guideFractional Leadership

The CTO Interview Question Bank

The questions I use to test CTO candidates, with what a strong answer sounds like and the red flags.

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About this resource

The questions Ganesh Kompella uses to test CTO candidates, full-time or fractional. Every question comes with what a strong answer sounds like and the red flags that should end the conversation. It covers leadership and judgment, architecture and buy vs build, delivery and incidents, team and hiring, security and compliance (including HIPAA and IEC 62304), and business and board communication, plus three questions to ask your current tech lead before you hire anyone.

What you'll walk away with

For every question, what a strong answer sounds like and the red flags that should end the conversation.
Seven core questions for when you only get one call, and a three-point scoring rule to use straight after it.
Regulated-domain questions on HIPAA, SOC 2 and IEC 62304 that separate people who have shipped under them from people who have read about them.

What's inside

01Start here: three questions for your current tech lead
02Leadership and judgment
03Architecture and buy vs build
04Delivery and incidents
05Team and hiring
06Security and compliance, including HIPAA and IEC 62304
07Business and board communication

WHO THIS IS FOR

Founders, MDs, boards and investors hiring a CTO, head of engineering or technical advisor, full-time or fractional.

Written by Ganesh Kompella, fractional CTO and CPO. Based on 75+ engagements across healthcare, fintech, and SaaS — these are the frameworks we actually use with clients, not a summary of someone else's.

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