Twelve questions to ask a development agency before you sign

Choosing a development agency is difficult because the thing you are assessing - judgement under uncertainty - cannot be demonstrated in a sales meeting. Everyone has a portfolio, a process diagram, and a testimonial page.

These are the questions we would ask. Several of them are uncomfortable to be on the receiving end of, which is precisely why they are useful.

On the people

1. Who exactly will be working on this, and what else are they working on?

You want names, seniority, and honest allocation. “A senior engineer and two mid-level developers” is not an answer; ask how many other projects each of them is on. Someone at 20% allocation across five clients is not going to hold your problem in their head.

2. Are the people in this meeting the people who will do the work?

If not, ask when you meet the people who will. The gap between the team that sells and the team that delivers is where a great many disappointments live.

3. What happens if someone leaves mid-engagement?

Small agencies have real key-person risk and should say so plainly. The answer to listen for is about practice - pairing, documentation, shared ownership - not a promise that it will not happen.

On the work

4. Tell me about an engagement that went badly.

The single most informative question in the list. Everyone has had one. What you are listening for is whether they can describe their own contribution to it specifically, or whether the story is entirely about a difficult client.

A good answer names a decision they got wrong and what they changed afterwards.

5. When did you last tell a client not to build something?

If the answer is never, they are order-takers. That may be what you want, but you should know that is what you are buying - you will be supplying all of the judgement.

6. How do you estimate, and how often are you wrong?

Ask for the shape of their misses, not their accuracy rate. Everyone is wrong: the question is whether they know their own bias and correct for it. “We are usually about 30% over on integration-heavy work, so we now scope those differently” is a much better answer than “we are pretty accurate”.

7. What does your first two weeks look like?

Onboarding and discovery reveal the seriousness of a team. An agency that starts writing production code in week one either has extraordinary context or is not looking for it.

On the arrangement

8. Who owns the code, the repositories and the cloud accounts?

The correct answer is: you do, from the first commit, in your own accounts. Any arrangement where the agency holds the infrastructure is leverage over you at renewal, whether or not they intend to use it.

9. What does the handover look like if we stop?

Ask specifically what you receive and how long it takes. If the answer is vague, the honest translation is that leaving will be expensive.

10. What is your notice period, and does it run both ways?

Symmetry matters. An agency that requires 90 days from you and offers 30 has priced their own flexibility above yours.

On the money

11. What is the rate, and what is billable?

Ask directly whether meetings, project management, code review and travel are billed. These can be a meaningful share of an invoice, and finding out in month two is a bad way to start a relationship.

12. What would make you turn this work down?

An agency with no answer will take anything, which means their pipeline decides their quality rather than their judgement. You want to hear real criteria - work outside their competence, timelines they cannot meet, projects where they think the premise is wrong.

What the answers are for

None of these questions has a single correct response, and a polished answer is not automatically a good one. What you are looking for is specificity. Agencies that have genuinely thought about how they operate answer with details and examples; agencies that have not answer with adjectives.

The other thing worth noticing is how they handle the questions they do not like. The reaction to being asked something uncomfortable in a sales meeting is a fair preview of the reaction to being asked something uncomfortable in month four, when it matters considerably more.