3 Tips to Make Upskilling Part of Your Workplace Culture

Younger generations are asking for ways to learn and build out their expertise, and employers who openly support that ambition are setting their teams up for success.

As new generations enter the workplace, new dynamics also come into play. Millennials now make up the largest share of the workforce, and Gen Z has officially surpassed Baby Boomers, which means the future of today’s workplace is already being shaped by these younger cohorts. It’s no surprise that employee expectations are changing, but with the broad differences between generational expectations and priorities, employers are being put in difficult positions when trying to keep their workforce happy.

In addition to most organizations actively trying to navigate “The Great Detachment” (where people feel increasingly disconnected at work), there is a growing sense of misalignment as younger generations step into environments tailored for older generations. For example, while older workers prioritize stability and compensation, Millennials and Gen Z are looking for meaning in their work and growth opportunities to advance their careers.

Companies know engagement is valuable—translating to higher productivity, reduced attrition, and stronger loyalty. And while the job market currently favors employers, smart businesses have their eyes on the horizon to ensure long-term compatibility with younger generations. One way to tackle this challenge? Upskilling.

Don’t Underestimate the Costs of Inaction

Upskilling is becoming essential for business success. Odds are your employees want to grow their skill sets and find meaning in their work. Companies that ignore these needs risk watching promising talent walk out the door to competitors who get it.

Upskilling gives employees a sense of purpose and momentum. It is also a cost-effective way for employers to nurture and develop existing talent as opposed to recruiting, hiring, and training new prospects. A full 70 percent of business leaders report that the skills gap is negatively impacting performance due to lack of basic competencies, and that doesn’t begin to address other issues such as disengagement and lost productivity.

The desire for growth is strong among younger workers. Research shows 17 percent of employees are actively asking for more professional development, and more than half of Millennials say they’ve been disappointed by the lack of personal development training in a new role. Yet, only 15 percent of employers report prioritizing personalized training programs for their workers.

Tips for Upskilling

This disconnect is a wake-up call for employers, and those looking to keep and engage top young talent can follow this roadmap to do so:

Tip 1: Start with conversations, not checklists.

Upskilling works best when it feels relevant and personal. That means starting with real conversations. Ask employees what they want to learn. Where do they want to grow? What skills feel out of reach right now? These questions can uncover a lot and often lead to development opportunities that might have gone unnoticed. Conversely, employers can fill gaps in skill sets that are limiting progress and performance—potentially impacting the bottom line—while nurturing young talent.

Most employees—including younger generations—aren’t just waiting to be told what to do. They want to shape their growth. In one survey, 58 percent of Millennials said they believe they can influence company culture, especially when it comes to things such as learning and development. That’s not a challenge. It’s an opening.

When leaders treat upskilling as something to construct together with employees, there is a shift in workplace dynamics. People feel heard and invested. That’s when real progress starts.

Tip 2: Tie skill development to business needs.

Training that happens in isolation rarely sticks. For learning to truly matter, it needs to connect to what’s happening in your business or industry right now. Whether you’re trying to boost customer experience, drive customer retention or improve service delivery, upskilling gives employees the tools to contribute more meaningfully. When people understand how their growth aligns with business priorities, they get more personally vested in business success.

Take AI, for example. With the right training, employees can use AI to make smarter decisions and help the business operate more efficiently—unlocking added value across teams. Research indicates that employees who are already using AI are making decisions faster and performing better overall.

This is especially true for younger workers. Gen Z and Millennials have grown up with technology and tend to be more open to learning and applying digital tools in their day-to-day roles. Their comfort with change and experimentation can give companies an edge, especially when those skills are tied directly to real-world business outcomes.

Tip 3: Use incentives to reinforce behavior.

People often work harder when they know their efforts are seen and appreciated. Recognition, whether public or private, monetary or not—goes a long way. Want to get people excited about building new skills? Tie trainings or certificates to some kind of reward, such as a digital gift card (also known as an eGift). These small gestures can send a powerful message that, as an employer, you value employee growth.

Timing really is everything with recognition. Research shows that rewards have the biggest impact when they come right after the achievement, as more than two-thirds of employees want to receive recognition within a week of earning it, and a third of employees reported that the value of rewards diminishes if received more than a week later. Luckily, technology exists that allows businesses to embed rewards directly into everyday workflows such as Microsoft Teams, so managers can send digital rewards near-instantly following an achievement.

Consistent, well-timed recognition keeps people learning and makes skill-building part of your culture. For younger employees especially, upskilling is a way to boost earning potential and shape their careers. And because they tend to value recognition more than previous generations, rewarding growth in the moment helps them feel seen and supported.

Invest in Your Future Leaders

Consistent engagement and recognition fuel ongoing learning. Younger generations are asking for ways to learn and build out their expertise, and employers who openly support that ambition are setting their teams up for success. Organizations that listen, train with purpose, and reward progress aren’t just upskilling. They’re building a culture where people want to stay, perform at their best, and grow with the company over time.

 

Jeff Haughton
Jeff Haughton is SVP, Incentives, Corporate Development & Strategy at Blackhawk Network. In this role, he leads the growth and development of Blackhawk’s employee, consumer, B2B, and B2B2C incentives business around the globe. Haughton is an expert on data strategy and the impact it has on overall growth across segments, specifically commerce and incentives.