The market for AI automation work is full of people who have done one or two projects and are presenting themselves as specialists in whatever you need. Getting proposals is easy. Evaluating them is harder.
What to ask before you sign
Work they've actually shipped. Not mockups or demos — automations running in production for real businesses. Ask to speak with a client who uses something they built. Ask what broke, what they fixed, and how long ago it's been running without major issues.
How they scope projects. Anyone who can quote a fixed price for a complex AI project on the first call either doesn't understand the complexity or plans to use the unclear scope against you later. Credible builders want a discovery phase — sometimes a paid session to understand your process properly — before committing to a number.
What happens when something breaks. Because things break. What's the response time? Is there a maintenance arrangement? Is there documentation that would let someone else step in if needed?
Who actually does the work. Some firms sell engagements that get delegated to contractors who've never built the type of system you need. Ask specifically who will be doing the implementation.
Red flags
Proposals heavy on AI terminology and light on specifics about how your actual business process will work.
Specific outcome promises — "we'll cut your processing time by 60%" — made before any discovery about your current process.
No mention of failure modes, edge cases, or what happens when the automation encounters input it wasn't designed for.
A timeline that's suspiciously short for the described complexity.
The right framing
An AI automation project is a collaboration. You know your business. The builder knows the tools. Neither of you knows exactly what the right solution looks like until you've spent time on it together.
A builder who asks good questions, acknowledges what they don't know, and is honest about tradeoffs is more likely to deliver something that works than one who has all the answers before they've heard the questions.
