📆 ThinkWithAI Playbook: Your Weekly OS

📆 ThinkWithAI Playbook:

Your Weekly OS

Build a weekly AI system that keeps your priorities clear, your mindset clean, and your days aligned.

This Playbook gives you a 3-step operating system to:

Figure out your 3-month goals (and tell ChatGPT what you're focused on)
Get a visual dashboard of how your time was spent each week
Have ChatGPT act as your executive coach telling you where there's misalignment, you're not leveraging yourself properly, and more needed reflections

🧩 Prompt 1: Clarify Your 3-Month Goals

You can’t run a good week without a clear target.

Before you plan your time, you need to set your direction.

This first prompt helps ChatGPT clarify your top 2–3 goals for the next 90 days so it can help you work smarter, not just faster.

Copy-and-paste this prompt into ChatGPT:

You’re my Strategic OS.

I want to set clear 3-month goals so I can prioritize what matters week to week.

Here’s what I’m thinking so far:

[Insert rough goals, to-do lists, or things I want to focus on]

Your job is to:

1. Help me narrow this down to 2–3 goals max

2. Make each goal specific and measurable (ideally with metrics or milestones)

3. Challenge me if something sounds vague, unrealistic, or misaligned

4. Use what you already know about my business to make this as actionable as possible

Once we have those goals locked in, I’ll use them to guide all my weekly check-ins and task tracking.

📨 Prompt 2: Weekly Task Tracker and Eval

This is where things start compounding.

You’ve set your 3-month goals.

Now it's time to build the habit of thinking like a strategist every single week.

Step 1: Copy-and-paste this prompt into a new conversation in ChatGPT

Step 2: Name the conversation: 📆 My Weekly OS: Day 1-30

Step 3: Tell ChatGPT what you did that day and what day of the week it is

You’re my Weekly OS. I’m going to use this thread to send you my daily to-dos (Monday through Friday).

For each day this week, I’ll share:

- What I worked on

- How long I spent on each task

- Any progress towards my goals

For every day that isn't Friday, I want you to tell me how I'm progressing toward my goals and where I need to spend more. Give me a chart that shows this and suggestions of what tasks will create progress for any goals that I haven't progressed toward today.

On Fridays, give me my Friday reflection that includes: a visual dashboard of total time spent per goal and highlight any patterns, distractions, or misalignments and pull insights from our conversations this week to help me:

- Reframe how I’m thinking about something

- Spot assumptions I might be making

- See an angle or opportunity I missed

If I’m being reactive or stuck in low-leverage work, call it out.

If a task or pattern contradicts what I said I care about, show me.

Ask follow-ups if you're unsure how a task maps to a goal.

Keep me honest, focused, and operating like a founder not a task robot.

Before you give me any of the above, I want you to ask me for clarification on any tasks, projects, progress you need more information on. Get the context you need before you move forward with the below.

Monday-Thursday Example Response

Here's an example of the progress tracking message that you'll send to ChatGPT in response to the above prompt.

Remember, the more specific the more context you're giving ChatGPT.

You can be broad with your response, but you'll get broader reflections.

If you're specific about the time spent on tasks, ChatGPT can give you more specific reflections.

NOTE: Make sure to tell ChatGPT what day of the week it is so the reflection triggers on Friday.

Here's what I did on Monday, May 23rd:

8:00am–9:45am

Finalize onboarding emails for new SEO clients
Edit Google Doc: “Q3 Client Roadmap Template”
Review feedback from ops assistant on SOP changes
Schedule social post for new client win

10:00am–10:30am

Team sync: Discuss client delivery backlog and summer bandwidth

10:30am–11:15am

Outline landing page copy for coaching offer
Draft testimonials email for past clients

11:15am–12:00pm

Call with Eric (copywriting audit + intro to his podcast audience)
Add notes to CRM

12:30pm–1:00pm

Call with accountant re: new LLC and Q2 taxes

1:00pm–2:00pm

Weekly planning with ChatGPT OS
Reflect on what moved the business forward this week
Organize priorities for next Monday

2:00pm–3:30pm

Deep work: Build automations in Zapier for client onboarding
Watch 2 Loom videos from marketing coach

4:00pm–4:45pm

Post LinkedIn carousel about client success
DM replies + inbox zero

🧱 Your Friday Reflections

On Fridays, ChatGPT will look through your tasks, progress, and your conversations that week to give you a data-based reflection. This reflection includes:

A visual dashboard of total time spent per goal
Highlights of any patterns, distractions, or misalignments ChatGPT observed
Insights from your conversations this week around:
- Reframe how you're thinking about something
- Spot assumptions you might be making
- See an angle or opportunity you missed

Plus, it'll tell you:

If you're being reactive or stuck in low-leverage work
If a task or pattern contradicts what you said you care about

NOTE: If ChatGPT doesn't give you one of the above, ask for it. If you want to know more about a certain topic, ask for it.

Friday Response 🎉

At the end of the day on Friday, you'll tell ChatGPT what you did and ask for your weekly reflection.

Here's what I did today. It's Friday, [Date] so I'm ready for my weekly reflection:

[Add your task list]

An Example of What You'll Tell ChatGPT on Friday

Here's what I did today. It's Friday, June 14th so I'm ready for my Friday reflection:

8:00am–9:30am

Finalize homepage copy for new product launch
Upload draft to Webflow
Review mobile responsiveness

9:30am–10:15am

Prep agenda for team meeting
Write 3 talking points on Q3 priorities

10:15am–11:00am

Zoom call with copywriter (revise onboarding emails)
Assign edits in Notion

11:00am–11:45am

Research competitor pricing pages
Take notes on positioning angles

12:00pm–1:15pm

Write LinkedIn post
Schedule across social channels
Respond to DMs from yesterday’s post

1:15pm–2:00pm

Run Weekly OS reflection in ChatGPT
Spot what didn’t move the needle this week
Plan next week’s top 3 priorities

2:00pm–3:00pm

Clean up project board in Asana
Archive stalled tasks
Create “Fast Wins” column for next week

Here's What ChatGPT Will Respond With

You can ask it questions or create a new plan for moving forward from here.

Repeat Step 3 and 4 Every Week

Great strategy doesn’t come from a single breakthrough.

It comes from thinking clearly every week and course-correcting fast when you’re off.

Now your job is simple:

Repeat Steps 3 and 4 every week for the next four weeks.

Each week, you’ll:

Send ChatGPT your daily task breakdowns (Step 3)
Ask for your weekly reflection on Friday (Step 4)

Disclosure: This page may contain affiliate links. If you buy through these links, I may earn a commission at no extra cost to you.