A facilitator's deck of perspective-shifting questions for governance and executive conversations about digital technology and AI. The good ones don't ask about technology — they force a room to reconsider where it stands. Browse them, filter by theme, or run present mode to put one big question on the screen at a time.
Most AI conversations drift in the abstract. The fastest way to make one real is to ask for a number — it turns "we should explore AI" into a statement of actual priority, and the answer (or the silence) tells you where the real conversation needs to go.
Blunt on purpose. A strategy with no number behind it is an aspiration, not a plan. Whatever the answer — a figure, a guess, or an awkward pause — you've just learned how seriously this organisation actually takes AI, and you've earned the right to ask everything that follows.
Pick three to five questions, not twenty. The aim is depth and discomfort, not coverage.
Use present mode to put one question on the screen and let the room sit with it before anyone answers.
Make people commit — a number, a position on a wall, a written answer. The commitment is the point.
Grouped by the shift each one creates. Filter to a theme, or hit "Present" on any card to open it full-screen for the room. Nothing here is saved.
A list of sharp questions is the easy part. The work is facilitating the room through the answers — surfacing where leadership actually disagrees, translating discomfort into decisions, and turning a single budget number into a governance approach the board can stand behind. That's what our facilitated AI strategy sessions are for.
Talk to us about a facilitated session