Before building
- Is there a specific task with a measurable outcome?
- Is an agent the right shape for the task, or would a deterministic workflow be safer?
- Who owns the result when the system is wrong?
- What is the cost of a slow, incomplete, or incorrect outcome?
- Which decisions must remain with a person?
Context and memory
- What does the agent need to know for the current step?
- Can the required information fit into the active context?
- If information is retrieved, how is relevance evaluated?
- How will stale, contradictory, or missing information be handled?
- What data should never be placed in a model context?
System map
The context preflight
Tools and permissions
- Does every tool have a narrow, documented input contract?
- Are tool arguments validated outside the model?
- Are permissions enforced by the application or only described in a prompt?
- Are retries safe for actions that can create side effects?
- Are timeouts and tool failures represented clearly in the next step?
- Is there a human approval step for irreversible actions?
Evaluation and operations
- Do representative tasks cover both success and failure cases?
- Can the team inspect the context, tool calls, and observations for a run?
- Are quality, latency, cost, and safety measured separately?
- Is there a way to stop, roll back, or disable the agent?
- Is there an owner for reviewing failures and updating the system?
A useful decision rule
If the answer to several of these questions is unknown, the next step is not more prompt experimentation. It is a short design exercise: define the workflow, identify the required information, narrow the capability surface, and choose the smallest evaluation set that can prove the idea works.