10 questions to ask your developer or agency (no technical degree required)

One of the hardest parts of commissioning software when you’re not technical is knowing whether you’re getting good advice. The good news: you don’t need to understand the code to ask good questions. You just need to listen carefully to how people answer.

Here are ten questions I’d ask, what a good answer sounds like and what should worry you.

1. “What’s the simplest version we could launch first?”

Good: A clear, confident answer about a smaller first release, with reasons. Worrying: “Well, we need to build everything properly from the start.” Big-bang builds are expensive and risky.

2. “What are the biggest risks on this project?”

Good: Specific, honest answers: a tricky integration, an unclear requirement, a dependency on a third party. Worrying: “There aren’t really any.” Every project has risks. If they can’t name any, they haven’t thought hard enough.

3. “Can you explain that without the jargon?”

Good: They happily rephrase and use analogies. Worrying: They get defensive or just repeat it louder. If someone can’t explain it simply, you can’t make an informed decision.

4. “Who owns the code, the designs and the hosting accounts?”

Good: “You do. Everything lives in your accounts.” Worrying: Vague answers, or code hosted only on their systems. You should never be locked in because someone holds the keys.

5. “How will we know how it’s going?”

Good: Regular, visible progress: working software you can try every week or two, not just status reports. Worrying: Silence for weeks, followed by “nearly there!”

6. “How do you test it, and how do you deploy changes?”

Good: Mentions of automated tests, a staging site to try things before they go live and a repeatable way to release. Worrying: “We test it manually” or “we just upload the files.” It works until it doesn’t, usually at the worst possible moment.

7. “What happens when something breaks after launch?”

Good: A clear support arrangement: who to contact, how quickly they’ll respond and what it costs. Worrying: “We’ll sort something out.” Software needs looking after; you want to know how before you need it.

8. “What will it cost to run and maintain, not just to build?”

Good: A realistic view of hosting, licences and maintenance, including what’s likely to change as you grow. Worrying: Only talking about the build price. The running costs are where surprises hide.

9. “What’s not included in this quote?”

Good: A clear list of exclusions and assumptions, with how changes will be handled. Worrying: “Everything’s included!” (Then the quote’s probably vague, and the scope arguments will come later.)

10. “What would you do if it were your money?”

Good: A thoughtful answer, even if it means building less, spending less or using an existing product. Worrying: Every answer happens to involve more work for them.

How to use this list

You don’t need to ask all ten, or to grade the answers like an exam. Just pay attention to whether you come away understanding more, and whether the person seems more interested in solving your problem than in selling you a project.

When you want a second opinion

If you’ve got a quote, a proposal or a half-built project and you’re not sure whether it’s sensible, an independent technical audit gives you a plain-English view of what’s good, what’s risky and what to do next. And if you’d like someone senior on your side throughout, that’s what a fractional CTO is for. Or simply get in touch and tell me what’s going on.