dgChoose a bounded job
Start with a task that has clear inputs and a recognisable successful outcome: routing an enquiry, checking a status or scheduling a follow-up.
Design for uncertainty
An assistant should be able to say it does not know. Define approved information, escalation conditions and what happens when a connected system is unavailable.
Make handoff part of the design
Pass relevant context to the person receiving the conversation. Avoid making a customer repeat details, and be explicit about whether a human has actually received the request.
Review after release
Check unresolved conversations and exceptions. Improvement comes from understanding where people get stuck, not from adding automation to every step.