Storytelling Techniques for Entrepreneurs

Tom Kelley seated on a set of stairs.

In the early days of IDEO, Tom Kelley recalls the challenges of expanding the company to Japan, where there was no office and no one there had heard of the company. All IDEO had, according to Tom, was the stories they could tell. They told stories about their design thinking work to media publications and businesses, who then began to share these stories with others. By the time IDEO opened an office in Tokyo, it had established itself as a brand. Tom believes that it was the power of storytelling that allowed IDEO to find success in Japan.

Tom Kelley is a Partner at IDEO and the bestselling author of Creative Confidence, The Art of Innovation, and The Ten Faces of Innovation. He works with IDEO Tokyo on its mission to expand creative leadership in Japan and co-founded D4V, or Design for Ventures, a Tokyo-based early-stage venture capital firm. Tom frequently collaborates with entrepreneurs and founders in Japan to help them bring human-centered design and storytelling to their businesses.

In our conversation with Tom, our team was blown away as he walked the walk, breaking down storytelling essentials and punctuating each of his lessons for entrepreneurs with great stories.

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Why storytelling matters

Storytelling is a skill that doesn’t get much attention in the business world, with data and analytics oftentimes taking the spotlight. Tom admits that early on, IDEO didn’t recognize the importance of storytelling—the group of mostly engineers at the time thought that data should speak for itself. They found out, however, that stories had an ability to bring their work to life. Now, storytelling is part of IDEO’s culture.

“It took us a while to realize this: the data, the message, the thing that you care so much about, does not speak for itself. You’ve got to think about how to wrap your data in the right story,” says Tom. Especially in the beginning, when a business doesn’t have an established brand, great stories can paint a picture in people’s minds. They help others understand your idea and believe in your idea.

From Tom’s experience, there are four major storytelling moments that are essential for any entrepreneur: the elevator pitch, the origin story, the pitch deck, and the internal story.

Icon representations of an elevator pitch, origin story, pitch deck, and internal story.

 


“It took us a while to realize this: the data, the message, the thing that you care so much about, does not speak for itself. You’ve got to think about how to wrap your data in the right story.”
Tom Kelley


 

Story #1: The elevator pitch

Think of a company you're familiar with—it might be your own company, an organization you work with, or one that you admire. Now, explain what's remarkable about that company in 15 seconds. Because you only have 15 seconds, and not 5 minutes, you need to make your story succinct and memorable.

The elevator pitch is a concise way of verbally communicating what your business does. Essentially, it’s the first opportunity to engage people around a story about the company. And because of that, it’s helpful to practice so that you’re ready to deliver it anywhere, whether it’s in a meeting or on a plane. It tells people what they need to know in a short amount of time, which is why it’s so important.

Tom gives airCloset, one of D4V’s portfolio companies, as an example of a startup with an effective elevator pitch: airCloset is a personalized fashion subscription service for busy women that combines the best of Stitch Fix and Rent the Runway, enabling customers to wear clothes before they buy them so that they can explore and experiment with new styles.

When giving your elevator pitch, remember to understand who your audience is and adapt it to them. An American football metaphor might work great in the U.S., but it might not work as well if the listener is from another part of the world. Context matters, and when you consider your listener’s life experiences, you can tell a more effective story. “In the elevator pitch, you’re throwing away 99.9% of what you know about the company. So in that 0.1%, you’re picking the stuff that fits and resonates,” explains Tom.

 

Story #2: The origin story

How did you first start your business or come up with your idea? That’s your origin story. Tom gives the example of the financial software company Intuit as a business with a great origin story. Intuit founder Scott Cook saw his wife managing their family finances and thought, “There’s got to be a quicker way to do that.” Soon after, he created a product to address it, and named it Quicken.

When sharing the origin story of your business or idea, it’s important to be authentic. Tom says that if you have an interesting story, share it—but that you don’t need to try to force it. For example, there’s the classic origin story of the startup beginning in a garage. While Apple, Google, and HP all started out of garages, only HP fully utilized that story because it aligned with their brand. What works for every organization will be different. Rather than looking for a story that will fit with others, embrace your own personal story with authenticity and vulnerability.

 

Story #3: The pitch deck

When you think of an entrepreneur, you might imagine someone persuasively presenting a pitch deck. It’s a key presentation that tells the story of how a company meets a unique need, and is generally used by founders to raise money from investors. “The elevator pitch opens the door for you, but your success or failure in raising enough money to make your enterprise fly is going to depend in large part on the pitch deck,” says Tom.

As an investor who manages D4V’s multi-million dollar fund, Tom emphasizes that there are a few crucial elements that you need to include and communicate with your pitch deck. First, tell the story of your team in a way that gives people confidence in your skills and capabilities—investors choose a team more than they choose a product.

Next, Tom says to describe the total addressable market, which is the size of the market that you’re targeting. Particularly in the beginning, when a venture firm is taking a risk by working with you, it needs to believe that there is the possibility of your company growing exponentially. Finally, show that your business will be financially viable, technically feasible, and distinct from your competitors. Beyond these few key points, everything else is extra and can be included in an appendix.

As you craft your pitch deck, it’s important to make sure that the pitch deck can live on its own, without you there to deliver it. While you’ll often present your pitch deck live, not everyone who needs to see it will be in the room, and it will likely be shared with others afterward. Because of this, you might think of a soundbite or takeaway that you can leave people with. It should be easy for your audience to summarize your pitch deck afterward. The clearer your message is, the more repeatable it’ll be to others.

 


“The elevator pitch opens the door for you, but your success or failure in raising enough money to make your enterprise fly is going to depend in large part on the pitch deck.”
Tom Kelley


 

Story #4: The internal story

The internal story is about motivating your team to work toward your mission, as well as a future that likely doesn’t yet exist. If people don’t feel aligned with a company’s values or purpose, they may choose to leave. “The internal story was always important, and I think it's gotten a whole lot more important because people now care so much about purpose,” says Tom.

One of the best examples of an internal story that Tom has seen is from Starbucks when the company first started. He remembers coming across an incredibly effective internal video about the concept of the “third place”—a place outside of the frenzy of home and work where you could relax and spend time with friends—and how Starbucks provided that space for their customers. It worked so well as an internal story because it made employees feel like they were working toward a mission.

 


“The internal story was always important, and I think it's gotten a whole lot more important because people now care so much about purpose.”
Tom Kelley


 

Tom’s favorite storytelling tips

Having worked with a speaking coach for the past 20 years, Tom continues to look for ways to improve in his storytelling. “I believe in storytelling as a craft. I think it's worth practicing and worth your time and attention, because as you go through life, storytelling can help your message get across in a different way,” says Tom.

A few storytelling tips have stood out to him. One piece of advice that Tom picked up from the book Made to Stick by Chip and Dan Heath is to take a “shortcut.” For example, saying that a company takes the best features of X and Y builds on knowledge that your audience already has and allows them to pick up what you’re trying to say quickly.

Another learning from his speaking coach has been that when you want to get information across and it’s really important, whisper it. While it has to be a stage whisper so that you listeners can actually hear, they’ll recognize that what you’re saying is significant. Similarly, you could also say something along the lines of, “If you don't remember anything else I said today, just remember this,” before going into your key message. These are tricks that you can use only once per presentation, but they can work well in getting people’s attention.

Last of all, Tom says he learned an important lesson from author Brené Brown in her book The Gifts of Imperfection. When you mess up or give a bad presentation, don’t be hard on yourself. Remember not to be overly critical of your mistakes. “You're not perfect and you'd be crazy to try to be perfect. But in spite of your imperfections, you're worthy of love and belonging,” says Tom.

As you go forward, think about how storytelling surfaces in your career:

  • What stories do you currently tell about yourself and your work?
  • Where might there be an opportunity for more intentional storytelling?

If you want to learn how to prototype business ideas or craft impactful stories, check out our online courses Designing a Business and Storytelling for Influence.


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