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.
Companion to The CTO You Actually Need · Updated 2026-09-29
Use a small, role-relevant selection. Asking every question creates fatigue and shallow answers.
- Six question sets test judgment, technical contact, leadership, candor, founder transitions, and fractional engagements.
- Four work samples and a debrief form test how a candidate reasons under a realistic brief and changed constraints.
In this section
- Six Question Sets Test Judgment, Contact, Leadership, Candor, and Transitions
Six interview question sets for CTO candidates, with follow-ups and additions for builder, enterprise, and physical-system roles.
- Four Work Samples and a Debrief Form
Four realistic work-sample briefs with changed-constraint tests, and a debrief form for recording evidence.