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Discussion Guides

Reading group and board discussion guides for every chapter. Six questions each, built for leadership teams, not book clubs.

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The End of Human Time — Discussion Guide

Human Time vs. System Time, the Ferrari-in-the-carriage trap, and grading your own AI initiatives honestly.

6 questions · 1 page

See all Introduction downloads→

The Latency Challenge Opportunity — Discussion Guide

Audit one real project against the Multi-Layered Latency Stack, the Reliability Tax, and where governance has become an excuse for hesitation.

6 questions · 1 page

See all Ch. 01 downloads→

The New Calculus of Scale in Competition — Discussion Guide

Calculate your own ARR/FTE against the AI-era benchmark, the McNamara Fallacy, and whether your org is bloatware or leverage.

6 questions · 1 page

See all Ch. 02 downloads→

The Node Architecture — Discussion Guide

Redraw your org chart with Carbon and Silicon Nodes, and test how much of your AI usage is really doing versus just chattering.

6 questions · 1 page

See all Ch. 03 downloads→

The Architect and the Moat — Discussion Guide

Captain vs. Architect, the Accountability Gap, and the Moral Crumple Zone — built for leadership teams and boards.

6 questions · 1 page

See all Ch. 04 downloads→

Business Models and Changing Buying Behavior — Discussion Guide

Seat-based pricing versus outcome pricing, feature fatigue, and whether your leaders think like users or orchestrators.

6 questions · 1 page

See all Ch. 05 downloads→

The Dial-up Era of AI — Discussion Guide

The Waiting Room Fallacy, building on rented AI infrastructure, and who on your team is still calling it a gimmick.

6 questions · 1 page

See all Ch. 06 downloads→

AI-Driven Enterprises: The New Model of Growth — Discussion Guide

SME vs. IDE vs. AIDE, Growth Purgatory and the Founder’s Dilemma, and benchmarking your revenue per employee.

6 questions · 1 page

See all Ch. 07 downloads→

Everywhere in Every Organization — Discussion Guide

Back-office automation first, where the human trust threshold actually sits, and which bottleneck falls to a competitor first.

6 questions · 1 page

See all Ch. 08 downloads→

The New Age Organization Chart — Discussion Guide

The Five Stages of Org Chart Transformation, the Merit Gap, and choosing between the Retrofit and the Phased Transformation.

6 questions · 1 page

See all Ch. 09 downloads→

Speed of Creation: The Entrepreneur's New Superpower — Discussion Guide

The 30-minute build, who plays System Architect on your team, and whether democratization is a threat to your talent moat or a gift.

6 questions · 1 page

See all Ch. 10 downloads→

Development Versus Distribution: The New Bottleneck — Discussion Guide

Your real moat versus your assumed one, the 80/20 R&D-to-distribution flip, and whether your CEO is a builder or a broadcaster.

6 questions · 1 page

See all Ch. 11 downloads→

The Rate of Entrepreneurial Experiments — Discussion Guide

Hypotheses versus babies-to-protect, the Wrapper Trap, and redefining what counts as failure when experiments are cheap.

6 questions · 1 page

See all Ch. 12 downloads→

Deep Tech, Medtech, and Pharma: A Different Timeline — Discussion Guide

Your own Valley of Death, the At-Bats Theory of capital allocation, and not mistaking a faster simulation for real-world proof.

6 questions · 1 page

See all Ch. 13 downloads→

The AI-Augmented SME — Discussion Guide

Operations vs. product investment, the L&H quoting-cycle math run on your own numbers, and whether you should be the acquirer of a "boring" business or worried about being the target.

6 questions · 1 page

See all Ch. 14 downloads→

AI and Private Equity: The Next Frontier — Discussion Guide

Running an AI diligence scan on yourself before a buyer does, the Systems Architect vs. the hatchet man, and whether you need an AI Operating Partner.

6 questions · 1 page

See all Ch. 15 downloads→

Venture Capital in an Age of AIDEs — Discussion Guide

Your burn multiple, Software-as-a-Service vs. Service-as-Software, and whether your compute spend is outgrowing payroll for the right reasons.

6 questions · 1 page

See all Ch. 16 downloads→

Economic Development and the Global Race — Discussion Guide

Your own Resilience Math, buffalo hunting vs. swarm farming, and how many high performers are one AI-powered weekend from leaving to found their own company.

6 questions · 1 page

See all Ch. 17 downloads→

Corporate Governance and Leadership — Discussion Guide

Scoring your own board’s AI literacy, the AIDE Maturity Cycle stage you skipped, and the dollar cost of faking it versus leading it.

6 questions · 1 page

See all Ch. 18 downloads→

Mapping the Organization: AIDE Matrix and Risk Asymmetry — Discussion Guide

Plotting yourself honestly on the AIDE Matrix, spotting ungoverned Stealth Adopter risk, and the new audit question every board should be asking.

6 questions · 1 page

See all Ch. 19 downloads→

Dear C-Suite — Discussion Guide

Running the job post test, epistemic debt on your own systems, and whether your own job description is already obsolete.

6 questions · 1 page

See all Ch. 20 downloads→

WTF Do I Do with AI? — Discussion Guide

Running the Friday Night Test on a live tool, the peer-review pivot for scoring AI opportunities, and whether your roadmap is disciplined Quick Wins or boiling the ocean.

6 questions · 1 page

See all Ch. 21 downloads→

Start with You — Discussion Guide

The v0 Rule tried once, the gap between your AI reputation and hands-on skill, and whether leadership is modeling Tinker Time or just mandating it.

6 questions · 1 page

See all Ch. 22 downloads→

Take a Day for Tinker Time — Discussion Guide

Blocking an actual Tinker Day, the regulated-industry excuse versus the Air-Gapped hour, and the Manager-to-Maker identity shift.

6 questions · 1 page

See all Ch. 23 downloads→

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Ctrl+Alt+Company: The Post-Human Organization — Discussion Guide

Which surviving human role fits you, whether you’re governing the machine or still one of its gears, and what gets deleted in your own company reboot.

6 questions · 1 page

See all Epilogue downloads→

About Paul Cheek

Paul Cheek is a global expert on AI-driven enterprises and enterprise innovation. He is a Senior Lecturer at the MIT Sloan School of Management and Senior Advisor for Entrepreneurship & Artificial Intelligence at the Martin Trust Center for MIT Entrepreneurship. As founder of the AI-Driven Enterprise Institute and Entonomy, he develops data systems and software that power AI agent-run businesses. A Forbes 30 Under 30 honoree, bestselling author of Disciplined Entrepreneurship: Startup Tactics, and recipient of MIT’s Monosson Prize for impact on entrepreneurship education, Paul has advised and built ventures from seed to scale, with his work featured in Bloomberg, CNBC, Forbes, CNN, Inc., Entrepreneur, and more.

Read Paul’s full bio →

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