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AI-First Edition

Questions on AI
your leadership is avoiding.

A workshop and discussion tool for leadership teams designing AI-first organizations. 92 cards. 6 categories. The questions nobody is asking.

One question. One play mode. Read both aloud.
Question
 
Context
This is a discussion prompt. No single data point defines it. Use it to surface perspectives and assumptions.
Click to flip back
How to play
 
Context
Play cards set the rules for how the table discusses the question. Follow the instruction exactly.
Click to flip back

Rooted in research from

Strategy

12 cards

Competitive positioning, business models, and the shift from AI experiments to AI operating models.

Are you competing for incremental improvement or exponential leverage?
AI-native startups generate $2.5M+ revenue per employee. What's your number?
What's your competitive moat — proprietary data, embedded workflows, or talent?
If a team of 15 with AI can outperform your department of 200 — what's the department for?
Sign up to see all 12 and customize your deck

People+

12 cards

Talent, roles, hiring, middle management, and what happens when AI reshapes the workforce.

Governance+

12 cards

Accountability, regulation, bias, oversight, and who owns the decisions AI makes.

Adoption+

12 cards

Pilots, ROI, workflow redesign, and why most AI investments fail to show impact.

Agentic+

12 cards

Autonomous systems, delegation, machine-speed decisions, and the line between copilot and agent.

Technology+

12 cards

Build vs buy, vendor lock-in, data architecture, open source, and infrastructure bets.

Gameplay+

20 cards

Quick Start

01
Open
Draw two cards — one black question, one white play mode. Read both aloud. The play card sets the rules for how the table responds.
02
Explore
Follow the play instruction. No right answers. The goal is honesty, not consensus. Let the question sit. Let silence happen. The best insights come from discomfort.
03
Close
Capture the sharpest insight from each round. Write it down. Pin it on the wall. At the end: review what surfaced. Decide what to act on.
People
6–30 people. Tables of 4–5. One moderator.
Time
5–10 min per round. Full session: 60–90 min.
Materials
Screen + Post-its + markers. Optional: print deck.
Ground Rules
No laptops. No hierarchy. What's said here stays here.

Gameplans

4 formats, ready to facilitate
15–20 min · 4–30 people · no materials needed
A rapid-fire warm-up. No preparation, no output, no pressure. Just honest reactions to provocative questions. Use it to open a meeting, break the ice, or close a workshop on a high.
1. Draw (30 sec)
All categories active. Hit “Draw Both.” Read the question aloud, then the play card. The play card is the rule for this round.
2. Discuss (3 min)
Follow the play instruction. If it says “60 seconds each” — enforce it. If “one word” — hold them. The constraint creates energy. No Post-its.
3. Repeat (5 rounds)
Draw again immediately. No debrief between rounds. After 5 rounds: “What surprised you?” One sentence per person. Done.
Facilitator tip: Speed is everything. If a round dies, skip to the next card. Energy matters more than depth. Keep under 20 minutes.

Services

From facilitation to custom decks
Workshop Facilitation
Want someone to run this for your leadership team? I facilitate AI strategy workshops using PromptDeck — from 90-minute sessions to full-day offsites. Remote or on-site.
Get in touch
Hard Copy
92 cards, professionally printed. Black and white. Built to survive workshops.
Coming soon
Custom Edition
Design a deck for your organisation, your customers, or your next conference. Tailored categories, industry-specific questions, your branding. Digital + print.
Inquire
Pay it forward
Free and open. If it helped your team, share it or buy me a coffee.
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