
You already govern gears: same input, same output. This is how to govern the one machine that guesses back.
Gears Don’t Guess: The Executive’s Practical Guide to Thriving in the Face of AI Hype and Risk
Right now you’re doing one of two things with AI. Saying no to everything while competitors pull ahead. Or saying yes and hoping nothing important breaks. Both are guesses.
Why AI is different
You’ve governed technology for years. Budgets, vendors, compliance, cybersecurity. You set the rules and walk away. AI feels different, and you can’t say why. Here’s why: it’s the first system you’ve ever been handed that guesses back. The same question gets a different answer on Tuesday than it did Monday. And the answer often looks right even when it’s wrong.
So you’re already managing a crisis. You just don’t know it’s one yet.
How this works
Step 1. Take the assessment
Twenty questions, about ten minutes, no email required.
Step 2. See where you stand
Your score lands in one of three zones, phase by phase.
Step 3. Close the gaps
The templates that match what your score exposed arrive with the book.
Advance praise
Kip has taken the complex topic of managing and using AI and created an easy-to-follow 'how to.' AI is everywhere. It's in the systems we use, buy, and build. We may not even know we are using AI when it's embedded in other products. Board members will find Kip's book especially useful because it turns a technical topic into a risk-management discussion that helps us perform our job of oversight.
Most AI security advice today is just wishful thinking wrapped in a system prompt, but Kip Boyle brings us back to reality. He uses a hard-hitting, real-world near-miss to prove why relying on an AI to follow its own instructions is a recipe for disaster. If you want to stop guessing and start securing agentic workflows, Gears Don't Guess is the pragmatic blueprint: hard data boundaries, rigorous logging, and actual human review, not just LLM-powered hope.
We built the Cloud Security Alliance to help organizations trust technology they don't run themselves. The AI you buy is the next version of that problem, and it's moving faster than cloud ever did. Gears Don't Guess shows leaders how to see the AI already inside their business, including what their suppliers bring in, and govern it without blocking adoption.
Read 17 more from the book’s advance praiseHide the rest
Most leaders can't yet measure the AI risk they've already taken on. Gears Don't Guess fixes that. Kip Boyle turns a vague worry into something you can see and quantify, covering both the AI you buy and the AI buried in your suppliers' tools. The chapters on board reports and outside vendors are what leaders need to help govern AI by the numbers, not by instinct.
I've worked alongside Kip Boyle to help my clients strengthen their cyber posture, and I trust how he thinks about risk. From an insurance perspective, cyber underwriters reward an organization that can see and prove its controls. Gears Don't Guess gives executives that capability for the AI they're now buying. Read it before your next renewal, not after your first claim.
A compelling read for anyone in technology today, Gears Don't Guess shows why the future of AI depends not on making machines smarter, but on making their behavior more predictable, secure, and aligned with human goals.
Gears Don't Guess makes the shift in AI risk immediately understandable for a non-technical executive audience, which is not easy to achieve. Kip's message is the right one: the risk is already here and unmanaged, not a future decision point. His data, tool, and use framing is practical and simple to put to work, and his stance that governance should enable adoption rather than block it is exactly where most organizations struggle. A great book, and one I'd recommend to our data and AI leaders.
Read Kip Boyle's Gears Don't Guess twice. Read it the first time to understand the strategy, the tactics, and the roadmap. Then read it a second time as instructions for writing and building your own AI governance program.
Gears Don't Guess is the rare AI governance book that actually meets organizations where they are. Kip cuts through the hype and focuses on the real work: understanding the AI you buy, the data boundaries you inherit, and the risks you're accountable for whether you realize it or not. It's a clear, pragmatic roadmap for leaders who need to make sense of vendor AI in the middle of a rapidly shifting risk landscape.
Instead of using fear, Kip uses real-life examples to guide you through the AI agents you buy but don't create. Don't guess, read it, then keep it and build your checklists.
Every leader is looking for the easy button to make AI safe for the workplace. This book is exactly that. It provides a helpful self-assessment, ready-to-use templates, and a crosswalk to the NIST AI Risk Management Framework to help any leader safely deploy AI. I highly recommend it!
When I asked an AI to apply the Balanced Scorecard framework to AI governance, the result was dense and abstract, useful only if you already knew what to look for. This book does the opposite. It cuts through the noise with clarity, concrete examples, and actionable specifics. The board report template alone is worth the read.
Gears Don't Guess provides excellent guidance on how to frame AI that is directly related to, and indirectly impacts, organization security and financial performance. It provides a comprehensive, actionable and clear roadmap for leaders making real-time decisions in a fast-paced and dynamic environment. An excellent read!
As a CFO, I found this book particularly relevant because it addresses the questions every executive team and board should be asking as AI becomes embedded in their organizations. Value is the subject on every CFO's mind. Kip Boyle moves beyond the technology itself and gives practical frameworks for measuring that value and reporting it to management and boards. His focus on visibility, business outcomes, and executive decision-making makes this an essential resource for leaders who want to balance innovation with control and oversight.
In an era of extraordinary uncertainty and change, Kip's real-world case studies and actionable next steps are reassuringly practical and well-suited to our time.
Whether you run a fleet, finance vehicles, or just get behind the wheel, Kip won't leave you guessing on how to manage AI risk. Gears Don't Guess captures the security and financial cost of poor privacy, even in cars, when we unknowingly hand our patterns of life to third parties who use AI to profile us.
Gears Don't Guess treats AI governance the way it should be: not as a one-time rollout or a cybersecurity veto point, but as a living process that lets you say 'yes,' 'no,' or 'not yet' fast enough that people keep bringing risk into the open. In three decades of cybersecurity and risk consulting, it's the most practical guide I've seen.
Gears Don't Guess is a PSA for any business using AI. I'd send this to everyone.
In Gears Don't Guess, Kip Boyle delivers a practical roadmap for navigating one of today's most complex business risks: AI-driven incidents. As someone who helps organizations protect and strengthen their reputations during crises, I appreciate Boyle's emphasis on preparation, disciplined response, clear communication, and executive-level decision-making. The reality is that AI incidents are no longer just cybersecurity events, they are reputation events. Organizations that respond with transparency, speed, and credibility will protect trust with employees, customers, regulators, investors, and the public. This book shows leaders how to do exactly that.
Gears Don't Guess is more than another book about cybersecurity breaches. Boyle removes the guesswork of building a responsive system, and he tackles the culprit most books ignore: the dynamic, unpredictable nature of human behavior and workplace culture. Every chapter delivers practical charts, templates, and assessments. An absolute must-have for any C-suite executive looking to protect and strengthen their organization.
What is on this site
The free self-assessment
The Lite Culture AIR-MAP from Appendix A, scored in your browser. Nothing you answer leaves your device.
The template library
The fill-in tools from Appendix B, as fillable PDF and editable Word. Free when you subscribe to Inflection Point, Kip Boyle's newsletter.
Opens with the book on September 28, 2026.
The blog
AI governance issues worth a leader’s attention, written for the person who answers for the decision.
Coming with the launch.
Get the book
Paperback and Kindle available September 28, 2026 on Amazon.
Tell me when it's out
Subscribing to Inflection Point, Kip Boyle's newsletter, starts right away: a short read every other week on what is actually changing in AI and cyber risk. You also get a note the day the book is out, with the links to both formats.
Email signup opens shortly. Check back, or reach Cyber Risk Opportunities directly at info@cyberriskopportunities.com.
ISBN 979-8-9973023-0-6 (paperback). ISBN 979-8-9973023-1-3 (ebook).

Kip Boyle is the founder and CISO of Cyber Risk Opportunities and the best-selling author of Fire Doesn’t Innovate. He hosts the Cyber Risk Management Podcast.
The template library
The fill-in tools from the back of the book, as fillable PDF and editable Word. They are free. Subscribing to Inflection Point, Kip Boyle's newsletter, starts right away, every other week, and a separate note goes out the day the templates open.
Email signup opens shortly. Check back, or reach Cyber Risk Opportunities directly at info@cyberriskopportunities.com.