Pastors carry weight that most of their congregation never sees — and rarely have anyone to process it with. Coaching changes that.
Pastoral leadership is one of the most demanding — and most isolating — roles there is. These are the situations coaching is built for.
Navigating the tension between vision and governance, building trust across different expectations, and leading a board that is meant to support — not stall — the mission.
Every church faces conflict. The question is whether the pastor has the clarity, the tools, and the outside perspective to lead through it without losing people, trust, or momentum.
Am I still the right leader for where this church is going? Coaching creates the honest, unhurried space to ask that question — and get to a real answer, whatever it turns out to be.
Alan Cleveland served as a Senior/Lead Pastor for 28 years — 7 years in Michigan and 21 years in Wisconsin, where he led a congregation of over 1,100 people. He knows what it is to carry a congregation, navigate elder relationships, lead through seasons of uncertainty, and wonder whether the next chapter belongs to someone else.
He currently serves as Executive Director of Church Strengthening for Converge Great Lakes, working alongside more than 100 churches across Wisconsin and the Upper Peninsula. That role keeps him embedded in the realities of church leadership at every size and stage — which means his coaching is shaped by what is actually happening in churches right now, not just what happened decades ago.
His Doctor of Ministry, combined with formal coaching training through the University of Wisconsin–Madison, makes him genuinely rare: a credentialed coach who has actually led a church.
Alan brings 40 years of ministry experience — and a genuine interest in what the next generation of pastoral leaders is navigating. The challenges facing younger pastors today are real and distinct, and Alan engages them with curiosity, not just history.
Start the Conversation"Alan Cleveland's coaching has helped me uncover and step into the calling God has already placed within me. His thoughtful questions consistently draw out clarity and direction I didn't realize I had. Through his guidance, I've gained confidence in pursuing what God has called me to do."
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