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Free Lesson

Nobody Said No: How Polite Rooms Kill AI Strategy

Hosted by Hussam Ahmad

Mon, Oct 19, 2026

6:00 PM UTC (30 minutes)

Virtual (Zoom)

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How to Diagnose and Overcome the Five Critical Dysfunctions of AI Transformation
Hussam Ahmad
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What you'll learn

See Why Silence Is Expensive

Trace the causal link from unchallenged ideas to technology-first commitments signed on enthusiasm, not alignment.

Run Your First Red Team Ritual

A step-by-step format where a designated team presents the anti-case for any AI proposal — why not, why not this vendor.

Respond to the Anti-Case Like a Sponsor

How executive sponsors publicly thank the Red Team for finding flaws instead of defending their own proposals.

Why this topic matters

People hide what they don't know about AI, so bad ideas go unchallenged and hype wins. McKinsey calls it strategic misalignment: commitments before the problem is clarified. Not for lack of intelligence — for lack of permission to dissent. This is Dysfunction 2 — Fear of Strategic Conflict — the cheapest to fix, needing no budget, only a ritual. You leave with the Red Team Ritual — dissent as a requirement, so commitments survive reality.

You'll learn from

Hussam Ahmad

AI Transformation, Leadership & Product Excellence and OKR Coach

AI transformation advisor and OKR coach, working with leadership teams on organizational readiness for AI. Developer of the Five Dysfunctions of AI Transformation framework and the AI

Transformation Health Check diagnostic. Diglab is currently running the first pilot sessions with select leadership teams — participants in this early phase shape the framework directly and receive preferred pilot terms.

See all products from Diglab Academy

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