The Courageous Conversations Compass, after Glenn Singleton
Institute for Courageous Leadership
A racial-equity leadership program for the people who run schools and districts, carried by a platform built for one thing: a place where leaders can be honest about race long enough to change how they lead.
The arc
Ten foundational sessions in Year One, deepening practice in Year Two. Each session opens in a direction on the Compass and carries one text, one instrument, one decision the leader takes back to their building.
The Compass, the Four Agreements, the Protocol. Before the work touches a system, it touches the leader holding it.
The Cycle of Socialization, white fragility, the creation of whiteness, the single story. The patterns you inherited, named.
Mindframes, implicit bias, High Operational Practices, the 60-second conversation, anti-Blackness. Practice that reaches kids.
Books distributed; the Compass, the Four Agreements, NSEW styles
The instruments
Identity work comes first because leadership decisions carry the leader. Each instrument is a private reflective tool inside the app, written and saved by the participant, never graded.
Trace how race was taught to you, from before you could choose to the moment you decide to interrupt it.
“What did the people closest to you teach you about race, directly or by their silence?”
Eight sentence stems that open a session. Who you are, what you carry, what you refuse for your students.
“I refuse… what you will not accept for your students.”
Your first memory of race, moving back to its source and forward to the decisions you make for kids now.
“Go back to your earliest memory of noticing race. Where were you? What happened?”
The five Loops
Each Loop takes something you actually wrote or decided, a memo, a transcript, a choice, and reflects the pattern back. Paired with one category scored in the Elements of Whiteness 360.
The words your district uses become the future your district builds.
Your authority reaches further than you can see.
Your voice carries weight in rooms where most people defer to it.
Some of your urgency is real. Some is inherited.
Your documents say what counts as truth in your district.
The Intelligence mirror
Across a cohort, the Compass check-ins, the Loop reflections, and the commitments compound into a private mirror for the facilitator: where the room sits across the four directions, which patterns recur, where the work is moving and where it has stalled. Aggregate by default. A participant’s words stay the participant’s.
The Fortress
None of this works if leaders perform. Every reflection a participant writes is theirs: their data is isolated by row-level security so only they and the coach they choose can read it, the facilitator sees patterns and not private text, and nothing leaves the cohort. The honesty the program asks for is protected by how the platform is built.
See how we protect it →A walkthrough is a working session: we show the participant app, the facilitator console, and the trust model, against your cohort and your calendar. No pitch deck, the real thing.
From paper to performance to practice.