Most people use AI like a slightly faster search engine. They type a vague question, get a smooth but generic answer, and wonder why it does not feel useful. The issue is almost never the tool. It is the brief. The prompts below are structured to give AI enough context to ask you clarifying questions before producing output — which consistently changes the quality of what comes back. Five situations. Five prompts. Each one designed to be filled in with your actual situation and used directly.
These prompts work best when you treat the follow-up questions as part of the process. The output you get after answering two or three clarifying questions is consistently more useful than any first response. Do not skip that step.
Before committing to a week, this prompt stress-tests your task list against your actual goals. It catches the busy work that feels productive but moves nothing forward, and asks you the questions that change your priorities before you have already committed to the wrong ones.
Planning in your head means planning in a vacuum. By externalising your workload and goals in one prompt, you give AI enough context to identify the misalignments you are too close to see. The questions it asks back are the ones a good senior colleague would ask before your Monday morning meeting.
For performance issues, salary negotiations, client disagreements, or any conversation where the stakes are high and the outcome is uncertain. This prompt forces you to think through the other person's position before you open your mouth.
Most difficult conversations go badly because one or both people have only prepared their own side. This prompt forces you to articulate the strongest version of the other person's argument before you build yours. It also identifies the fear underneath your stated concern, which is usually what is driving the conversation going off the rails.
Every project has a moment where it stalls. This prompt does not give you a generic list of things to try. It challenges your framing of the blocker first, because the thing you are calling the problem is often not the real problem.
When you are too close to a problem, you tend to describe the symptom, not the cause. The most valuable thing AI can do here is not suggest solutions but reframe the problem. Once the framing shifts, the path forward often becomes obvious. This prompt forces that reframe before it goes anywhere near solutions.
Most people walk into performance reviews and speak in generalities about effort. The ones who get what they want speak in specifics about outcomes. This prompt builds the commercial case for your contribution before you are sitting in the room.
Managers and senior leaders respond to impact, not effort. The challenge is that most people describe their work in terms of what they did, not what happened because of what they did. This prompt finds those gaps before the review and gives you time to fill them with actual evidence.
For any significant decision you keep circling without committing to. This prompt surfaces what you actually know, what you are assuming without realising it, and what fear is disguising itself as caution. Better decisions start with better questions about the decision itself.
Most indecision is not a lack of information. It is a lack of clarity about what you actually value, what you are genuinely afraid of, and which assumptions you are treating as facts. This prompt forces all three to surface before it offers any framework. The output changes substantially based on your answers.
Use these prompts with Claude, ChatGPT, or any capable AI model. The placeholders in brackets are yours to fill in. The more specific and honest you are, the more useful the output. Vague input produces generic output. That is true every time.
Founder & Strategic Director, The Avenella Agency
Tom has 15+ years of senior marketing experience, including building the EMEA escalation framework at Google and YouTube, and directing social strategy for DWTC, Petronas, Dubai Duty Free, Sony PlayStation, and the NBA Abu Dhabi. These prompts are drawn from the frameworks he uses daily with clients across the UAE and UK.
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