--- title: "Write your executive's operating manual into files so AI drafts follow the rules" description: "Record calendar rules, meeting protocols, stakeholder tone, travel standards, and priorities in files so AI drafts fit your executive on the first pass." canonical: "https://scalewithsearch.com/articles/ai-for-executive-assistants" date: "2026-01-28" modified: "2026-09-25" --- ## Site navigation - [Scale With Search](https://scalewithsearch.com/) - Real estate - Real estate - [Real estate](https://scalewithsearch.com/for/real-estate) - Work - Start here - [Send your brief](https://scalewithsearch.com/work#send-your-brief) - [Prepare your six-question brief](https://scalewithsearch.com/work#prepare-your-six-question-brief) - Build - [Site build, content library with SEO, signal desk](https://scalewithsearch.com/work) - For your business - Trades and home services - [Auto body and collision shops](https://scalewithsearch.com/for/auto-body-and-collision-shops) - [Foundation and home repair contractors](https://scalewithsearch.com/for/foundation-and-home-repair) - 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You manage the CEO's calendar. A board member wants a meeting. You ask AI to draft the scheduling email. It returns generic politeness: "Would next Tuesday at 2 p.m. work for you?" That is wrong three ways. The CEO takes no meetings after 3 p.m. Board members get executive-level formality, not a casual tone. This board member prefers a morning phone call to a calendar invite. You know all of this because you have been the executive assistant (EA) for two years. The assistant knows none of it. You rewrite the email. Tomorrow a different stakeholder brings the same problem. The assistant saves you no time, because each day you teach it from scratch. An EA does not need generic scheduling help. You need an assistant that knows the executive as well as you do. ## Why a generic assistant fails an EA ChatGPT does not know your executive's calendar rules, communication style, travel preferences, or the unwritten protocols that keep the day running. An EA manages rules like these: - calendar: no meetings before 9 a.m., deep work blocks on Tuesdays, 15 minutes between calls; - meeting length: board members get 60 minutes, vendors 30, internal teams 15 unless flagged urgent; - tone: formal for some people, casual for others; - travel: aisle seat, one preferred hotel chain, no red-eye flights, car service instead of rideshare; - relationships: who gets priority, who can be rescheduled, who gets the executive's time readily; - decision habits: no evening events booked more than two weeks out, yes to every customer call, no video meetings before coffee. When you ask for an email, a meeting, or a trip plan, the assistant has none of this. It cannot write in the executive's voice or rank requests, because it does not know the voice or the relationships. It is not bad at the job. It is uninformed. ## What the assistant needs to remember The executive's operating manual comes first: when they take meetings, how long each type runs, and which days are protected. It also records the executive's time zone for the current week. Tone by stakeholder comes second. Board members get formal. Direct reports get warm and direct. Customers get energy. Vendors get polite and brief. Travel standards come third. Record the full set, not only "aisle seat": preferred airlines, hotel chains, car services, dietary needs, meeting room setup, and AV needs. Relationships come fourth: who gets priority access, who can move, who gets a personal callback, and who gets a delegated reply. Meeting preparation comes fifth. Before a board meeting the executive wants the full deck, financials, and talking points. Before a customer call they want account history, recent contact, and open issues. They do not want long briefing documents they will not read. ## Build five context files Keep a folder of Markdown files. Claude Code reads a file named `CLAUDE.md` when a session starts. Use it to list the five files below and the rules for drafts. `exec-preferences.md` holds calendar rules and communication preferences: email, call, or text, and the expected reply time. It also records decision patterns (what gets approved at once, what needs more information). Working style goes here too: short emails, bullet points, no small talk. `meeting-protocols.md` holds meeting length by stakeholder type, what gets scheduled and what gets delegated, prep material per meeting type, and follow-up expectations. `stakeholder-map.md` holds the key people: board members, direct reports, top customers, key vendors. For each, it records priority level, tone, and context notes such as current projects and recent contact. `travel-standards.md` holds airline, hotel, car service, and dietary preferences, plus meeting room and AV needs. `current-priorities.md` holds what the executive is focused on this month, what gets priority, and what waits. ```text ## BOARD-2 (board member) Tone: formal. Opens with "Good morning." Prefers: morning phone calls, not calendar invites Meeting length: 60 minutes (board standard) Prep: full deck and financials 48 hours before Last contact: 2026-09-10, audit committee follow-up (notes: meetings/0910.md) ``` When you ask for a scheduling email to a board member, the assistant reads three files. The preferences say the executive is available 9 a.m. to 3 p.m. The protocols say board meetings run 60 minutes. The stakeholder map says this member prefers mornings and a formal tone. ## Before and after Before: "Draft a scheduling email for the board meeting with BOARD-2." The assistant writes: "Would Tuesday at 2 p.m. work?" You rewrite it: formal tone, a morning slot, 60 minutes, and a phone call instead of an invite. You correct the same mistakes on every email. After: the same prompt. The assistant reads the three files and drafts: "Good morning [first name], would you be available for a 60-minute board call on Tuesday at 10 a.m.? I can place the call from the CEO's line." You send it. Next request: "Prepare the CEO's travel for the Austin conference." The assistant reads `travel-standards.md` and produces a booking checklist. The checklist names an aisle seat on the preferred airline and a downtown property in the preferred chain. It adds car service from the airport and a meeting room with the AV setup the CEO uses. You book it in your travel tool and confirm. The assistant does not book anything itself unless you connect a booking system and approve each action. ## Resolve a scheduling conflict Two requests arrive for Thursday at 10 a.m.: a vendor renewal call and a customer escalation. You prompt: "Two requests want Thursday at 10 a.m. Rank them and draft both replies." The assistant reads `current-priorities.md`, where customer escalations sit at the top this month. It reads the stakeholder map, where the vendor is marked "can move." It keeps the customer in the slot. It drafts a short reschedule note to the vendor with two morning options. You check both drafts against the live calendar and send them. A fail looks different. If the assistant keeps the vendor in the slot, check the date on `current-priorities.md`. A priorities file that is three weeks old ranks last month's work. Put the month at the top of the file. Then add a rule to `CLAUDE.md`: if the month is not the current month, say so before you rank anything. ## A worked setup An EA to a CEO sets up the five files once. When she drafts emails, schedules meetings, or plans travel, the assistant follows the executive's rules. Priorities shift: a product launch jumps the queue, or board prep turns urgent. She then updates `current-priorities.md`, and the drafts shift with it. The files become the executive's operating manual. A new EA reads them to onboard. The assistant reads them for every task. The executive stops explaining preferences twice. When the executive corrects a draft, the EA writes the correction into the right file. The [AI correction log template](/articles/ai-correction-log-template) keeps the date and the reason with the rule. Decisions from meetings belong in a dated record too; see [AI memory for meeting notes](/articles/ai-memory-meeting-notes-decisions). ## Discretion and approval These files describe a person. Keep them discreet. Record working preferences, not health details, family matters, or private opinions about named people. "Gets a delegated reply" is enough; the reason stays with you. Claude Code sends the content it reads to the model provider over the network ([Claude Code: Data usage](https://code.claude.com/docs/en/data-usage)). Use your company's approved account and follow its policy on executive and board information. The assistant drafts. You send, and anything written in the executive's name follows the executive's rule for what you may send on their behalf. [Who approves what an AI agent sends](/articles/who-approves-what-an-ai-agent-sends) shows how to write that rule down. An executive who keeps a company-level record can pair these files with a [company context file](/articles/ai-for-ceos). ## Test the files Run three checks in a fresh session. 1. Ask for a meeting at 4 p.m. with a vendor. Pass: the assistant flags the 3 p.m. rule. Fail: it books the slot in the draft. 2. Ask for a board email. Pass: the tone is formal and the length is 60 minutes. Fail: fix the stakeholder map. 3. Ask for a trip plan. Pass: every preference from `travel-standards.md` appears. 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