When I plan with AI, I don’t treat it like a search engine. I treat it like a junior engineer during a handoff.

Here are 2 rules I live by to get production-ready plans:

1️⃣ Serialize Your Decisions (The “One Thing” Rule)
I don’t dump a paragraph of questions on an AI. It leads to shallow, hallucinated answers. Instead, I serialize the flow:
Me: “Here is the context. Do you have questions?”
AI: (Asks 5 questions)
Me: “Let’s tackle each question one-by-one. For question 1…”
Result: Deep, verified thinking on every single point. No skimming.

2️⃣ The “Agent Handoff” Test
I draft every plan assuming a totally different agent will execute it. Here is the critical difference: When a human junior engineer hits ambiguity, they have a built-in safety mechanism – they stop and ask you a question.
AI agents generally lack this. They don’t have a reliable internal metric that says, “I am only 40% sure what ‘single source of truth’ means here, so I should stop and ask.”
Faced with vague requirements, they don’t pause, they confidently execute a guess. The “Handoff Test” forces me to remove that ambiguity before I hit “run”, because I know the AI won’t raise its hand to ask me about it later.
The Insight: Strict precision isn’t just “nice to have,” it is the only defense against silent failure when you don’t have a human loop to catch the confusion mid-flight.

Managers & Leads: Are you finding that working with AI is highlighting gaps in your own documentation or requirements gathering?

Originally posted on LinkedIn