5 People & Culture Lessons from My Time in Prison

No hugging. No cash. No chewing gum. No blue colored clothing. No running. No phones. No jewelry.

It was about ten days before I was being admitted into Solano State Prison outside of San Francisco as a volunteer for a leadership and entrepreneurial rehabilitation program organized by Defy Ventures. However, the instructions I had received seemed almost cryptic. I skimmed through the note, not really absorbing what I signed up to do — or knowing just how much the experience would teach me about empathy, acceptance, and connection. As I have dedicated myself to creating change in the workplace in my role as CEO at Live in the Grey, I have tried to distill this profound experience into five lessons for every organization and team leader.

Lesson 1: Invest in Your People

Nurture strong relationships, so everyone can share what’s really going on in their lives. Be a place of trust.

As I first crossed the barren yard at Solano State Prison, I wondered, what have these people done? If I’m honest, “they” looked quite scary. Tattoos, some scarred and weathered faces with squinting eyes and jaws lifted. Then the doors to the gym opened to welcome us with 100 waving EITs, or “Entrepreneurs In Training,” as Defy Ventures calls them — not “criminals” or “inmates.” Their smiles stretched from ear to ear. I couldn’t help but smile back.

In order to get to know each other, the first activity was an icebreaker questionnaire. As I moved around, comparing answers and getting to know the EITs, one question about personal flaws struck a chord. It helped me reevaluate my views of myself and the people around me. As I read what others wrote with such raw honesty, and saw the blank space I had left, it hit me how crazy it was that I was still trying to hide some part of me. I wrote down “perfectionism” as my flaw — and then realized that was like answering the interview question of “what’s your weakness” with a strength. I’d been on the receiving end of that before and it wasn’t authentic. I called bullshit, and wrote down “judgment of myself and others.” The walls between us were crumbling, bit by bit. The space between black and white was turning “grey.”

Lesson 2: Give Second Chances…for the Right Reasons

We all deserve another chance, but support out of understanding and care, not out of pity. Pity sets up a condescending dynamic that is as unhealthy for you as it is for them.

One of the most impactful and emotional moments came during an exercise probing our similarities and differences. Our program leader had us stand on a line, EITs on one side, volunteers on the other. A visual representation of separation. She then read out revealing true or false statements: step forward for “true,” and backwards for “not true.” There was only one additional instruction: you must make eye contact — and keep it.

During the exercise, people admitted to anxiety, illegal behavior, etc. but the biggest division between volunteers and EITs was over years in prison. My lips began quivering as I saw how their expressions changed at this question. A grey-haired man, with tears slowly puddling in his eyes, revealed that he’d been in prison for nearly 66 years. I reached for the tissue in my pocket and started sobbing. Catherine reminded us to stay put, to keep gazing…“with empathy.”

I was sad and furious, and wanted to run across the line to hug this man who seemed so different from me on the surface. Though many EITs had committed crimes, Catherine’s words stayed with me: “What if you were judged for the remainder of your life for the worst thing you have ever done?”

Lesson 3: Teach Your People to Connect Authentically

Start by simply making eye contact — it’s the birthplace of authentic connection. Listen quietly and actively when someone is sharing something meaningful. Expressing empathy and vulnerability make for stronger bonds professionally and personally.

Have you looked directly into someone’s eyes recently? Not just a casual glance, but a deep gaze? No words are necessary to connect and empathize with another person. We teach empathy and vulnerability when we work with companies at Live in the Grey, but I now understand the power of empathy in a way I never have before, despite teaching the concept to so many teams.

Lesson 4: Create a Truly Inclusive Team

We all want to feel like we belong, at home and at work. Change has to happen on so many levels, but your people can start by learning, practicing, and believing in acceptance at work.

When the day started, I saw the EITs as criminals — frightening, and somehow less than me. I am not proud of this, but to deny it would be inauthentic. I had to remind myself not to judge at first, but by the end of the day our commonalities bonded us, rather than our differences dividing us. This sense of empathy is at the heart of inclusion, in every organization and setting, from schools to neighborhoods to companies. I’ve spoken with Heads of People and CEOs about the importance — and benefits — of creating welcoming and accepting teams in their organizations.

This experience taught the importance of an inclusive culture in a whole new way. I never expected to find such warmth, to experience such empathy and vulnerability, or to confront so many of my own judgments during my time at Solano State Prison. But nothing teaches humanity like finding similarities in the face of superficially stark differences. It was a gift for the EITs to let us in their minds and hearts, a gift that I believe we can all learn from, and use to grow and improve personally and professionally.

Lesson 5: Express Gratitude Daily

Grateful employees are happy employees, so create time for people to check-in and share the things that are making their hearts sing.

Despite their struggles, the EITs showed the power of perseverance and gratitude. Instead of giving up, they’re striving for a better future, honing new skills and most importantly, forming new connections with enthusiasm. Their strength, warmth, and positive attitude was inspiring. Not a single day has gone by since my experience in Solano State Prison that I haven’t been grateful for even the simplest things in life, like sharing meals with loved ones. Appreciating these keeps us in touch with what really matters: each other.

The biggest lesson from my time in prison was the importance of human connection. The bonding among the volunteers and the EITs, even in such a short time, reinforced the power of empathy to overcome differences and create connection. People form the foundation of every organization, from prisons to companies, and as leaders we must make them a priority. From encouraging empathy to teaching authentic communication and introducing inclusion initiatives, it’s on us to make our offices into authentic workplaces, where people feel able to bring their whole selves every day.

Grey Matters is the online publication of Live in the Grey, a company that creates authentic workplaces where people bring their whole selves to work everyday. Click here to learn more!