B2Shift · Published 27 August 2026 · Updated 27 August 2026
Automation proposals are hard to compare because the underlying work varies enormously behind similar-sounding language. The questions below surface that variance before you sign anything.
Ask what they will actually build, not what the demo shows
A live demo proves a model can produce a good-looking output. It does not prove the system can read your CRM, write back to it safely, and recover when an API call fails. Ask specifically which systems the proposal connects to, with what permissions, and what happens on a failed step — see AI agent vs chatbot vs workflow automation for the vocabulary this question depends on.
Ask for a measurable scope and its explicit assumptions
A quote without a defined success metric and a list of assumptions has simply moved the risk onto you. Ask what happens if the process turns out more exception-heavy than described, or if an integration's API has undocumented rate limits — a serious partner has an answer, because they have hit this before.
Ask who owns escalations and how mistakes are found
Every automation will eventually be wrong about something. Ask who is notified, how quickly, and what the audit trail looks like when a customer disputes an automated decision. An agency that has not thought about this has usually not built anything that survived contact with real customers.
Ask about data residency, access and what happens after the contract ends
Where does your data go, is it used to train anyone's models, and do you own the workflow logic if you switch providers later? Vendor lock-in is not inherently wrong, but it should be a decision you made, not one you discovered.
Ask for a reference for a comparable, not just any, project
A reference for a chatbot tells you little about a vendor's ability to build a workflow that writes to your ERP. Ask for a reference in the same category of complexity as what you are buying, and ask that reference specifically what went wrong and how it was handled — the answer to the second question matters more than the first.
Discuss your workflow