Leading the Confident Generation with Clarity and Purpose

Be honest—did the title of this article bring to mind a smartphone-wielding, social-media-scrolling twenty-something? If so, you’re not alone. The term “entitled” has become synonymous with younger professionals, often unfairly. But research tells a different story. In a long-term analysis of nearly half a million high school students, psychologists Brent Donnellan and Kali Trzesniewski concluded that today’s youth aren’t any more self-absorbed than previous generations. Entitlement, it turns out, tends to decline with age—not rise with the times.

That said, every workplace has its share of personalities who seem overly confident, demand constant recognition, or struggle to see past their own priorities. And it’s not limited to the youngest employees. These behaviors can show up across generations, from fresh hires to long-tenured veterans. The challenge—and opportunity—for leaders is not to dismiss these individuals, but to guide them with intention. The best managers learn to engage, challenge, and develop even the most self-assured contributors.

A Look Back to Move Forward
While “back in my day” stories may not land well in every setting, there’s value in connecting employees to the journey of the organization. Many newer team members don’t know what it took to build the company they now work for. Consider adding a visual milestone wall or storytelling session that highlights key turning points, struggles, and victories. This context fosters gratitude and helps reframe today’s work in the larger narrative of growth and resilience.

Appreciation Over Adoration
Language has power. Telling someone they’re “the best hire we’ve ever made” might feel motivating, but it can fuel a sense of superiority. Instead, shift your vocabulary to emphasize appreciation over admiration. Try: “I appreciated the strategic thinking you brought to that client pitch,” or “Thank you for stepping up when the team needed leadership.” These types of comments keep the focus on the effort and impact—not on feeding a sense of personal exceptionalism.

Building Team Accountability
When someone believes their success is self-made and self-contained, the best approach is to tie their outcomes to others. Link part of their incentives to team performance, mentorship, or shared project goals. Give them a mentee to coach. Celebrate the team’s achievements over the individual’s. When done well, this creates a subtle but powerful shift—moving from “I succeed when I win” to “I succeed when we all do.”

Expectations That Leave No Room for Ambiguity
With confident or self-focused employees, clarity is essential. Broad or vague performance goals can be interpreted in self-serving ways, so define what success looks like at every level: What’s unacceptable? What’s adequate? What’s exceptional? Paint a clear picture—quantifiable when possible—and stick to it. Wavering on expectations teaches people how to exploit the gray area. Set the bar, make it visible, and uphold it consistently.

Growth Through Challenge
It might sound counterintuitive, but one of the best ways to develop an overconfident employee is to assign a stretch goal—one they’re likely to fail at, or at least struggle through. Not to punish, but to invite humility, learning, and growth. Give them permission to experiment, fail forward, and reflect on what they could improve. The goal isn’t perfection; it’s resilience.

Even better? Tell them why you’re giving them the challenge: “This is tough. I know it’s a reach. But I believe you can handle it.” This communicates seriousness, trust, and the kind of meaningful opportunity that high-performing individuals crave. Risk builds capability—and often, deeper loyalty.

The Real Opportunity
Entitlement isn’t necessarily a flaw—it’s often just confidence without enough experience behind it. And when you see it that way, it becomes easier to lead with purpose. Help these employees direct their energy toward growth. Clarify what matters. Challenge them to rise. That’s how you turn strong egos into strong leaders—and how you build teams that grow from the inside out.