E X E C U T I V E B R I E F I N G & C O M P A N I O N A P P / 2 0 2 6
AI Fluency for Boards and Executive Teams
Sixty minutes to a half day, plus the companion app that makes it stick
AI is now on every board's agenda, every executive committee's agenda, every audit and risk committee's agenda. The directors and senior leaders who navigate the next five years well will be the ones who knew what to ask. The 214ID Executive AI Fluency briefing prepares them to ask it. The companion iOS app keeps the discipline current.
Director-grade. Live. Defensible.
Delivered personally by Matthew Sanfilippo, scaling from a 60-minute board briefing to a half-day leadership session. Five sections: a working mental model of how AI behaves at executive depth, the Six Dimensions of a Strong Prompt as a delegation discipline executives already know from briefing humans, a method for stress-testing AI output, the governance surfaces directors now own, and a closing on the practice that follows.
Practice that survives the meeting.
An iOS companion published by 214ID. The Prompt Refinery takes a director's actual prompt and evaluates it against the Six Dimensions, returning a refined version with structured feedback. A signed Trust Receipt shows a general counsel exactly what happened to the data: nothing retained, nothing trained on. Eight lessons cover what AI is and is not, delegation, evaluating output, adversarial stress testing, data value chains, board-seat governance, agents, and the CTO conversation.
Director-grade, not technology-grade.
We treat directors as directors. The frame uses board vocabulary, not engineering jargon: governance, accountability, exposure, recourse.
Built on lived governance.
214ID leadership sits on operating boards across engineering, technology, finance, manufacturing. Peer-tested by directors who can check the claims.
Practice that outlasts the meeting.
The app keeps the framework with directors and executives between meetings. AI questions get handled differently, not lost by Tuesday.