Workshops
Transform how you think about AI. Move beyond tools and prompts to develop the calibrated judgment leaders need in the AI era.
AI for Leaders
In collaboration with Jamie-Leigh Blake, Principal Technical Program Manager, AI at Amazon in Seattle, we’re offering a focused workshop that builds real AI judgment for executives and technical leaders.
What You’ll Learn
This isn’t about becoming an AI expert or learning which buttons to click. It’s about developing the judgment to lead effectively when AI is everywhere—and knowing where it belongs (and where it doesn’t).
In 3 hours, you’ll build the frameworks to answer: “Should AI do this, and where do I stay in the loop?”
Mental Models for AI
Learn frameworks like the mirror, intern, and dog models to reason about what AI can and can’t do, without the hype or fear.
Why AI Fails
Understand the failure modes: hallucinations, authority transfer, and confidence without correctness. Learn verification strategies that work.
Human+AI Workflows
Design workflows where humans and AI each do what they’re best at. Know when to delegate and when to stay in the loop.
The Format
- 3-hour live virtual session via Zoom
- Real-time interaction with CDS (Chief of Digital Staff), an AI system designed to fail in front of you so you can see how AI breaks down and build real judgment instead of false confidence
- Hands-on exercises with immediate feedback
- Access to private Clarity Intelligence community for ongoing peer discussion
- No recording (supports candor and psychological safety)
Who Should Attend
- Executives, CTOs, and AI leaders who need calibrated AI judgment
- Leaders asked to “figure out AI” for their organization
- Anyone who wants to understand where AI belongs, and where it doesn’t
Investment
Free for a limited time as part of the January 2026 Founding Cohort (limited to 12 leaders). We suggest a donation to The Trevor Project, supporting LGBTQ+ youth in crisis.
About the Instructors
Jamie-Leigh Blake brings 20+ years building technology that changes how humans interact with computers. Co-founded Orbbec (IPO’d), founded OpenKinect, wrote the book on natural user interfaces, and now works at Amazon on AI and inclusive technology.
The hard part isn’t building AI—it’s thinking clearly about it. Most AI training teaches tools. Jamie-Leigh teaches judgment.
“Authority never transfers to AI, only delegated tasks do. And the appearance of confidence is a matter of formatting, not a matter of correctness.”
Learn more about Jamie-Leigh →
Gian Paolo Santopaolo brings 24+ years in software engineering with deep expertise in production-grade AI systems. Built AI platforms serving 100+ million users, developed CogniX (enterprise RAG platform), and deployed multiple agentic systems including ReforgeAI and Sentinel-AI.
Microsoft MVP (2012–2022) and Regional Director (2018–2020), with hands-on PyTorch expertise spanning custom neural architectures, LLM/diffusion model fine-tuning, multi-GPU distributed inference, and RAG systems at scale.
The gap between research prototypes and production systems is where most AI projects fail. Gian Paolo bridges that gap with battle-tested engineering patterns.