In my dual role as both chaplain and Executive Director at Chicagoland Prison Outreach, I’ve come to believe that hiring is one of the most spiritual decisions we make as a ministry. Not because of the job descriptions, but because of the people behind them. The work we do—whether in vocational training or spiritual discipleship—rises and falls on our staff’s ability to be present, to build trust, and to carry the Gospel with both conviction and compassion.
What follows is not just a philosophy. It’s a reflection of what I’ve learned in the field—inside jail cells, across desks from staff candidates, and in the sacred space of lives being changed.
Relationship Is the Core of Our Mission
Ministry at CPO is not transactional. It’s relational. Whether someone is stepping into a classroom or entering a cell block, our expectation is the same: be present. Be real. Be ready to listen before you teach. The people we serve are not projects. They’re men and women made in the image of God—many of whom have never experienced what it means to be seen, heard, or discipled.
If our staff aren’t anchored in that belief, this work becomes mechanical. We risk turning restoration into a task list, discipleship into a curriculum. But ministry, the kind that truly transforms, begins when we slow down and stay with people—even when it’s messy, even when it doesn’t fit a schedule.
Hiring People Who Are Called to Walk With Others
I’ve come to realize that the best staff don’t just teach welding or preach in chapels. They build trust. They ask hard questions. They sit with someone for forty minutes just to help untangle the spiritual chaos behind the behavioral one. They see moments of emotional breakthrough not as interruptions to the day—but as the point of the day.
That kind of presence only comes from people who understand the “why” of what we do. It’s not about keeping programs running—it’s about remaining faithful to people, even when discipleship doesn’t follow a clean arc. That’s what we look for when we hire: individuals who carry both the resilience and the compassion to walk with people long after others would have walked away.
Ministry That Continues—Because People Matter
At CPO, we believe that relationships are not a byproduct of our programs—they are the heart of the ministry. That’s why, even years ago, our chaplaincy team wrestled with a hard question: When does ministry to someone end? The answer we kept returning to: it doesn’t—not if we’re serious about discipleship.
So we continue to hire with that commitment in mind. We look for people who are not only available to serve—but are also willing to stay. People who bring hospitality into every space they enter, who see their role not as a job, but as a calling to walk faithfully with the brokenhearted, the overlooked, and the returning.
This work isn’t easy. But it’s holy. And I count it a privilege to serve alongside people who understand that.
