04-06-2025
Why Most Companies Fail At Storytelling—and How To Fix It
Storytelling is an art companies should pay more attention to.
There's nothing as off-putting as realizing you're being sold to halfway through what you thought was a genuine conversation.
It's the ultimate corporate act of objectification: it's not you the salesperson is interested in, it's the content of your wallet.
Salespeople walk a delicate tightrope when it comes to the stories they tell.
If a client senses that every friendly laugh and personal anecdote was just bait on the hook, the entire relationship collapses into a transaction. Mental barriers go up, defensiveness kicks in, and no one leaves the conversation any happier or wealthier than they arrived.
But it doesn't have to be this way.
First of all, some buyers want to be sold to. They come with specs in hand, hunting for the right product until they find who can give it to them. For them, the no-nonsense Grant Cardone approach where we embrace the transaction and skip the fluff works brilliantly.
For everyone else, there are the stories companies tell, even if they don't realize they are telling them.
A well-told story does much more than entertain a client.
It places them inside a larger narrative, where the product becomes a tool to further their own journey. Where Simon Sinek starts with why, great storytellers start with the who - who is the customer, what are they trying to become, and how do we help them get there?
Stories are what sold the first iPhone. They're what sell you most of the ideas you hold in your head today. They are an antidote to poor salesmanship.
Why, then, are so many companies still so terrible at telling them?
Here's a secret most marketing professionals won't admit: sales, marketing, product, and branding are not separate functions.
They're all just fragments of the same essential task of contextualizing the company to its clients and selling a story from the first engagement to conversion.
The connecting thread across all these disciplines is so simple that many miss it entirely: who we are, what we do, and why it matters to you is ultimately nothing more than the story the company tells to its customers.
Abhay Parasnis, founder & CEO of Typeface and former CTO at Adobe, sees this particularly clearly.
"Companies often think of storytelling as marketing's job," he says. "But every touchpoint tells a story, your onboarding flow, your contract terms, even your product roadmap. It's one giant conversation with the customer, whether you realize it or not."
Parasnis is a strong believer in integrating storytelling across the company.
"If product is telling one story, marketing another, and sales yet another, you're not multichannel, you're in chaos," he jokes.
He warns that the customer notices dissonance far faster than executives do.
"Today's buyers are trained experts. They sense inconsistency immediately," Parasnis explains.
At the heart of all successful storytelling, according to Parasnis, is radical coherence.
"You have to be so aligned internally that no matter which team the customer touches first, the narrative feels inevitable. Like gravity."
That coherence doesn't happen by itself, nor does it thrive when the storytellers are locked up in their silos. It demands ruthless clarity about who the customer is, and what they actually want.
It also requires us to go further than bare-bones personalization and make a real connection to engage with the customer.
'We've become spoiled by how well everything is personalized to us as consumers, with brands like Netflix and Spotify, to the point where these companies know what we watched, what we like and our values are now a given' Parasnis begins. But most enterprises do not have the ability to tell personalized stories, especially at scale which led Parasnis to founding Typeface.
'We all have fond memories of companies making an intimate connection with us in ways that go beyond simply knowing us. These companies saw us, connected with us, in ways that others didn't, and that feeling sticks,' Parasnis continues before adding how the best companies enroll the customer as a co-creator of their stories.
Ryan Chesterfield, a seasoned client strategist, reflects on why so many companies don't hit this mark by noting how 'the biggest gap in most companies is that they don't actually know their customer's story. They know their own, and often even that is muddled and jumbled in jargon and technospeak."
Look around you and you can join Chesterfield who sees this all the time.
"Sales decks are filled with 'we' statements, we built this, we raised that, we are the best. But the customer's sitting there wondering: What about me?"
Indeed, too often the client comes in only when we get to the pricing sheet. If your clients' only contribution to the story is whipping out their credit card, don't be surprised if they jump ship and leave town with someone who brings them along the entire journey.
This is why Chesterfield believes great storytelling is an act of empathy, not self-promotion. "You have to deeply understand the customer's life and tell the story from their point of view," he says. "If your pitch isn't secretly their diary entry, it's dead wood all the same."
Understanding the customer, deeply and humbly, is the starting point.
Even companies that master storytelling often falter when it comes to truly building customer relationships that endure.
One reason is that what motivates a buyer is rarely what motivates a seller.
Shahar Silbershatz, CEO of Caliber, a stakeholder intelligence firm that helps organizations build trust, argues that client-centrism is often preached but rarely practiced.
"Everyone claims to put the customer first," Silbershatz notes. "But most companies still optimize for their quarterly KPIs, not the customer's journey."
The solution, according to Caliber, is to better understand how customers perceive your organization so you can align your actions with their expectations.
Silbershatz believes the best brands don't just tell stories, they live inside the customer's internal narrative of success.
"The difference between an average brand and a beloved brand is actually rather simple. One is an interruption. The other is a character in the story you're already telling yourself," Silbershatz says.
He points out that the emotional connection often outlasts rational calculations.
"You can be 50% cheaper than your competitor and still lose if the customer feels they understand them better."
But that emotional connection has to be earned, and backed by operational truth.
Jeremy Burton, CEO of Observe, shares lessons he learned working alongside legends like Larry Ellison and Joe Tucci.
"You can have the best story in the world, but if your product doesn't back it up, it's just a lie waiting to be exposed," Burton says.
He cautions against empty storytelling. "The great mistake companies make is thinking marketing is magic dust you sprinkle after the fact. No. Storytelling starts with what you build, not what you say."
Burton believes the best marketing is simply telling the truth, but telling it elegantly.
"At the end of the day, the companies that win at storytelling are better at identifying the substance the story points to."
The most enduring brands are ruthlessly consistent between what they say and what they sell, and they build the narrative around the client. A client, that is much more than an account to be managed.
If storytelling was as easy as making the customer the hero of it all, we could stop here and call it a day. But it's not.
In fact, sometimes the customer relationship and the stories around it aren't always what matters most.
Sometimes, it's just the transaction, plain and simple.
Grant Cardone, one of the most loudly heard voices in sales today, flips conventional wisdom on its head.
"The idea that every customer wants a relationship is a straight up myth, perpetrated on up-and-coming salespeople for decades," Cardone says. "Some customers just want a suit, not a new best friend."
For Cardone, selling is about clarity and speed, not manipulation or faux intimacy.
"I don't think I'm in any kind of relationship with the customer until money actually trades," he explains. 'Only then, can I provide the product or service to the customer and only then can they benefit from it.'
He argues that transparency, even brutal transparency, builds more trust than artificial rapport.
"Put the price on the table. Show the product. Make it simple. Remove the friction. You want trust? Give people the truth—fast," he says.
Cardone scoffs at the idea that a sale becomes "dirty" if it's treated as a transaction.
"If we become friends after the deal, great," he concedes. "But the idea that I have to create some fake relationship first? That's the real trickery here."
For Cardone and his followers, sales isn't an act of seduction, it's clinical surgery.
Get in, fix the problem, and get out. Clean, fast, and with the customer's dignity intact with both parties benefiting from the exchange.
However, here's a secret.
Even the simplest transaction tells a story: Here's what I have. Here's what it costs. Here's what you get. Come back again.
Sometimes, the best story is the simplest one, which is why many are finding Cardone's process brutally effective.
If even the simplest stories would do, why do so many companies still suck at storytelling?
The easy answer is because storytelling is hard, particularly when you don't know the story you are telling in the first place.
Matt Davies and Pieter-Paul von Weiler, co-founders of BetterBriefs, have spent years studying why most marketing storytelling falls flat, and they trace much of the failure back to one overlooked source: the brief.
"Current estimates say 30% of marketing spend goes to waste," Davies notes. "In any other profession, the way marketing briefs are written would be considered incompetent."
BetterBriefs' research shows that when better briefs enter the system, teams produce deeper, richer work with less wasted effort. 'A good brief reduces rounds of rework,' von Weiler explains. 'In a typical Super Bowl campaign, you can have 150 people involved across five or more rounds. Better briefing would cut that waste dramatically.'
Their diagnosis is blunt.
Marketers, they argue, have lost the language of business. "Too many marketers can't tie creative output to commercial impact," Davies says. "And without a clear idea of what results we want, storytelling collapses into either vanity or noise."
The solution, according to Davies and von Weiler, isn't simply focusing on making better ads.
Instead, companies need to learn how to start better internal conversations about what stories they tell.
"Before you tell a better story to the market," Davies says, "you have to tell a better story to yourself."
Great storytelling requires coherence between teams, empathy with customers, humility about your product's real strengths, and a willingness to tell the truth even when it's less flattering.
Storytelling is hard because it forces leaders to confront not just what they sell, but why it matters to others.
But companies that master it, those that align product, marketing, and sales into a single narrative flow, are the ones that do more than simply close deals and fill sales pipelines.
And if your company hasn't nailed great stories yet, don't worry. It's never too late to rewrite yours.
