Last week, during a leadership workshop at a high-tech startup, we touched on something that felt reflective—how we box people in with our judgments and, in doing so, trap ourselves too.
Alex, a Director-level executive at the startup, had become a focal point of our discussions. His reputation was complex: a brilliant strategic thinker who struggled with relationships.
Some colleagues described him as intense and driven but also prone to micromanaging. At 42, he had a track record of leading innovative projects but also a history of high team turnover.
"He's a micromanager," one colleague said. "He never sticks around for long," said another. The comments were infused with that subtle judgment: "He's not a good leader," "He burns people out," "He doesn't care about his team's well-being."
I listened, and I felt the urge rising in me to protect Alex and reset the narrative. So, I told them a story—one from my own life.
Years ago, I volunteered for Alliance For Smiles, an organization that helps children born with cleft lips and palates. I worked with a team in Africa and China, giving kids a chance at a different life. These children often faced a lifetime of exclusion—bullied, shunned, and denied opportunities simply because of how they looked. A simple two-hour surgery gave them what we take for granted—a smile that allows them to fit in, to be seen beyond a surface flaw. Just like that, these kids had a shot at life without judgment holding them back.
Alliance For Smiles - China - 2014
And so here we are, in front of Alex, and we have a choice. We can either create a "smile"—an opportunity for change—or we can continue to look at his past and deny him that chance.
But here’s what we often miss: what makes us think Alex isn’t aware of his past mistakes? What if he’s worked on himself—maybe with a coach, maybe with a mentor—and he’s showing up now, hoping for a different outcome? What if he wants a fresh start?
While the spirit of giving second chances is powerful, transformation is not simple or guaranteed. Not all behavioral patterns change easily, and personal accountability is critical.
Giving them that opportunity doesn't mean:
· Ignoring past harmful behaviors
· Allowing continued toxic workplace dynamics
· Sacrificing team well-being for individual redemption
True transformation requires:
· Genuine self-reflection
· Consistent effort to change
· Willingness to take responsibility for past actions
· Active engagement in personal and professional development
As I recently read in The Power of Now, when we let go of the past, we allow ourselves to fully experience the present.
Let me ask you: if you assume someone is incapable of change, what does that say about your own belief in transformation?
I told the group: If we hold on to those old judgments—if we see Alex only through the lens of his past—we deny him that chance to become someone different. Worse, we might even be the reason he falls back into those old patterns.
But what if we chose differently? What if we saw him as capable of change? What if we became the light that he needed, the reflection that invited a different story?
By letting go of our judgments, we move into a space of giving. And by giving—whether encouragement, support or simply our belief in someone—we experience the "feel good" hormone, oxytocin, within us. It's in that giving that we not only heal relationships but also ourselves.
You might be thinking, "But Roberto, we’ve heard it before—the past is often a prediction of future behavior." And yes, there’s truth in that. But here’s what I’d ask you to consider:
When did you last grow and transform? Was it when someone saw only the worst in you? Or was it when someone saw your potential and gave you a chance?
Looking back, I realize that the times when I've held on to old perceptions of someone rarely ended well. We stayed stuck, and nothing changed. But when I made room for something new—for a different version of that person—the shift was real. They showed up differently, and so did I.
Three Practical Steps to Create Change
1. Challenge Your First Thought:
When you catch yourself judging someone, pause and ask, "What if I'm wrong?" Give room for an alternate possibility.
2. Look for One Positive Quality:
When interacting with someone you've previously judged, actively look for one positive quality they bring to the table.
3. Offer the Opportunity - Approach possible transformation realistically:
Provide clear feedback
Set measurable goals for improvement
Maintain accountability
Be prepared to call it out if genuine change doesn't occur
The truth is, how we perceive others is the reality we end up creating. When we choose connection, growth, and opportunity, we create an environment where everyone can thrive—including ourselves.
So what do you say? Is it time to create more "smiles"?
Until next time 👋🏼
Love 💙 Roberto
PS: If you find this challenging, share your story and let me know how I could help.
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