School to Prison Pipeline

A school’s climate is about fostering meaningful relationships among all stakeholders.

The School to Prison Pipeline is a process by which students are pushed out of schools through disciplinary policies like “zero tolerance” and potentially end up in prison. Leonard Webb is one of the foremost speakers on the “School to Prison Pipeline”. He has used his experience to provide practical approaches to address reductions in the overall use of exclusionary discipline but also focuses on issues of implicit biases and structural racism. By treating students and one another as creative thinkers and creative beings, we expand what is possible. The mission is to inspire, empower, and motivate the enhancement of personal, professional, and educational performance. School is a place where childhood happens for each child. Each child has the right to learn in a supportive environment that respects their humanity, upholds their dignity, and responds fairly to mistakes and mis-steps. Instead, zero tolerance and other exclusionary school discipline policies are pushing kids out of classrooms and into the criminal justice system at unprecedented rates. Some districts are prioritizing putting police into schools, harming students who are Black, Brown, LGBTQ, or disabled for making mistakes that are disciplined more frequently and harshly than their white counterparts. Leonard believes by joining parents, administrators, students, Black, White, Brown, that we can make every public school a place where each child can learn, grow, and thrive.

About Leonard Webb

Mr. Webb retired from law enforcement to focus on improving education outcomes of students and improving relationships between administration, teachers, parents, and students. He is focused on directly addressing the school to prison pipeline by providing equity-based solutions, bringing accountability to school leaders while increasing attendance and decreasing suspension/ expulsions. His work with schools and community led to him being appointed by Governor Hogan (Md.) to the Juvenile Justice School Board for the State of Maryland.

He offers a unique perspective about the School to Prison Pipeline as well as solutions. He spent 19 years as an adjunct professor at Potomac State College of West Virginia University and 27 years with the Federal Bureau Prisons counseling men.   He has seen both ends of the pipeline.  He has seen young people enter his office in prison and people with similar demographics enter his college classroom.  Leonard supports criminal justice and educational reform but he has learned investing in young people’s “off hours”, building relationships, and supporting SEL (social emotional learning) are pragmatic and consequential ways to end the school to prison pipeline. His perspective has been borne from a simple and commonsense insight: if you want to see young people succeed in the classroom, then you need to invest in the relationships and in their lives outside of school.


Leonard highlights the pressing need for addressing issues of school discipline, building administration/ teacher / parent, and student connections, and nurturing student’s purpose will help end the school to prison pipeline.  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