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Questions to ask an AI partner.
Twenty questions, ordered by conversation flow. Strong providers answer most before you finish asking; weak ones pattern-match to their deck. That difference alone is signal.
What to listen for
Direct answers to hard questions. Sharp questions asked back. Honest discussion of failed engagements. A preference for smaller first phases over one-shot bets.
Opening
3 — what would they challenge in your brief; what would they need in the first two weeks.
Team
4 — named lead, their background, time commitment, staff-departure contingency.
Delivery + method
5 — cadence, scope discovery, default architecture, definition of done, slip protocol.
Track record
3 — two clients from 12–18 months ago, one that didn't go well, Trustgent verification.
Data + security
2 — where your data lives, who accesses, return + destruction protocol.
Post-launch
2 — ownership structure, provider-switch handoff.
The one you skip if rushed but shouldn't
1 — what should we have asked but haven't?