They always have a reason why things are so hard.
There’s some circumstance, or some decision someone made, that caused them to be stuck

And the story is (usually) mostly true.
That’s what makes it so dangerous.

Because a story doesn’t have to be a lie to be a trap. It just has to be incomplete. And the part that’s missing - the part where you had more influence than the story allows - is almost always the part nobody explores.

Until now.
This prompt finds the part of your excuses that are all on you - but you don’t see them.

It exposes you the role you’ve written for yourself, and pulls the curtain back on your Omission Bias, and that Confirmation Bias that’s cowering in the corners of your Unconscious Operating System.

What if you have more ability to change your life than you’ve been letting yourself believe?

You don’t know what you don’t know, but this prompt is going to reveal it.
Run the prompt below. 👇🏽

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Maybe you know what it is, but if you’re anything like my leadership coaching clients, you most likely don’t.

It’s not that you made a bad decision. You’re a smart person with good intentions, so let’s assume it was a good one.

It’s also not that the decision was too important for other people to handle.
It wasn’t.

The problem is that you made a decision simply because you thought it felt wrong to have somebody else do it.

So you did it yourself.

Maybe you told yourself it’s faster that way. Maybe you convinced yourself that nobody else has the context needed to decide effectively.

Or maybe you keep promising that you’ll delegate more as soon as things settle down a little.

Meanwhile, other people on your team are wondering why you’re doing their job for them. They’re wondering what decisions are actually theirs - and which ones you’ve just pretended are theirs.

And you don’t even know this is happening.
It’s all going on in your leadership blind spots.

It’s time you saw your decision-making the way that everybody else does.

This prompt isn’t about how you delegate better - that’s a whole different cup of coffee.

This prompt will reveal what you’re actually protecting by not letting go. What you believe about yourself that makes hoarding control feel better than trusting others.

Are you ready for the truth?
Because I’m not sure you can handle the truth.

You might want to brace yourself for this one.
Run the prompt below. 👇🏽

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Your team already knows what you think of them.
They figured it out a long time ago.

Not from what you said, but from how you said it.
From who you called first when something went wrong.
From the micro-expressions you think nobody catches.

They know. Trust me on that one.

The only person in the room who doesn’t, is you.

At some point in the leadership coaching relationship, I ask each of my clients to describe their teams to me. It’s not because I want to know about the team members.

It’s because the words they choose tell me more about the leader than the people they’re describing.

Some employees may be described as “sharp” and “reliable” while others may be described as “trying” and “needs development”. Since I don’t know the employees, I can’t pretend to know how they act, but I can understand how their boss views each of them.

Here’s the thing most leaders don’t realize: what you believe about the people around you becomes a self-fulfilling prophecy.

It’s a brain shocker the moment you realize that your underperforming employee isn’t failing - you are.

It’s time to learn the truth.

Run the prompt below. 👇🏽

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It’s the thing a good leadership coach would see immediately.
The thing people talk about after you leave the room.

It’s that thing that shows up in every one of your reviews, maybe dressed in different language, but always hinting towards something “you might want to work on".”

Most people have been carrying their thing around for years.
I’m guessing you have too.

Not because you lack self-awareness - I’ll give you the benefit of the doubt there.

You’ve been carrying the thing around because nobody in your life has the guts to tell you directly. Your boss softens it. Your peers work around it.

I’m not that type of guy.
It’s time to tell you the thing that you need to hear.

This prompt doesn’t beat around the bush.

It understands your actual patterns, your actual behavior, and your actual blind spots.

Then it tells you the one thing — not five things, not some silly framework — the One. Thing. that could change everything else for you, if you actually worked on it.

Make it your number one priority for the next ninety days… and your life will be transformed.

Are you ready…?
Lets do it.

Run the prompt below. 👇🏽

These mind-blowing AI prompts are exclusively for The Inner Circle.

Join The Inner Circle for access to this prompt and all the others.

If you’re ready to learn about your Unconscious Operating System, these prompts are you gateway drug.

Once you see it, you’ll never be able to unsee it again.

Get The Prompt Now

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The problem isn’t that you don’t know what matters most. I’m pretty sure you do.

The problem is that you’re remarkably talented at building your life around the things that don’t matter that much in the end.

You know better - you just don’t prioritize it.

You are no doubt like most people. You focus on the urgent things and postpone the important ones.

You promise to go to the kids next sporting event. You vow not to forget your anniversary again. You will build out that strategy, start that idea or take that class later.

You continually convince yourself that you will do the important things tomorrow.

But tomorrow never comes. Or, at best, it shows up after it’s far too late.

My friend’s father was an emotionally and verbally abusive alcoholic for the 50 years of my friend’s life. When his father turned 80, he finally got sober. And just as he began to try to mend the family relationships he destroyed, he got cancer and was dead in 3 months.

Thats how things work when you’re always waiting for tomorrow.

I don’t mean to be brutal to you here, but I just don’t want you waiting until you’re in your 80s to figure out your regrets.

We are going to bypass that problem right here, right now. Cause I’ve got a prompt. And it could change everything for you.

So if you are ready for a firm thwack across the face by a fist full of reality, run the prompt.

Have the conversation and give yourself the chance to make the changes today that will avoid the regrets tomorrow.

Because by the time you are on your deathbed, it will have been far too late.

Run the prompt below. 👇🏽

Want powerful prompts in your inbox every week?

Every Tuesday, mind-blowing AI prompts are sent to The Inner Circle. Each prompt is designed to reveal the Unconscious Operating System running your life.

The patterns, the person you really want to be, the things that go bump in your brain at night…

Join The Inner Circle to get access to this prompt and all the others.

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There’s no warning. You don’t prepare for it.
You just get hit hard and - boom - you break down. Psychologically speaking.

I’ve watched it happen to all types of people. I’ve had it happen to me.

There’s one conversation, one situation, one realization that will tear you apart.

And the crazy thing? It isn’t random.
It is completely predictable.
It is surgically designed to undo you.

You just never asked anyone to predict it.

This prompt will tell you exactly what it will take to hit your psychological breaking point… and what you need to do to prepare for it.

It’s a ten-minute conversation.
It’s also the thing most people spend years in therapy talking about.

Forget therapy - this prompt is the solution you need.

Because it’s time you knew your breaking point.
Check it out below 👇🏽

Want powerful prompts in your inbox every week?

Every Tuesday, mind-blowing AI prompts are sent to The Inner Circle. Each prompt is designed to reveal the things about yourself that you can’t see. The patterns, the person you really want to be, the things that go bump in your brain at night…

Join The Inner Circle to get access (at any price level)

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Now imagine you time traveled back to now. But you brought back a letter from the future you to the present you.

The letter outlines all the things you need to know to ensure you become that future version of yourself.

It turns out you can time travel. It works.
And it’s triggered by the prompt below.

This isn’t another goal-setting exercise or vision board. It’s a letter from the version of you who already did the things you want to do - writing back to the version of you who’s still deciding whether you’re capable of doing them.

It’s time travel.

The future you has opinions because it knows you better than you know yourself.

It know’s what you’re overthinking. It knows what you’re undervaluing. And it knows what you already know but keep pretending you don’t know. You know?

Everybody wishes they could tell their younger self the things they know now.
This is your chance.

All you have to do is run this prompt… and listen.

Let’s go do some time traveling.

Want the powerful weekly prompts in your inbox?

Every Tuesday, a mind-blowing leadership therapy AI prompt is sent to The Inner Circle. It is designed toreveal all the things about yourself that you can’t see. The patterns, the person you really want to be, the things that go bump in your brain at night…

Join The Inner Circle to get access (at any price level)

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Nobody told me about the patterns in my life that were holding me back.

Nobody is telling you about yours either.*

[Editor’s Note: except in the free Leadership Diagnostic Workshop]

For my entire adult life, I was convinced I kept learning from my mistakes. But with every new job - every new relationship - I somehow always ended back in the same place I started.

It took one AI prompt to uncover the me I’ve been hiding from.
It hurts, but it’s true.
And I really wish somebody told me this stuff 20 years ago.

The prompt below isn’t about who you are - it’s about who you’re quietly terrified to become.

The response you’ll get will be a cement-truck worth of self-insight, but it will drop its load right on your head. Be careful, it might hurt.

Run this prompt below.
But don’t expect to like everything you learn.

IMPORTANT NOTE: You need to fill in everything in brackets with your own information. And don’t forget to delete the brackets once you add your info.

Want the powerful weekly prompts in your inbox?

Ready to reveal all the things about yourself that you can’t see on your own?The blind spots, the patterns, the person you really want to be, the things keeping you up at night…

Join The Inner Circle to get access (at any price level)

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I have only two invites left for Overclock.work.

It’s an amazing AI tool that replaces your busy work. I use it daily. Right now it scans the internet every morning for relevant leadership coaching conversations and sends me links. Saves me hours per day.

It’s a game changer - and it’s invite only.

Want one of the invites? Email me.
I’ll announce the winners on Monday’s newsletter

IMPORTANT NOTE

Every Tuesday, paid members get a new AI prompt that’ll let you see all the things you can’t see on your own — the blind spots, the patterns, the things keeping you up at night.

This one’s free, so you know what you’re missing.

[Join The Inner Circle for more →]

CEOs rely on advisory boards.
They have rooms full of smart and expensive experts with decades of knowledge.

They critique their ideas.
They poke holes in their plans.
They ask the questions that no one else will.

Many senior leaders have expert advisory boards too.

You don’t.

Not because you don’t need it.
You do need it.

You just don’t have the time, money or rolodex to put that group together.

So you do what the rest of us do: you think about your big decisions alone.

Maybe you ask a friend.
Maybe a colleague who knows slightly more than you.
Maybe that mentor who may text you back three days later with a thumbs up emoji.

Meanwhile, Fortune 500s are running your same decisions in front of a room full experts who are paid to disagree with each other.

They have the advantage.
Until now.

You can have that exact same room of expert advisers.
Right here. Right now.

Because I’ve got a prompt for you.

One of my leadership coaching clients tried it and said:

This turns ChatGPT or Claude into your personal, senior-level advisory board.

• Brand strategist.

• Growth marketer.

• Sales leader.

• Product maven.

• Whomever you need, whenever you need them - all debating your idea like it’s the most critical board meeting of the year.

And the cool part?

They’ll argue with each other while you sit back and watch. Which is exactly what the CEO’s pay all that money for.

Here you go…

IMPORTANT NOTE: You’ll need to alter any thing in the [ ]s to fit your situation. Examples are at the bottom.

You are facilitating a [growth strategy meeting, expert advisory meeting] about [describe your specific goal, challenge or decision]. Create four experts who will debate this by asking me questions and challenging each other based on my answers:


1. [Define expert #1 - their specialty and years of relevant experience. Examples are below]

2. A [growth marketer with 10 years running paid campaigns and optimizing ROI]

3. A [leadership content creator with 10 years in online courses, virtual workshops, newsletters, social media and audience growth]

4. A [sales director with 7 years in selling leadership coaching services, courses and workshops]


Here's how this works:

- Each expert asks me specific questions about [what they need to know -ideal customer, goals, current activities, current situation, etc.]

- Based on my answers, they debate with each other to help me [your specific outcome - define a strategy, make a decision, solve a problem, etc.]

- They identify gaps in my thinking, missing data or blind spots I haven't considered

- They challenge assumptions I'm making about [whatever's relevant - my market, my team, my timeline, my approach, etc.]

- When someone spots a problem or overlooked concern, they call it out directly to me and the other experts.  

- They continue debating and questioning me until they reach a consensus or a clear recommendation.


Start by having each expert introduce themselves and ask me their most important questions.  Limit to 3 questions each in the first round.



My primary goal is to:

- [add bullet points of your specific goals and what success looks like]


Additional context for the debate:
- [Your constraints, resources, current situation, deadline, relevant background, processes - anything that will helm them give you better guidance]

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IMPORTANT: Helpful Tips For Defining Your Experts

Choose experts whose real-world experience directly relates to the different angles of your actual problem - not just who sounds impressive. You want people who actually have useful stuff to tell you.

Here are some ideas.

For a product launch:

1. Product strategist with 15 years in B2B SaaS launches

2. Customer research specialist with 10 years in user behavior analysis

3. Go-to-market consultant with 12 years in product positioning

4. Pricing strategist with 8 years optimizing SaaS business models

For a solopreneur growing their business:

1. Solopreneur business strategist with 12 years helping one-person businesses scale to six figures

2. Content marketer with 10 years building audiences organically on constrained budgets

3. Conversion copywriter with 8 years optimizing landing pages and email sequences for small businesses

4. Systems designer with 7 years helping solopreneurs automate operations and eliminate bottlenecks

For an organizational change initiative:

1. Change management consultant with 15 years in enterprise transformations

2. Organizational psychologist with 12 years studying adoption patterns

3. Internal communications director with 10 years managing stakeholder alignment

4. Operations leader with 8 years implementing cross-functional initiatives

For career positioning:

1. Executive recruiter with 15 years placing senior leaders

2. Personal brand strategist with 10 years in professional positioning

3. Career transition coach with 12 years in mid-to-senior pivots

4. LinkedIn strategist with 8 years building executive presence

Get the idea?

Let me know if you have any other questions! I’d love to help.

Want more powerful prompts in your inbox every week?

Join The Inner Circle (at any paid level)

Every week you’ll get a new AI prompt that will let you see all the things you can’t see on your own — the blind spots, the patterns, the things keeping you up at night.

I stumbled upon the Tiimo app about a month ago because it won 2025 App Of The Year from Apple. Basically, it combines the To-Do list and Calendar in the way I’ve been hoping somebody will figure out. I love it.

I quickly became a partner of theirs - which allows me to give you 50% off a yearly subscription.

1. Just go here

2. On checkout, use the code “PARTNERPROGRAM”.

3. Once you purchase the web app, you can download the mobile app for free.

You may want to sit down for this one.
If you’re already sitting… maybe strap on your seatbelt.

I could explain to you how profound this prompt was for me - but we’d need a bigger bottle of bourbon and a therapist on standby.

When I ran it, it changed my life.

I’m not being dramatic. I’m totally serious.

For 20 years, I was on one path in my career. This prompt made me realize - like a wet noodle thwacking me in the face - is that I’d been repeating the same pattern throughout it all. Same moves. Same issues. Same me. Just different scenery.

I didn’t see it.
Now I can’t unsee it.

I’m now annoyed that I didn’t have this prompt 20 years ago. Then again, there was no magic AI machine back then to make it useful. It still would’ve been nice anyway.

I’m genuinely hope the results impact you the way it hit me.

Advanced Warning: This one doesn’t whisper in your ear. It gets right up in your face and yells.

Here’s the prompt…

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Not *wrong* wrong. I mean, I showed up every week, talked about the thing I thought was the thing, got some insights, felt better, left.
Rinse, repeat.

Then one session my therapist said: “You’ve been coming here for months. You haven’t once brought up your need to be a master at everything.”

[record scratch]

Wait whaaaat?!

That’s the thing about self-awareness. Whatever perspective you have is biased by your perspective. You can’t really see you outside of your perception of you.

You’re trying to read the label on the pickle jar while you’re stuck inside the darn pickle jar.

You know what you need? Someone outside the jar.

There are parts of your body everybody else can see, but you will never see with your own eyes. You need a mirror. You need something to reflect yourself back on you.

That’s what honest, direct feedback does. It shows you the patterns you can’t see because you’re living in the middle of them.

Problem is, that kind of feedback is really rare.

Your team won’t give it to you.
Your colleagues won’t give it to you.
Your friends might give it to you, if you ask directly and have the psychological safety in that relationship.

Your therapist might help a little, but it doesn’t really translate well to the nuance of leadership

So you’ve got a few options:

1. Hire a leadership coach who will tell you the truth you’re not hearing. Like this guy

2. Join a diagnostic workshop where you can learn the patterns getting in your way. Sign up here to learn more.

3. Or - and stay with me here - you could talk to my really insightful friend, Claude. Or his equally compelling cousin ChatGPT.

If you are a regular user of an AI tool, this prompt is amazing Leadership Therapy

I had a client run this prompt last week. Here’s what they said after:

It’s simple. It’s uncomfortable. And it works (as long as you use an AI tool often)

Here’s the prompt.

The AI Prompt That Explains You To You

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You can’t see yours. If you could, they wouldn’t be called blind spots. They’d just be called spots.

Heres the problem - I talk with hundreds of leaders who tell me they’re self aware because they think a lot.

Thinking isn’t self-awareness.
It’s just thinking.

It’s hard to see the things you can’t see about yourself by just thinking. As Albert Einstein said,

“We cannot solve our problems with the same thinking we used when we created them.”

In order to solve your behavioral problems, you first need clarity on what they are. That requires honest feedback.

And that’s where things begin to break down.

Very few people will tell leaders the truth. There have been multiple studies about this.

• People avoid giving honest feedback to avoid conflict1

• People avoid giving feedback when the outcome feels risky2

• Employees are far less likely to give honest feedback to someone with authority3

And the list goes on.

The fact is, that most leaders believe they are open to feedback, but research suggest that most employees and colleagues don’t believe it’s safe to give.

So leaders end up doing detrimental things simply because they don’t know any better

• Maybe you’re talking too much and not listening enough.

• Perhaps you continue to change priorities

• Maybe you’re not communicating enough and getting frustrated with others because they couldn’t read your mind.

Self-awareness is where growth happens. But self-awareness doesn’t happen unless you see yourself through something other than your own biased perspective.

Fortunately, there are three ways you can solve this

1. Hire a leadership coach who will tell you the truth you’re not hearing. Like this guy

2. Join a leadership workshop where you can learn the patterns getting in your way. Join here.

3. Use a good AI prompt

The good news? I can help you with all three.

I already gave you the links above for 2 of them, so let’s now focus on the AI prompt.

Here it is:

The AI Prompt That Exposes Your Blind Spots

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