The four questions that matter most
One: "Who owns the integrations, prompts, and data?" The only acceptable answer is you — in writing. Agencies that keep ownership are building a hostage situation, not a system. Two: "What happens after launch?" Monitoring, alerting, and iteration should be included; "we hand it off" means you own 2 a.m. failures alone. Three: "Show me a reference workflow with before/after numbers." Not a logo wall — a workflow, a metric, a delta. Four: "What is your compliance story for my sector?" HIPAA, TCPA, GLBA — the answer should include audit trails and specifics, not "we take security seriously".
An agency that answers all four crisply is rare. That is the point of asking.
Eight more that separate builders from resellers
Five: "What will you tell me NOT to automate?" Honest scoping kills bad projects early. Six: "Fixed quote or open retainer?" Scoped projects with written quotes beat "AI strategy" retainers. Seven: "Who does the work — the people on this call?" Layers of account managers slow everything. Eight: "What stack do you build on, and why?" Listen for reasoning, not brand loyalty. Nine: "How do you handle my customers’ languages?" If multilingual is an afterthought, so is your market. Ten: "What is your typical time to production?" Weeks is the modern answer; quarters is a consulting model. Eleven: "How do failures reach me?" Alerting and SLAs, not customer complaints. Twelve: "Can I start with one small workflow?" The right agency says yes eagerly — proof beats promises.
Red flags that end the meeting
Guaranteed results before seeing your data. Pricing that only exists after a "strategy engagement". No production system they operate themselves. Contracts that lock your data or integrations to their platform. And the subtle one: an agency that never says "that part, you shouldn’t automate" — because it means they are selling everything to everyone.