3 Mistakes Leaders Make When Trying to ‘Relate’ to Young Employees

In an age when talent retention is as critical as innovation, leaders are under increasing pressure to engage their younger employees—not just manage them. But too often, well-meaning efforts to “relate” to Gen Z and Millennial employees fall flat, or worse, backfire entirely.

At the core of the disconnect? A misunderstanding of what young professionals actually want from their leaders.

The answer isn’t ping pong tables or TikTok references. It’s empathy.

Empathy, defined as the action of understanding, being aware of, and vicariously experiencing the feelings and perspectives of another, has become one of the most powerful yet underutilized tools in leadership. And when done right, it drives results. In fact, companies where managers show sincere interest in Millennials as people see an 8x improvement in agility and a 7x increase in innovation.

So what are the most common missteps leaders make—and what can you do instead?

Mistake #1: Thinking Relatability Means Being “Cool”

It’s tempting to try to relate to younger employees by mimicking their slang, referencing pop culture, or casually name-dropping social media trends. But this strategy can quickly feel disingenuous—and young employees can spot it a mile away.

Instead: Ask what energizes them.
As leadership researcher Marcus Buckingham explains in his book Love + Work, great leaders begin by asking questions like:

“What is it about what you do that you love?”
“When does time fly by for you?”
“What are you most looking forward to in your role?”

When leaders ask sincere, curiosity-driven questions about what makes someone come alive, they build trust—and open the door to better engagement.

Mistake #2: Substituting Grand Gestures for Consistent Connection

Leaders often think employee engagement means organizing big events or flashy initiatives. But for young employees, meaningful engagement is less about intensity—and more about consistency.

Buckingham puts it this way:

“Frequency trumps intensity. The best managers check in every week—15 minutes, two questions: What did you love last week? What did you hate? And what are you focused on this week? How can I help?”

52 conversations a year. That’s the framework.

Instead: Prioritize weekly check-ins.
At Generation Distinct, we’ve adopted this rhythm as a cultural value. These check-ins aren’t status updates—they’re moments to truly see, support, and guide each team member. And they’ve transformed our culture.

Mistake #3: Assuming Performance Is Separate from Personal Passion

Some leaders hesitate to talk about what their employees love outside of work—assuming it’s irrelevant to their performance. But ignoring those passions sends the message that employees must compartmentalize who they are to succeed.

Instead: See your employees as whole people.
Ask about their side projects, their weekend hobbies, their big dreams. Then, celebrate those things—even if they don’t directly tie to your bottom line.

At Generation Distinct, we train leaders to value the full humanity of their team members. Because when people feel seen, known, and genuinely valued, they show up more fully—and more powerfully—to the work that matters.

Action Step

This week, ask the young adults on your team:

“What is it about what you do that you love?”
“When does time fly by for you?”
“What do you look forward to in your day?”

Then—and this part is crucial—listen. Let their answers shape how you lead, how you develop them, and how you show that you care.

When leaders lead with empathy, they don’t just “relate” to young employees. They unlock their full potential.