1. Who stays?
Ask who from the first conversation is still there at delivery. A senior person who understands your business should be present throughout. If the people who framed the problem leave once the build starts, the result will drift from the reason you started.
2. How senior is the team, and how is it staffed?
Ask for the experience of the people who will do the work, not the firm. Teams that scale with junior engineers under a new title are a recipe for rework. Look for senior leaders who stay involved, with specialists from each discipline as the work grows.
3. How will we know it is working?
Ask what is measured, against what baseline, and when you will see it. Each phase should end with evidence you can check, and you should decide whether to continue.
4. What will our people learn, and what happens after the engagement?
The best teams work alongside yours, so your people learn by building and keep building. Ask how the work fits your standards, who approves what, and how governance is built in from the start rather than added at the end.