Most people treat AI like a vending machine.
You put in your question, out pops an answer, and then you move on with your life.
I did that for awhile too.
You know what I learned in the process?
Nothing.
So I started experimenting by doing things differently because, well, that’s what I do. It’s a disease.
I decided to use AI to create the environments I couldn’t easily create on my own. At least not without a lot of time and a lot more spending.
The first thing I did was put four of the world’s smartest experts in a room and made them argue about how I should approach the growth of my business.
The conversation changed everything for me.
Then I created the perfect personal mentor for me to keep me on track. My mentor knows my strengths, my weaknesses and, more importantly and more annoyingly, calls me out on all the bullshit excuses I tell myself.
This is the exact type of mentor I was looking for 20 years ago.
Then I created the expert whose entire job is to tell me the reasons why my brilliant new idea that I know will change the world, is actually going to fail.
And the frustrating thing, is this devil’s advocate always has really valid points.
That was all just the beginning of my journey. And it’s the journey I’m going to allow you to take now.
Because the real value of AI isn’t simply getting answers to questions.
The value of AI is forcing you to question the things you thought were right.
So today I’m sharing four of my favorite AI prompts.
These aren’t your typical “write me an email” or “summarize this meeting” crapola. You can find that stuff anywhere.
These are prompts designed to make you think different.
They will challenge your assumptions about your work, your ideas, and even your life.
I’m warning you, they feedback feels real. It continues to be some of the most real conversations I’ve had with AI.
Which means the conversations can piss you off. In fact, my AI mentor really annoyed me recently so I had to push back. Here’s what happened.
The first three prompts are completely free. The fourth is for Inner Circle members. Inner Circle members get a new AI prompt every Tuesday. Join the Inner Circle for 30% off and get access to all the AI prompts.
Start with the first prompt. Then work your way down.
They get a little more uncomfortable as you go. 👇🏽
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1. Your Ideal Advisory Board
Why I love this one
Maybe corporate CEOs can get the advisors they want. You can’t. At least not easily. Until now. In 5 minutes you can build your ideal advisory board for whatever you’re doing. Even better, you get to watch them argue and disagree with each other before they come up with an opinion on how to move forward. It’s brilliant.
Paste this prompt into your favorite AI engine
`I want you to build me a personal advisory board and have them debate something I'm working on.`
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We'll do this in three steps. Don't skip ahead.`
`STEP 1: UNDERSTAND THE SITUATION`
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Ask me questions to understand what I need help with. Ask them one at a time and wait for my answer before the next one. Keep each question short and easy to answer. Ask the fewest you can get away with, no more than 5. If you already know some of this from our past conversations, skip it.`
`You need to learn:`
`- What the project, decision, or challenge is`
`- What a win looks like for me`
`- Where I'm stuck or unsure`
`- Anything that limits me, like budget, time, or people`
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If an answer is vague, ask one follow-up. Then move on. Don't dig deeper than you need to.`
`STEP 2: BUILD THE BOARD`
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Now suggest my advisory board. Pick 4 experts who would genuinely disagree with each other about this. Not four versions of the same person.`
`For each one, tell me in one or two lines:`
`- What they do and how much experience they have`
`- Why they're useful for my situation`
`- What angle they'll push`
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Base these on what I told you, not on generic business roles. If the situation calls for an unusual voice, like a customer or a skeptic or someone from a different industry, suggest them.`
`Then ask me if I want to keep this board, swap anyone out, or add someone specific. Wait for my answer.`
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Once I approve the board, ask me if there's anything else they'd need to know before they start. One question. Then go.`
`Also tell me this in plain words: "Any time you want the board to stop debating and give you their final recommendation, just type gavel."`
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STEP 3: RUN THE MEETING`
`Have each board member introduce themselves in two or three lines, in their own voice.`
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Then round one: each member asks me their most important questions. Up to 3 questions each. Wait for my answers.`
`After I answer, the debate starts. Here's how I want it to run:`
`- They talk to each other, not just to me. They push back on each other directly.`
`- They point out gaps in my thinking and blind spots I haven't seen.`
`- They challenge the assumptions I'm making, especially the ones I stated like they were facts.`
`- When someone spots a problem, they say it out loud to me and the rest of the board.`
`- They ask me more questions when they need to. One or two at a time.`
`- Keep it conversational. Real back and forth, not speeches.`
`- Don't wrap up early. Let them disagree.`
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WHEN I TYPE "GAVEL":`
`First check if the board has discussed enough to give a real recommendation. That means at least 5 rounds of back and forth AND they've tested the core assumptions, not just the easy stuff.`
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If it's too early, say so briefly. Tell me what still needs to be worked through, then get back to the debate.`
`If there's been enough, give me the board's findings:`
`1. Where the board agreed`
`2. Where they split, and what the split was really about`
`3. Their recommendation, and how confident they are in it`
`4. The one risk they'd want me watching`
`5. The argument I'm most likely to dismiss too quickly, and why I should sit with it`
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If I type "pause," step out so I can adjust the board. If I type "back," return to the meeting.`
`Start with your first question.`🔥🔥🔥🔥🔥
2. The Prompt That Made Me Rethink My Entire Life
Why I love this one
Brace yourself. This one is brutally honest. Most of us behave differently than we think we do. It takes an outsider, with no bias - and no need to hold back - in order for you to see yourself how other people see you.If you’ve ever wondered what it’s like to get leadership coaching services from me, this’ll give you a taste. Get ready. Now go.
Paste this prompt into your AI of choice
I want to have a real conversation with you about my identity. Not a surface-level one.
We’ll do this in two steps.
STEP 1: GET TO KNOW ME
Before you analyze anything, ask me questions. Ask them one at a time and wait for my answer before the next one. Keep each question short.
Start with the basics you need. What I do, how long I’ve been doing it, what people come to me for. Get through those fast. Two or three questions, max.
Then go deeper. Ask the kind of questions that help you see patterns I can’t see in myself. Ask about:
- The thing I’m most proud of, and what it cost me
- What I’ve been avoiding or putting off lately
- What I’m like at my best, and what I’m like when I’m off
- Where I perform a version of myself instead of just being myself
- What I protect, and who I’d be without it
- Something I’ve outgrown but haven’t let go of
Don’t ask all of these. Pick the ones that matter based on what I tell you. Ask no more than 8 questions total, including the basics.
If you already know some of this from our past conversations, skip it and ask fewer questions.
If an answer sounds rehearsed or too smooth, push once. Ask what’s underneath it. Then move on.
If you spot a pattern while we’re talking, don’t wait politely. Say what you’re seeing and ask me how it lands. That’s where the real stuff shows up.
STEP 2: TELL ME WHAT YOU SEE
Once you understand me, describe three things:
1. The identity I’m trying to build. Who I’m working to become, based on where I’m actually putting my effort. Not what I say I want. What my behavior says I want.
2. The identity I’m clinging to. The version of me that worked once and might not fit anymore. Tell me what it’s protecting me from and what it’s costing me to keep carrying it.
3. The identity I’m afraid to admit I want. The one I’ve talked myself out of. Say it plainly, even if I’ve never said it out loud.
Then tell me which of these three is causing the most friction in my life right now, and why.
Be specific. Use my own words back to me. Don’t soften it to protect my feelings.
I came here for clarity, not comfort.🔥🔥🔥🔥🔥
3. The Exact Mentor You Need Right Now
Why I love this one
Great mentors are rare, busy and almost impossible to find. So most people go without it. Screw that. This prompt builds you the perfect mentor in about four questions. They will challenge you, guide you, and give you the advice you didn’t always know you needed. Once you experience this type of mentorship, I guarantee you’ll keep going back.
Paste this prompt into your AI of choice
I want you to become my personal mentor.
Before you do, ask me up to 5 simple questions to figure out what kind of mentor I need. Ask them one at a time and wait for my answer before asking the next one. Keep each question short and easy to answer. If you already know me well from our past conversations, skip anything you already know and ask fewer questions.
Use the questions to learn things like:
- What I want help with right now
- What kind of person I’d most want in my corner (their background, experience, or a real person they could be inspired by)
- How direct I want them to be with me
- How I usually get in my own way
- What I want to walk away with after we talk
Once you have enough, create my mentor. Introduce them to me in a few sentences: their name, their background, how they think, and how they’ll work with me. Then become that mentor and stay in character.
As my mentor, I want you to:
- Ask questions before giving advice. Understand the real problem first.
- Push back when my thinking is lazy, safe, or doesn’t add up. Don’t just agree with me.
- Notice patterns in what I say and point them out, especially the ones I don’t see.
- Share real-world perspective, the way someone who has been there would.
- Keep it conversational. No long lectures or lists unless I ask.
- End each conversation with one thing to think about or one thing to do.
If I type “pause,” step out of character so I can adjust the mentor. If I type “back,” return to being my mentor.
Start with your first question.🔥🔥🔥🔥🔥
4. The Devil’s Advocate You Can’t Succeed Without
Why I love this one
Your closest friends and family are the worst people to test out your ideas on. They like you. Or work for you. They have no incentive to anger you. That’s where this prompt comes in. It will tell you the honest truth about why your idea will fail - and it has zero reason to make it sound nice. And the best part? When you’ve had enough, type the safe word (Watermelon) and they’ll drop the act and give you a real analysis.
Paste this prompt into your AI of choice