Humble Leadership Behind Prison Walls
I have been volunteering in a women’s prison for nearly a decade. Two Saturdays a month, I leave home at 6:00 AM, arrive at the facility by 7:00 AM, and begin the lengthy entry process. I’m greeted by a massive gate, which feels like something out of Jurassic Park. My belongings are scanned by an X-ray machine, I’m asked to show the bottoms of my feet to check for contraband, and then I’m patted down. With my Bible and supplies in hand, I walk the long hallway past the visitation room and the segregation housing unit.
When I first started volunteering in prison, I thought my job was to “minister” to the women. I went through multiple training sessions, knew what needed to be done, and did most of the talking. But over time, I noticed something: the residents rarely recalled my points. However, what they did remember was when I asked about their stories.
One evening, instead of relying on my own conversation game plan, I shared something vulnerable. I admitted that I had been wrestling with anxiety, specifically, a fear of failing on a project and letting others down. I asked whether anyone else had ever felt that way. The room shifted. Women who had sat silent began nodding. One shared her fear of being released without a place to go. Another spoke about the fear of her children rejecting her.
“Tell me more,” was the phrase God placed on my heart. I couldn’t pretend to know what it was like to face a parole hearing or carry a felony record. However, I did know what it felt like to be insecure, rejected, and even invisible at times. The Spirit gave me the right words about how God meets us in our fear. By the end of the evening, the women were praying for each other. My role wasn’t center stage; I had simply created space for honesty, vulnerability, and hope.
According to Edgar and Peter Schein, authors of Humble Leadership: The Power of Relationships, Openness, and Trust, this experience exemplifies a “Level 2” relationship, where empathy serves as the guiding sentiment. They identify four levels of relationships:[1]
| Relationship Level | Associated Sentiment |
| Level minus 1 | Antipathy |
| Level 1 (transactional) | Apathy |
| Level 2 (personal) | Empathy |
| Level 3 | Compassion |
Why does it matter?
The Scheins suggest that naming and distinguishing relationship levels can help leaders respond appropriately in varied circumstances. Misunderstanding the level can create miscommunication, misguided expectations, and ultimately distrust.[2]
Relationships are messy, and surely Jesus didn’t categorize them, but He lived them well, navigating volatility, uncertainty, complexity, and ambiguity with a non-anxious presence. Edwin Friedman, in A Failure of Nerve, defined this as the ability of a leader to remain calm and grounded in the midst of others’ anxiety and chaos.[3] This is also the heart of humble leadership: authentic relationships that build trust.
How did Jesus navigate relationships in a challenging world?
In the midst of volatility, Jesus brought stability without resorting to force or control, instead offering peace grounded in prayer and presence. Through frequent bouts of uncertainty, He clarified identity and mission to his disciples, “You are the light of the world.” Even when His words or parables were confusing, He consistently reminded them of who they were and their purpose. He gained their trust through his authenticity.
In complex situations, Jesus simplified the dynamics in ways that everyone could understand. He condensed over 600 laws into two simple commands: Love God and love your neighbor. Schein teaches that humble leaders replace rigid, top-down answers by asking “What can we learn together?”
Ultimately, in the face of ambiguity, Jesus demonstrated vulnerability while remaining grounded in faith and discernment. He modeled dependence on God and invited us, His followers, into faith, rather than pretending to control the future.
In Closing –
My years in prison ministry have provided me with enormous opportunities for learning. Working alongside the residents taught me that leadership is not about holding the spotlight or having all the answers. It’s about the ministry of presence, humility, and creating space where other voices are welcomed. Despite the often-dehumanizing environment, these women are able to grow in their walk with Christ and in building trusting relationships.
Jesus modeled this type of steady leadership in a turbulent world, and the Scheins provided a framework to understand what humble leadership means. In times of volatility, uncertainty, complexity, and ambiguity, we don’t need louder voices or tighter control. We need leaders who listen, show empathy, and walk together through the unknown. That kind of leadership fosters relationships that transform lives within prison walls and beyond.
[1] Schein, Edgar H., and Peter A. Schein. Humble Leadership, Second Edition: The Power of Relationships, Openness, and Trust. Second Edition. Oakland, CA: Berrett-Koehler Publishers, 2023. P. 15
[2] Ibid. XIII
[3] Friedman, Edwin H., Margaret M. Treadwell, and Edward W. Beal. A Failure of Nerve: Leadership in the Age of the Quick Fix. 10th anniversary revised edition. New York: Church Publishing, 2017.
About the Author
Jennifer Eckert
Operations and fundraising director, people connector, believer in second chances, fights poverty, supports justice reform, lives a life integrated with Matthew 25.14 responses to “Humble Leadership Behind Prison Walls”
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Hi Jennifer, welcome to the final year of the program. I have appreciated reading about your experience visiting and serving in prisons.
It seems like you have intuitively done what the Scheins are describing in the book.
How might those in authority in a prison, characterized by Level -1 relationships put something like this into practice without giving up the need for order, structure, and authority.
Thank you, Graham. Yes, year 3 – it’s hard to believe.
I have seen a major culture shift taking place across U.S. prisons. Residents can attend school, learn technical trades, and participate in life/character/faith programs that all have a restorative element. Traditionally, staff have maintained a hard attitude, with compassion mainly coming from the chaplain. However, these days, wardens can be seen giving high-fives, celebrating good behavior, and even acknowledging women by name. What they are finding is a less hostile environment. Corrections officers (CO) can not only maintain order and safety, but they can also be seen as trusted coaches. In the women’s prison where I serve, a CO recently transferred to a newly created position as gym coach. He is leading exercise programs and other initiatives to help these women grow while they are in the facility. The women are happier, the staff are happier, and there are far fewer infractions overall. Calm begets calm. It’s pretty remarkable and helpful in an environment that is severely understaffed everywhere.
Hi Jennifer,
Thank you for your post. Your post radiates humility, transformation, and the sacred power of presence. I believe sometimes the most profound ministry begins not with answers, but with vulnerability and the courage to listen.
In what ways can leaders and volunteers reframe their role from “fixer” to “fellow traveler,” allowing the stories of others to shape their own growth and understanding?
Thank you, Shela. Serving in a prison is difficult for so many reasons. But once you begin talking with the ladies, you immediately recognize that they are no different than me.
About two weeks ago, I was in a small neighborhood grocery store when I saw a woman I recognized who was working there. I wasn’t sure I was seeing correctly, so I went aisle to aisle looking for her. Sure enough – it was Christina, a beautiful sister I had known for some time behind razor wire. She was free! And working at the grocery store! My eyes filled with tears to see her wearing street clothes for the first time. She grabbed my shoulders and looked me right in the eyes and said, “I want you to know how much you and the other volunteers helped me. I couldn’t do this outside if it wasn’t for you.”
No doubt, re-entry after prison is extremely difficult. I have been blessed by those experiences, too. But the truth is, Shela, we are all redeemed sinners living in the prison of this challenging world or the prisons of our minds.
Jesus paid for all of our sins as he hung on that tree.
Forgiveness is what his redemption allows us to do, and part of that means preparing incarcered men and women to live life differently when they get out so they can flourish the second time around.
Thank you so much for sharing these stories, Jennifer! How do you model those authentic relationships in your ministry while still keeping the focus on the people you are serving?
Thank you, Ryan. Of course, as volunteers, we are required to go through annual state-level training as well as facility-specific training. It’s good to have those reminders because you still have to operate with boundaries. People are people in prison just as they are outside. They are trying to be seen as credible, many are battling personal trauma and demons of their own. But what keeps me centered is Christ.
I’ll share a quick story –
I once served on a four-day team event held in the prison gym. On the final day, we were cleaning up and needed to wash dishes (without a kitchen or sink). Being resourceful, we filled a plastic tub with soapy water from the bathroom sink and, since there was no table, I sat on the floor scrubbing dishes by hand. It wasn’t anything I ever thought I’d be doing, but here I was – the work needed to be done and this was the only option.
But the craziest thing happened. Sitting there on that prison gym bathroom floor, an overwhelming sense of love washed over me. It was Jesus – no doubt about it. It was one of those rare times when you could feel him standing there – literally! I heard him say in that still small voice that washing those dishes for the women was the same as if I were washing His feet. Thinking about these details to even write them for you gets my eyes watery.
God often meets us in the most unlikely moments and places, stripping away comfort and ego. In prison, He not only works in the lives of residents but also in the hearts of volunteers. To be honest, volunteers often grow and benefit as much, if not more, than those we come to serve.
Jennifer,
I am struck by your level 2 relationships within the prison walls while the inmates themselves have -1 relationships with the guards. This kind of relationship building takes time and effort and I am glad that you have put in the time, month after month, year after year. You might be one of the few level two relationships many of these women have.
Thank you, Adam. My soul is fed significantly in prison with people who need Jesus as much as I do.
Jennifer, your service in prisons always sounds so powerful. Thank you for doing that.
I’m wondering though, how can leaders who are in positions of formal authority, rather than volunteers, replicate the “ministry of presence” and trust-building you describe?
My sweet friend,
The best example I can give you is to show you this short YouTube video of the Oklahoma Dept. of Corrections Director, who joined the women’s praise and worship concert at the prison where I serve. What he did was demonstrate humanity. The bonus is that trust was built among everyone there, and it was done through the love language of music. We need more leaders to do things like this in prisons across the U.S. It’s happening, but not everywhere. Enjoy the video. It’s pretty cool.
https://www.youtube.com/watch?v=BnxbCP9Lgps
Jennifer, your story behind the prison walls deely moved me. I believe it was Elie Wiesel who said that the opposite of love is not hate, but apathy. Reading about your experience makes me wonder how many of these women have never experienced love in their lives. I suspect many of them have only had level 1 or -1 relationship. Your vulnerability pointed them to the love of our Heavenly Father.
Thank you, my friend. It’s a joy to learn from them, but you are right. Many have never seen a healthy relationship of any kind before. You should hear the curiosity and questions that Doug and I get when we serve together in prison. For women, they marvel at how kind he treats me (and them). I am hoping to get a program started next year that will help married couples with a spouse in prison. Re-entry for those folks is doubly hard.
Jennifer,
Thanks for describing your experience working with these wonderful women over the past ten years. Others have already asked questions or made comments that were going through my mind. Taking this idea of Level 2/3 relationships building trust, have you considered how your modeling of Level 2 relationships will impact some of these women as they are released back into the outside world. Will they be open and willing to be vulnerable with others or will they function using Level Minus 1 or Level 1 relationships?
Thank you, Jeff. I’m going to paste a response I made to Shela’s question, which was similar to yours.
(Pasted)
Serving in a prison is difficult for so many reasons. But once you begin talking with the ladies, you immediately recognize that they are no different than me.
About two weeks ago, I was in a small neighborhood grocery store when I saw a woman I recognized who was working there. I wasn’t sure I was seeing correctly, so I went aisle to aisle looking for her. Sure enough – it was Christina, a beautiful sister I had known for some time behind razor wire. She was free! And working at the grocery store! My eyes filled with tears to see her wearing street clothes for the first time. She grabbed my shoulders and looked me right in the eyes and said, “I want you to know how much you and the other volunteers helped me. I couldn’t do this outside if it wasn’t for you.”
No doubt, re-entry after prison is extremely difficult. I have been blessed by those experiences, too. But the truth is, we are all redeemed sinners living in the prison of this challenging world or the prisons of our minds.
Jesus paid for all of our sins as he hung on that tree.
Forgiveness is what his redemption allows us to do, and part of that means preparing incarcered men and women to live life differently when they get out so they can flourish the second time around.