Storytelling as a Craft: Advice from 5 Experts on How to Tell a Compelling Business Story
PR & Marketing

Storytelling as a Craft: Advice from 5 Experts on How to Tell a Compelling Business Story

Every startup leader should practice flexing their storytelling muscles. To help warm these muscles up, we’ve rounded up some of our best advice about storytelling in business that’s been featured in the Review.

As a startup founder, you're constantly telling stories. You tell the story of your company's origins when you pitch to investors. You craft narratives about your product when marketing to customers. And you shape an inspiring vision to rally your team. Storytelling is woven into every aspect of building a startup.

But in the midst of building the product and all of the other things on a startup founder's plate, it's easy to lose sight of the impact your stories have on your business — how you narrate your startup's journey influences everything from funding and sales to morale and team cohesion.

It’s why every startup leader should practice flexing their storytelling muscles and carefully hone this skillset. To help warm these muscles up, we’ve rounded up some of the best advice about storytelling in business that’s been featured in archives of the Review.

Learn from folks like Oren Jacob, the man behind the storyboarding process at Pixar, to First Round’s own Marketing Expert in Residence Arielle Jackson on how to position and present a successful startup story. We’ll feature tested frameworks for leveling up your business storytelling skills for all sorts of different audiences.


Storytelling isn’t just the domain of content creators, marketers or PR pros. The ability to tell stories that inform, persuade or inspire supercharges every part of company building.

“When we look at what visionaries really succeed at, they give us a confident, consistent and coherent plan that makes us feel safe,” says longtime Google product leader Tyler Odean. “We trust them not because their vision is perfect, but because they have it under control. They communicate clearly without giving us all the answers. What most people think of as vision is actually persuasion.”

And when it comes to persuasion, companies typically appeal to the left side of the brain, like logic, pricing and specs, says Andy Smith (a startup marketer, advisor, and expert storyteller). Emotion, however, has proven to be the better marketing tool. Simply put, well-told stories earn attention. Storytelling in business can be a powerful tool to help you connect with people emotionally, simplify complex ideas, humanize your brand, inspire action and spark creativity.


But the way you architect and tell a company’s story is (and should be) quite different from the way you’d tell a story at a party. Here is the four-step checklist for crafting a compelling business narrative.

1. Identify The Purpose

Are you trying to persuade investors to take a chance on your startup or convince top talent to leave a BigCo job to take a chance on your startup? Start by narrowing down the purpose of your story — think of this as sketching out the story structure.

For advice, we turn to Arielle Jackson, our Marketing Expert in Residence at First Round and a former marketing leader at Google and Square. Jackson has advised hundreds of startups over the years to communicate the exact story they want to tell, and she asserts that the bulk of this comes down to proper positioning.

“Aligning teams, hiring the right people, developing the best product, communicating the value of your work — the list goes on. It all starts with positioning,” she says. “You need to position yourself in the mind of your user. That requires taking your potential audience into account, assessing your strengths and weaknesses, and considering your competition. People are busy. You have to know who you are.”

2. Pinpoint The Audience

Once you have the purpose of your narrative nailed down, the next piece of the storytelling puzzle is to fine-tune the details so it resonates with the right audience. Just as a product manager zeroes in on a customer persona, expert storytellers do the same with narrowing down an audience persona.

But for the times that it’s not so obvious who the target audience of your story is, this may take a bit of pre-work. Jackson offers some helpful questions to ask yourself before formulating your next business story:

3. Sculpt a Structure

We’ve all been twisted up listening to a rambling story, with no discernible beginning, middle, or end in sight. At the very mildest, it’s a nuisance to the listener. At its worst, a poorly told story can have the exact opposite effect on your audience; it can persuade folks why they shouldn’t listen to you.

It’s critical to follow some sort of structure to anchor whatever narrative you’re telling. “You need to take the whole room on a journey together,” says Oren Jacob, the founder and CEO of the entertainment company PullString and former CTO at Pixar. “This means there has to be a narrative arc with a beginning, middle and end. When you’re in command of your material, creating this structure is in your control.

One tactical way to make sure you are landing on a structure that weaves in all the points you want to hit home is to ditch chronology altogether. “Chronology matters much less than having your story follow an interesting arc,” says Smith. "And as luck would have it, the stuff you need to hook people doesn't tend to happen early on.”

Unless you’re telling the story of how to land a plane safely or the proper assembly of an IKEA bookshelf, resist the urge to begin at the beginning.

Smith argues that events need to build, one after the other, emotionally rather than sequentially.

4. Weave the Storytelling Elements Together

So you called a cab, but no one’s showing. The only thing the cranky dispatcher will say is “He’ll be there in 15.” You call back in 15, and he now says, “Driver’s on the way. Any minute now.” Click. It’s cold, it's getting dark, and you’re already late. Wouldn’t it be great if there was an app that let you tap into an unused supply of empty cabs and cars to get you where you want to go, perhaps with a little style?

So goes the legendary inspiration behind Uber, a story now encapsulated in a single tagline: “Everyone’s private driver.”

It’s also a near-perfect example that combines steps 1-3 seamlessly. Andy Smith argues this anecdote followed the proper business storytelling formula.

Uber took into account its purpose (a private taxi competitor and startup) sprinkled in messaging for a hand-picked audience (potential customers who had felt the pinpoint that Uber was solving) and used a clear beginning, middle, and end structure to tie it all together. The result painted a compelling picture that a real problem in this area existed while also offering itself as a solution. Blending in elements like conflict, a main character and relatability made this an even stronger pitch.


Like the Uber example above, sometimes, the best way to get a grasp on storytelling skills is to listen to a terrific one. So we’ve rounded up four storytelling experts who have shared their hard-won wisdom with us on the Review over the years for additional tips to help boost your storytelling abilities.

Practice how your story will land by running the Bar Test

Nicole Kahn knows a thing or two about delivering a compelling presentation. Now the VP of Design at Carta, Kahn has spent her entire career carefully crafting thoughtful designs and projects for innovative workplaces like IDEO and WeWork.

One of her favorite tips to lean on when starting from scratch on a new presentation is to run the Bar Test. “Something really important happens when you’re at a bar,” says Kahn. “You use direct language. You make sure that what you’re saying is entertaining and engaging. You don’t quote tons of data. You don’t use overly corporate language — except maybe in air quotes.”

Kahn argues that this proves that we all have an innate sense of what makes a good story, but we tend to forget it once we walk into the office or join a Zoom room. She challenges anyone taking on business storytelling to think: how would I give my presentation at a bar?

By bringing the Bar Test into the work environment, we answer this question: What’s the point?

To run the Bar Test, Kahn has her team talk to other people — often strangers — before they start putting presentations together. “We tell them our story. We verbalize it. We grab a colleague who’s completely unfamiliar with what we’re doing and buy them a beer or a coffee and spend 15 minutes to see if they understand the point of the presentation,” she says.

Lean into your authenticity to boost your credibility

Storytelling in business isn’t just about being able to tell tales of success, but it’s also about knowing the power of telling stories of failure or doubt.

Don Faul, CEO of Crossfit and former Head of Operations at Pinterest has spent the better part of his career leaning on authentic storytelling as a way to establish trust as a leader. He learned from his early career at the U.S. Naval Academy that all good leaders need to be able to tell what he calls the “failure story” to be credible.

“If you’re willing to tell everyone on your team about your mistakes, your shortcomings, what you’re currently working on to get better, you seem more human. It’s easier for people to connect with you. They have an easier time believing what you say, and that you’re taking their wellbeing into account,” Faul says.

Being vulnerable is one of the most powerful things you can do as a leader because it shows you’re genuine. Being genuine builds trust. Trust is the key to getting anything done.

Commit it to memory

Sketching out the beats of a story is just one part of telling a compelling narrative. But if your delivery is stilted or you’re just reading off your notes, even the most well-designed stories can fall flat. As Oren Jacob puts it “A pitch is a live performance. You have to know it so well that it seems spontaneous.”

This spontaneity is key to helping your audience pay attention, remember the information, and be persuaded to take action. Committing your story to memory, in whatever form that takes, will help inject the necessary emotion and authenticity to persuade your audience. If that means practicing your pitch, presentation, or speech in the mirror at home for a few hours each night, do it, says Jacob.

Never read your slides. If you find yourself doing that, you've already lost.

Finally, remember that great stories are inspiring.

“You have to make investors believe how much you believe in it, and how much you want to go on that journey with them — even if neither of you knows how big it can get," Jacob says.

Image credit: Constantine Johnny for Getty Images