Software projects rarely fail in development. They fail in the fortnight before the contract, when nobody asks the questions that would have revealed the mismatch.
These are the questions we would want asked of us. They are not adversarial — a good vendor will answer them readily, and the answers will tell you more than any demo.
Ask how they will learn your process
A vendor who cannot describe how they will learn your operation will build against an assumption. Ask what happens in the first two weeks, who they need time with, and what document comes out of it.
The answer you want is specific: names of roles, hours of access, and a written problem statement you get to correct. The answer to be wary of is a discovery call followed by a proposal.
Ask what they would refuse to build
Every honest vendor has a version of this answer. If everything you describe is possible and nothing gives them pause, you are talking to a sales process rather than a delivery team.
Ask who stays on the engagement
The people who scope the work are often not the people who build it. That is where intent gets lost. Ask which named people remain through delivery, and what happens if they leave mid-project.
A vendor who cannot tell you what they would refuse to build has not understood your problem yet.
Ask what you own at the end
Source code, data, documentation and deployment access. Get the answer in writing before contract, not after go-live.
If the answer is that you own the data but not the code, that can be reasonable — but you should know it, price it, and understand what happens if you change vendor in three years.
Ask what happens when scope changes
Scope always changes. What matters is whether change is handled as a conversation with a price attached, or as a dispute. Ask to see how the last three change requests on someone else’s project were handled.
Ask about the project that went badly
This is the most useful question on the list. Everyone has one. A vendor who describes it plainly — what went wrong, what they changed afterwards — is telling you how they will behave when yours gets difficult.
Ask what support looks like on day 31
Handover is not the end of the relationship, and the month after go-live is when the real defects surface. Ask what is included, what is billable, and how quickly someone answers.
The short version
- Who is on the engagement, by name
- What the first two weeks produce
- What you own at handover
- How scope changes are priced
- What support covers after go-live
Before you sign, get these in writing:
- who is on the engagement, by name
- what the first two weeks produce
- what you own at handover
- how scope changes are priced
- what support covers after go-liveIf a vendor answers all seven of these well, the remaining risk is ordinary delivery risk, which is manageable. If they answer three, the price is not the thing you should be negotiating.