The 30-Day AI Starter Plan
From "I should really use AI more" to an assistant that reads your inbox, your calendar, and your to-do list.
You do not need to code anything, and you do not need an engineer. You need three things: standing context, connected tools, and a review habit. This plan builds them in four weeks, about twenty minutes a day. It's written for Claude (claude.ai), which is what I use and what I demo in the session; if you'd rather use ChatGPT, the appendix at the end maps every step, and every prompt works as written in either tool.
Week 1: Give it standing context
The single biggest upgrade available to you is to stop re-introducing yourself in every conversation. In Claude, that container is called a Project: a workspace with standing instructions that every chat inside it already knows.
- Day 1-2. Sign in at claude.ai and create a Project. Name it "Chief of Staff." That name is a decision about what you're building.
- Day 3-4. Build your context document with Prompt 1 below, then paste the result into the Project's instructions. Aim for one page: who you are, what your business does, who your customers are, how you like things written, what it should never do without asking.
- Day 5. Test it. Ask for something you'd normally have to explain ("draft a reply to a customer asking about turnaround time") and see how much it already gets right. Fix the instructions, not the prompt.
Prompt 1: The context interview
"I want you to build a standing context document about me and my business, so future conversations start with you already knowing me. Interview me one question at a time: my role, what the business does and for whom, my top three recurring responsibilities, how I like my writing to sound (show me two style options and let me pick), and the things you should never do without asking me first. Then write it up as a one-page brief I can paste into my Project instructions."
Week 2: Connect your tools
This is the week that separates an AI you visit from an assistant that knows your day. In Claude's settings, under Connectors, you can connect Gmail and Google Calendar (and more: Drive, Notion, others). Each one is a checkbox and a permission screen, not a project. Connectors need a paid plan; see the cost box below.
- Day 8. Connect Gmail and Google Calendar. Read the permission screens; you are deciding what it can see, and you can disconnect any time. That control is the point.
- Day 9-10. First connected asks: "What's on my calendar this week?" then "What's sitting in my inbox that actually needs me?" Notice you pasted nothing.
- Day 11-12. Run Prompt 2 each morning and read the result with coffee. This is the habit the rest of the plan builds on.
Prompt 2: The morning brief (connected)
"Read my calendar and my inbox for today. Give me a one-page brief: the three things that matter most today and why, anything in the inbox that needs me before noon, what can slip without consequence, and one thing I appear to be forgetting. Be direct. If something on the calendar collides with something in the inbox, lead with that."
Week 3: Automate one task
Not five tasks. One. Pick the recurring task you complained about most recently: the weekly customer email, the meeting recap, the quote follow-up. Frequency beats size: a daily 10-minute task is worth more than a monthly 2-hour one.
- Day 15-16. Do the task WITH Claude once, inside your Project, conversationally. Notice what you had to correct: that's missing context. Add it to the Project instructions.
- Day 17-18. Turn it into a repeatable prompt with Prompt 3. Save it wherever you'll actually find it.
- Day 19. Run the saved prompt on a fresh instance of the task. Time it. Write the before and after numbers down; you'll want them in week 4.
Prompt 3: The task recipe builder
"I just did [task] with you. Turn what we did into a reusable prompt I can paste any time this task comes up. It should state the job, the format I want back, my standing preferences from context, and end by asking me only for the inputs that change each time. Show me the prompt, then test it by running it on a new example."
Week 4: Close the loop, and draw the line
Two moves this week: add the end-of-day close so your mornings and evenings share memory, and write the boundary rules that make the whole thing safe to rely on.
- Day 22-25. Add Prompt 4 as your last two minutes of the workday. By midweek, the morning brief opens with what yesterday's close left unfinished. That loop is the system; everything else is decoration.
- Day 26-27. Write your rules of the road (Prompt 5). Decide what it drafts but never sends, and what data never goes in.
- Day 28-30. Tally it: compare your week-3 timing notes to now. Most people find 3-5 hours a week. Then pick the next lane, because by now you'll have a list.
- Bonus, day 30: make it a routine. In Claude's app, look for scheduled tasks and turn Prompt 2 into one: every weekday, 6:45 AM. Now the morning brief is waiting with your coffee, without being asked. That's your first routine, and the first time the system works while you sleep.
Two words you'll meet next: routines and skills
A routine (Claude calls them scheduled tasks) is a prompt that runs itself on a clock: the morning brief at 6:45, a Friday afternoon week-in-review, a monthly "search the web for [your industry] news." A skill is a saved recipe: a process you teach once, in your way, that Claude then applies without being re-told. The prompts you saved in week 3 are starter skills in spirit; when you're ready, Claude lets you install pre-built skills and write your own. Between routines (when) and skills (how), you stop being the person who has to remember to ask.
Prompt 4: The end-of-day close
"Day's over. Here's what happened, in fragments: [talk or type freely]. Update my running to-do list: mark what's done, add what's new, flag anything I promised someone. Then tell me the first thing tomorrow-me should do."
Prompt 5: Rules of the road
"Help me write a one-page AI policy for how I work with you. Cover: what you draft but I always review before it goes to another person, what categories of information I will never give you access to (customer personal data, passwords, anything under legal privilege), and how I'll spot-check your work. Keep it short enough that I'll actually follow it."
The three rules that keep it safe
- Nothing leaves the building without your eyes. AI drafts, you send. Every email, every post, every quote. This rule never expires, no matter how good the drafts get.
- You decide what it can see. Connectors are permissions you grant and can revoke. Some things never go in: customer personal details, financial credentials, anything a lawyer is involved in.
- Trust is earned per task, not granted to the system. Let a workflow prove itself five times before you stop checking every line. And keep checking occasionally, forever.
What it costs, honestly
Claude's free tier is enough to try Week 1. Connectors and steady daily use need Claude Pro: $20 a month, or $17 a month billed annually, and the annual toggle is the only discount that always exists. Teams run $25 per seat annually. There are no promo codes, so ignore the coupon sites; when Anthropic runs a real promotion it shows up as a banner inside claude.ai. Weigh $20 against the 3-5 hours a week this plan typically returns.
One Claude, three places it lives
Everything in this plan happens in the chat at claude.ai, in your browser: that's the front door, and it's plenty. Claude Cowork is the desktop app, where it can work with the actual files on your computer. Claude Code is the deep end: it runs on your machine and powers scheduled routines, like a morning brief that builds itself before you wake up. Start in chat. The other two are where the second session lives.
When you outgrow this plan
Everything here runs in a browser tab. The next level runs on your computer: your texts in the loop, scheduled routines that build your brief before you wake up, an assistant that works while you sleep. That's a second session, if this group wants one, and it's the version I run my own life on. Tell Kate, or tell me.
Want help building your version?
This plan gets a system started. If you want one built around your business, that's the work I do. Tell me what you're hoping to build and I'll follow up personally, or email me at hello@shannonowens.com. I read everything.
Appendix: Using ChatGPT instead
Every prompt in this plan works word-for-word in ChatGPT. The containers have different names:
| In this plan (Claude) | ChatGPT equivalent |
|---|---|
| A Project with instructions | A Project, or Custom Instructions in Settings for an account-wide version |
| Connectors (Settings, then Connectors): Gmail, Google Calendar | Connectors (Settings, then Connectors or Connected apps), availability varies by plan |
| Claude Pro, $17-20/month | ChatGPT Plus, about $20/month |
| The morning brief reads your connected tools | Same idea once connectors are on; otherwise paste your calendar and to-do list into Prompt 2 and it works fine |
Feature names and plan details in both tools change often; the three rules and all five prompts don't care which tool you pick. Pick one, not three: switching costs more than any tool difference.