication about career paths and what it takes to move forward, so team members can see their employer is invested in their performance.
- Investment in leadership training, particularly in EQ and coaching, to ensure this direction comes from the top and is skillfully led.
Ultimately, careers are not static; they are learning journeys. Organizations that thrive will be those that empower their people not just to keep pace, but to lead change.
A Final Thought
The pace of change won’t slow down. Skills will continue to evolve, new technologies will emerge, and FOBO will remain a reality. But leaders have a choice. You can leave employees to manage their fears alone, or you can invest in reskilling and upskilling to turn that anxiety into confidence.
So, to return to my opening question: which team would you rather lead? The stagnant, hesitant one, or the agile, optimistic one that’s ready for the future?
Rebecca McNeil is a Senior Advisor for People and Culture at MC Advisory, where she helps organizations build stronger, people-first workplaces. When she’s not partnering with leaders on strategy and culture, you can find her salsa dancing, throwing pottery, or playing a fiercely competitive game of pickleball. Look for her free webinars on trending topics in HR and culture.