Ending the School to Prison Pipeline

Leonard Webb is one of the foremost speakers on the “School to Prison Pipeline” and he is focused on ending the “School to Prison Pipeline” by providing equity based solution, helping school leaders with accountability while improving attendance and decreasing expulsions/ suspensions. He has used his experience to provide practical approaches to uncovering implicit bias while addressing issues in discipline, criminal justice, and mental health.

About Leonard Webb

Mr. Webb is a retired law enforcement professional turned life coach/ youth advocate.  Leonard is also an adjunct faculty member teaching Criminal Justice at Potomac State College of West Virginia University.  He offers a unique perspective about the School to Prison Pipeline as well as solutions.  He has seen both ends of the pipeline.  He has seen young people enter his office in prison and young people with similar demographics enter his college classroom.  This led him to find out, “Why ?”.  

He learned those students who drop out of school exit the school door eventually take to the streets, away from any structure, probably away from any responsible adults, looking for something but not knowing exactly what.  It doesn’t take long before they follow the prison pipeline.  Some don’t drop out but they are involved in school discipline.  Due to zero tolerance policies and being identified as “at risk” they are sent to alternative schools or court programs which are set up like prisons.   

Leonard’s hope is to highlight the pressing need for addressing these issues and ending the pipeline to prison.  He provides coaching and strategies to young people to break this cycle and focus on academic success and resilience.  He consults and trains educators with strategies to help them connect with students, focus on student’s strengths, and provide the support that improves behavior rather than relying on discipline.

Who We Have Served


Ladonna Shankle Harlan

Judge, Dallas, Texas

Mr. Webb’s inspirational and interactive discussions were fantastic. His message and method resonated with many

Heidi Laupert

Principal, Cumberland, Md.

We will continue to use Leonard Webb as a speaker for our professional development as we continue to confront our implicit biases. He is a breath of fresh air.

Laura Nedd Shelton

Testing Coordinator, Bladensburg, Md.

His presentation was purposeful and for many will be impacting their decisions. His presentation will help shape their future

Contact/ Book Leonard