Companion to The CTO You Actually Need
The worksheets, scorecards, interview library, checklists, and glossary the chapters point to
Companion to The CTO You Actually Need · Updated 2026-09-29
The book argues for defining the CTO job by the decisions it owns, writing the mandate, and testing candidates against evidence. This companion holds the working material: the dossier templates, the checklists, the AI prompts, the scorecards, the role cards, the interview library, six composite hiring cases, and a glossary.
Nothing here replaces the book. Each tool assumes you have read the chapter that builds the argument for it. Use a small, role-relevant selection; a scorecard or question set applied in full to every CTO produces fatigue and shallow answers.
Start Here
- Fill in the hiring dossier in order. If a search is already active, fill the gaps before the next major candidate decision.
- Run the checklists at each stage, from opening the search to the first year.
- Pick a scorecard for the role you are hiring, and replace its measures with evidence from your mandate.
- Choose from the interview library and the role cards.
- Use the AI fieldbook for the prompts, and read the composite scenarios to see the tools work together.
The glossary defines the words hiring teams argue over.
In this section
- Fill In the Hiring Dossier in Order
The seven templates that make up the CTO hiring dossier, from the one-page need statement to the first-year evidence file.
- Eleven Checklists Take a Search From Opening to the First Year
Eleven checklists for the hiring search and the CTO’s first year: opening, screening, interviewing, diligence, offer, days 30, 90, 180, and one year, fractional engagements, and founder transitions.
- Fourteen Reusable Prompts Survive Changes in AI Products
Fourteen reusable prompt patterns for CTO hiring and management decisions, each with its best use and the failure to watch.
- Start From a Role-Specific Scorecard and Replace the Measures
Eight scorecards for CTO roles: startup, founder replacement, growth and scale, SME, business unit, enterprise, a regulated overlay, and fractional or interim.
- Twelve Role Cards Name the Base Role and Any Overlay
Twelve CTO role cards, each with setting, mission, what the role owns, what good looks like, evidence to seek, the failure pattern, and a hiring caution, plus a template for combining them.
- Ask a Small, Role-Relevant Set of Questions
How to use the interview questions and work samples: a small, role-relevant selection, not every question for every candidate.
- Six Composite Hiring Scenarios Show the Tools Working Together
Six composite hiring cases, from a first startup CTO to a failing appointment, showing how the dossier, scorecards, and interviews connect.
- Define These Terms Once So Everyone Means the Same Thing
Plain-English definitions of the terms hiring teams argue over, from architecture and decision rights to technical option value.