Find your reading path
This book has 37 chapters. You don't need all of them first. Find your role below, then follow the path — the other chapters will be there when you need them. Everyone reads Part I (Chapters 1–3) first; it is short and is the argument the rest of the book rests on.
Find your role
Read each description and check the one that fits. If none fit, see the note at the bottom.
- ☐ The Ops Leader — You run operations (COO, VP Ops, Director of Ops, or the person who actually makes things run). You've been handed "figure out AI" on top of everything else. Your questions are operational: which process first, who owns it when it breaks, how do I measure it.
- ☐ The Tech-Pressured Executive — You're the CEO or owner. The board is asking. Competitors are announcing. You don't have a CTO, or the one you have wasn't hired for this. You're taking briefings from vendors with every incentive to oversell.
- ☐ The Technical Leader — You're the IT Director, Head of IT, or VP of Engineering. You're watching leadership make commitments faster than the infrastructure can support. You've been here before with other technology waves. You want to move carefully; leadership wants to move fast.
- ☐ The Knowledge Work Leader — You lead a function: Finance, HR, Customer Ops, Marketing. You know where the manual work is. Your team has probably been quietly using AI tools already, without a policy. Your questions are function-specific.
- ☐ The Peer or Referral Source — You're not the one implementing. You're an advisor, board member, operating partner, or fellow CEO trying to be useful to someone in the middle of an AI decision — or deciding whether to recommend this book.
My role is: ______
Role-based reading paths
| Role | Where you start | The chapters for you |
|---|---|---|
| Ops Leader | Part I (Chapters 1–3), then Chapter 7 (Assess) | Part I → Chapter 7 (Assess) → Chapter 25 (Change Management) → your vertical in Part VII → Chapter 37 |
| Tech-Pressured Executive (CEO/no-CTO) | Chapter 5, then Chapter 37 | Chapter 5 → Chapter 6 (Operating Stack) → Chapter 37 (First 90 Days) → Appendix A (board slides); Chapter 24 on who to hire; Chapter 17 on when expensive models earn their cost |
| Technical Leader | Part IV (Chapters 11–17), then Chapter 36 | Part IV → Part V (Chapters 18–20, governance) → Chapter 36 (If You Lead IT) |
| Knowledge Work Leader | Chapter 35, then your vertical in Part VII | Part I → Chapter 35 (If You Run a Function) → your vertical in Part VII → Chapter 21 (workflow redesign) → Part V for compliance |
| Peer or Referral Source | Part I, then Chapter 5 | Part I → Chapter 5 → Appendix G (How to Work With a vCAIO); Part III for the method |
What each destination gives you
| Chapter / section | What it delivers |
|---|---|
| Part I (Chs. 1–3) | Why most mid-market AI projects fail; why the boring work is where the money is; why you start with operations, not the tool |
| Part III (Chs. 6–10) — Assess, Illuminate, Accelerate, Sustain | The core method: from "where do we put AI" to a ranked list, a scoped pilot, a 90-day rhythm, and quarterly re-validation |
| Chapter 5 | The CEO-without-a-CTO reality; what the conversation with your IT director should actually look like |
| Chapter 35 | Function-specific use cases, compliance backstop, and a framework for bringing the conversation to your CEO |
| Chapter 36 | Augment-don't-replace posture; the IT reference architecture you can implement incrementally |
| Chapter 37 | Your first 90 days, week by week; the five slides your board actually needs |
| Part IV (Chs. 11–17) | How agents actually work; the plumbing; evals; the parts vendors gloss over |
| Part V (Chs. 18–20) | Governance, security, OWASP LLM risks — compliance framing for both technical and functional leaders |
| Part VII (verticals) | Industry-specific use cases calibrated to your sector |
| Appendix G | When fractional AI leadership makes sense; the engagement rubric; when to refer someone on |
Notes on firm size
This book targets firms running 50–500 employees. The smaller the firm, the more the bottleneck is human capacity and process documentation, not technology. The larger the firm, the more the bottleneck is integration, data quality, and change management. The method handles both — the emphasis shifts.
This book is not written for Fortune 500 enterprises (different operating realities, different governance scale) or for companies below about 50 people (different questions, different answers).
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