Most “questions to ask” lists give you 8-10 generic items. This is the full bank — organized so you can pull exactly what you need for the conversation you’re having, not a vague checklist.

Technical capability (ask these to verify, not to test trivia): Can you show me production code from a completed, similar-complexity project? Who specifically will work on my project, and what’s their direct experience? What’s your approach when a technical decision turns out to be wrong mid-build? How do you handle code review — is there a second person checking work, or does one developer’s code go straight to production? What’s your testing process before a feature ships?

Scope and estimation: How do you arrive at a quote — hourly estimation, historical data from similar projects, or something else? What’s included in “done” for a milestone — a working demo, or fully tested and documented code? How do you handle scope changes mid-project — a formal change request, or informal adjustment? What’s your typical variance between initial estimate and actual delivery time?

Communication and process: What’s your standard communication cadence — daily updates, weekly calls, both? What tool do you use for project tracking, and can I see a real (not sanitized) board from a past project? What’s your timezone overlap with me, specifically, not just “flexible”? Who’s my main point of contact, and what happens if they’re unavailable?

Contract and risk: Is payment milestone-based, and what are the acceptance criteria for each milestone? Who owns the code and IP — is this explicit in the contract, not just assumed? Where does the code live during development — your repository or mine? What happens to work-in-progress if either party wants to exit the contract early? Do you carry any liability insurance relevant to what you’re building for me?

Red-flag questions (their answer quality matters as much as content): Tell me about a project that didn’t go well — what happened, and what changed afterward? What’s a type of project you’d turn down, and why? Can I speak directly with a past client, not just read a written testimonial? What happens if I’m not satisfied with a delivered milestone?

Fintech/healthtech-specific, if relevant: Have you built products handling this type of regulated data before? What’s your approach to compliance requirements you’re not fully certain about — do you research and confirm, or guess and proceed? Can you name a specific compliance requirement relevant to my product, unprompted?

How to actually use this list: don’t ask all 50 in one conversation — that’s an interrogation, not a vetting process. Pick the 8-10 most relevant to your specific situation and industry, and pay closer attention to the quality and specificity of the answer than to whether they “pass.” A vague answer to a good question tells you more than a confident answer to a generic one.

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