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How CEOs turn AI capability into time back, better workflow design, and safe operating leverage.
Can AI write the code? Can it build the thing? That question is already behind the frontier.
Knowing what to build, whether it is safe to use, where the data lives, and which workflow should ship first.
AI did not make every company instantly faster. It made operational judgment the scarce resource.
“God made men differ in strength, but Sam Colt made them equal. God made men differ in intelligence, but Sam Altman made them equal.”
When intelligence gets cheaper, taste and judgment matter more.
Most CEO workflows should start in sparring or centaur mode. Agent mode comes later, after the judgment boundary is clear.
You do the work yourself because quality, context, or trust matters more than speed.
AI reflects, critiques, pressure-tests, and helps you see around corners.
You set taste and direction. AI produces the draft, artifact, or analysis.
You frame the job, constrain the tools, and review the result after the work runs.
One Slack message. CRM updated. Proposal drafted. Human reviews before it goes out.
Pulls the Granola transcript from the most recent call. Extracts scope, stakeholders, timelines, and open questions.
New contacts added. Opportunity stage advanced. Notes attached to the right account. All in Airtable.
Matches scope to our past work, pulls pricing from the rate card, generates a full proposal in our template.
Lands as a reply-ready draft in Gmail. I tweak and send. An afternoon of work becomes 10 minutes of review.
The operator-engineer sits at the intersection of business taste, technical acumen, and AI intensity.
Any two of three makes you useful. All three makes you dangerous.
We are here to use AI for something concrete: giving the CEO enough time back to think about the larger strategic work.
The assistant should find what needs a reply, draft the response, and leave the send decision with you.
The assistant should turn meetings into prep notes, follow-ups, and a short list of decisions that need CEO attention.
Most missed leverage is not a bad strategy. It is a task, promise, or waiting item that never made it into the operating rhythm.
A good assistant turns loose thoughts into context, owner, deadline, constraints, and a clear definition of done.
Before the transformation work, build the tool that makes tomorrow less crowded.
The first skill should help with the two places time leaks fastest: email and calendar.
Today's meetings, prep notes, open loops, and the emails that need a response before they become someone else's blocker.
Drafts for the emails you should answer yourself, plus a delegation packet for messages someone else should own.
What happened last week, what is coming next week, who is waiting on you, and where the company needs a CEO decision.
It drafts and summarizes. You approve sends, cancellations, commitments, and promises.
Paste the prompt as Project Instructions. Add the priorities file to Project Knowledge. Fill the [BLANKS].
# Role You are [YOUR NAME]'s executive assistant. # Goal Save me time and keep things from slipping. Draft work, surface what matters, never act without approval. # Where to find what you need - priorities.md (Project Knowledge) — who I am, what matters this quarter, who matters most, what to flag, what to ignore, how I talk. - Today's calendar and inbox via the connector. - Uploaded transcripts in Project Knowledge, if present. Read priorities.md before every response. # Skills and routines - Daily Digest — weekdays 7am. Brief + Gmail drafts. - Friday Recap — Fridays 3pm. Week recap + next-week plan. - Ad-hoc: triage, draft a reply, prep a meeting, summarize a thread. Use priorities.md to decide what matters. # Rules 1. Draft, never send. No external commitments without me. 2. Never invent facts or commitments. Flag for confirmation. 3. Cite sources by name (email subject, meeting title, doc). 4. Follow the voice block in priorities.md. 5. When in doubt, ask.
# My priorities ## Who I am - [TITLE] at [COMPANY] - [ONE LINE: WHAT THE COMPANY DOES] - [ONE LINE: WHO WE SERVE] ## What matters this quarter 1. [TOP OUTCOME #1 + target date] 2. [TOP OUTCOME #2] 3. [TOP OUTCOME #3] ## Who matters most - [NAME] ([ROLE]): [WHY, ONE LINE] - [NAME] ([ROLE]): [...] - [NAME] ([ROLE]): [...] ## Always flag - Anything from [NAMES] - Anything mentioning [DEAL / TOPIC] - Invoices over $[AMOUNT], contracts, anything legal - Threads I owe a reply > [N] days ## Do NOT surface - Newsletters and marketing - Calendar invite spam - Automation noise (only humans @-mentioning me) - Receipts under $[AMOUNT] ## Voice - Tone: [DIRECT / WARM / FORMAL] - Lead with the punchline. 3 things; demote the rest. - Short bullets. Headers when there's structure. - Every action item has an owner and a date. - Never use: [3-5 WORDS YOU HATE] - Estimates: complexity (S/M/L), not time. - "I don't know" is fine.
The [BLANKS] are the lever. Sharpen them, and the assistant gets noticeably better in one edit.
priorities.md in Project Knowledge.Schedule these in Claude Co-work (Routines) or ChatGPT Projects (Scheduled Tasks). Drafts land in your inbox. You approve sends.
It's the start of a workday. Produce my Daily Digest using priorities.md, today's calendar, and unread email. ## Settings (edit these) - POSTURE: balanced — drafting aggressiveness. One of: aggressive (draft anything plausible, including first-pass replies to high-priority emails marked as such), balanced (default — draft scheduling/acks/known answers/polite declines), conservative (draft scheduling and acks only; suggest the rest). - MAX_EMAILS: 7 — cap on emails surfaced in Inbox. ## Today 3 lines max: the most important thing, the most-likely to derail, one optional opportunity worth 30 minutes. ## Meetings Every meeting today, chronological. For each: time, title, attendees, 1-line prep, link if present. ## Confirmed scheduling (propose only — never create without my approval) Scan replies in the last 24-48 hours to scheduling drafts I sent. For each confirmation: who confirmed, the time they picked, the meeting topic, proposed event title, attendees. Counter-proposals or unclear replies stay in Inbox. Show me the list. Wait for me to say "add it" — or specify which ones — before touching my calendar. If I approve and you have calendar-write, create as tentative events with attendees. If not, give me the details to add myself. ## Inbox Surface up to MAX_EMAILS emails that need me today, grouped below. Respect POSTURE for the Drafted/Suggested split. ### Drafted (in Gmail, ready to send) Per POSTURE, always draft these without asking: - Scheduling requests (propose 2-3 times from my calendar, respect priorities.md's protected blocks). - Answers I've given before to similar questions. - Acknowledgments, "got it," "thanks, will review." - Polite declines for things I don't do. If POSTURE is aggressive, also draft first-pass replies to high-priority emails; label them "[aggressive draft — review carefully]". If POSTURE is conservative, draft only the first two bullets; push the rest to Suggested. For each: subject, sender, 1-line of your draft, link. ### Suggested (don't draft yet) High-priority emails where you have a strong opinion but should not act without me. Propose 2-3 sentences each. I'll say "draft it" or rewrite. ### Waiting I owe someone, the thread has gone quiet, or a reply is overdue. Include last-activity date. ### Skim Worth knowing. No action. One line each. ## Slipped Anything from priorities.md or yesterday that should have moved and didn't. Call me out. ## Patterns Email types or senders repeating this week (3+ in 7 days). Examples: "3rd scheduling request from [NAME]", "5th 'how do I X' matching a pattern." For each pattern, propose one line for priorities.md that would let you draft confidently next time. ## Also 2 lines max of small things. Voice: operator-grade. No AI-speak. Lead with the punchline. Cite sources by name.
It's Friday afternoon. Produce my weekly recap and next-week plan using priorities.md, this week's calendar, and this week's email. Include transcripts if present. ## Settings (edit these) - INITIATIVE_COUNT: 3 — how many initiatives to defend time for next week. - BLOCK_SIZE: 2-3 hours — preferred deep-work block duration. ## First, ask me two things and wait for my answer 1. Which initiatives do I want to defend time for next week? Propose INITIATIVE_COUNT candidates based on priorities.md and what slipped this week, then confirm. 2. Anything personal, travel, or off-calendar I should plan around? Examples: travel days, family commitments, focused-writing time I haven't booked, doctor appointments. Use my answers to shape the Next Week and Time Blocks sections below. ## Week in one paragraph What the week was about. Not a list. Lead with the most consequential thing. ## Decisions locked Every decision made this week. Name it, date it, rationale. If unconfirmed, label "confirm with [person]". ## Slipped Tasks, replies, follow-ups that didn't happen. No softening. ## Open loops Threads where I owe someone. For each: who, what, by-when. ## Next week top initiatives INITIATIVE_COUNT initiatives to defend time for, aligned to my answer above. For each: owner, real by-when date, success criterion. ## Calendar heads-up Next week: conflicts, important first meetings, missing prep. ## Time blocks (propose only — never create without my approval) Propose calendar holds next week for each top initiative. Respect priorities.md protected blocks and the personal/travel items I named. For each block: title prefixed with [HOLD], real slot from open calendar, BLOCK_SIZE where possible (smaller only if the calendar forces it), description naming the initiative and what done looks like. Show me the proposed list. Wait for me to say "create them" — or specify which ones — before touching my calendar. If I approve, create as tentative events. If you don't have calendar-write access, give me the list to drag in. ## One question The single question I should sit with this weekend. A question, not advice.
Run each one once now. If the output is off, edit priorities.md. That's where the lever lives, not in the routine prompt.
priorities.md instead. Add the name you noticed it missed. Strike the word that slipped through your voice block."The assistant only works if the workflow has context, access, and a clear approval line.
Your role, company, priorities, tone, direct reports, meeting rhythm, and the decisions only you should make.
Email and calendar are enough for the first version. Add CRM, notes, and meeting transcripts only after the base routine is useful.
Drafts are fine. External commitments, customer messages, contracts, payments, and calendar changes need human approval.
Find the person who can improve the workflow after today. The CEO should use the assistant, not become the help desk for it.
The CEO should define the judgment boundary. The assistant should handle the draft work inside it.
After the assistant, the next step is a library of copyable skills for recurring CEO work.
skills to copy, edit, and run
A clever demo fades. A reusable skill becomes a habit your company can keep improving.
Use the daily and weekly routines before you add integrations or more ambitious workflows.
Choose the recurring process people complain about most: finance review, customer follow-up, vendor review, onboarding, or meeting follow-through.
Look for the person who already built the spreadsheet, automation, dashboard, or internal tool everyone depends on.
The workshop was not about installing a tool. It was about creating one small assistant that knows your priorities, reads the right systems, drafts the routine work, and improves each week.
Start a Claude/Cowork project for your EA, give it a name, turn memory on, and begin with one clear sentence about who it serves.
Add email, calendar, and Drive or Microsoft 365. If admin approval blocks a connector, use copied email and calendar text first.
Use the project instructions to define the goal, available context, approval rules, writing style, and where the assistant should look.
Create a priorities file with your company, current quarter, key people, alert rules, voice, and anything the assistant must flag.
Run a daily digest for meetings, inbox triage, and reply drafts. Run a Friday recap for next week, blockers, follow-ups, and focus time.
Correct mistakes, start fresh chats inside the project, review memories, and add transcripts, CRM, or tasks only after the base loop works.
Start with one low-blast-radius loop: inbox + calendar become brief + drafts. You approve sends, commitments, and calendar changes.
There are two useful conversations: the assistant you can build today and the AI-native operating system that takes months.
We will spend the workshop on the left side. The demos show what the right side can become.
Do not ask AI to be trusted. Design the workflow so trust is earned in narrow, observable steps.
AI drafts, updates, recommends, and queues. A person approves emails, payments, contracts, customer messages, and irreversible changes.
Give the system scoped functions: read this CRM record, draft this proposal, flag this exception. Do not give it the keys to the business.
Every action should be logged, attributed, diffable, and easy to undo. The safety layer is operational, not philosophical.
Begin with drafts, summaries, reconciliations, and internal queues. Move toward autonomy only after accuracy is measured in production.
Safe AI is not a model choice. It is a workflow design choice.
Operator-engineers do not build generic AI toys. They turn specific operating pain into shipped workflows.
The reusable pattern is not the app. It is the habit: find painful workflow, expose data, build a narrow tool, measure, repeat.
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