Procuring custom software is genuinely hard when you're not technical yourself — you're trusting someone's word on quality you can't directly inspect. These are the questions that reliably separate a serious partner from one you'll regret hiring, asked from the buyer's side of the table.
"Who actually owns the code and the accounts when we're done?"
Listen closely to the answer. A partner who owns your domain registration, your cloud account, or the only copy of your source code has quietly built themselves permanent leverage over you — leaving becomes expensive or impossible, no matter how the relationship is going. The right answer is unambiguous: everything is registered in your name, from day one, and you could walk away tomorrow with everything you need.
"Can I speak to a client whose system has been live for over a year?"
Any vendor can produce a happy client from a launch three weeks ago, while the honeymoon is still on. A reference from someone who's lived with the system through a year of real use, staff turnover, and at least one thing going wrong tells you far more about how the partner actually behaves once the invoice is paid.
"What happens when something breaks at 11pm on a Saturday?"
Get the actual answer in writing, not a reassuring shrug in a sales meeting: is there a documented support agreement, a defined response time, and does it cost extra? "We'll sort it" is not an SLA, and the gap between the two only becomes visible during your first real emergency — the worst possible time to discover it.
"What don't you know yet about our organisation, and how will you find out?"
Be wary of anyone who claims to fully understand your business after a single meeting and jumps straight to a fixed quote. A partner who takes real ownership asks more questions than they answer early on, and is upfront that the specification will sharpen as they learn how your organisation actually works.
"Can you show me undocumented code you've inherited from someone else, and how you handled it?"
Every serious developer has taken over a messy, undocumented system at some point. How they describe that experience tells you a lot: someone who complains bitterly about "bad code left by amateurs" may be less generous with your team's understanding a year from now than someone who talks calmly about documenting, refactoring and moving forward.
"What would make you tell us not to build this?"
A partner who has never talked a client out of a project, a feature, or an unnecessary expense is either extremely lucky or not being straight with you. The willingness to say "you don't actually need this" — even at the cost of a smaller invoice — is one of the clearest signals of a partner who's optimising for your outcome rather than their own billing.
How we'd answer these ourselves
We wrote this list from the buyer's side deliberately, including the questions that are uncomfortable for a vendor to answer honestly. If you'd like to put them to us directly, our About page covers how we work, and we're glad to give straight answers — including telling you if we're not the right fit for what you need.