The Question Got Smart Before We Did

A guy three stools down asked the bartender what was good. He listened to the whole rundown. House lager, a stout the brewer was proud of, a sour they only had for two more weeks. He nodded the whole time, looked engaged, then ordered a Coors Banquet.

The question got smart. The order didn’t.

That’s been the year, hasn’t it. Everyone I work with has developed a new reflex. They open a draft and ask “could this be better?” They look at a deck and ask “is this the strongest version?” They forward an email to a friend or to a model and ask “what am I missing?” The reflex is real, and on its face it is an improvement. We used to ship the first thing that wasn’t embarrassing. Now we run it through one more loop.

The trouble is the loop.

Asking is cheap. Answering is expensive. The tools we’re using will happily expand, condense, polish, restructure, tighten, soften, sharpen, anything you want, in any direction, on demand.

Every one of those moves feels like progress because it cost effort. None of them are actually better. They’re just different.

The deck gets longer or shorter. The email gets warmer or cooler. The post gets more clever or more sincere. And then we ship it, and the work we produced this year looks almost exactly like the work we produced last year, except we feel more thoughtful while making it.

The question moved. The output didn’t.

There’s a marketing version of this, and it should bother you. When the reflex “could this be better?” gets applied to a campaign, what usually shows up is twelve variants of the same hollow premise. A subject line test on an offer no one wants. A landing page rewrite for a category that’s dying. A new tagline for positioning that was wrong before the model touched it. It appears that the tool will not, ever, tell you the foundation is rotten. It will help you decorate that foundation in seventeen different finishes and let you pick your favorite.

A smarter question deserves a harder answer. The harder answer is almost always “this needs to be rethought, not rewritten.” But rethinking is slow and lonely and looks, from across the room, like not working.

Rewriting is fast and feels like motion and produces a fresh artifact you can show a colleague by 4pm.

So we rewrite. Over and over. And we tell ourselves the inflection point has happened because we changed how we ask, even though we have not yet changed how we work.

I have done this. I did it twice this month. I asked the model to help me sharpen a positioning doc that needed to be scrapped and started over. I knew, by the second pass, that I was decorating a wall that should have been demolished. I kept going because the decoration was easier than the demolition. By the end I had a beautifully worded version of an idea that was never going to land. That isn’t the model’s failure. That’s mine. The model gave me exactly what I asked for. I asked a smart question and accepted a polished answer instead of a real one.

The reflex to ask “could this be better?” is a gift. Right now we need to stop wasting it.

The Coors Banquet isn’t the problem. Ordering it after the bartender’s whole speech is.

Stay Positive & Demolish The Thing You’ve Been Decorating

He Wasn’t Performing. He Was Pouring.

I performed energy at a feature launch once. The release was an enhancement at best. The product underneath was on its last breath, and everyone in the meeting room knew it, including me. So I cranked up my own voice. I leaned in harder. I delivered the talk track like the thing was bigger than it was, because somebody had to fill the room with something, and I thought volume might pass for momentum.

It didn’t. People can smell manufactured momentum the same way they can smell a steak that’s been microwaved.

A few weeks later, I sat at a bar and watched a beertender work the rail.

He was not chipper, not bubbly, not asking anyone how their day was in the tone of a children’s television host. He was also not phoning it in. He was just there. When a guy three stools down said something quiet about his week being long, he heard it. When a woman ordered a sour, he nodded and made it without making a moment out of it. When someone asked what was new on tap, he answered the question. Not the question he wished they had asked. The actual one.

He listened. He didn’t perform listening, which is the part that has been bothering me ever since.

There is a kind of engagement that is real. It looks like attention. It sounds like attention. It is, in fact, attention. And there is a kind of engagement that is theater, and the theater version has won most of the territory in modern business because we measure smiles, response times, exclamation points, and the energy in the room, and we mistake those signals for the thing they are supposed to be signaling.

Most service training pushes people toward the theater. Most hiring pushes them there too. We interview for warmth, eye contact, the firm handshake, the prepared question about the company. We are choosing, mostly, for people who can perform being interested. We rarely interview for whether they can actually be interested.

When you hire performers, you get a team that knows how to project energy when there is none. They are very good at the launch where the product is just an enhancement. They are very good at the all-hands where the quarter was rough. They are very good at the customer call where the renewal is shaky. They look great. They sound great. And they cost you the one thing real engagement gives you, which is the ability to notice that something is wrong before it gets loud.

The performer fills the room. The present person hears it before it gets loud.

If you want a team that can catch a product before it dies, you need fewer people who can sell foam and more people who can pull a clean pint. They are quieter in the interview. They will not look like the obvious hire. They will not high-five your CEO at the offsite. They will be the ones who notice that the customer is hesitating, that the engineer is exhausted, that the launch is thinner than the deck claims.

I think about him sometimes. Not because he was extraordinary in a way that you would write a LinkedIn post about. The opposite. Because he was completely ordinary in the rarest possible way. He was doing his job, with all of his attention turned on, and no part of it turned outward as a show.

The product I was cranking energy for did die, by the way. Not because of the launch. The launch was a symptom. We had been performing for it for a long time before we admitted it was sick.

Stay Positive & Pull A Clean Pint

Someone’s Kid Just Threw Up

You’re sitting in the Zoom waiting room. The candidate is ten minutes late. Then fifteen. Then twenty.

Your phone is the only thing in the room with anything to say, and it’s not saying it.

The story your brain wants to write is short and tidy. They’re flaky. They don’t respect your time. They got a better offer and didn’t have the decency to cancel. You can already feel the email you might send, the friend you might vent to, the small hardening that happens inside you when you decide a stranger has wronged you.

But you don’t actually know.

Maybe their kid just threw up on the carpet. Maybe their phone fell between the car seat and their hands are too big to grab it. Maybe their mother called from a hospital. Maybe they typed the meeting into their calendar for tomorrow, not today, and right now they’re at a coffee shop feeling responsible and prepared and entirely wrong.

You don’t know which movie is playing on the other end. You only know the part of yours where the chair is empty.

The same thing happens when a piece of content goes out and nothing happens. No comments. No shares. The little dashboard sits there like a houseplant nobody waters. The temptation is to blame the audience. They didn’t get it. They’re not paying attention. They were too busy looking at someone’s vacation photos.

That posture is comfortable because it puts you at the center of every story. The audience either showed up for you or failed you. The candidate either honored you or wronged you. The customer either bought or rejected. You become the sun. Everyone else is a planet that either orbited correctly or didn’t.

Here is the quietly true thing about marketing, leadership, and most of human life: you are not the sun.

Most of the time you are a small thing happening on the edge of someone else’s enormous day. Their kid is sick. Their dog is old. Their grief is a year old this week. Their mortgage just went up. They got your email but they were standing in line at the pharmacy. They wanted to respond but felt embarrassed about how long they had taken to respond.

The discipline is to hold the silence loosely. To leave it unexplained until it explains itself. To do the next useful thing instead of the next angry thing.

The leaders who burn out fastest are the ones who insist on filling in the blanks. They write the story before the facts arrive, and then they spend the rest of the week defending that story when the facts contradict it.

The leaders who last hold the blank space open. They send the follow-up. They check on the teammate. They re-read the email with a kinder eye. They wait.

Once you know the truth, you act on the truth. Simple as that.

If the candidate ghosted you on purpose, fine, you act accordingly. If the campaign actually missed the mark, you fix the campaign. But you don’t get to act on the story you invented at minute fifteen of the waiting room. That story is almost always a worse version of what actually happened, because it’s a story written by your most insecure self with no editor in the room.

There’s a small grace in this, and it runs both ways.

Somewhere out there, someone is sitting in their own waiting room wondering why you didn’t reply to their email. They don’t know what’s happening on your end either.

Stay Positive & Admittedly, I Still Catch Myself Writing The Worst Version First Sometimes, Too

But, What Is Better?

Nobody wakes up craving “more efficiency.”

Nobody rolls out of bed, kisses the dog on the forehead, pours coffee into the sacred bean chalice, and whispers, “Today, I hope someone improves my workflow by 14 percent.”

People say they want better.

They say they want easier.

They say they want more time, more money, more control, more visibility.

Fine. Those are the acceptable words. The words allowed into conference rooms wearing slacks and a hoodie with an evil bunny icon stitched on the sleeve.

But underneath them are the real beasts.

Status.

Relief.

Confidence.

Safety.

Pride.

Belonging.

The feeling of walking into a meeting with the answer before the question has finished putting on its pants. (You’ve never said those words but they resonate, don’t they?)

That is what people are actually buying.

“More time” is rarely about time. It is about not being the parent answering Slack messages during dinner while a child explains, in heartbreaking detail, why the moon is following the car.

“More money” is rarely about money. It is about permission. Permission to hire the person. Permission to say yes. Permission to stop making every decision feel like choosing which limb to sell to the spreadsheet goblin. And permission? That’s just a blend of agency and the feeling of fulfillment that actually helps us sleep at night better than a melatonin pill.

“Easier” is rarely about laziness. It is about dignity. It is about not needing seven tabs, three spreadsheets, a hallway conversation, and a blood oath to answer one simple question. With those removed, it doesn’t actually make our life easier, it makes it harder because we’re finally free to tackle the problems that are worth us waking up late at night to jot an idea down.

“Better” is the cardboard mask.

The human desire underneath is the face.

This is where mediocre marketing gets stuck. It points at the feature and shouts, “Look, it saves time!”

Congratulations. So does skipping lunch.

Great marketing keeps digging.

What does saved time become?

A calmer team.

A leader who looks prepared.

A customer who feels remembered.

A finance person who does not have to play archaeological detective in the ruins of bad data.

A sales rep who finally stops guessing and starts knowing.

A CEO who can tell the board, “We see what is happening, and we know what to do next.”

That is not efficiency.

That is authority.

That is status.

That is oxygen in a room that used to smell like burnt toner and quiet panic.

As for customers? Customers do not just want the thing.

They want the version of themselves the thing makes possible.

Sharper.

Calmer.

Trusted.

Promoted.

Less embarrassed.

More necessary.

Able to leave work on time without feeling like a criminal fleeing the scene.

This riff is important because it drives home this point: build the product that makes life better, easier, sharper, richer, calmer, and less like wrestling a printer in a thunderstorm.

But do not stop there.

Ask what that improvement gives them emotionally.

Ask what fear it removes.

Ask what story it lets them tell about themselves.

That is where the sale lives.

Not in the feature.

Not in the benefit.

In the little private human victory hiding underneath both.

Stay Positive & Willing To Discover It?

The Market Doesn’t Owe Your V1 Applause

It is possible your first product is exactly what customers were secretly wishing for while brushing their teeth and staring into the little porcelain oracle above their sink.

Possible.

Also possible a goose walks into a board meeting with a better Q3 plan.

The first version is usually not the answer. It is the question wearing shoes. It walks into the market, trips over a chair, spills coffee on the prospect, and comes back with priceless information.

They did not want that.

Good.

Now you know.

Failure is not the opposite of progress. Failure is the crude lantern that shows you where the path is not. Every flop is a customer whispering, “Not this. Not quite. Try over there.” And if you are paying attention, if your ego is not wearing a crown made of wet cardboard, that whisper becomes strategy.

The hard part is not iteration. The hard part is emotional sobriety.

Ship something. See what happens. Do not faint when the market shrugs. Do not build a cathedral around your first idea just because it took six months and three executive offsites to name it. Customers do not care how beautiful the internal deck was. They care if the thing makes their life better, easier, sharper, richer, calmer, or less like wrestling a printer in a thunderstorm. (What this exactly means deserves it’s own blog post, perhaps tomorrow…)

This is where leadership matters.

A great leader/CEO says, “Here is where we are going. Here is why it matters. And yes, we are going to learn along the way.”

Because there will be shifts.

Not maybe.

Always.

Something will not work. A customer segment will surprise you. A feature you loved will sit untouched like a decorative zucchini that you let grow too much and no longer has any nutrients. A small request from one frustrated customer may turn out to be the doorway to a bigger market.

That tension is not a bug in the business. It is the business.

You are trying to be more useful to the customers who already trusted you, while becoming more relevant to the customers who have not noticed you yet. That is a delicate circus act. One foot on loyalty, one foot on discovery, juggling flaming assumptions while the market changes the music. No wonder marketers are needed more than ever!

The only sane way through is real customer curiosity.

Not fake curiosity. Not survey theater. Not the kind where you ask questions only to confirm your own cleverness.

Real curiosity.

The kind that listens. The kind that gets excited by being wrong because wrong is finally specific. The kind that says, “Wonderful, we found another wall. Now where is the door? Maybe here instead?”

Ship. Learn. Pivot. Even when it works, pivot toward what could work better.

That is how new projects grow legs.

That is how companies stay alive.

That is how you turn failure from a funeral into fuel.

Stay Positive &

Let The Broken Thing Be Broke

When something breaks, the first instinct is to grab the duct tape, sprint toward the smoke, and start yelling heroic little phrases like, “We can still save this.”

Maybe you can.

But the more useful question is whether you should.

A broken campaign. A busted process. A launch that limped into the world like a shopping cart with one haunted wheel. A friendship with too many unpaid emotional invoices. A product nobody understands. A meeting culture so bloated it needs its own cardiologist.

The default move is rescue.

Rescue feels noble. Rescue feels urgent. Rescue makes us look busy, which is the business world’s favorite Halloween costume.

But sometimes saving the thing is just preserving the wrong lesson.

The better move is often slower, stranger, and more useful.

….learn from it.

Ask what cracked first. Ask who saw it coming and stayed quiet. Ask what assumption was dressed up as strategy. Ask what the thing was trying to teach you before it fell off the shelf and made everyone pretend they weren’t involved.

Broken things are generous… if you can tolerate their honesty.

They show you where the glue was weak. They reveal the gap between the story you told yourself and the reality that walked in wearing muddy boots. They point to the system beneath the accident. And damn, does it gift you with a whole lot of empathy. (Ask me about my new appreciation for hand-carved wooden bowls … and my broken bowl.)

This is especially true in marketing. Not every message needs a refresh. Some need a funeral. Not every campaign needs more budget. Some need a coroner’s report. Not every idea failed because execution was poor. Some failed because the audience never cared, and no amount of confetti can convince a room to become a parade.

There are things worth saving. Absolutely. The dented chair. The weird tradition. The scrappy idea with a pulse. The person who made a mistake and owns it. (Especially that person… you?)

But when something breaks, do not confuse urgency with wisdom.

Pause before the rescue mission.

Look at the wreckage.

Take notes.

Stay Positive & Sometimes The Gift Is The Truth You Tell, Not The Broken Thing You Fixed

The Holy Voltage Of Giving A Damn

Let’s set aside the idea that the brain is a beige little office with a tiny man inside alphabetizing your ambitions.

Let’s imagine the brain is a bonfire… and it remembers what has heat.

Learning a language gets easier when you give a damn about the work. Not “I downloaded the app and now I am being emotionally blackmailed by a cartoon owl” giving a damn. Real giving a damn. The kind where you want to order wine in Greece without sounding like a malfunctioning toaster. The kind where you want to understand your grandmother’s recipe card, your lover’s joke, the insult someone muttered beautifully under their breath.

Care is a cheat code in the way that it gives the work somewhere to live.

The same thing happens in marketing.

It is almost impossible to write a sharp positioning statement for an audience you have not bothered to love, fear, study, or respect. You can still write one, of course. The internet is full of sentences wearing AI-polished business shoes. “Empowering teams to optimize outcomes.” Wonderful. Call the priest. The sentence has no pulse.

When you actually care about the person on the other side, the language changes.

You stop saying “streamlined operational efficiency” and start saying “stop losing Friday afternoon to the spreadsheet nobody trusts, least of all, you.”

You stop saying “better customer engagement” and start saying “give people a reason to come back before they forget why they came in the first place.”

You stop saying “AI powered insights” and start saying “ask the question before the meeting and walk in with an answer instead of a hunch dressed in cologne.”

Care creates specificity. Specificity creates trust. Trust creates action.

A bartender who gives a damn remembers that someone likes pilsners but hates anything too sweet. A product marketer who gives a damn knows the CFO is not buying software. They are buying fewer surprises. A teacher who gives a damn does not teach grammar as grammar. They teach it as the difference between being understood and standing there with your mouth full of alphabet soup.

It’s worth stating again: work gets better when it matters to you.

Stay Positive & Giving A Damn Isn’t Just Sentimental; It’s Strategic