Decision Support

Judgment, red-teaming, weighing options, decision-quality

Decision Support

Jun 19, 2026

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5 min read

Context Engineering for Chiefs of Staff

The judgment layer: how to frame AI work going in, supervise it, and catch what's wrong before it ships. Members only.

Agentic AI

You've sent AI work you never checked. It looked done.

Jun 11, 2026

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3 min read

You've sent AI work you never checked. It looked done.

Steer it or dispatch it, plus a prompt that catches what slipped.

Stephanie Lewis-Bennett

Decision Support

May 21, 2026

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3 min read

How to get AI governance funded

The conversation that gets AI governance funded

Stephanie Lewis-Bennett

Meetings

When Legal, IT, and Finance disagree on AI

May 14, 2026

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4 min read

When Legal, IT, and Finance disagree on AI

The prompt that turned a three-week governance debate into a 40-minute meeting

Stephanie Lewis-Bennett

Decision Support

Argue against your own recommendation first

Apr 16, 2026

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4 min read

Argue against your own recommendation first

The AI Habit That Makes You Right More Often

Stephanie Lewis-Bennett

Decision Support

Mar 26, 2026

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10 min read

The day my CEO didn't get his brief

The day my CEO didn't get his brief (and what he said when he found me)

Stephanie Lewis-Bennett

Decision Support

Context Engineering for Chiefs of Staff

You've sent AI work you never checked. It looked done.

How to get AI governance funded

When Legal, IT, and Finance disagree on AI

Argue against your own recommendation first

The day my CEO didn't get his brief

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