24 questions to ask a software development company

In short: the questions that tell you most about a software development company are not about technology. They are about what happens when something goes wrong. Below are twenty-four questions in six groups, what a good answer sounds like, and what a weak one gives away. Send them in writing and compare the answers side by side.

How to use the list

Ask every vendor the same questions in writing. A good answer is specific, names people or numbers and admits limits. A weak answer is reassuring and vague. The best signal of all is a vendor who contradicts you before signing.

1. Track record

1. Tell me about a project that went badly and what you did. Good: a specific case with a fix. Weak: "we have never had one".
2. Can I speak to a client from that project?
3. How many projects like mine have you delivered, and how long did each take?
4. How many projects does the lead on mine run at once?

2. People

5. Who exactly will work on my project, and what share of their time?
6. Will the people in the pitch be the people doing the work?
7. What happens if one of them leaves?
8. Who is my single point of contact?

3. Scope and change

9. What did you assume that I did not tell you? Good: a written list.
10. What is not included in this quote?
11. What happens if I change my mind about a feature mid-project? Good: impact costed in time and budget, in writing. Weak: "no problem".
12. What would you remove from my scope to hit the budget?

4. Quality and acceptance

13. Who tests, and against which criteria? Good: criteria written before development and tested by my side.
14. How are defects found after delivery handled, and for how long?
15. How do you handle security: authentication, secrets, file uploads, tenant isolation?
16. How do releases reach production, and can they be rolled back?

5. Ownership and exit

17. Who owns the code, and from when?
18. Will the repository and hosting accounts be in my name from day one?
19. What documentation will I receive, and how will I accept it?
20. What do I get if the engagement ends early? See the ownership checklist.

6. Working together

21. How much of my time do you need, in days, during the project? Weak: "very little".
22. How and how often will you report? Good: per deliverable, with a percentage and what remains.
23. How fast do you answer my questions, and how fast do you need answers?
24. Do you have any financial interest in what you recommend (referral fees, resale)?

How to score the answers

Give each answer 0 (no answer), 1 (a general answer) or 2 (a specific, written answer). There is a ready eight-line grid in how to choose an IT vendor. The goal is not a perfect vendor; it is to see how each one behaves under questioning, which predicts how they will behave under pressure.

If you cannot judge the answers

An independent reader is cheaper than one change request. Build Oversight grades the vendor's work against written criteria, and one prepared hour with the Architecture Power Hour can review a single vendor proposal. Before you send the questions, make sure the scope is written; see the PRD template.