Good Leaders are Great Storytellers — Our 6 Tips for Telling Stories That Resonate

Good Leaders are Great Storytellers — Our 6 Tips for Telling Stories That Resonate

Storytelling isn’t just the domain of marketers or PR — the ability to tell stories supercharges every part of company-building and leadership. We sifted through wisdom from founders and experts to gather the Review's six best tactics on telling stories that inform, persuade and inspire.

When “Toy Story” premiered to glowing reviews and box office success in 1995, there was one theme among the chorus of praise that made the Pixar team especially proud.

"We took pride in the fact that reviewers talked mainly about the way 'Toy Story' made them feel and not about the computer wizardry that enabled us to get it up on the screen,” Ed Catmull, co-founder of Pixar, recounts in Creativity, Inc. “We believed that this was the direct result of our always keeping story as our guiding light.”

In fact, this detail was so foundational that the phrase “story is king” has since become something of a motto for this animation studio in Emeryville. And the lesson isn't confined to the storyboards — it extends far beyond the heartfelt scripts and pioneering animation, permeating all the way down to how its software development teams operate.

Startups, too, can take a page from Pixar’s playbook: 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. Founders pitching the next big startup idea need to nail the narrative that compels investors to care. Sales reps leading demos have to create scripts that win customers, and recruiters need to tailor their company pitches to close stellar candidates.

Stories aren’t just for external audiences, either. Structuring an All-Hands agenda requires telling the story of the company’s progress. When you’re presenting a strategic plan, you’re laying out the story of the company’s future. From making a case for promotion in a performance review, to conveying a shared vision for a project, every operator in every function benefits from being able to communicate ideas that connect people.

Storytelling is the not-so-secret ingredient that makes the difference between being a manager and being a leader, between closing a customer and winning a lifelong fan.

It's the tool that everyone — leaders especially — should be constantly sharpening. To help you tell stories that cut through the noise, we’ve rounded up the Review’s six best tactics on storytelling. From founders to engineering leaders, marketing experts to design directors, our experts each approached the notion of “storytelling” from a slightly different angle. But taken together, they highlighted a key common thread: Good storytelling isn’t about fanciful language. It’s about conveying a message clearly and simply. It’s about connecting with your audience not as customers, executives or investors, but as humans.

After all, what’s company-building but a series of stories? Every established company has its celebrated origin story, every startup is authoring its valiant underdog story — and with any luck, all of it culminates in a success story. We hope these tips can help you tell yours.

1. Find your story at the local watering hole.

Perhaps the most obvious storytelling opportunity at companies comes in the form of presentations. Whether you’re sharing a status update at a meeting or giving a talk for an audience of thousands, you want to make sure that you refine your delivery so that your story lands.

Take the example of a design agency presenting their work. “We know that our designs don’t live on with our clients without a good story attached to them,” says Nicole Kahn, the former Senior Director of IDEO’s Design for Change Studio. “Stories are the way our teams get excited, aligned, and rallied around the same goal.”

Hoping to ensure that all of their designers would also see themselves as storytellers, Kahn and her team held a series of events at IDEO offices across the country, sharing their set of best practices for giving high-impact presentations. The goal: to provide a model for what good presentations look like, while also giving designers a chance to talk about what inspires their creativity, and get solid feedback from an audience of their peers.

Here are two of those tested tactics:

Find your story at the bar

“Bars are friendly, social places, sure, but something really important happens when you’re at a bar,” says Kahn. “You use really 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.”

These experiences show that we all have an innate sense of what makes a good story, but we tend to forget it at work. So, how would you give your presentation at a bar? What if you only had the backs of napkins for graphics? How would that change the way you related information?

When we tell stories to our friends, we prove we're all natural born storytellers.

By bringing the Bar Test into the work environment, we’re more able to answer this question: What’s the point?” Kahn says. “When we’re in the middle of a project, the sheer number of stories we could tell about it are as numerous as stars in the sky, and we get really excited to share them all to show what we’ve done, but we can’t do that.”

To run the Bar Test, IDEO designers 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.”

When you do this with your colleagues or friends and family, pay attention to the little things, Kahn says. “We look for when they lean in, or when they look away or reach for their phone. We look for nods and ‘uh huhs’ — we look for what surprises and delights. That’s how we figure out what’s sticky and resonating.”

It doesn’t have to take much time at all — just the 15 minutes it takes to drink a coffee and get one or two pieces of feedback. “Force it to be succinct. That’s the magic of verbalizing your story. You’ve invested nothing and there’s no reason to get stuck. You can redo it again and again.”

Build your skeleton

“After a good Bar Test, the skeleton of your story should emerge: the main points you know you have to hit to make it memorable," Kahn says.

It only takes three essential elements to make a great story:

  • Your through-line that connects everything together — the point of you telling the story in the first place.
  • “Put me in the room” anecdotes that provide a tactile sense of experience, take your audience on a journey, and create drama.
  • Moments of reflection — telling your audience how you feel in order to cue them to feel a certain way.

Similarly, moments of reflection should be scattered throughout your talk to grab attention, create intimacy with your audience, and give them a window into your process. “I might say something like, ‘I knew we were onto something the moment I met Sandy and she said this one thing.’ This cues the client to pay attention.”

Tell your audience 'this is a point that is important to me' to tell them 'this is a point that should be important to you.’

“When we meet with new clients, we often say things like ‘Hey, this is where we know a lot of other clients get hung up or stuck,’ and they will always listen really hard to those ideas. It gives you a sense of expertise,” says Kahn.

When you bring all of these elements together — the through-line that you’ve found in conversations with others, anecdotes that ignite the imagination, and reflection points that call people’s attention back to how you’ve approached the work — you’ve found your story.

Read more about the advice from IDEO’s Nicole Kahn that will transform the way you give presentations.

2. Use the art (and science) of persuasion to tell stories that change minds and rally teams.

Tyler Odean stands by his contentious outlook on leadership:

For startups and founders, being persuasive is way more important than having vision.

In other words, leadership is less about having a perfectly-engineered vision, and more about telling a compelling story that convinces others to join you. “The reality is that visionaries like Steve Jobs weren’t successful because they thought of something amazing and original out of thin air,” he says. “Rather, they were gifted at constantly persuading many people to follow them on their journey to something amazing and original.”

As a long-time product leader for Chrome at Google, former Director of Product at Reddit and current Product Lead at Pinterest, Odean found himself using persuasion as a tool to herd massive organizations — engineers, designers and executives — toward product decisions and developments. He realized how powerful it was to be able to rally people to his and others’ points of view.

To harness the power of influential storytelling, he researched the science behind how brains process information and form opinions. “When we look at what visionaries really succeed at, they give us a confident, consistent and coherent plan that makes us feel safe,” says 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.”

Trouble is, most tech operators express themselves with complexity, nuance, facts and figures. That’s their default, and it doesn’t appeal to people's unconscious processors. To help folks tell stories that resonate, Odean shares his top tips for smart, simple storytelling:

Distill your story into a highlight reel

After any experience, humans create a representative image or memory of what happened — and they reason off that image. For instance, if they have an argument with someone, they’ll take away one or a handful of representative images of how that went down. No one gets to choose what sticks, it just happens.

For founders and marketers, this hits on one important point: “People will remember a totally random sample of the information you give them about what you do.” It won’t be the best sample. It won’t be the summary you wish you could hand them. It’s a random set of data.

Many people, given the opportunity to get in front of an important audience — like investors or an industry reporter — think they need to say it all. They have to tell a full story about their company or product so that it can be well understood in the exact context you want.

People pack presentations with every selling point they can think of. But that’s actually the worst thing to do.

“They’re going to remember hardly anything you cram into that hour,” says Odean. “Because they’ll remember random parts, you want to construct a message that — when sampled at any point — reinforces your argument and remains persuasive. Keep it to the highlight reel and stick to a very short, simple message that you repeat in different ways again and again. When there are fewer things to remember, your audience is more likely to remember what matters.”

Stick to only your strongest points, too. The way the brain works, even if you’ve made a ton of extremely compelling arguments, one weak one can spoil the whole thing. Think of two hypothetical sets of goods:

  • The first includes 5 iPhones, one of which is broken.
  • The second includes 3 iPhones in good condition.

We all know that the first set is the best choice, and most people will choose it when presented with both options side by side. However, when they’re only shown one set at a time, they tend to put a higher price on the undamaged set. Even though they intellectually understand the value is the same, they still emotionally respond to the damaged goods.

To tell stories that persuade, emphasize possibility and potential

“People hate losses much more than they like gains,” says Odean. But they don’t evaluate losses and gains relative to what they have — they evaluate them relative to what they feel like they have. “If you’re totally convinced you’re going to get a promotion, and then it falls through, you might experience that as a loss, even though — technically speaking — you didn’t lose anything. You just didn’t gain anything.”

When you need to persuade someone, you can purposefully adjust their reference point — alter what they feel like they already have locked in — to get them to do what you need them to do. If you talk like something is already true, and you do so simply, continuously, and in a way that’s easy to visualize — people will start to feel like it is true.

“You see this all the time in sales pitches,” says Odean. “Rather than telling customers to buy something, the campaign tells them that their time is running out to purchase. They therefore have the opportunity to buy in hand, but are about to lose it if they don’t act. This is why brands always incentivize you to try on clothes or test drive a car. Once people start contemplating their ownership and see it in action, that’s their mental reference point. They’ll have to suffer a loss if they decide not to buy.”

Imagine talking to a job candidate deciding whether to join your startup. Start speaking to them as if they’ve already made the decision to join. “Say, ‘You’ll have this much equity, and this will be your desk, and these people will be on your team.’ Start using the collective first person — ‘We have this opportunity ahead of us,’ ‘We can solve this problem together.’ It will sound like they already have something concrete — and they’ll have to willingly give up all those things by turning down your offer.’ People don’t like to give up things if they can help it,” says Odean.

Read more about the five cognitive biases that Odean says founders can harness to master the art of persuasion as a skill and habit.

Headshot of Tyler Odean
Tyler Odean, Product Lead at Pinterest

3. Great leaders are storytellers — and the best leaders know how to tell stories about failure.

When it comes to the must-have tools in a manager’s arsenal, astute decision-making or motivating reports might come to mind. Storytelling, on the other hand, doesn’t usually make the cut.

Don Faul is here to rewrite that narrative — and give storytelling its rightful place in the leadership toolkit. The CEO of Athos and former Head of Operations at Pinterest got his start at the U.S. Naval Academy. Throughout his impressive journey from the Marine Corps to Silicon Valley, he’s noticed one skill that made leaders stand out: being able to tell good, personal stories. In particular, good leaders need to be able to tell what Faul calls the “failure story.”

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,” says Faul. “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.”

It also gives people permission to take bigger risks in their own work. If your team knows about times you tried to do something and failed, they will also see that you recovered and went on to succeed. They won’t feel hard-pressed to be perfect or place small bets so they always win. When you’re at a startup, you can’t afford to play it safe.

Faul remembers when he first started leading people in the Marines, being vulnerable was very difficult for him in the same way it’s hard for many new tech managers. “You don’t want to show any sign of weakness because you want to convince everyone — maybe mostly yourself — that you’re there for a reason, you’re not a fraud, you don’t have any doubts,” he says.

His attitude toward vulnerability and sharing failure didn’t start changing until he arrived in Silicon Valley and saw examples set from leaders he’s worked with. Now he feels responsible for modeling this approach to the managers on his own team. It’s one of the most powerful ways to pass these skills along to more people and strengthen your entire organization.

I saw firsthand the way my relationship with people changed once I started talking about mistakes. The entire environment of my team changed. Everyone started sharing more openly.

One of the key failure stories Faul shares draws from his time at Pinterest. Early on, he worked on major projects related to the company’s culture. “I know there were many pieces of this I approached the wrong way. I made some bad decisions, including one that didn’t get the response we wanted at all inside the company — it just didn’t land,” he says. “It was my first big, visible failure as an executive, and I knew it reflected poorly on me. I had to work through that, acknowledge the failure, apologize for it, discuss it over and over again. It was incredibly hard for me to do.”

Instead of sweeping the episode under the rug, he now tells this story again and again. Whenever his team confronts a similar situation or makes a mistake, he recalls it. Because the truth is, he did get through it. His team at Pinterest not only survived but went on to other successes. Knowing that recovery is possible on this level generates productive psychological safety for everyone involved.

“I can tell people, ‘I’ve been through this and I legitimately know that you’re going to make it through this and be fine, be better, do more,’” he says. “Now I have three or four stories over the course of my career like this that I tell to soften these hard moments for the people I work with and give them the confidence to endure and stay excited.”

Being vulnerable doesn't weaken your authority. It strengthens everyone else around you.

Here are his two tips for getting started:

  • Open up to just one or two people you trust. See how they respond and how it changes their work style and ethic. Chances are, you’ll get a positive reaction. Plus, it will give you a chance to strike your own balance between vulnerability and confidence.
  • Choose your words carefully in advance. “When I feel people getting worried around me or not taking the big risks, or trying to rebound from a mistake, the first thing I do is sit down and write out the story I want to tell them,” says Faul. “It’s so important that I find the right language that will make it clear I know what their feeling and that there’s a solution. I’ll even practice with my wife. I don’t think people should expect to be good at this spontaneously. And it’s so important to get right.”

Read more of Faul’s wisdom on the pivotal stories every startup leader should be able to tell. If you’d prefer to read his Review piece in print, you can order a copy of our first book, First Round Essentials: Management.

4. Sometimes, the most important stories are the ones that are told within your startup.

If anyone can speak about storytelling from the frontlines of scaling startups, it’s Molly Graham. She managed Culture and Employment Branding at Facebook, and she scaled sales and marketing as COO of Quip before becoming a founder herself.

She has an eagle eye for spotting the challenges that acutely afflict startups, from the dangers of not “giving away your legs” to the monstrous emotions that lurk at startups. She’s spied another pitfall that startups all too often stumble into: failing to construct the company’s culture and distinct story. “When you’re small, the focus is always on product product product, but building a strong team and a strong culture is a hugely important part of building a great product long term,” says Graham.

Take Amazon's well-known practice of writing press releases for products, before they even build a prototype or write a spec. “They take the time to first think through what they want to say to the world when they launch the product. How are they going to explain it?” says Graham.

She challenges founders to port this product approach over to their culture. “Take a minute to write down your story. What do you stand for? What do you want people to say about you?”

Your company's story is the backbone on which everything else is founded.

This story doesn’t have to be long, Graham emphasizes. “It can be four sentences or one paragraph or 3 values. But it needs to make it clear what you are and what you aren’t as a company,” she says. It also needs to give you language that you can re-use again and again in the press, in hiring, in product announcements, and at all-hands meetings to reinforce what your company is about, who you want to attract, and why you’re doing what you do.

Here are two specific tips for polishing your company story.

  • Remember your story isn’t for everyone. “Most job descriptions aren’t actually very honest,” says Graham. “They’re written so that everyone will read it and think ‘Yes! I am definitely qualified to do that. I want that job!’” This happens because job descriptions are written like pitches, practically selling the idea of the job to prospective candidates. “I once got some amazing advice to write your job description for the one person that should absolutely 100% be in that role,” she says. “You want everyone who isn’t right for the job to think, ‘Oh my god, I definitely don’t want that job.’ The same is true of your company's culture narrative: When you have a well-crafted, specific, controversial company story, it can guide everything from who you shouldn’t hire to how you settle arguments.”
  • Steer clear of clichés. “Many of my first attempts at writing Facebook’s story could have described any company — think ‘we hire smart people who are fast learners and team players.’ I would read what I had written and need to take a nap because it was so boring,” says Graham. “Don’t just rehash what every other company has written — watch out for words like ‘innovative’ and ‘impact’ — you should only write down your story if you are willing to stick your neck out and make it controversial.”

Read more from Molly Graham about why 80% of your culture is your founder — and what founders and leaders can do to build a strong foundation for culture for years to come.

5. Your brand is your story. Tell it simply.

One of the most important stories a startup can tell is the tale of what you’re building, why you’re doing it and who it’s for — a narrative better known as brand positioning.

“A lot of people are intimidated by branding. They think, ‘I'm not an artist, I'm not a writer. I can't come up with something,’” says Gibson Biddle, a seasoned startup advisor who’s shared his product knowledge with companies like NerdWallet and Reddit.

What those people don’t know is that there are concrete steps to unraveling the black box of “branding.” For Biddle, Lean Branding author Laura Busche comes closest to an actionable definition:

A brand is the unique story that consumers recall when they think of you.

“This story associates your product with [your customers’] personal stories, a particular personality, what you promise to solve, and your position relative to your competitors,” Busche writes. “All human aspirations are opportunities for brands to build relationships.”

Biddle’s worked firsthand on some of the toughest positioning projects. When he joined Netflix in 2005, he was faced with the daunting task of positioning a product that was breaking completely new ground in technology. The product expert still had focus groups asking him, “Wait, I don’t get it. Do you mean streamlining?” No, streaming, he would say. No one knew what that meant. In the early days, building the company’s brand meant not only finding ways to promote and position the “brand promise” of Netflix, but also introducing language that was fundamental to an incredibly new business.

In other words: He had to break down an innovative concept and turn it into a story that users would not only understand, but endear.

Aligned with Busche’s thinking, Biddle proposes a positioning model to help you locate the place your brand should occupy in a consumer’s mind. First, answer these three questions about your company:

  • What is it? Be descriptive.
  • What are the customer benefits? How does it improve customers’ lives?
  • What is its personality? If your product, company or service was human and you met at a cocktail party, how would you describe him/her?

Of course, there are levers and pitfalls to consider when answering each of these questions. To address these, Biddle has suggestions and illustrative examples to guide your process. Here, he uses snack subscription service Naturebox, which he’s advised, to illustrate concepts that have worked for him at Netflix and throughout his career.

Avoid positioning exercises alone or in silos.

Biddle works with startups in ways that leverage many minds at once. For example, during a workshop with employees at Naturebox, he divided the group into teams of six to apply his positioning model to the business. All participants reconvened to share their thoughts at the end of the hour. The objective of this exercise is to capture and articulate what others value about a company, so it’s critical to get many perspectives. It’s also helpful to track shared language across teams. Here are the initial answers from three of the groups at Naturebox:

Chart from Naturebox branding workshop
Selected answers from a Naturebox branding workshop with Gibson Biddle

So how can you start with something like this and arrive at crisp, unanimous positioning language?

Describe it to a sixth grader.

“Aim to be succinct and clear. Pretend you’re speaking with a sixth-grader. Your customers are busy so they don’t have time to parse fuzzy concepts. Your goal is not to dumb it down, but to tighten it up. ” Biddle challenged Group A to unpack “custom subscription snackbox.” One person offered: “Snackbox Delivered to Your Door.” That was too “salesy” for Biddle. “Snackbox Subscription Service.” That works. What would someone with zero context and limited knowledge of your business understand right away? Go with that.

Decide on one word to own.

Companies that have successfully positioned their brand own a specific word in a consumer’s mind. “What’s the one word that you associate with each major car brand?” asks Biddle. “Honda is ‘reliability,’ Mercedes is ‘luxury,’ Volvo is ‘safety,’ BMW is ‘performance’ and Tesla is ‘innovative.’ We all instinctively relate these companies to these words, but it can take many decades for companies to ‘own’ a word — that is why I’m so impressed by Tesla as a young brand, this idea that they own innovation in the car industry at a relatively young age.”

Ten years from now, what word do you want to own?

Read more about the three simple and powerful tools that Netflix used to build its world-class brand here.

6. Structure your fundraising pitch like a hero’s journey.

Finally, we return to Pixar, the company that’s even come to be associated with the “rules of storytelling.”

Before spending 20 years of his career at Pixar, Oren Jacob was a child surrounded by a family of storytellers. His parents were teachers who were constantly hosting family, friends, colleagues, passersby from around the world, each with their own story to tell. So it’s not surprising he’s built his career around compelling narratives — whether it was developing movie pitches at Pixar or raising $16 million as co-founder and CEO of PullString (which has since been acquired by Apple).

In all of these endeavors, storytelling was a crucial part of Jacob’s work to make pitches memorable and resonant. Whether you’re talking about your product or your company, Jacob recommends several specific storytelling tactics to both appeal to your audience for the first time, and to forge successful long-term relationships.

One key lesson he has for founders: Great stories have structure.

A pitch meeting should have a natural cadence, like a screenplay.

“You need to take the whole room on a journey together,” says Jacob. “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.”

Headshot of Oren Jacob
Oren Jacob, former co-founder and CEO of PullString

The best meetings are the ones where the VCs in the room want to take this journey with you — and to ensure this, you have to hit all the stops they’re anticipating. “Lay out the map for them at the beginning: ‘I am going to talk about engagement; I am going to talk about monetization; I am going to talk about our team and features and potential competitors,’” Jacob says.

You may walk into a meeting with 12 slides — he recommends 12 — with the plan to touch on each of them sequentially. But more often than not, an investor will ask to skip slide two or jump ahead to slide eight.

“You might be in control of how to tell your story, but you also need to read the room. If they are trying to pull you toward one topic, listen to them and adjust accordingly but keep the story’s structure intact. You have designed the story to build toward the conclusion that they have to invest in you. You have to build that case no matter what.”

When you design your presentation, you want to make sure to emphasize the points that will drive people to the conviction that they should back your idea. If you believe the market opportunity is the most compelling thing you have to share, spend more time on it. If you believe the strength of your team is unmatched, take the time to dive into their bios and experience. You want to build your presentation and slides so that your argument only gets stronger and gains momentum as you go along.

“You might have 10 slides of nerdy graphs in the appendix that you can use to answer questions, but your story should be condensed to the point that you’re never even reading your slides.”

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

Tactically, Jacob says it’s also critical to not plan a full hour of material. You should be able to tell your whole story, in a compelling and detailed fashion, in just 20 minutes. “This will almost always expand to fill the hour. You’ll be interrupted. You’ll answer questions. You’ll decide in that moment to flesh something out a bit more or add more detail to something. You’ll get the sense that someone in the room wants to dwell more on product construction or this stat or that stat. You don’t want to end up running out of time

At the same time, you want to have hours and hours of nerdy details squirreled away in your head, Jacob says. “Through practicing you can feel better and better about leaving those details out, but should the conversation go that way, you can bring them to the forefront if necessary. Have some well-known short stories as examples — a user who loves what you’re doing, for example. Those can be useful answers to general questions. When you tell stories like that you can find ways to move the conversation to other points you want to hit.”

The important thing is to make the words your own. “You should be able to give your pitch with no slides. Cold,” says Jacob. “Hit every key point you want, unrushed in 20 minutes. Practice as if the projector bulb blew out several times and make sure you can still do it then — and don’t wait until the night before. Be able to recreate any idea you have on a white board in less than one minute. Label the axes and call out the three to four critical points on the graph that characterize the point you are trying to make.”

Finally, remember that great stories are unexpected.

“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. "When you’re in pitches, you should make your case not to raise money, but because you’re so excited about what you could possibly accomplish.”

Read more about Oren Jacobs on how to take fundraising pitches from mediocre to memorable.

Looking for more wisdom on storytelling? Recognize (and avoid) the seven deadly sins of startup storytelling. Learn to craft a sales narrative that will help you build an amazing sales team. Get to know why software engineers should be storytellers.