A real chief of staff costs $180,000 a year and takes six months to ramp. A good prompt stack costs nothing and works the first time you paste it. The two are not the same. They are also not as far apart as you would expect.
A chief of staff does six things. They run your morning brief. They triage your inbox. They prep your meetings and chase the follow ups. They stress test your decisions. They build the briefings you need before a conversation. They run the weekly review that keeps you honest. Six categories. The rest is judgement.
Below are 30 prompts grouped into those six categories. Every prompt is structured for ChatGPT, Claude, or Gemini. Copy, paste, swap in your specifics, and you have a working draft. Together they form what we call the Chief of Staff Stack. Treat them as a starter set. Calibrate them to your voice over a week and they become yours.
What Is the Chief of Staff Stack?
The Chief of Staff Stack is a framework for using AI the way an executive uses a chief of staff. The point is not to automate your judgement. The point is to free up your judgement by handing the surrounding work to AI.
The stack splits the surrounding work into six pillars. Daily Planning, Inbox Triage, Meeting Mastery, Decisions, Research, and Weekly Review. Each pillar has five prompts that handle the repeatable parts of that pillar. Thirty prompts cover roughly the same surface area a junior chief of staff would cover in a typical week, minus the parts that need a human in the room.
The model does not replace you. The model gives you the first draft, the structured analysis, and the chase email so you can spend your time on the thinking and the relationships.
Pillar 1: Morning Brief and Daily Planning
The first hour of the day is where chief of staff support pays for itself. A good brief tells you what matters before you start reacting to what does not.
1. Daily Brief Generator. "Act as my chief of staff. Here is my calendar for today: [paste]. Here are the top three emails or messages I flagged: [paste]. Here are the projects I am leading: [list]. Produce a one page morning brief with: top three priorities for today, three potential time sinks to avoid, two decisions I will likely face, and one question I should think about before my first meeting."
2. Top Three Selector. "Here is my task list for today: [paste]. Help me pick the three tasks that will produce the most leverage. For each, explain in one sentence why it ranks above the others. List the rest as either delegate, defer, or drop, with one sentence reasoning for each."
3. Time Block Planner. "Convert this task list into a time blocked calendar for the day, given that my available focus blocks are [list times]. Each block should specify the task, the goal of the block, and the artifact that should exist when the block ends. Leave 15 minutes of buffer between blocks. Tasks: [paste]."
4. Energy Matched Scheduling. "Here are my tasks for the week: [paste]. Classify each as high focus, medium focus, or low focus. Then propose when in the day each should happen, given that my peak focus hours are [time] and my low focus hours are [time]. Output as a table."
5. Day End Review. "Run my end of day review. Here is what I planned this morning: [paste]. Here is what actually happened: [paste]. Output: three things that worked, two things that wasted time, one thing to start differently tomorrow, and one question I should sleep on."
Pillar 2: Inbox Triage and Email Drafting
The inbox is where most knowledge workers lose the morning. The Chief of Staff Stack handles triage in minutes, not hours.
6. Inbox Priority Sort. "Act as my chief of staff. I am pasting the subject lines and first sentences of unread emails. Sort them into four buckets: respond today (needs my voice), respond this week, delegate (and to whom), and archive. For each in the first bucket, draft a one sentence response I can edit. Emails: [paste]."
7. Polite Decline Drafts. "Draft three versions of a polite decline for the following request, each with a different tone: warm, neutral, and firm. Each should be under 80 words, acknowledge the request specifically, decline clearly, and offer one alternative if appropriate. Request: [paste]."
8. Two Line Response. "Read the following long email and draft a two line response that addresses the sender's actual question, confirms the next step, and includes nothing else. No greeting, no signoff. Email: [paste]."
9. Follow Up Nudge. "Draft a follow up email for the following stalled thread. Tone: warm, professional, not passive aggressive. Reference the previous exchange in one sentence. Restate what I am asking for. Make the next step easy. Maximum 90 words. Original thread: [paste]."
10. Thread Summary. "Summarize the following email thread. Output: who said what (one line each in chronological order), what was decided, what is still open, and what the next action is with owner and due date. Thread: [paste]."
Pillar 3: Meeting Mastery
Meetings are the highest density part of an executive day. The Chief of Staff Stack covers prep, structure, and follow through so the meeting actually produces something.
11. Pre Meeting Brief. "Build a one page pre meeting brief for the following meeting. Cover: stated purpose, my goal for the meeting, what each attendee wants, the three questions I should ask, the two decisions that might come up, and the artifact I want to leave with. Meeting context: [paste]."
12. Agenda Builder. "Build an agenda for a [duration] meeting on [topic] with [attendees]. Output: time blocks summing to the total duration, the goal of each block, the question or decision each block should produce, and the assigned facilitator. Reserve the last 5 minutes for next steps."
13. Note Structure. "Generate a note taking template for the following meeting. Sections: Attendees and roles, Stated goal, Key points raised (with attribution), Decisions made, Open questions, Action items (with owners and due dates), and One sentence summary. Meeting: [describe]."
14. Action Item Extractor. "Read the following meeting notes or transcript. Extract every action item. For each, output: owner (named person), action (one verb starting sentence), due date if stated (or propose one), and dependency if any. Output as a table. Notes: [paste]."
15. Post Meeting Recap. "Draft a post meeting recap email to send to the attendees. Open with one sentence summary. Then sections for: decisions made, action items (with owners and dates), open questions, and next meeting if any. Tone: brief, factual, no padding. Notes: [paste]."
Pillar 4: Decisions and Analysis
A chief of staff stress tests decisions before they get made. The Chief of Staff Stack does the same.
16. Decision Framework. "Act as my chief of staff. I am facing the following decision: [describe]. Walk me through a structured decision framework. Output: the options on the table, the criteria that matter and their weights, a score for each option against each criterion with one sentence reasoning, the weighted total, and a recommendation. Then list the two things that would change the recommendation."
17. Counterfactual Stress Test. "Here is a decision I am leaning toward: [describe]. Stress test it by answering: what would have to be true for this to be the wrong call, what is the evidence for and against each of those conditions being true, and what is the cheapest way to test the riskiest assumption before committing."
18. Two Path Comparison. "Compare these two options against my goal of [state goal]. Option A: [describe]. Option B: [describe]. Output a five row table: criterion, Option A score (1 to 5), Option B score (1 to 5), winner, why. End with a one paragraph recommendation including the trade off the loser forces me to accept."
19. Risk and Mitigation. "Identify the top five risks for the following plan. Plan: [describe]. For each risk output: description, likelihood (low/medium/high), impact (low/medium/high), early warning sign I should watch for, and a mitigation I can put in place now."
20. Devil's Advocate. "Argue against the following proposal as if you were the smartest critic in the room. Proposal: [describe]. Output: the three strongest objections, the evidence behind each, and the one objection that would most change my approach if it held up. Be specific. No hedging."
Pillar 5: Research and Briefings
Before any high stakes conversation a chief of staff produces a one page brief. The Chief of Staff Stack does the same, in minutes.
21. Company Brief. "Build a one page brief on the following company before my meeting with them: [company name]. Cover: what they do in one sentence, who their main customers are, recent funding or major news, top three competitors, their three likely priorities right now, and three questions worth asking. Use only widely reported information and note any assumptions."
22. Person Brief. "Build a one page brief on the following person before my meeting with them: [name and role]. Cover: their background in three lines, what they likely care about right now, what they have publicly said in the last year, and the two topics that would resonate. Note any assumptions and avoid speculation about private matters."
23. Topic Crash Course. "Give me a 15 minute crash course on [topic] for someone with general business background but no specialist knowledge. Structure: what it is in plain language, why it matters now, the three or four concepts I need to understand, the most common misconceptions, and the one question that will separate a real expert from a generalist when I meet one."
24. Competitor Analysis. "Build a structured competitor analysis for the following set of companies in the [category] market: [list]. For each, output: positioning, pricing approach if known, target customer, one stated strength, one likely weakness. End with a one paragraph synthesis of where the market has gaps."
25. Industry Update. "Summarize what has changed in the [industry] industry in the last 90 days. Cover: major announcements, regulatory or macro shifts, two emerging trends with evidence, and the one development that is likely overhyped. Cite sources where possible and flag where you are uncertain."
Pillar 6: Weekly Review and Strategy
A weekly review is where most executives intend to do strategic work and instead drift back into the inbox. The Chief of Staff Stack forces the review to actually happen.
26. Week in Review. "Run my weekly review. Here is what I committed to last Monday: [paste]. Here is what actually got done: [paste]. Output: a one paragraph honest assessment, three things that worked, two things that did not, one pattern I should change, and three commitments for next week. Use plain language. No hedging."
27. Goal Progress Tracker. "I have the following quarterly goals: [paste]. Here is where I am at the end of week [N] of 13: [paste]. For each goal output: progress percentage (with reasoning), on track / at risk / off track, the single most important action for next week, and the decision I would have to make if things did not improve in two weeks."
28. Backlog Prioritization. "Here is my project backlog: [paste]. Rank them using a weighted scoring: impact (1 to 5), confidence (1 to 5), effort (1 to 5, lower is easier). Score each, calculate priority as impact times confidence divided by effort, and output as a table sorted by priority. End with a one sentence reason to start with the top item."
29. Quarterly Check In. "Run a midpoint quarterly check in. My Q goals were: [paste]. Halfway through, where I am is: [paste]. Output: which goals are on track, which need acceleration, which should be killed or rescoped, and the one structural change I should make to the second half of the quarter."
30. Strategic Question. "Based on the following week of context, generate the one strategic question I should focus on next week. The question should be hard to answer in one sentence, point at a real decision, and force me to choose between two genuinely different paths. Context: [paste]."
How to Use the Chief of Staff Stack
The 30 prompts are designed to be used selectively, not all at once. A working setup looks like this. Prompts 1 and 6 run every weekday morning. Prompts 11 and 15 run around every meeting that matters. Prompts 16 through 20 run before every decision worth more than 20 minutes of your time. Prompts 21 and 22 run before every first conversation with a new company or person. Prompt 26 runs every Friday afternoon.
That covers roughly 80 percent of what a chief of staff would do for you. The remaining 20 percent is judgement, escalation, and relationship work that should stay with a human.
The prompts also get better the more you use them. After a week, each prompt becomes your prompt. You will adjust the format, add your team's vocabulary, swap in your default tone, and remove the parts you never use. By month two the stack is calibrated to your operating style and runs without thinking. That is the point.
Frequently Asked Questions
Can AI really replace a chief of staff?
No. AI replaces the documentation, structuring, drafting, and analytical work a chief of staff would do. It does not replace the relational work, the escalation judgement, the political navigation, or the trust that comes from a long term human partner. The Chief of Staff Stack is best understood as the part of the role AI handles well, not the whole role.
Do these prompts work in Claude and Gemini too?
Yes. The structure works in any modern instruction following model. Claude tends to follow long structured prompts more precisely. ChatGPT has the broadest integration ecosystem. Gemini ties cleanly to Google Workspace. The prompts in this post are written generically and work across all three.
How do I know which prompts to start with?
Start with prompt 1 (Daily Brief Generator). Run it for three days. Once the format works for you, add prompt 6 (Inbox Priority Sort) the next week. Add a third only when the first two feel automatic. Most people who try to adopt all 30 at once stop within a week. Most people who adopt one per week have all 30 in regular use by quarter end.
Should the same prompts work for a founder, an executive, and a senior manager?
Yes, with calibration. The structure of the work is the same across roles. The specifics change. A founder calibrates the brief generator around fundraising and product. An executive calibrates around their P&L and team. A senior manager calibrates around their function and their boss. The prompt scaffolding stays the same.
What about confidentiality?
For sensitive content (HR matters, customer data, vendor contracts, confidential strategy), only use a model under an enterprise agreement that covers data handling. Most enterprise plans of ChatGPT, Claude, and Gemini meet this bar. Free consumer tiers usually do not. For everything else (drafts, structuring, research, planning), the productivity gain compounds.
How long does it take to learn to write prompts like this?
A week of practice gets you to functional. A month gets you to natural. The 30 prompts in this post are calibrated examples to study and copy. Once you have run them a dozen times each, you will start writing new prompts in the same style without thinking.
Get the Full Chief of Staff Prompt Pack
The 30 prompts above are the working starter set. The PromptLeadz Chief of Staff Prompt Pack expands the stack to 100 plus prompts across the same six pillars, every prompt formatted three ways (XML for Claude, Markdown for ChatGPT, PTCF for Gemini) so you can drop them straight into your preferred model.
Browse the Chief of Staff Pack and the rest of the PromptLeadz role library in the shop. Every pack is delivered as instant download.
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