Every software vendor sounds similar in the first meeting: experienced team, modern stack, happy clients. The differences that will actually shape your project live one layer deeper — and they surface fast if you ask the right questions. Here are the seven we’d want answered if we were the ones buying, and what a good answer sounds like.

1. “How do you arrive at a price?”

Good answer: a structured discovery process with deliverables — requirements, wireframes, a ranked feature list — and a price built on them. Warning sign: a confident number in the first hour. An estimate without discovery is a guess with a signature, and someone will pay for the gap later.

2. “When do I first touch working software?”

The answer should be a number of weeks, followed by “and every few weeks after that.” Screenshots and status decks are not software. If the first hands-on moment is launch day, all the risk has been saved up for the most expensive possible moment.

3. “What do you test against, and who tests?”

Listen for two things: test cases written from the agreed requirement (not improvised at the end), and your team included as reviewers each release. Quality that isn’t a process is a hope.

4. “Who owns the code?”

The only acceptable answer is you. Ask specifically: if we part ways, can another team pick this up — repository, documentation, credentials and all? Vendors confident in their work don’t need lock-in to keep clients.

5. “What does year two cost?”

Hosting, patches, API changes, small improvements — a real vendor quotes the ongoing picture with the build. Silence about year two is how “affordable” projects become expensive ones. (Our accountant wrote a whole maintenance budget guide.)

6. “Tell me about a project that went sideways.”

Everyone has one. What you’re evaluating is the honesty of the telling and what changed afterward. A vendor with no such story is either brand new or not being straight with you — both are answers.

7. “Will you tell me if I shouldn’t build this?”

Sometimes the right answer is off-the-shelf software, an integration, or nothing at all. Ask for an example of a time they talked a client out of a project. The vendors who can answer are the ones whose recommendations you can trust when they say build.