Webinar: Boards Must Start Thinking with AI, Not Worrying About It

Boards are rightfully pushing their organizations to adopt AI to drive efficiency, effectiveness, and competitive advantage. But while management teams race to deploy AI across operations, marketing, and product development, one question remains largely unexamined:

How can boards using AI to strengthen governance itself?

Join Dr. Patti Fletcher and Brendan McSheffrey from The Kendall Project for a live session introducing a governance infrastructure approach that enables boards to leverage AI, not simply oversee it from a distance.

This webinar explores how boards can move beyond AI anxiety and effectively address the strategic reaction time lag that companies must address to stay competitive in the age of AI.

Date: March 26th 2026
Time: 11AM - 12PM ET

AI Strategy Workshop for Transportation Leaders

Rethinking Governance in the Age of AI

A webinar for boards and enterprise leaders navigating AI-driven change

Boards meet quarterly. AI capability evolves monthly. Strategic assumptions break silently between meetings. This is not a leadership problem. It is a governance infrastructure problem 

Most boardrooms still operate on slide decks designed for persuasion, not interrogation. Directors see conclusions, but not the structured reasoning underneath them 

When strategy remains implicit:

  • Assumptions cannot be pressure-tested
  • Misalignment hides beneath polished narratives
  • AI tools generate analysis disconnected from real strategic logic
  • Regulatory exposure increases

The Kendall Framework starts from a simple premise: strategy is language

When that language is structured into inspectable Context Blocks, boards can examine assertions, trace dependencies, test scenarios, and document reasoning in real time. Context360 operationalizes this approach into a practical governance platform designed for modern board oversight

What You’ll Learn

-Why 'Reasonable Oversight' is more than a quarterly slide deck
Discover how governable language enables strategic oversight

-Why traditional governance breaks under AI velocity
Understand the systemic failures of opacity, rigidity, and misalignment that limit board effectiveness 

-Why strategy must become structured language
See why AI cannot reliably reason over unstructured narratives and how structured context changes that dynamic

-How Context360 enables real-time interrogation
Explore how Context Blocks encode strategic assertions, assumptions, evidence, dependencies, and revision triggers 

-How RAPID-AI transforms board sessions
Learn how boards can reason from context, expose hidden assumptions, pressure-test across multiple lenses, and document decision trails 

-How governance becomes competitive advantage
Examine how cumulative strategic knowledge, faster adaptation cycles, improved execution alignment, and regulatory readiness create durable differentiation 

Why Attend

  • Move from worrying about AI risk to actively using AI to interrogate strategy
  • Replace quarterly slide reviews with structured, inspectable reasoning
  • Strengthen alignment between strategy, capital allocation, and execution
  • Improve regulatory readiness for ISO/IEC 42001 and EU AI Act requirements 
  • Build documented decision trails that create institutional memory and reduce governance exposure 
  • Walk away with a practical 90-day pilot roadmap to introduce Context360 inside your boardroom 

Who Should Attend

  • Board directors
  • CEOs and executive leadership teams
  • Chief Strategy Officers
  • Governance, risk, and compliance leaders
  • Enterprise AI transformation sponsors

If your board is demanding AI adoption from management but has not yet equipped itself to think with AI at the governance level, this webinar is for you.