Start with a bounded task, usable information and a clear way to evaluate the result.
Choose a task you can describe
A strong first project has a clear beginning and end. Answering a defined set of internal questions or summarising a standard document is easier to evaluate than an open-ended instruction to run the business.
Check the information
An assistant depends on the material it can use. Identify the approved sources, their owners and how they will stay current. Decide which information should remain outside the workflow.
Define when a person takes over
An assistant should have a clear route for uncertainty, exceptions and decisions that require approval. Plan that route before the workflow is used by customers or colleagues.
Create a practical evaluation set
Collect representative examples, including awkward cases and questions that should be escalated. Compare the output with the result you actually need, rather than judging only a polished demonstration.
Plan ownership after launch
A workflow needs someone responsible for access, updates, feedback and monitoring. Include the time and cost of that ownership when deciding whether the project is worthwhile.