The Critical Thinker Who Sharpened My Mind
The Mentors Who Made Me
"How does it work?"
Tomas looked at me, calm but firm.
Then he started tearing my idea apart—gently, but without mercy.
I wanted to fight back. It's my idea. I believed in it.
By the end of our conversation, I realized he hadn't tried to destroy it.
He had helped me make it stronger.
It was my first startup.
And the discovery of the power of critical thinking.
A lesson that changed the way I think, lead, coach, and mentor.
Hard From the Very Beginning
It was 2007. A snowy April vacation in Paris.
Tourists were exploring the city using The Da Vinci Code as a guide. And they were all getting lost, obviously.
"They are crazy", I thought, "But what if they are not?"
That sparked a connection in my mind between games, stories, and cities.
"What if we could use narrative games to explore the real world?"
I immediately fell in love with the idea. So much so that I wanted to build a startup around it.
At the time, I was working in H-Farm, one of the first incubators in Italy. They were crazy enough to support my idea, but first, I had to get it past Tomas, the guy who validated business models.
I was naive. Tomas was practical. Both of us were stubborn.
He challenged my assumptions. I resisted a bit. Then, we dismantled and rebuilt the idea piece by piece.
Until it was stronger and better.
I didn't just pass the test: Tomas decided to join me in the adventure.
That's how our partnership—and our legendary debates—began.
The Magic of Intellectual Combat
From the outside, our conversations looked like chess matches. Sometimes even battles.
Tomas pushed me to look at ideas from unexpected angles. He asked hard questions. He demanded clarity, evidence, and honesty.
Gradually, I learned to do the same with him.
And we had our fair share of bouts.
But these weren't debates to win.
They were excavations! Digging until we struck gold.
That process was only possible because of one thing: trust.
I knew Tomas had my best interest—and our team's—at heart.
That safety made it possible to question everything, even my beloved ideas.
From Ideas to Impact
The results? Together, we created WhaiWhai—narrative treasure hunts that helped people rediscover cities, earning us an Innovation in Tourism award from the Italian presidency. We developed Frammenti, Italy's first blend of interactive fiction and alternate reality gaming.
These weren't flukes. They were the result of ideas that had been stress-tested, refined, and sharpened.
Even now, though we're no longer business partners, I still seek out conversations with Tomas to sharpen my thinking.
But that's not all.
Critical thinking is a valuable tool, but to accomplish anything, you need more.
Critical Thinking Is Not Enough
Tomas also taught me something many overlook: Clarity is only half the job.
Once an idea survives the challenge, it needs to be brought to life with grit, energy, and commitment.
You can't just think clearly. You have to act relentlessly.
That's what Tomas modeled: vision sharpened by challenge, then made real through relentless work.
Years later, as I began mentoring others, I realized what Tomas had really taught me: The greatest gift a mentor can give isn't validation—it's the courage to think clearly, and the energy to act on that clarity.
That's what I strive to do now.
Help people sharpen their vision and then stay with them to turn insight into action.
From Intuition to Method
Tomas's gift for critical thinking came naturally. But to apply that effectively in a mentoring relationship, we need more. We need the structure, competencies, and techniques of professional mentoring to truly help others think deeply, without creating resistance or defensiveness. And to help them act relentlessly and meaningfully without getting overwhelmed or frustrated.
Here are five lessons I carry into every mentoring session:
The strongest ideas welcome scrutiny. If they break, they weren't ready. Strengthen, don't protect.
Challenge with care. People open up when they feel safe enough to be wrong and grow.
Questions are more powerful than statements. Insights come from asking questions that help us see the possibilities ourselves.
Critical thinking is an act of love. It's not about being right. It's about caring enough to help someone grow and thrive.
Challenge first. Then go all in. Once the idea holds, pour yourself into it fully. Think clearly. Then act with fire.
For Managers Reading This
If you're a manager, ask yourself:
Are you helping your team sharpen their thinking or just keeping things smooth?
Are you validating ideas or helping people make them stronger?
Are you willing to be a Tomas for someone else?
Mentoring isn't about giving advice.
It's about creating the friction that ignites growth. Then go all in.
In Closing...
The true gift of a mentor isn't answers.
It's clarity. Challenge. Courage. Support.
It's staying with someone through discomfort until they become who they're meant to be.
For that gift, I'll always be grateful to Tomas, one of the few who can push through my stubbornness and bring out my best.
Who challenged you to think more clearly? Who do you challenge with care?
If you're ready to become that kind of mentor, or want to experience it for yourself, meet Scarlett and Nemo in Becoming The Mentor, a story of how real mentoring changes not just work, but lives.
This story is part of an ongoing series: "The Mentors Who Made Me." Want to meet more of them?