🦉 ThinkWithAI Playbook: Turning AI into Your Advisor

AI isn’t just for automation.

Used the right way, it becomes something far more valuable:

A business advisor that never gets tired, always asks the hard questions, and helps you make smarter, faster, more confident decisions.

This ThinkWithAI Playbook gives you 5 Strategic Prompts designed to do exactly that:

Create your business vision that drives every decision
Turn challenges into money making opportunities
Create a visual of how your business is actually doing. (and use ChatGPT Task’s to update it)
Prepare for the problems your goals come with
Use the 80/20 rule to figure out how to get more leverage without more work

Each prompt is a guided conversation.

One question at a time. Built to pressure-test your thinking, surface what you're not seeing, and unlock moves that compound.

The goal isn’t to get answers from AI.

It’s to think better. Using AI as the advisor that helps you move forward, faster.

Pick-and-choose the most relevant prompts for you to go through based on where you are in your business.

💬 Strategic Prompt: Use the Entrepreneurial Operating System to Get Clear on Your Vision

EOS is used by thousands of growth-stage companies to get aligned, stay focused, and make faster decisions.

But most founders treat the Vision section like a form to fill out.

This prompt treats it like what it actually is.

A strategic lens for everything you build next.

You’ll walk through your 10-Year Target, 3-Year Picture, and 1-Year Plan.

Not to check a box, but to make sure each one is connected, clear, and actually helps you say no to the wrong things.

ChatGPT will act as your advisor asking one question at a time, challenging soft spots, and helping you spot gaps you might not see.

By the end, you won’t have a vision doc.

You’ll have a North Star that makes it clear to you, and others, what you’re doing and where you’re going.

Copy-and-paste this prompt directly into AI to have a curated conversation on the below topic.

I want to work through my EOS Vision to make sure it’s clear, aligned, and actually useful for decision-making. I’m not looking for vague goals—I want to map out a real direction I can build toward.

In this prompt, act as my advisor. Ask me one question at a time to understand the following. Also give your two cents based on what you know about me and my business already.

- What future I’m building toward (10-Year Target)

- What success looks like in 3 years (3-Year Picture)

- What my 1-Year Plan is and whether it sets me up to get there

Once you have that context, help me connect the dots.

- Does this vision make sense based on what I’ve told you?

- Is anything missing or unclear?

- Where am I playing it too safe or setting goals that won’t move the business forward?

Keep your answers short and concise—just one bullet per idea until we’ve mapped everything out. Don’t elaborate. If something sounds vague or weak, challenge me to back it up or rethink it.

At the end of the conversation, give me:

- A clean version of my Vision, 3-Year Picture, and 1-Year Plan

- A short list of what I should revisit or make stronger

- One sentence I can use to stay focused on this vision every week

Always ask one question at a time. Keep your answers short and simple. Write at a third grade reading level or below. Act as a business advisor who challenges assumptions, points out gaps, and helps build a direction worth committing to.

At the end of the conversation, say, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

💬 Strategic Prompt: Turn Challenges into Opportunity (Advice from a Billionaire)

This prompt comes from How to Make a Few Billion Dollars by Brad Jacobs.

It’s the perfect reminder that within adversity there are opportunities.

Embrace everything that comes your way, the good and especially the bad. And don't just accept adversity - figure out how to capitalize on it. Brad Jacobs

A great example of this is Jeff Bezos who is infamous for building products around the most inconvenient parts of his business.

Problem: Amazon’s internal infrastructure for handling web services was slow and inefficient.
Inconvenient Business Reality: Scaling a website required massive server investments, making it hard for startups to compete.
Bezos’ Solution: Amazon turned its internal cloud computing technology into Amazon Web Services (AWS) in 2006, offering it to other businesses.
Impact: AWS became the backbone of the internet, powering Netflix, Airbnb, and countless startups. It now generates more profit than Amazon’s retail business.

Inconvenience = Opportunity

If you think about it through that lens.

Copy-and-paste this prompt into ChatGPT:

I want to embrace everything that comes my way, good and especially bad. Specifically, I want to think through the approach from How to Make a Few Billion Dollars by “not accepting adversity but figuring out how to capitalize on it.”

I want you to ask me for one challenge I’m facing right now that is extremely frustrating. Ask me one question at a time to get the context you need before giving me creative ways to turn this adversity into massive opportunity.

Keep your answers short and concise and write at a third grade reading level. The goal is that you get so much context that when you tell me a creative way to turn this adversity into opportunity it is perfectly aligned to my business, the time I want to spend on this, and my experience.

Make your opportunity suggestion realistic (example: don’t tell me to open a venture fund with $100 million if I’m making $40,000/month). Work with me to figure out the best possible way to see this adversity through a new lens.

If I say that I can’t do something, ask me for the data and context you need to prove that I’m not making assumptions and using my false cognitive biases to see this challenge as opportunity.

At the end of the conversation, say, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

💬 Strategic Prompt: Create a Visual Representation of How Your Business is Doing

I love listening to the Founders Podcast.

It reminds me that business is always challenging.

Despite what the internet has us thinking - most of the time business is a slog.

It’s not this easy multi-million dollar result from cashing in on a quick trend.

It’s more like wack-a-mole. But each mole is a problem. And each time you wack one (successfully solve the problem) another pops up.

And somehow.

In some way.

It’s awesome.

Instead of thinking that every single part of your business has to be going well for it to be successful, let’s get realistic.

There will always (always) be somethings going great and others going terribly. Instead of aiming for perfect aim to have a clear understanding of where you are.

Cue the visual representation. 🖼️

This prompt shows you how to see how your business is doing. You’ll figure out what’s going well, what’s going okay, and what’s going terribly.

ChatGPT will put it all into a neat little spreadsheet and you can take that spreadsheet and put it into your project management software (I use Notion). Now you can visually see how things are going (and remind yourself that not EVERY part of the business is a catastrophe).

Copy-and-paste this prompt into ChatGPT to start the conversation:

I want to create a visual representation of how my business id doing. I want to do this by first going through the thought exercise of answering the below 3 questions. Each question may have several answers (for example: What's going well: networking, organic content, and partnerships). Note that some questions may only have one answer. To figure out the answer to these questions get the needed context from me and through what you already know about my business. When you ask each of the 3 questions, always fill in what you know about the business so that we’re working together to find the answers. Only ask me one question at a time and keep your answers short and concise here.

1. What’s going well (green)

2. What could be better (yellow)

3. What’s going terribly (red)

For each answer, I want to say a specific KPI that I'm aiming to reach that makes it green and what KPI would make it red. For example, networking is going great because I have 5 meetings on average per week. Organic content marketing isn't going well because I only get 10 leads from organic traffic per month and the goal is 100.

Once we have this figured out, I want you to create a spreadsheet for me that showcases each topic and it's status (green, yellow, or red), the associated ideal KPI, and a note about why it's going well, what will be improved, or what needs to change/get implemented.

Once we have this, I want you to prompt me to create a Task inside of ChatGPT to update this spreadsheet in two weeks. Tell me to switch my model over to GPT-4o with scheduled tasks (beta) and tell ChatGPT to "Create a Task titled "Update Performance Spreadsheet" that occurs every two weeks on Friday at 10am."

Once this is done, I want you say "You've finished this ThinkWithAI Strategic Prompt conversation. Congrats on upgrading your thinking. 💡 If you want to continue this conversation, feel free to send another message with how you'd like to move forward."

💬 Strategic Prompt: Preparing for The Problems You’re Saying Yes To

What happens when you make a decision to reach a certain goal in your business?

You take action…and inevitably run into problems.

Your mind starts to tell you that the other options would have been easier.

You’ve made a mistake in your decision making.

But is that actually true?

Realistically you agreed to these problems when you decided to go for, and reach, this specific goal.

If you want your business to make $1 million/month…that is guaranteed to come with a list of problems you’ll have to work through.

This week’s strategic prompt shows you the problems you’re agreeing to by:

Going through the process of reaching your goals (ex. on the road to $1M/month your systems will break)
Reaching your goals (ex. now we’re paying massive software fees to upkeep this customer base)

You’ll use ChatGPT to talk through your business goals (or reference them from the 2025 Business Goal Setting prompt you already went through) and get a list of problems coming your way.

Now, when you reach those problems they won’t make you think, “Damn it the other decision would have been better.”

Instead, you’ll realize that these problems are 1) totally normal, and 2) mean you’re on your way to reaching this goal.

Copy-and-paste this prompt into ChatGPT:

Based on my business goals, I want to figure out the problems that I'm saying yes to by agreeing to reach for and accomplish these goals. If you know my business goals, write the list here as one sentence bullet points.

Ask me if the goals are correct and make updates as needed based on my response. If you don't have my business goals, start the conversation by asking me to list my business goals before moving forward.

Once you have my goals, I want you to create a 6 bullet list of the problems I'm saying yes to by agreeing to each of these goals.

So for each goal there should be 6 bullets. The first 3 bullets of the list should be about the problems I'm saying yes to by going through the process of reaching these goals. The other 3 bullets should be about the problems I'm saying yes to when I have reached these goals.

After you send the bullets ask me if I want to add any bullets to the list.

Once we have the final list, create a statement that says "I know X will be a problem as I reach for Y goal," and "I know X will be a problem once I have reached Y goal."

Give me an easy copy-and-paste message that I can put somewhere to remind myself that these problems are normal and expected as I reach for and accomplish these goals. Remember the conversation we had.

At the end of the conversation, say "You've finished this ThinkWithAI Strategic Prompt conversation. Congrats on upgrading your thinking. 💡"

💬 Strategic Prompt: The 80/20 Decision Rule

You don’t need more effort.

You need more leverage.

This prompt is built for moments when you’re busy but not moving fast. When it feels like you’re working all day but not getting closer to what matters.

It’s designed to help you:

Cut through noise
Spot high-leverage decisions
Stop wasting time on the wrong work

If you're chasing every task, you're not thinking clearly.

This prompt slows you down just enough to speed you up by forcing ruthless clarity on what actually drives results.

Use it when you're stuck in motion but need momentum.

The prompt starts with a few quick questions to get context. Then it walks you step by step through:

Finding the 20% of actions that drive 80% of outcomes
Killing low-value decisions
And making one shift today to move the needle

Copy-and-paste this prompt into ChatGPT:

I don’t just want to work harder. I want to make decisions that multiply my results. I need a way to filter through distractions and focus on the few moves that will drive the biggest impact.

Start by asking me:

What I’m working on that requires decision-making.
What I think are my most important priorities.
Where I might be spending too much time on things that don’t really matter.

Once you have that context, guide me through:

How to find the 20% of actions that create 80% of my results.
How to cut out the 80% of decisions that are slowing me down.
How to shift my strategy so I’m only making high-leverage moves.

If I’m focusing on the wrong things, push me to prove why they actually matter. If I’m missing an opportunity, make me see it.

At the end, give me:

A ruthless way to prioritize my decisions for impact.
A system to stop wasting time on low-value choices.
One immediate change I can make today to get better results.

Only ask me one question at a time throughout the conversation. Keep your answers short and concise. Write at a fourth grade reading level or below the entire time.

At the end of the conversation, say "You've finished this ThinkWithAI Strategic Prompt conversation. Congrats on upgrading your thinking. 💡"

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