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Darts illustrating curiosity and challenging assumptions in marketing strategy.
Marketing Strategy

The Most Dangerous Thing in Marketing Isn’t What You Don’t Know. It’s What You’re Sure You Know.

Chris Kelly
Chris Kelly
September 22, 202612 min read

One of my favorite scenes in Ted Lasso takes place in a pub over a game of darts.

Rupert Mannion thinks he has Ted figured out. He's watched him long enough to form an opinion about who Ted is, what he knows, and what he's capable of. So when Ted challenges him to a game of darts, Rupert confidently accepts.

What Rupert doesn't know is that Ted grew up playing darts with his father every Sunday afternoon from the time he was ten until he was sixteen. More importantly, Rupert never asks. As Ted prepares to finish the game, he talks about a quote he once saw attributed to Walt Whitman:

"Be curious, not judgmental."

Had Rupert been curious, Ted points out, he might have asked one simple question:

"Have you played a lot of darts, Ted?"

That question would have completely changed Rupert's understanding of the situation.

Marketing organizations do versions of this constantly. We collect enough information to form an opinion, turn that opinion into an assumption, repeat it until it becomes accepted wisdom, and eventually make decisions as though it were an established fact.

Sometimes we're right. Sometimes we're spectacularly wrong. The problem is that once we're certain, we usually stop trying to figure out which one it is.

Judgment closes the investigation. Curiosity starts it.

And in marketing, closing the investigation too early can get very expensive.

When an Assumption Becomes "Something We Know"

Every organization has a collection of things everybody seems to know.

"Our customers won't pay for that."

"Paid advertising doesn't work for us."

"Our audience isn't on that platform."

"We tried that before."

"Organic is the only way to build trust."

"Our customers are too cheap."

"That campaign failed because of the creative."

Any one of those statements could be completely accurate. Curiosity isn't about automatically assuming the opposite is true. It's about being disciplined enough to distinguish between something we've demonstrated and something we've repeated. That distinction gets lost surprisingly easily.

Someone makes an observation in a meeting. It sounds reasonable. Someone else repeats it. Eventually it makes its way into a strategy deck. Six months later, nobody remembers where the conclusion originated or what evidence supported it. It has simply become something everybody knows.

Then budgets get allocated around it. Audiences get ignored. Channels disappear from the strategy. Offers change. Customer journeys get built around behaviors customers may or may not actually exhibit. That's when I come back to one deceptively simple question:

How do we know?

Not "Why do we believe it?"

Those are different questions.

There is usually a perfectly reasonable story behind what an organization believes. The more valuable question is whether there's enough evidence to distinguish that story from what's actually happening.

I Was Sure This Campaign Was Going to Work

I wish I could tell you I've always been the person asking that question. I haven't. Years ago, I developed a product promotion that I absolutely loved. Customers could build their own combination of products and save up to 33%. They could mix and match colors, sizes, products and fabrics, and we included flat-rate shipping.

As someone who loves to shop, I thought it was fantastic. And that was exactly where I screwed up.

I thought it was fantastic.

I was thinking like myself instead of our ideal customer.

Because of margin requirements, not every product could be included. We had plenty of popular products in the promotion, but not one true bestseller from any category. Customers had a lot of choice. We just hadn't given them the choices they wanted most.

The campaign failed.

Nearly ten years later, the lesson I remember isn't what I should have discounted differently or which products I should have swapped. That's Monday-morning quarterbacking, and buyer behavior has changed far too much for me to pretend I can rerun that campaign today and know exactly what would have worked.

The lesson is that I had fallen in love with my own idea.

I wasn't looking at the promotion through the customer's eyes anymore. I was looking at it through mine. I liked the flexibility. I liked the discount structure. I liked the ability to mix and match. And because it checked the boxes that mattered to me, I became convinced it would check the boxes that mattered to them.

That's not customer insight.

That's confirmation bias with a marketing budget.
Your ICP is not you.

Experience gives us instincts, and good instincts are incredibly valuable. But an instinct should tell you where to look, not give you permission to stop looking. That's the distinction I missed.

The market doesn't care how much YOU love YOUR idea.

The Hardest Question Might Be: "What If I'm Wrong?"

There's a reason experienced marketers can stop asking questions.

Certainty is comfortable.

When you've spent years building expertise, people expect you to have answers. Clients expect them. Executives expect them. Your team expects them. Eventually, you expect yourself to have them too. And experience matters. Years of watching campaigns succeed and fail, analyzing marketing performance, managing budgets and solving problems create valuable pattern recognition.

But there's a trap hiding inside it. The more you've seen, the easier it becomes to believe you've seen this before.

"I know why this failed."

"I know what these customers want."

"I know that channel doesn't work."

Maybe you do. Or maybe you recognize the shape of the problem without understanding this particular version of it.

The moment expertise convinces us we have nothing left to learn is the moment our expertise starts becoming a liability.

That's why one of the hardest things to say when you're supposed to be the person with the answers is:

"I don't know yet."

It doesn't mean you don't have a hypothesis. It means you're leaving room for new information, for the customer to surprise you, the data to contradict you, and someone else to notice something you missed. And ultimately, it leaves room for the harder question:

What if I'm wrong?

Being wrong isn't particularly dangerous. Every marketer who has done this long enough has been wrong. Needing to be right so badly that you stop looking for evidence that you aren't?

That's dangerous.

Sometimes We Create the Customer Behavior We Complain About

I've heard versions of this throughout my career:

"Our customers will never pay for that."

"They're too cheap."

"They always want something for free."

"We've tried charging for that before."

Maybe they're right. But again: How do we know? Did customers reject the price, or did we fail to communicate enough value to justify it? Did we test different positioning? Different customer segments? And here's the uncomfortable one: have we spent years teaching them not to pay?

Constantly discount, and customers learn to wait for discounts. Repeatedly give something away, and customers learn to expect it for free. Lead every marketing message with price, and you're going to disproportionately attract people who make decisions based on price.

Then one day somebody sits in a conference room and says, "Our customers are price-sensitive."

Maybe. Or maybe your marketing spent years attracting price-sensitive customers and rewarding price-sensitive behavior.

Be careful calling something customer behavior when it might actually be customer conditioning.

Assumptions don't always describe reality. Sometimes they help create it.

You Can't Build Strategy Around Someone You Don't Understand

This is why I have such a strong reaction when marketing strategy starts before customer research does. Don't even sit down to draft the strategy until you understand who you're going after and who your client truly is. Having an ICP slide isn't enough. A title, age range, company size and industry give you attributes. They don't necessarily give you understanding.

What pressure is your customer under? What are they accountable for? What are they afraid of getting wrong? How do they research solutions? What problems are they actually trying to solve? What makes them trust a company? What makes them skeptical? And critically: where are they actually willing to engage with you?

I saw this with a startup client who came into the relationship convinced paid advertising didn't work. She had been told repeatedly that organic was the way to grow, and by the time we started working together, that advice wasn't something she wanted to test anymore. It was something she believed.

The problem was sitting right in front of us.

This was a startup. The brand was largely unknown, the offering was untested in the broader marketplace, and it had virtually no market share. We could continue changing organic tactics, and we did, but changing the tactic didn't change the fundamental problem.

You can't build awareness among people who don't know you exist by waiting for them to find you.

For months, we had the conversations. We showed the dashboard data. We adjusted organic tactics when she wanted to try something different. We kept coming back to the same recommendation: we needed to put the brand in front of the right people instead of relying entirely on those people to discover it themselves.

Eventually, she was willing to test it. And I mean test it. The paid media budget she approved was tiny, almost insignificant. We weren't suddenly flooding the market with advertising dollars. But in roughly six weeks, that small paid media test created more movement than we'd seen from organic efforts in the entire quarter before it. That's when the assumption finally had to compete with evidence. The lesson isn't that paid media works and organic doesn't. That's just replacing one absolute with another, and it would miss the entire point.

The lesson is that a belief had been allowed to dictate the strategy long after the results were giving us reasons to question it.

Sometimes the smartest thing you can do in marketing isn't defend your recommendation harder. It's create a test small enough that everyone is willing to learn from it. Because once you have evidence, the conversation changes. And that brings us back to the question underneath this entire article:

How do we know?

Not what have we been told. Not what worked somewhere else. Not what we prefer. Not what we've always done. What does the customer, the market and the evidence in front of us actually tell us?

A strategy built before you understand the customer is a collection of guesses with a budget attached to it.

Curious on the Way In. Decisive on the Way Out.

But knowing the customer isn't the end of curiosity. The same discipline matters in the room, especially when the evidence is telling you that something needs to change. Because finding the right answer is one challenge. Getting people to hear an answer that challenges something they already believe is another. Some of the best leaders I've worked with share one trait:

They listen more than they speak.

Not the performative version of listening where you're checking email during the meeting or waiting for someone to stop talking so you can deliver the answer you've already decided on. They are actually engrossed in the conversation. They ask questions. They pay attention. They don't talk over the client or stakeholder because their experience tells them they know better.

And before challenging someone's thinking, they make sure that person knows they've been heard. Something changes when people genuinely believe you've listened to them. Defensiveness comes down. The conversation becomes calmer.

Then you can drop the bomb.

You can introduce the disruptive idea, challenge the long-held assumption or explain why something they've done for years needs to change.

People are much more willing to have their thinking challenged once they believe their thinking has actually been heard.

Curiosity doesn't make leaders indecisive. The best ones are curious on the way in and decisive on the way out.

Leaders Aren't Supposed to Know Everything

Unfortunately, saying "I don't know yet" has become increasingly difficult for leaders. Corporate culture talks constantly about learning and development. We tell employees we'll train, coach, mentor and help them grow. Then someone reaches an executive role and the expectation can suddenly change. You're here because you're supposed to know.

When an executive doesn't know something, they're too often made to feel guilty, inferior or ill-equipped to handle their responsibilities. But if leaders believe admitting they don't know is professionally dangerous, what are we teaching them to do?

Answer anyway. Project certainty. Lean harder on experience. Avoid questions that might expose a gap. Defend an answer longer than they should because changing their mind might look like they didn't know what they were doing.

There's a difference between expecting leaders to know how to find the answer and expecting them to already have every answer. Good leaders should bring expertise, recognize patterns, make decisions and accept accountability.

But expertise isn't omniscience. Especially now.

AI is changing how people discover information. Search behavior is evolving. Paid media platforms are increasingly automated. Attribution, privacy, customer journeys and buyer behavior continue to shift.

There has probably never been a worse time to decide you have nothing left to learn.

Curiosity isn't the absence of expertise. It may be one of the highest expressions of it.

Ask the Darts Question

That's ultimately what makes the Ted Lasso scene so powerful. Rupert had plenty of information about Ted. The information wasn't necessarily wrong.

The conclusion was incomplete.

And one question could have changed everything:

"Have you played a lot of darts, Ted?"

Every marketing organization has its own version of that question. What haven't we asked because we think we already know the answer?

About our customers. Our strategy. Our campaigns. Our data. Our people. Or ourselves.

The dangerous part isn't not knowing. You can fix not knowing. You can research. Listen. Test. Measure. Experiment. Ask. The dangerous part is becoming so certain that you stop doing any of them.

Rupert's biggest disadvantage at that dartboard wasn't that Ted knew how to play darts. It was that Rupert had already decided who Ted was. And once he made that decision, there was nothing left for him to learn.

Be curious, not judgmental. Pretty good advice for a game of darts.

Turns out, it's pretty damn good advice for marketing, too.

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