Claude Skills: Use Grill Me to Question a Project Plan

Grill Me is a Claude skill that asks hard questions about a plan instead of accepting it at face value. You provide a plan, invoke the skill and Claude returns a set of probing questions aimed at the assumptions, gaps and risks that the plan does not address. The skill does not provide answers — it forces you to find them.

The value is in what those questions surface. A plan that holds up under questioning is more reliable than one that was never challenged. Tools like fenbs store the decisions and unresolved questions that come out of a Grill Me session so the next session starts from what was answered rather than revisiting the same ground.

What Grill Me does and does not do

Grill Me is a questioning skill, not a planning skill. It reads your plan and generates questions in categories — assumptions, dependencies, risks, success criteria, rollback steps. It does not rewrite the plan, suggest solutions or tell you whether your answers are right.

That is deliberate. A skill that both questions and rewrites tends to soften its own questions to make the rewrite look better. Keeping the roles separate means the questions are not influenced by what answer would be easiest to incorporate. For how to use Claude interactively to challenge plans, see how to use Claude Grill Me. For where skill files live, see claude skills files.

When to use a questioning skill

Use it before you commit to a plan. The earlier you run it, the cheaper the changes it reveals. Running it on a plan that is already in execution reveals problems you may not be able to fix without significant rework.

• Before starting a project: surface the assumptions you have been carrying as facts.
• Before a client handoff: check whether the plan addresses the client's actual constraints, not just the ones you know about.
• After a major change: a plan that was sound before a scope change may have new gaps.
• When something feels off: if you have a nagging doubt about a plan, Grill Me can turn that intuition into a specific question.

How to run a Grill Me session

1. Write the plan in plain language before invoking the skill. A vague plan produces vague questions. Write it as if you are explaining it to a new team member: goal, steps, assumptions, what success looks like.
2. Invoke the skill: type /grill-me (or the skill's actual command name) and paste the plan.
3. Read through all the questions before answering any of them. Some questions will overlap; grouping related ones lets you answer the underlying concern once.
4. Answer each question as specifically as you can. "We have not thought about that" is a valid answer — it tells you where the gap is.
5. Identify which questions revealed a gap you need to address before proceeding. Those become tasks or decisions.

Acting on the questions

Not every question requires a change to the plan. Some questions confirm that the plan already addresses something you thought was a gap. Others reveal that an assumption is correct but was never stated explicitly. Both are useful outputs.

Distinguish between a question that requires immediate action and one that would be useful to resolve but is not blocking. Addressing every question before proceeding can stall a project unnecessarily. If a question reveals a risk you can mitigate as you go, note it and continue. If it reveals a risk that would require discarding significant work to fix later, address it first.

The questions that do require action fall into two categories: decisions that need to be made now, and open questions that need more information before they can be answered. Record both. An open question left in a chat history will disappear. A decision made in response to a question is worth more when you can see what prompted it.

Keeping the skill in your library

A questioning skill is only useful if the questions are genuinely challenging. Before relying on a community Grill Me skill, run it on a plan you know well and check whether the questions surface something real. A skill that asks only obvious questions adds no value over a checklist.

If the standard Grill Me skill does not go deep enough for your domain, add a domain-specific section to the skill file. A legal team's version should ask about jurisdiction and enforceability. A product team's version should ask about user discovery and rollout risk. The base skill covers general patterns; domain additions cover the gaps specific to your work.

How to do this with fenbs

1. Create a free account and add a project for the plan you are reviewing.
2. Add the plan as a task in fenbs before running the skill. That way the plan itself is recorded, not just the questions.
3. After the Grill Me session, record each decision that came out of it in Decisions and rules, linked to the plan task. Mark unresolved questions as open decisions.
4. Add the approved Grill Me skill text to Skills and prompts in fenbs. Connect your AI app over MCP from Integrations so it reads the skill and existing decisions when you start the next planning session.