Second Chances, Stronger Teams: Leadership Lessons From Prison

Forbes

28-04-2025

April is Second Chance Month, a national effort to recognize the importance of giving people with criminal records a fair opportunity to rebuild their lives. But it's also a chance for leaders—of companies, communities, and families—to examine our own beliefs about talent, trust, and what it means to grow.
I have had the rare privilege of volunteering inside York Correctional Institution, a women's prison in Connecticut. I joined Defy Ventures, a national nonprofit that equips incarcerated individuals with the tools, mindsets, and support to succeed as entrepreneurs and leaders.
The women of York Correctional Facility have a lot to teach us about leadership.
The people I met through Defy's in-prison program taught me lessons about leadership as potent as any business school course or retreat.
Their lessons were raw, real, and—if we're willing to learn from them—deeply relevant to how we build stronger individuals, teams, and organizations.
The women in this program have made serious mistakes. Some are serving long sentences. But they've also made a different kind of choice—one to reflect, to forgive, and to rebuild.
One participant had become an expert in creating full meals using a paper bag, chip wrappers, and a hair dryer. Another aspired to launch a funeral transportation business for underserved families. A third hoped to be chosen to give the graduation speech at the end of her cohort's entrepreneurship training.
They each displayed what psychologists call a 'growth mindset,' paired with extraordinary resilience.
In a world that often values speed and scale, their commitment to self-awareness, creative expression, and joy—even behind bars—was a powerful reminder: leadership begins with how we lead ourselves.
When we talk about diversity of thought, we rarely imagine a prison gymnasium full of women in khaki uniforms, brainstorming mobile party planning businesses or repair services. And yet, what I witnessed was some of the most inspiring collaboration I've ever seen.
The mutual support and collaboration among the Defy participants is a model for any team.
These women practice active listening. They build each other up. They share real-time feedback with a spirit of generosity and accountability.
It's the kind of culture every team claims to want—and few actually build.
Great leadership isn't about charisma or control. It's about creating the conditions for creativity, trust, and shared growth. And that's exactly what Defy fosters inside the walls of correctional facilities.
One of the most important leadership mindsets is long-term thinking. And there's perhaps no more powerful long-term investment than the one Defy is making in people who society often writes off.
Nearly one in three Americans has a criminal record, according to the Brennan Center. And recidivism remains a costly challenge: within three years of release, two-thirds of people are rearrested, contributing to $80 billion annually in incarceration-related spending in the U.S. alone.
But with the right interventions, that pattern breaks.
Defy Ventures' graduates have a recidivism rate up to 85% lower than the national average, and 90% find employment within 90 days of release. Many launch small businesses—over 200 to date—significantly outperforming typical reentry outcomes.
These are not outliers—they are untapped assets. If you care about performance, equity, or social impact, second chances are not charity—they're strategy.
Over 200 Defy graduates have started small businesses.
What I saw at York wasn't a feel-good field trip. It was a profound reminder that potential is everywhere—and that the systems we design, fund, and lead can either unlock or suppress it.
Second Chance Month challenges us to ask not just who deserves another shot, but also what kind of leaders we want to be.
The women I met may have made mistakes, and lost years of their lives. But they have not lost their capacity to lead—with clarity, courage, and commitment.
As executives and employers, we can choose to see that potential—not just in them, but in everyone we meet.