Speaking That Challenges Systems and Moves Leaders to Action
Keynotes that combine lived experience with systems insight — giving audiences both the diagnosis and the implementation path.
Request AvailabilitySentenced to Prison
(During my Second Incarceration)
the Blueprint
NARP
Why Event Leaders Book Khalil Osiris
In my keynotes, I challenge everything your audience thinks they know about reentry — and introduce the corrective architecture: the 2Generation Economy Blueprint.
The system measures the wrong thing. Reentry programs fail because they focus on individuals. Household stability is the outcome we should be measuring.
Signature Topics
"Stop Calling It Reentry. It's Reinvention."
Why individual employment isn't enough — and what we should be building instead. A challenge to every assumption your audience holds about workforce reentry.
"The 2Generation Economy Blueprint"
Building household stability, not temporary jobs. The corrective architecture that changes what we measure, what we fund, and what we call success.
"The 1976 Story"
Lived experience and the corrective architecture. Arrested at 16, sentenced to prison, 20 years incarcerated, two Boston University degrees — and 27 years building the solution.
"Measuring What Matters"
Shifting from individual to household outcomes. Why your current metrics guarantee failure — and what to measure instead.
Delivery Formats
Keynote
30–60 minutes
Workshop
Half or full day
Panel
Moderated discussion
Training
Multi-session series
Built for These Audiences
Workforce development conferences • Reentry and justice reform summits • Nonprofit leadership events • Government agency trainings • University symposiums • Corporate leadership teams
Board Member, National Association of Reentry Professionals (NARP)
Speaker Credentials
50 years studying criminal justice and workforce systems from both sides
20 years incarcerated across two sentences
2 Boston University degrees earned during my second incarceration
27 years in consulting, research, and advocacy
Creator, Psychology of Incarceration curriculum
Author, "Stop Calling It Reentry. It's Reinvention"
Trusted By
Reentry Professionals (NARP)
Ready to Book Khalil?
Let's discuss your event and how the 2Generation Economy message can transform your audience.
