30 questions across six areas — for PE and VC investors, acquirers, and board members who need a grounded view of a technology company before making a decision.
Technical due diligence is often the least structured part of an investment or acquisition process. Engineering is hard to evaluate without domain knowledge — and most financial or legal teams lack the vocabulary to press on the right questions.
This checklist is designed for non-technical readers. It does not require you to read code. It gives you the questions to ask, and — more importantly — the answers to watch out for.
Engineering Team & Organisation
Headcount, key-person risk, attrition, and leadership capability.
5 questions
Architecture & Technology Stack
Documentation, stack currency, modularity, CI/CD, and vendor dependencies.
5 questions
Technical Debt & Code Health
Debt visibility, test coverage, build stability, and maintenance burden.
5 questions
Security Posture
Pen testing, secrets management, access controls, and incident history.
5 questions
Scalability & Performance
Load testing, bottlenecks, autoscaling, and cost projections.
5 questions
Operational Maturity
Observability, incident response, disaster recovery, and on-call.
5 questions
Sample questions from the checklist
Is headcount appropriate for the current roadmap and projected growth — or is the team chronically under- or over-staffed?
Are critical technical domains covered by at least two engineers, or does the organisation have dangerous key-person dependencies?
What has voluntary engineering attrition looked like over the last 12 months? Any recent departures of senior or founding engineers?
Is there an active, documented engineering hiring process — and how long does it typically take to fill a senior role?
Does the CTO or VP Engineering have experience operating at the company's current stage — and at the next stage of scale?
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