7 Deadly Sins Of Startup Storytelling

Find more conflict, don’t start from the beginning–some of these might surprise you.

7 Deadly Sins Of Startup Storytelling
[Image: Flickr user Fernando Kokubun]

When it comes to persuasion, companies have traditionally appealed to the left side of the brain–logic, pricing, specs. Emotion, however, has proven to be the better marketing tool.


As Daniel Pink, author of Drive, writes, “Right-brain dominance is the new source of competitive advantage.” Appealing to the right side of the brain allows for deeper engagement by uniting an idea with an emotion. The best way to do this: Tell a story.

Too often business stories fall flat. And while I can’t tell you how to tell your unique company story, I can tell you the major things that you shouldn’t do.

1. Telling, not showing.

One of the most fundamental maxims of storytelling is “Show, don’t tell”–and for a good reason. Rather than talking at your audience, telling them what to do or feel, share the story so that it unfolds naturally and your audience comes to their own conclusion themselves. People don’t just absorb facts and information. They actively listen to stories and make their own inferences.

When you’re sharing a story, do so in a way that lets your audience envision the setting, picture the protagonist, and really feel the conflict that he or she is facing. Describe what’s happening as if the action is unfolding right now in front of you.

The right way: Go to the “About Us” section on your website. Is it mostly text? Is the information pure data or are you using stories, personality and perhaps even humor to illustrate who you are?


Also take an inventory of the tools you’re using to share your company’s story. Done well, video is the most powerful tool. It can convey complex ideas quickly, or emphasize subtle but important differences.

2. Using too much jargon


We have all read countless press releases and seen presentations filled with nonsense words like synergy, platform, paradigm. What do they mean, anyway? It’s you and your product that need to fit your customer, not the other way around. Filling a story with technical terms, acronyms and superfluous words is the best way to lose your audience.

In his introduction of the famous Think Different campaign, Steve Jobs told his audience, “To me marketing is about values. This is a very complicated world, it’s a very noisy world, and we’re not going to get a chance to get people to remember very much about us–no company is. So we have to be very clear about what we want them to know about us.”

The right way: Companies like Square (“Sell on the go.”), Venmo (“Make and share payments.”), and Evernote (“Remember everything.”) make important and often elaborate capabilities accessible. They do this by filling in the blank for their customers: “I really want to _______.” Then they do it.


3. Your Message is too impersonal.

It doesn’t matter if your company sells razors, builds cloud infrastructure, or designs medical devices, human beings are still driving the action. Personalize the protagonist of your story. Make her seem real enough so that the audience feels a stake in (and wants to know) what happens to her next.

The right way: Subway famously took the opportunity to turn a true story into pure gold. College student Jared Fogle demonstrated that you can lose a ton of weight on a diet of Subway sandwiches. Much more compelling than promoting a slate of healthier new sandwich choices, here was a real-life story of a guy who Subway customers could connect to, who was using their products to be healthier.

Jared became the quietly charismatic spokesperson for the brand, and the Jared story ran as the lead campaign for Subway for 10 years–during which sales doubled.

4. Starting from the beginning.

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. Chronology matters much less than having your story follow an interesting arc. Often the stuff you need to hook people doesn’t tend to happen early on. Events need to build, one after the other, emotionally rather than sequentially. To really impact people, your story should describe increasing risk and increasing consequences until the final, inevitable conclusion–but not necessarily the one that the audience expects.

As you think of the elements of the story you want to tell, imagine them as modules, first capturing them on Post-Its, then mixing them up. This easy exercise will break you of the oppressive habit of presenting things in order. Now, Post-Its in hand, think like a movie-maker. Open on a moment of truth. Make people feel it. Engage the senses.


Then reach back to the past to savor the contrast. Even if people know how your story ends–it’s usually the product you’re asking them to buy–you can breathe life into the journey of how you got there, how your other customers discovered you, and why it’s made a difference.

The right way: Bank of America chose to flip chronology in its recent Portraits campaign. Opening on an old couple taking a photo together, we start to go back in time with the couple’s extended family setting up and taking photos, reaching back in time through significant, often challenging events. Grandchildren disappear, adults become children, and we’re left at the beginning: a young couple on a couch with their whole lives ahead of them. The effect is mesmerizing. What might have been a cloying, overly-sentimental ad is elevated with visual interest, a rare combination of creativity and familiarity that grabs attention and warms the heart.

5. Lack of conflict.

Something always goes wrong in companies, particularly startups. But screw-ups also present opportunities to shine by telling a story of responsibility, apology and remedy. Not only are customers more loyal to brands that readily apologize, the backlash to brands that don’t own their mistakes are disproportionately costly. Engaging stories do not chronicle a straight line to success. Hone in on your protagonist’s problems or barriers to achieving his goal. What is standing in his way?

The right way: While some accused her of being slow to respond, Marissa Mayer seized the opportunity to humanize Yahoo’s brand and demonstrate leadership while offering a clear, sincere apology for last month’s widespread email outage. She empathized with people and the problems the outage caused and took responsibility without making excuses.

She even offered insight into the problem itself that anyone could identify with: “Unfortunately, the outage was much more complex than it seemed at first…” Hearing these few words, most people can think of a time when something similar happened to them. That’s where empathy begins. And only then can you recover.


6. You Fabricate Your Story.

Your story needs to be authentic. A major cancer center in Washington once asked a customer named Audrey, if they could use her photo in a cancer awareness campaign. When the bus and magazine ads launched, much to the surprise of Audrey, she was positioned as a cancer survivor. How much more powerful would this campaign have been if the featured image were that of an actual cancer survivor? For everyone who heard the story, this reputable institution has now tarnished its credibility forever. People want to hear and be moved by real stories.

Make stories part of your culture–and more than that, the integrity of your culture. All-hands meetings can be pivotal here. Stories are often the best way to relate how a company is doing, what people are doing well, and what they could be doing better. And when leaders do this with transparency, honesty and humility, they make their employees feel good about their work–even if things aren’t all peachy.

The right way: Capturing moments, good or bad, in story form can authentically connect your employees to your company, and increase their commitment to their work. Consider kicking off staff meetings with stories instead of progress reports.

There are a few ways to do this. As you go around the room, ask everyone to briefly talk about the strangest thing that’s happened to them since the last meeting, or a customer story that involved the greatest amount of surprise. Did someone use your product in a new way? Did a hater become a believer?

7. You try to hold onto proprietary.

Companies with a stranglehold on what their corporate story is and who can tell it are missing a world of opportunities. And they’re doing so at a time when social media makes it easier than ever to connect and share. Stories told by employees and by customers are incredible, sometimes invaluable assets (see Jared for Subway). Recognize the value in stories from internal and external sources, design ways to collect them, and enable your customers, advocates and employees to be storytellers too.


The best tactic is to create an internal database of stories, where employees and even customers can write and submit stories complete with titles. These stories can then be tagged by keyword, so that people looking for particular anecdotes or examples can easily find them. This also makes it easy for employees browsing through customer stories to reach out to the authors.

The right way: Nike, Apple and eBay all harness stories as tools to crowdsource ideas — especially what their consumers are really passionate about. In doing so, they give employees the language and initiative to tell personal stories of meaning, and to amplify and distribute brand initiatives in story form.

As content marketing increasingly becomes the norm, tactical storytelling is sure to be broken down to a science. But there’s danger in being overly reductionist. What makes good stories work is the same unpredictable, creative, unintuitive quality that makes humans human. Breakout success won’t follow from the rote application of step-by-step guides or how-tos. Design your strategy to avoid the seven sins above, however, and you’ll be in good shape to forge a voice of your own.

This article originally appeared in First Round Review and is reprinted with permission.

Andy Smith is an entrepreneur and startup advisor who built winning teams at Dolby, Intel and Polaroid, focused on how to execute a strategy that engages and monetizes customers. He is also the author of The Dragonfly Effect.