Quit Guessing & Train Your AI Like a 7 Figure CEO Coach (in 90 seconds)
If your AI doesn’t have one clear brain, it has none. Most execs stuff random PDFs into ChatGPT and pray it spits out magic. Then they wonder why the answers fall flat.
Here’s the 6‑step super simple playbook I use with my Legend Media clients & partners to turn ChatGPT into a personalized laser‑focused "CEO Coach" AI—and it works even if you’ve only got 10 minutes between calls.
To keep it fun, I've programmed mine with brains plus max memeability of my two fave CEOs 👇 – you do you.
The 6 Step "One Brain" SOP
1. Create → One Project to Rule Them All
Spin up a fresh ChatGPT project (model o3 working best in June 2025) and name it after the function you want—e.g., “CEO Coach.”
This does two important things – it keeps your chats organized for future data mining and walls off the context so every answer compounds without getting "poisoned" by other chats (you know, like when your kid gets on your YouTube account and who knows what your feed shows you when you open it next!).
2. Compile → Rip & Load the Best Intel
Imagine your AI is a superhero who can read only what you hand it. If you give it a messy pile of old homework, receipts, and doodles, it wastes time digging for the good stuff. So:
- Grab only today’s most important papers —think of your OKR sheet, the score-card with your big numbers, the latest org chart, and your strategy slide.
- Leave the clutter at home —no dusty appendices, outdated drafts, or giant image files.
- Fit everything into one slim folder —fewer than 20 files, all together smaller than about three songs (15 MB).
Now your superhero AI can skim the folder in seconds and jump straight to solving your real problems.
3. Clean → Lose the Lard
Picture your AI like a kid packing a lunchbox. If you stuff it with six identical sandwiches, old apple cores, and crumpled napkins, there’s no room left for the good snacks.
- Toss the duplicates. If a page shows up twice, keep the freshest copy and bin the rest.
- Skip the ugly pictures. Old screenshots and giant images just take up space and slow your AI down.
- Delete dummy text. Anything that says “lorem ipsum” or placeholder headers is junk—ditch it.
- Get a quick summary. Still too long? Open ChatGPT, drop in the document, and say, “Summarize the key points.” Now you’ve got a neat, lightweight version the AI can chew through fast.
Clean lunchbox = happy kid. Clean files = faster, smarter AI.
4. Chunk → Slice for Recall
Think of a giant PDF like a 500-page cookbook. If you hand the whole thing to your assistant and ask, “Find me the pancake recipe,” they’ll spend forever flipping pages. Instead:
Slice it up. Copy-paste about 600–700 words (roughly 800–1 000 “tokens”) from each section into its own little text file.
Give each slice a sticky note. Name the file something obvious—“Finance-Q2”, “Ops-Hiring”, “Culture-Values”.
Save as plain text. No images, no fancy formatting—just the words.
Now, when ChatGPT looks for “quarterly burn-rate,” it jumps straight to the Finance-Q2 slice instead of wading through the whole book. Faster answers, fewer hallucinations.
5. Preface → Force the Model’s Eyeballs
Imagine your AI is an eager student who sometimes blurts out answers without looking at the textbook. By starting every question with:
“Research the project files first, then…”
you’re basically saying, “Open the book, find the right page, then speak.”
That little reminder forces the AI to read your neatly-tagged docs before it guesses, so the answer comes from your facts instead of its imagination.
6. Iterate → Version Like a Savage
Think of your files like your favorite video game saves.
When you beat a new level, you save as Level 2, not overwrite Level 1. That way, if something glitches, you can jump back to the last good checkpoint instead of starting all over.
- Make a tiny name change each time—add v1.2, v1.3, etc.
- Swap the old file in your AI project for the new one so the AI always reads the latest version.
- Keep the old saves in a folder in case you need to rewind.
Do this every update and nobody—AI, teammates, or future-you—gets lost in file chaos.
“Ask AI” Prompts That Deliver Board-Level Value in < 60 Seconds
Now you can "Ask AI" by copy + pasting instructions or questions like these into your next chat.
- “Scan all project files and surface three ‘dead’ goals we need to kill this quarter.”
- “Draft a 5‑bullet investor update that only references KPIs in the uploaded files.”
- “Identify missing data that prevents you from forecasting runway with 95 % confidence.”
- “Given our 2025 plan and P&L (links), give me the ONE decision that adds $1 M ARR fastest—tweet‑length.”
- “Audit these docs and list the top 3 gaps that block board‑level forecasting.”
- “Role‑play my CFO: push back on my hiring plan using embedded data only.”
- “Scan the org chart and P&L—show me one role we should eliminate or outsource first.”
- “Turn Q2 metrics into a 3-sentence investor brag + 1 clear ask.”
- “List the top 5 customers by lifetime gross profit and the ONE action to grow each 20 %.”
- “From our OKRs, identify the single KPI that predicts churn 30 days out.”
- “Rewrite our product vision deck as a 90-second all-hands speech—no jargon.”
- “Generate a 90-minute deep-work calendar invite titled with the ONE THING for this week.”
- “Using uploaded Slack export, surface the three biggest blockers engineers mentioned > 2×.”
- “Forecast runway if we freeze hiring today versus after closing one AE—show months left.”
- “Draft a customer-win tweet thread citing only success metrics in our case-study folder.”
- “Audit onboarding docs—list the top 3 knowledge gaps that cost new hires > 4 hours.”
Copy‑paste into your CEO Coach AI and watch the magic – it'll hand you immediate, CEO-level decisions with stats and citations, ready to tweak and execute today.
The big unlock
Think about CEO Coach like your own personal coach, not like an intern that just does what you tell it.
What Happens Next
- Ship this SOP to your team—make it law.
- When the AI starts answering like a board‑ready CEO, screenshot and share the win. After you get comfy with using it, incentivize your team to use it by rewarding the most creative uses, biggest win of the day/week, etc.
Want the one‑page cheat sheet? Grab it below, laminate it, and tape it to your screen.
📝 One‑Page Cheat Sheet – "Train Your AI in 6 Brutal Steps"
Step | Command | Tool / Reminder |
---|---|---|
1. Create | New ChatGPT project → name it CEO Coach | Model o3 |
2. Compile | Drag top docs only | Keep it < 20 files |
3. Clean | Strip fluff, images, dupes | Smaller size = faster |
4. Chunk | Split into <700 word files | Tag by topic |
5. Preface | "Research project files first, then ___" | Forces RAG* |
6. Iterate | Version v1.1, v1.2 … | Replace uploads |
*RAG = Retrieval-Augmented Generation.
Translation: the AI must retrieve answers from the files you gave it before it starts “generating” new text. Telling it “Research the project files first …” is like saying, “Open the binder, find the fact, then speak”—so it cites real data instead of guessing.
Print. Execute. Profit. NO excuses. – Daniel
🔥 Ready to let AI run your Monday‑morning sprint? Get on the waitlist for early access to the free CEO Coach App—When it saves you an hour a day, trade your email for unlimited prompts + the full CEO Coach OS.
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