Khalil Osiris
Founder & CEO, Khalil Osiris Consulting | Board Member, National Association of Reentry Professionals | Nationwide Consulting: Workforce Development, Reentry & Economic Mobility | 50 Years of Lived and Professional Experience
The Path to This Work
Arrested at 16. Turned 17 in jail. Sentenced to prison — all in 1976. Twenty years incarcerated across two sentences. Not a footnote. The foundation.
Inside prison, Khalil earned a bachelor's and master's degree from Boston University. He developed the Psychology of Incarceration curriculum. He studied the system that held him — and began designing how to change it.
Released at 40. Twenty-seven years later, that firsthand experience navigating broken systems is the engine behind every consulting engagement.
This is not theory. It is architecture built from the inside out.
Core Belief
The unit of change is the household — not just the worker.
You cannot stabilize a returning citizen without stabilizing their family. Employment without household stability is a revolving door. Measurement is destiny: change the metric, change the outcome.
The Framework
Every engagement is built on the 2Generation Economy Workforce Ecosystem — a systems-level model that treats the household as the unit of change. Two generations. One coordinated system. Measurable outcomes at 12 months, not 30 days.
Where This Work Meets Yours
Consulting: Systems redesign for employers, workforce boards, corrections agencies, and funders. Every engagement starts with a diagnostic and ends with a measurable implementation plan.
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Speaking: Keynotes, workshops, and executive briefings that challenge assumptions and move leaders to action.
Book Khalil to Speak →
Ideas: Author of Stop Calling It Reentry: It's Reinvention and Psychology of Incarceration. Research-driven insights published weekly.
Read the Latest →
How This Work Shows Up
Every engagement is tailored to the organization, the system, and the outcomes that matter. Here are the three ways Khalil works with leaders ready to build what lasts.
Consulting & Systems Design
Workforce boards, employers, and agencies hire Khalil to redesign coordinated career pathways — with retention infrastructure and measurable household outcomes.
The 2Generation Economy invests in two generations simultaneously — parent careers and child development, coordinated into one household-centered system. Employment gains for one generation become mobility gains for the next.
Khalil translates research into action — redesigning metrics, building accountability frameworks, and creating implementation roadmaps that bridge the gap between policy intent and on-the-ground results. Read the latest thinking on workforce, justice, and economic mobility.
Ready to Build Something That Lasts?
The workforce system measures activity.
You want to measure outcomes.
If you're ready to redesign your approach — to build systems that stabilize households, produce durable employment, and change trajectories across generations — there's a way forward.
