You can’t practice for a tug-of-war without somebody on the other side pulling back.

But that’s exactly how most of us prepare for difficult conversations.
We rehearse what we’re going to say.
We work through our arguments.
We imagine all the brilliant responses we’re going to give when the other person pushes back.

And, of course, we always win.
Because we’re playing both sides.

We think we’re preparing for a conversation. We’re actually preparing to deliver a speech.

And there’s a big difference between the two.

But I figured out a solution.
I figured out how to have the entire conversation before actually having the conversation.

And it’s already saved me from making a fool of myself.
Here’s what happened.

I’ve got a meeting this week with a publisher about my upcoming book.

I’ve been thinking about this conversation for weeks. I know what I want. I know why it makes sense. I’ve got my arguments all worked out in my head.

So I built an AI prompt to play the publisher.
And I had the conversation three days before the actual conversation.

It sucked.
She asked questions I hadn’t thought about at all.
She challenged my assumptions that I fully believed were reasonable.

I even gave a long monologue that had sounded brilliant in my head, and like complete buffoonery when it came out of my mouth.

Which is exactly what I needed.

Because now I can change what I plan to say.
And I can try it again.
And again.

And here’s my favorite part.

Whenever the conversation starts going sideways, I just type three words:

I LOVE PIZZA.

AI immediately drops the character and tells me what I did well, what I screwed up, and what I should do differently.

Then I can jump right back into the conversation.
Or start over.
Or make the person even more difficult to talk to.

I dare you to try doing that with your boss.

So what’s your next big conversation?

Maybe you’re asking your boss for a raise.
Maybe you’re confronting an employee who’s not performing.
Maybe you’re pitching an idea to someone who has already told you no.

You can keep rehearsing both sides of the conversation in your head.
Or you can finally find out what happens when someone pushes back.

Here’s the prompt. 👇🏽

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It’s time to tell the world how great it is.

But Jeff Bezos figured out something interesting a long time ago.

We’re doing it backwards.

At Amazon, they started writing the press release before building the product. Which sounds a little ridiculous at first blush.

I mean, how the hell are you supposed to announce something that doesn’t even exist yet?
Turns out, that’s exactly the point.

Because if you can’t explain what you’re building, who it’s for, and why anyone should give a shit about it, you probably shouldn’t be building it in the first place.

And if you can’t come up with a compelling headline, Well, maybe your big idea isn’t quite as big as you think (a devil’s advocate may help)

I love this approach. Because I have a tendency to get excited about new ideas. Lots of them. All the time. And sometimes I get so caught up in the excitement of creating something, that I forget to ask whether it’s actually worth creating.

And that’s why I built this AI prompt.

It asks you five simple questions about the thing you think you’re building. Then it writes the press release announcing it’s successful launch.

You can use this for a new product, a service, a workshop, a book, a career move. Anything where you want to figure out what success looks like.

We both know you don’t have time to write the press release any more than I do.

I gotchoo.

Write the ending first. Then go build it. 👇🏽 👇🏽

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You see, I’ve been working on a new business idea lately. I like the idea.

A lot.

Which is exactly the problem.

Once you fall in love with an idea, you become the worst person to assess how good it is. You just start looking for evidence that it’ll work instead of evidence that it won’t.

And AI can make this worse.

Tell ChatGPT about your brilliant new idea and it will treat you like the smartest person in the universe.

“That’s the best idea I’ve ever heard from you!”
“Brilliant! Here are 5 ways to make it even better!”

But I don’t need my butt kissed.

What I need is someone who is trustworthy trying to kill the idea before I waste six months learning the hard way that I should have killed it myself.

So I created a prompt that does that.

It asks AI to figure out who the right person would be to challenge your idea. Then it becomes that person.

This isn’t a generic devil’s advocate.

It’s an actual subject-matter expert with the experience to know how ideas like yours tend to fail.

Then you debate them.

They push.
You defend.

They challenge your assumptions.
You push back.

And if you give them a bullshit answer, they will not politely move on. They will tell you it’s bullshit.

And here’s the part I really like.

The AI isn’t allowed to tell you whether it thinks your idea is good.
Not yet.

You have to respond thoughtfully to it’s feedback. After all, it’s the same feedback you’re going to get from potential users and customers.

The difference is, your users won’t be direct with you. The devil’s advocate will.

Then, when you’re done with the debate, you type one word:

Watermelon.

That ends the debate.

AI steps out of character, looks at everything you’ve argued, and tells you what it actually thinks.

It analyzes the strongest cases for and against your idea. How it could succeed and how it would fail.

And it tells you what you have to do to make it work.

I used it yesterday.
It’s amazing.
It changed the entire way I’m thinking about the business I’m building.

If you have an idea - any idea - you shouldn’t move forward without this.

Create your own devil’s advocate 👇🏽

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It wasn’t because I couldn’t find one. It was because I was too scared to ask.

I thought asking for help would be proof that I didn’t know what I was doing.

Which, to be fair, I didn’t.
I just didn’t want anybody elseto know that.

It took me a lot of years and a lot of mistakes to understand the importance of a good mentor. They don’t just give you answers. They ask the hard questions you’ve been avoiding, and they see the patterns you can’t see because you’re standing too close to them.

And every once in awhile they’ll tell you the truth that everyone else is being way too polite to mention.

One of my leadership coaching clients said it perfectly last week:

“I don’t need more advice. I need someone to call me on my shit.”

Exactly.
That’s a good mentor.

The problem is that good mentors are hard to find.

They’re busy. They may not have time for you. And even if you find the right person, you’re not going to call them at 11:37pm because you’re having an existential crisis about a meeting tomorrow morning and really need to talk to someone.

So I started wondering:

What if you could build the exact mentor you need?

Not some generic AI both that tells you to believe in yourself and then gives you seven bullet points you don’t really care about.

I’m talking about an actual mentor.

Someone with the background you need. The personality that works with you. Someone who knows when to encourage you and when to call you on your shit.

So I created a prompt that does exactly that.

It asks you a few simple questions and then builds a mentor specifically for you.

And then you talk to them. Whenever you want.

No calendly link to schedule three weeks out. No awkwardness when you ask an awkward question. And no worrying that you’re wasting their time.

You’re not.

So you’ve got a pretty simple choice.
You can keep trying to figure everything out on your own.
Or you can put someone in your corner.

Both are options.
One is lonely.
The other is faster.

Meet your mentor. 👇🏽

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Ideas I was truly excited about.
Ideas I was absolutely convinced were going to work.
In retrospect, they were ideas that probably would have been a huge success if somebody else had been in charge of them.

Unfortunately, I was.

Because when it comes to your next big goal or project, there are a thousand things that can screw it up. Bad timing. Bad assumptions. Other people. The economy. Money. Your horoscope on the day of the big meeting.

It could be anything.

But there’s one potential problem that you probably aren’t spending nearly enough time thinking about.

You.

You bring the same person, the same thinking and the same identity to every new project.

Your need for control. The way you get bored halfway through. Or how you expand one simple concept down so many different roads you’re not sure how to even get started.

Whatever your thing is, it comes with you. Always.
It’s like those leech-like sucker fish that attach to sharks. Wherever you swim, the sucker is still with you.

This is why I love the idea of a pre-mortem.

A post-mortem happens after something dies. You look back at the body and try to figure out what killed it.

A pre-mortem is much more helpful for people like you and me.

The basic idea is that you assume the thing you’re about to do has already failed. An embarrassingly spectacular failure.

Then you work backward and figure out what is going to kill it while you still have time to avoid the problem.

That’s what this week’s AI prompt does.

But wait… there’s more. Because isn’t there always?

The prompt doesn’t just ask AI to figure out what could kill your project. It asks AI to figure out how YOU are probably going to kill it.

And then it will tell you what to do before you even get the chance to screw up yet another great idea.

So don’t take one more step towards your project or goal, run this prompt first. Before you start. Otherwise, you’re just going to regret it and come back to me to tell me how you should’ve listened.

Don’t say I didn’t warn you.👇🏽

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Somewhere in your life there’s a thing you’ve fully figured out.
I don’t know what it is.

Maybe the new hire isn’t going to work.
Or the strategy’s off.
Maybe it’s time to change jobs.
Or maybe the relationship that you’re pretending is still working hasn’t really been feeling good for a long long time.

You know what it is.
You’re just not saying it. Not even to yourself.
Because the second you say it out loud, you have to do something about it.

So you stay busy. You gather more evidence.

But you’re just trying to sweep something under a rug that’s already been swept to death. Nothing more can fit.

I once kept a senior leader two years past the point I knew I should fire him. I told myself that things could turn around.

But I knew it wouldn’t.
And I realized that the very minute after I fired him. I was just two years too late.

This prompt uncovers the thing you already know and won’t admit.

It’s time to run the prompt. No more stalling.👇🏽👇🏽

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They’d already raised a pretty hefty Series A (an amount that rhymes with “men tillion”), they had at least a couple years of runway left and their product was headed in the right direction. Needless to say, I was a bit surprised to hear about the worry.

I asked him what he was afraid of.

“If we can’t raise the money,” he said. “I’d have to lay people off.”

And so….?

“They’d think I failed them,” he admitted.

OK. And what if they did think that?

He paused. He either had to think about that one or had to consider how vulnerable he was ready to be.

And then he spoke.

“I guess it would mean that maybe I’m not actually good at this after all. Maybe I’ve just been lucky.”

Ka-POW!

That’s it. That’s the whole thing.
A five minute fear-of-funding conversation finally revealed the real feelings: He feels like a fraud.

That’s how it always goes in almost every one of my executive coaching relationships.

The thing you’re worried about is never the thing you’re afraid of.

The worry is just the symptom. The deadline, the conversation, the number - none of that is the actual fear.

The fear is three questions down.
It’s hiding in a dark corner and hoping you won’t notice it’s there.

But it is.

And the sooner you uncover it, the more confident you’ll feel.
And the more productive you’ll be.

This prompt dives down and finds the fear underneath the worries.

Strap on your seatbelt.
We may hit some turbulence as we descend into your psyche.

Run the prompt. 👇🏽👇🏽

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I prided myself on being direct and efficient.
I’d give feedback in a few words and move on, proud of not wasting anyone’s time.

In my head, I was respecting people enough to skip the fluff.

Eventually somebody on my team told me that people found me “hard to read, and a little scary.”

Scary?!
Me?!?!
WTactualF?!
I’m the guy who is always being helpful. How could I be scary?!

Here’s what eventually messed me up about it: I wasn’t wrong about my intentions. I really was trying to be respectful.

But my intention lived in my head, and everyone else only ever experienced my behavior. It turns out they couldn’t read my mind - and I didn’t realize they needed to.

The brief, efficient feedback that I felt was helpful, felt to them like I just slammed a door in their schnoz.

I’m not the only one who has this gap - the one between what you think you’re communicating and what other people hear.

The frustrating part is that most people blame others for not understanding what was communicated.

“They’re too sensitive.”
“They took it wrong.”
”They’re not paying attention.”

This prompt finds where you’re most misunderstood - and the thing you’re doing that causes it.

Turns out it’s usually not them.
Run the prompt now.

👇🏽👇🏽👇🏽👇🏽👇🏽

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“I’m just not good at this.”

Business.
Leadership.
The whole vulnerable-human-being thing.

I said it so often that nobody questioned it.
Including me.

It sounded humble. Like I was just being honest about my weaknesses.

Until a decade or so later when it all hit me like a ton of spiraled zucchini.

I wasn’t describing myself.
I was protecting myself.

If I wasn’t “naturally good” at something, then it was ok to fail.
By claiming to not be good at something, I was lowering everyone’s expectations. Including my own.

It wasn’t humility.
It was a wall to protect my fragile ego.

The scary part wasn’t that I believed it.
The scary part was that I never bothered to wonder whether it was actually true.

(Spoiler alert: it wasn’t. I’m actually pretty good at the stuff I said I wasn’t good at)

That’s what happens with the stories we tell about ourselves.
Do you know what your story is?

• “I’m terrible with money.”

• “I’m not creative.”

• “I’m not a people person.”

• “I’ve never been good at conflict.”

• “I’m just not confident.”

At some point those sentences stop becoming opinions and start becoming your identity.

The problem is that most of them aren’t based on fact.
They’re conclusions you reached years ago that you never bothered to re-confirm.

This prompt is designed to uncover one of those stories.
The one you’ve repeated so many times that it feels like part of your personality.

Then I will challenge you with this simple question:

What if that story isn’t true anymore?

Be warned…

This prompt is surprisingly uncomfortable.
Run it anyway.
👇🏽👇🏽👇🏽👇🏽

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You know what I’m talking about.
Maybe it’s the parent who goes quiet and cold when they’re upset.
Or the one who yells and complains for no reason.
There’s some behavior from your parents that you’ve sworn you’d never replicate.

And you don’t do it.

Until one day your significant other makes you realize that you act exactly like your parents.

Shit.

Here’s the thing… you learned how to deal with money, conflict, love, and work before you were old enough to have an opinion about it. You watched. You absorbed. And now you’re doing the same exact thing, whether you know it or not.

And you usually don’t know it.

Some of it works to your benefit.
Some of it has been guiding your life in the wrong direction without you knowing.

I created a prompt to uncover all the stuff you learned from your parents that unconsciously guides your life.

Fair warning: this is the one that makes you call your therapist. Or your mother. Possibly both. Especially if your mother is a therapist (like mine)

👇🏽👇🏽👇🏽👇🏽👇🏽

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That’s not my voice, you think. That’s not what I sound like.

Except it is.
It’s exactly what you sound like.
It’s the only voice anyone else has ever heard come out of your mouth.

The one you’re used to hearing is the fake one. It’s the one that reaches your ears through your own skull, filtered through bone and cartilage until it sounds nothing like what actually leaves your body.

You’ve been mishearing yourself your entire life and you never knew it.

As it turns out, you do the exact same thing with your personality.

You think you’re patient. You think you’re a good listener. You think you handle pressure well, delegate clearly, give considerate feedback.

You’ve been listening to yourself this whole time, and the version you hear sounds pretty reasonable, right?

But that’s like the bone-conduction version. That’s not how other people experience you.

Your team has their own experience of you.

It’s the one where you interrupt before someone finishes a thought because you’re already three steps ahead. The one where your “quick feedback” is really just bossing them around. The one where your calm exterior during a crisis makes them feel like you don’t care.

You didn’t build that version on purpose.
Nobody ever does.
You’ve just never seen it. Because you can’t see the label when you’re stuck inside the pickle jar.

I put together a prompt that reveals the version of you that other people actually experience. Not the polished 360 review written by someone protecting their own job. The real one.

What it’s actually like to sit across from you, report to you, get an email from you.

It’s not going to feel like your voice.
But that’s the whole point.

Run the prompt below.

👇🏽👇🏽👇🏽👇🏽👇🏽

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When I asked him what he was doing about it, he said to me, “Fortunately, I’m a really patient person. So I’m letting him do his thing. It will eventually work itself out.”

I paused.
Because I could see through what he said.
You can probably see through what he said.
Everybody can probably see through what he said.

He couldn’t.
Because he convinced himself he’s being patient.
He’s really just being avoidant.

We all do some version of this - and I’m not exception.
We all convince ourselves at some point in our lives that looking the other way is the better decision.

Do this enough and you start believing that looking the other way is the right thing to do.

And that brings us to you.

There’s something you keep tolerating.
Maybe it’s a person, a dynamic, your own behavior or a situation that you believe will “eventually work itself out.”

Do you know what it is?
Most people don’t - because you’ve disguised the tolerance as something more positive.

But I guarantee you’re tolerating stuff in your life that is holding you back.

Are you ready to hear the truth about what you’re tolerating and how to change it?

Your simple solution is below.

👇🏽👇🏽👇🏽👇🏽👇🏽

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We talk about the climb. The grind. The sacrifices nobly made in service of something bigger.

But that’s closer to a Disney dream than reality.

Trevor Noah talks about the loneliness.
Jerry Seinfeld talks about the perpetual dissatisfaction.
Elon Musk talks about the stress and isolation.

Robin Williams and Matthew Perry… well… they can’t talk about it any longer.

I had a leadership coaching client last year who was successful by every external measure. In the middle of our call, she stopped and said: “I don’t think I know who I am outside of this job anymore.”

It wasn’t a complaint. It was a discovery.

That’s what this prompt is about.

Not whether you’re successful.
Not whether the sacrifices were necessary.

But whether you’ve ever actually figured out what you’ve sacrificed to build the life you’re building.

Most people never bother to face this. Because reality means sitting with the stuff that’s poking at your unconsciousness.

The only question is whether you’re actually ready to face your truth.
I ran this on myself (as I do all the prompts) and… wow, what a wake-me-up.

Run the prompt below and find out what you’re pushing aside.

👇🏽👇🏽👇🏽👇🏽👇🏽

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You know you need to have it - you should’ve had it already.

Yet here we are.

Most people think you just don’t understand you need to have the conversation, but not me. I believe in you.

The problem isn’t about awareness. The problem is that you know exactly what you need to do - who the conversation is with, what it’s about, what needs to be said - but you’re still not having it.

You’ve got reasons. I know you do.
They’re probably even good reasons.

Maybe the timing isn’t right. Or it’s not that urgent. Maybe you don’t want to damage the relationship and it’s better to handle it after this quarter, after this project, after that thing in the future works itself out.

Meanwhile all the stuff you’re not saying is taking up space. Not just in your head, but in the room every time you’re with that person. Whether you can sense it or not (and you probably can’t), it’s impacting the dynamic between you two, and turning it into a new normal that’s much more destructive than the old normal.

I’ve watched leaders avoid conversations for months. Sometimes even years. Most of them cover it in the belief that “I’m a really patient person.”

You’re not patient.
You’re avoidant.

This prompt not only points out the conversation you need to have, but it tells you exactly why you keep not having it.

You already know what needs to be said.
Let’s figure out why you’re still not saying it.

Run the prompt below.

👇🏽👇🏽👇🏽👇🏽👇🏽

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They learn from it.
They own it.
They move forward.

It’s all bullshit.

Because when something actually goes wrong, the real version of them shows up.

The one that gets defensive, but doesn’t see themselves playing the victim.
Or the one that assigns blame and believes it’s accountability.

Most often it’s the leader who, once again, works twice as hard to make sure nobody - including themselves - has time to think about what is actually failing.

You are telling yourself a story about how you handle failure.

It’s just not the true story.

This prompt uncovers your real relationship with failure, and what you can do about it.

It’s time to see the thing you’re hiding from yourself.
Run the prompt.

👇🏽👇🏽👇🏽👇🏽👇🏽

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You are doing work right now that AI should be doing for you. I guarantee it.

I’m not the first one to tell you that you should be using AI more. I’m just the one you’re finally going to listen to

Because it’s time to stop writing that same type of email. It’s time to stop summarizing that same type of report.

You probably don’t even recognize all those things you do that take 45 minutes and produce the same output every. single. time.

There’s a reason you haven’t let go of it.
And it’s not because you haven’t found the right tool.
And it’s not because you haven’t found enough time.

It’s because of you.

It’s the same reason you haven’t let go of certain decisions.
The same reason you’re still in meetings you shouldn’t be in.
The same reason you tell yourself you really should delegate more.

Today is the day that all changes.
Yup, today.

In just 2 minutes I’m going to help you uncover the tasks you should stop doing yourself.

But wait, the tasks alone aren’t the problem.
The problem is you. But we already talked about that.

So I’m also going to tell you why you haven’t been letting that stuff go.
Because it’s not just time to transform your productivity, it’s time to transform your life.

Welcome to freedom.
The prompt is ready for you

👇🏽👇🏽👇🏽👇🏽👇🏽

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But great therapy actually changes things (which is why I’m flattered whenever my executive coaching clients call me their leadership therapist.)

I’m not here to tell you to fire your therapist. However, there’s something you need to know if you don’t know already.

When you ask AI the right questions in the right way, you’ll be able to see into your blind spot infinitely more clearer and faster than any therapist can ever provide.

The catch? Most people don’t know how to ask the right questions.

Well, my friend, that’s why we’re here together. I gotchoo.

Here are 7 of the most important prompts to help you understand your behavior better than a weekly $300 therapy session will ever provide.

1. The Other Perspectives

You’re in a situation that’s stressing you out - but you can only see it one way. Your way. That’s not a thinking problem, that’s a perspective problem. This prompt gives you three other ways to look at your specific situation - then it points to the one you’re resisting the hardest. Turns out, that’s usually the one that will allow you to exhale.

2. The Energy Audit

Your tired. You’re drained. You think it’s the workload or your commute or lack of sleep. It’s probably something else.

This prompt goes through your week and finds what’s really draining you. It’s almost never what you think.

3. The Stuck Point

There’s that something you’ve been “thinking about” for weeks. Maybe months. But you’re not actually thinking — you’re circling. Something specific is holding you back, and you probably can’t name it. This prompt names it for you… and tells you if your waiting is worth it.

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You’re not the person people complain about when they leave work.
You’re not the one creating the dynamic that makes other people want to quit.

Still… here’s what I know after years of leadership coaching for both men and women in leadership:

The gap between how leaders see themselves and how their teams experience them, is one of the biggest blind spots in leadership.

I run a fair bit of Culture & Leadership Surveys for companies and free leadership diagnostic workshops for leaders.
In every single instance, people in leadership rate their behavior 30-40% higher than their team does.

It’s not about being bad leaders. Most of the leaders I work with genuinely care about this stuff. The reason is a lot simpler:

Most people never actually ask how they’re doing - or they never ask it to somebody who will give them a direct and honest answer.

I’m not talking about the performance review version.
And not the useless “got any feedback for me?” closer to your weekly one-on-one. Everyone knows that’s a rhetorical question.

The AI prompt below gives you the truth.
It reveals the conversations about you that you don’t get to hear.

This prompt will tell you how your company will remember you if you quit right now.

You’ve spent years thinking about the leader you want to be.
It’s time to get the truth about the one you actually are.

Run the AI prompt now. 👇🏽👇🏽👇🏽

Inner Circle members get this for free. Join here.

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There’s no moment where you sit down and decide that this behavior is acceptable now, that this dynamic is just how things are, that this is the version of your team - or your life - you’re going to settle for.

It happens in invisible increments.

Something bothers you, you let it go.
It happens again, you let it go again.
After a while you stop noticing.
After a longer while you can’t remember what bothered you in the first place.

That’s the danger of compromise. It’s a slippery slope and you don’t notice you’re sliding until you’ve fallen off the precipice.

The crazy thing about the process, is that it feels like growth.
It feels like you’re getting a new perspective and maybe even maturing past the things that used to bother you.

Sometimes that’s true.
But it’s also not.
Sometimes, you’ve just lowered your standards in a way you’ll wish you didn’t.

I had a client who spent twenty minutes telling me everything was fine.

Great team, good culture, no major issues.
Then I asked: “What have you stopped bringing up in meetings because it’s not worth the conversation anymore?”

Long pause.
Then he rambled off a list that was ripe with meaning.

This prompt finds your list.
It shows you exactly what non-starters you had that you’ve quietly allowed to fade away.

Not everything you’re tolerating is a problem.
But some of it is.

And it’s about time you realized how you’re compromising your standards.

Run the prompt now. 👇🏽👇🏽👇🏽

Inner Circle members get this for free. Join here.

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Success has a cost.
Nobody really talks about the cost.

We talk about the climb. The grind. The sacrifices made.

We make success sound noble.
Like it’s actually worth it.

Was the cost worth it for Robin Williams and Matthew Perry?
I doubt it. They paid everything.

I have a leadership coaching client - successful by every possible measure - who recently confided in me:

“I don’t think I know who I am outside of this job anymore.”

It wasn’t a complaint, more like a realization.

That’s what this prompt is about.

Not whether you’re successful.
Not whether the sacrifices were necessary.

But whether you’ve ever actually added up the cost you’ve been paying for what you’re building.

The relationships that quietly fade away, the versions of yourself you slowly forget, the life that was happening while you were focused on work.

Most people haven’t thought about it.
Not really.

Because doing the real accounting means sitting with a number you’ve probably been rounding down for years.

This prompt does the accounting.
The question is whether you actually want to see the bottom line.

Run the prompt now. 👇🏽👇🏽👇🏽

Inner Circle members get this for free. Join here.

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