Every organisation buys technology. Very little of it gets properly questioned first: the demo dazzles, the deadline looms, and the contract renews itself while everyone is busy. This book exists for the moment between the promise and the signature.

Inside are 200 questions, one per page, each with a short case for why it matters and a practical test you can run this month, plus space for your own notes. They follow a real evaluation workflow, built and refined over thirty years of technology decisions: the work and the technology as parallel tracks, each with gates, where any honest ‘no’ stops the process.

The twenty chapters walk those gates in order. Strategy, fit and wellbeing. Data protection and the rules on monitoring staff. Security certifications, and how to read the scope statement where the truth actually lives. AI, including the tools your people are already using that appear on no register. Accessibility, usability and evidence. Pilots designed so they can genuinely say no. The full cost, counted from first invoice to final export. Implementation, adoption, resilience. And the discipline most estates never reach: reviewing, renewing and retiring on purpose, including the licence audit that is reliably the best-paid hour in the technology calendar.

I have spent my career on both sides of this table, as a technology CEO answering these questions for a living, and as a chair and director asking them before signing. These are questions a good vendor should welcome: a fair standard, applied consistently, that rewards the suppliers who do the work and protects the organisations who ask.

You will not need all 200 at once. Nobody does. But somewhere in these chapters is the question that saves your organisation a bad contract, a wasted year or a security incident, and it costs a page to find it.

The final question asks whether, a year from now, anyone would actually miss what you bought. The other 199 exist so that the answer is yes.