Choosing an AI automation partner: questions worth asking
Evaluate a provider by the workflow they can explain, the evidence they show, and the operating responsibilities they clarify.
Choosing an automation partner is partly a technical decision and partly an operating one. A useful provider should be able to explain how the workflow fits your business, where it can fail, and what your team will need to own after implementation.
Ask for a concrete process, not a promise
Describe a real task and ask how they would approach it. Look for questions about your inputs, existing tools, exceptions, and decision boundaries. A proposal should distinguish the demonstrated capability from assumptions that still need testing.
Clarify access and ongoing ownership
Ask which systems the workflow needs, what permissions it requires, and who maintains those connections. Establish how changes to your process will be handled. Understand what happens if you stop working together, including how you retain the instructions and records needed to operate or replace the workflow.
A useful question for your first conversation
Ask: “Can you show what happens when the input is incomplete or the connected system is unavailable?” A strong answer explains the boundary, the evidence retained, and who picks up the work. Ask the same question about an ambiguous external send and a change to your business rules. These discussions reveal whether a provider is designing an operational process or only demonstrating that a model can produce a plausible answer.
Agree the evidence for acceptance
Choose tests that represent the actual work, including failure and recovery. Ask how completed external actions are verified and how mistakes are corrected. Decide how scope changes are handled before they occur. A clear small project is a stronger starting point than a broad guarantee with no testable finish.
A reality check before you hit run
Anthropic’s evaluation guidance provides a practical topic for supplier due diligence: ask how proposed agents will be tested. [1]
NIST’s voluntary framework offers a structured way to discuss risk across the system lifecycle. Ask who owns those decisions after launch. [2]
Implementation checklist
- Ask the provider to map a real workflow.
- Separate proven capability from assumptions.
- Clarify access, maintenance, and handover responsibilities.
- Agree acceptance evidence before implementation.
The sources behind the sauce.
Primary research and official documentation behind the cited points. The workflow examples and checklists are Croissant’s own guidance.