What I Learned in Jail

When I sat down to talk to the warden, I had a burning question to ask him about what I had just observed.

Over the previous few hours, I had participated in an inmate training workshop. The course focused on leading yourself to better results and was designed to teach inmates how to be more effective and lead successful lives.

I was asked to attend the session to observe the training and offer my thoughts and insights into improving it.

The training was held in the library’s annex. Six round tables were wedged in the space. Each table seated a handful of participants. At the front were a projector, screen, and facilitator. Had it not been for the cinder block walls, correctional officers milling about, and participants dressed in orange, it would have resembled most corporate workshops I had attended over the years.

I found the experience interesting on several fronts, but one issue intrigued me most. It was the source of the question I intended to ask the warden.

When the facilitator directed the participants to complete a small group discussion at their tables, he asked the designated table leaders to facilitate the conversation. I turned to my host and asked how the table leaders were selected. I learned that they had all completed the course in the past, applied to be table leaders, and been selected by the warden.

“Oh yeah,” the host added, “they are all serving life sentences for murder.”

I thought to myself, Why would an inmate who had no possibility for parole offer to serve as a leader? After all, much of the discussion in the training focused on how people were going to more productive and successful after they left the correctional facility.

This is the question that I asked the warden. He answered that the table leaders knew that they would never get out of the correctional facility themselves, but we’re committed to helping those who would get out never to return. He said that they received no perks to perform the role. They did it because they wanted to.

I have often reflected on that day. I’ve thought about the table leaders who spend most of their time in a cell with no expectation of living outside the facility walls. I think about their motivations and their choices. I have also thought about how I learn so much about things when I step into new, often unexpected places. My perspective changes as I process new information.

Such was the case for recent podcast guest Allison Schrager. She penned the bestselling book, An Economist Walks Into a Brothel. Much like my experience in a correctional facility, her time in a brothel opened her eyes to a different world with unexpected lessons.

You don’t have to visit a brothel or a correctional facility to gain new insights. But, you do have to step out of your comfort zone and into some new places. Fortunately, there are new places all around you. You can find them in an office down the hall where another team works, at a customer site, inside a competitor’s store, or a range of other spots that you simply don’t frequent.

Spending time in those places, asking questions, and listening can provide you tremendous insights about your people, customers, competition, and more.

This week’s tool is designed to help you to identify a few places worth exploring. Doing so will increase your understanding of others, inform your thinking, and generate empathy. These lessons and more are critical to becoming the leader you are meant to be.

Make it a great day!  -Patrick

Photo by Hédi Benyounes on Unsplash

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