Paolo, what’s most important to you when coaching Gen Y, and how do you approach it?

For me, when I’m coaching Gen Y, what’s crucial is igniting something inside them. Not a gentle nudge, not a pat on the back, but a fire—a fire that pushes them to rethink the rules they’re living by, the paths they’ve been told to follow, and the limits they don’t even realize they’ve set for themselves.

Gen Y has this incredible, unique position in the world. They’ve lived through a time of massive transformation, from the analog world to this fully digital, constantly connected reality. But here’s the problem: they’re still often stuck navigating systems and structures built for a world that no longer exists. That’s where I come in. My job is to help them break free from that outdated thinking. I want them to see that the ability to understand both the old world and the new is their superpower. And they need to stop trying to fit into a playbook written for a time that’s long gone.

When I’m coaching them, it’s about teaching them how to thrive in a world that’s messy, unpredictable, and full of chaos. I push them to stop clinging to control because the truth is, control is an illusion. The real power comes from embracing the unknown, from seeing the opportunity in the chaos rather than running from it. If they can get comfortable in the uncertainty, they’ll be unstoppable.

Another thing I focus on is helping them trust in their own voice. So many Millennials are still chasing validation—they want approval from the corporate world, from societal norms, even from the expectations their parents had for them. I push them to unlearn that. They need to stop looking outside for permission and start trusting their own instincts. Their perspective is not just important, it’s necessary for shaping the future. They need to own their voice, stop trying to mold it to fit someone else’s expectations, and let it be as bold as it needs to be.

Failure comes up a lot, too. There’s such a fear of failure in Gen Y because they’ve been taught that failing means you’ve done something wrong. But I flip that on its head for them. Failure isn’t the enemy—it’s the path forward. If you’re not failing, you’re not taking big enough risks. My job is to help them reframe failure, to see it as a stepping stone to success, not something to avoid. They need to be willing to fall, and then get up quicker, stronger, and smarter each time.

And then there’s leadership. I’m always pushing them to think about leadership differently, not as something you do from the top down, but from the inside out. Gen Y is in the perfect position to mentor Gen Z, to guide them without trying to control them. They understand both worlds—the one before everything went digital and the one we live in now. They have the ability to bridge that gap. But they need to step into that role with confidence. It’s not about being the boss or dictating the way forward—it’s about leading with empathy, creativity, and agility.

But more than anything, I push them to challenge the status quo. Too many people in Gen Y are still playing by the rules that were set by the generations before them. But those rules were made for a different world. I help them see that it’s okay to ask hard questions. Why are we doing things this way? Is this still relevant? And when the answer is no, I encourage them to break the rules, to rewrite the script, and to create something new that aligns with the future they want to build.

At the heart of all of this is my belief that Gen Y has the power to be incredible disruptors, innovators, and creators—but only if they unlock themselves first. They need to shake off the conditioning that tells them to play it safe, to follow the path, to seek approval. I want them to realize that true success isn’t about fitting into the system—it’s about breaking it open and building something entirely different.

So, for me, what matters most is that Gen Y steps fully into their power. Not just for themselves, but for the generations coming up behind them. They need to see that they’re not here to follow; they’re here to lead, to be the bridge between where we’ve been and where we’re headed. And to do that, they need boldness, vision, and a willingness to walk straight into the unknown. That’s what I’m here to coach them to do.