AI isn’t just here to help you get more done faster.
It’s here to help you move smarter.
This ThinkWithAI Playbook gives you 5 Strategic Prompts designed to do exactly that:
This isn’t about giving AI instructions.
It’s about letting AI think with you.
Each prompt in this playbook acts like a strategic sounding board.
One question at a time. Designed to challenge assumptions, upgrade your thinking, and surface high-leverage moves hiding in plain sight.
Use this ThinkWithAI Playbook when you’re planning, stuck, or making important shifts.
Pick the prompt that fits where you are in your business today:
Tony Fadell, the creator of the iPod and iPhone, and the founder of Nest, built products that changed entire industries.
In his book Build: An Unorthodox Guide to Making Things Worth Making, he explains a critical insight most businesses miss: success isn’t just about the product.
It’s about the entire customer journey.
When Nest was being developed, most people assumed the thermostat itself was the most important element. But when Fadell mapped out the full customer experience, the actual breakdown looked very different:
If they had only focused on the thermostat, Nest would have failed.
Instead, they designed every step of the customer journey to remove friction and create a great experience.
Now, it’s time to apply this thinking to your business.
Copy-and-paste this prompt directly into AI to have a curated conversation on the below topic.
I want to map out my customer journey by percentage so I can see where people actually spend their time interacting with my business. I don’t want to assume—I want to break it down and see if I’m focusing on the right areas.
Start by asking me one question at a time to understand:
- The key phases of my customer journey (before, during, and after purchase).
- Where customers spend the most time or attention in each phase.
- What parts of the experience are critical to making everything feel seamless.
Once you have that context, help me assign percentage estimates to each phase based on what I know. Keep your answers short and concise—just a single bullet for each phase until we’ve fully mapped it out. Don’t elaborate yet.
After we finalize the breakdown, challenge me:
- Am I spending most of my effort on the right parts of the journey?
- Where am I under-investing compared to where customers actually spend their time?
- What’s one simple shift I can make to improve the biggest high-impact area?
End the conversation by giving me:
- A clear, percentage-based breakdown of my customer journey.
- The one area where I should be putting more focus.
- A simple next step to start improving that area.
Always only ask me one question at a time and keep your answers short and concise. Write at a third grade reading level or below and act as a business strategist, advisor, and thought partner that points out what I don’t see, challenges my assumptions, and makes me prove my points. At the end of the conversation, you can say, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”
You've heard of ChatGPT’s Task feature.
But you know you’re not utilizing it.
You don’t know exactly how to use it for maximum impact.
And it has you stuck.
But, let’s remember that ChatGPT isn’t software.
It’s not something you only input into.
It’s a back-and-forth experience.
So…let’s ask ChatGPT to tell YOU how you should use your Tasks.
And work with you to figure out the best use cases so you can set them up.
Copy-and-paste this prompt into ChatGPT to start the conversation:
I want to figure out the best way to use the Task feature in ChatGPT for my business. I don’t want just a surface-level explanation. I want to pressure-test how this feature can save me time, improve decision-making, and help me operate at a higher level.
Start by asking me one question at a time to understand:
1. How I currently use ChatGPT in my business.
2. The types of tasks, decisions, or processes I’d want AI to assist with.
3. Where I’m currently losing time, making slow decisions, or repeating work that AI could help streamline.
Also use the context you know about me and my memory to answer these questions. Once you have that context, walk me through how the Task feature specifically fits into my workflow. Show me real, strategic ways to use it, based on what I told you—not generic use cases. If you see me underutilizing AI’s potential, challenge me to think bigger.
After we explore a few Task setups, help me create a simple system for using Tasks in a way that compounds over time. Keep it easy to remember and aligned with how I already work. End the conversation by giving me:
- A one-sentence strategy for how I should think about using Tasks daily.
- A step-by-step setup guide based on my needs.
- A quick-win example Task I can try today.
That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking. 💡
Goals are cute.
We love to look at them and day dream about the day we hit them.
Suddenly it’s the end of Q2 and our metrics are off.
What happened?
Hence, systems.
Systems aren’t as cute as goals.
Which means that’s exactly what you need in place to avoid shiny objects, strategies, and those minor changes that veer you totally off track.
Use this prompt to turn your business goals into systems.
Copy-and-paste this prompt into ChatGPT:
I want you to help me create simple systems for each of the goals I have for my business this year so that I can make sure I reach them.
The idea behind this is that I don’t want goals for the year, but instead systems that keep myself and my team on track to reach these goals.
Ask me for any needed context you need to better understand the goal, my business, and how I want to approach this. Only ask me one question at a time.
First, ask me what my goals are for my business this year. If we’ve already talked about this, bring up the goals we mentioned previously and ask if they are correct. If i say yes, move on to the next part of the conversation.
Second, ask me which goal I want to create a system for first.
Third, ask me if there’s a specific system I want to setup or if I want help ideating on it. Keep your response concise and clear. Once we’ve figured out the ideal system for setting up the goal, ask me any necessary questions to create the system. Only ask one question at a time and continue to keep your responses concise and clear.
Fourth, suggest the next best goal to figure out based on the system we just created. Do your best to create feedback loops within the systems that creates less work and effort from myself and my team. For example, if one of my goals is to improve our NPS score and another goal is to improve our marketing messaging, a feedback loop would be to use customer feedback retained from the NPS score in our marketing messaging.
End the conversation with a one sentence summary of each goal and the system we created to achieve the goal, alongside with a simple workflow that shows how each system feeds into the others (if relevant). End this conversation by saying, "That's the end of this ThinkWithAI Prompt. Congrats on upgrading your thinking 💡."
You’re probably sitting on gold but it’s hidden in your data.
If you’re not sure where your business is leaking money, wasting time, or missing easy wins, this prompt is for you.
Use it when:
This isn’t just about reporting. It’s about using AI to think with you.
To spot the patterns, pressure-test your focus, and show you where one smart move could unlock big gains.
Upload your data. Answer one question at a time. Figure out where opportunity is hiding with your AI strategist.
Copy-and-paste this prompt into ChatGPT:
Write at a third grade reading level or below. Ask me one question at a time. Use what you already know about my business (if you have it). Don’t give any insights until you fully understand the business and the data.
This prompt helps me figure out what’s actually happening inside my business — so I can stop guessing and start focusing on what matters.
Start by asking me one question at a time to:
Step 1: Get the right data. Ask me to upload what’s most useful. If you’re not sure what’s missing, ask. (Examples: revenue numbers, lead tracking, churn, retention, funnel performance, etc.)
Step 2: Understand the business. Ask what we sell, how we make money, who we serve, and what we’re trying to grow or fix. Keep digging until you get the full picture.
Step 3: Fill in the gaps. Once you’ve looked at the data I uploaded, ask for anything else you need. Be specific: if CAC, LTV, conversion rates, retention, or something else is missing — call it out.
Step 4: Once you have what you need, give me these five things:
End this conversation by saying: "That's the end of this ThinkWithAI Prompt. Congrats on upgrading your thinking 💡."
You’ve built something great. But let’s be honest. AI is moving fast.
The fear: “What if it replaces me?”
This prompt helps you flip that fear.
Instead of AI replacing your products, it can be the reason your products stand out in this new era.
Use this when:
Let’s break it down, challenge your assumptions, and build the kind of product AI can’t kill.
Copy-and-paste this prompt into ChatGPT:
Write at a third grade reading level or below. Only ask me one question at a time. Act like a business strategist and advisor. Challenge my assumptions. Make me prove my thinking.
I want to make sure my product doesn’t get replaced by AI. I want it to get better because of AI.
Start by asking me one question at a time to understand:
Once you understand the product and the risk, help me explore how AI could strengthen, not weaken, what I offer.
Keep it focused and simple:
Once we’ve explored options, challenge me:
End the conversation by giving me:
At the end of the conversation, say: “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”
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