My coaching clients often ask for help becoming better storytellers, one of the most important skills for product leaders. What follows is everything I’ve collected over the years.

My number one recommendation is to become a better story consumer. Read fiction, comic books, children’s books, fairy tales, and folktales. Watch movies. Go to the theater, the opera, and musicals. Play video games. Write your own stories! The more you immerse yourself in storytelling, the more you’ll understand what makes a good story from the audience’s point of view. Why did you love that story? Why didn’t you like that other one? What narrative choices did the writer make? How did they structure the story? How did they develop the characters? What made you connect to them? How did it make you feel?

You’ll learn more about becoming a better storyteller from reading to your children than from any book with a title like “How To Deliver a TED Talk.” Steve Jobs was an incredible storyteller because he was immersed in the liberal arts, not because he went to corporate media training.

From my end, I’ve probably gained more storytelling skills from my liberal arts degree and my lifelong hobbies, such as tabletop roleplaying games¹, learning to perform card magic, and my love of theater, than from anything I’ve learned in the workplace. So get out there.

Understand the shape of stories. One common narrative arc in mythology is The Hero’s Journey.

Popularized by Joseph Campbell in his 1949 book, The Hero with a Thousand Faces, the narrative structure is simple and familiar:

A hero ventures forth from the world of common day into a region of supernatural wonder: fabulous forces are there encountered and a decisive victory is won: the hero comes back from this mysterious adventure with the power to bestow boons on his fellow man

From the Odyssey to Jane Eyre to The Lord of the Rings to Star Wars, it’s a tale as old as time. What’s your version? Who is the hero? Is it you? Is it your company? Your customer? Your audience?

The brilliant Kurt Vonnegut took things a step further and identified Eight Shapes of Stories.

Designer: Maya Eilam

Watching Vonnegut explain it himself is much more fun, so watch the video:

Which story shape do you want to use?

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Who is your audience? This is the first question you need to answer. You might be quick to answer, “The entire company.” Or “the potential customer.” But you need to be more specific. If you’re speaking to the company, who is your primary audience in the room? The new employees who joined in the past month? Or the curmudgeonly veterans who have been most skeptical about your vision in the past? Be specific. What are their motivations? What are their biases? What do they already know? Not know? What are their challenges, values, and beliefs? How do they feel coming into the room. How do you want them to feel when they leave?

What is your core message? The bottom line is that in one sentence, what do you want your audience to walk away with? Think of it this way – if someone were to walk up to them 24 hours after you spoke to them and ask them, “What did you learn?” how do you want them to answer? This might be the most challenging part of your preparation. Think very carefully, and understand that there can only be one primary bottom-line message that you can convey.

Look for metaphors. Metaphors are shortcuts to understanding. They take something familiar from another part of our world that we already understand well and help our audience connect with this new thing we want them to learn. A powerful metaphor can deliver the whole story to you on a silver platter. One myth of good storytelling is that it requires dreaming up something entirely new from scratch. That’s not necessary. I once gave an extremely well-received keynote speech based around a small anecdote I discovered in a biography about Miles Davis. I used that as a metaphor for how creative teams work, and it formed the backbone of my talk. Everything flowed from there. An uncharitable critic might say my talk started as a glorified book report. I would respond that such criticism merely demonstrates how easy storytelling can be.

Stories are all about emotion. Pay attention to how you feel when you’re immersed in a story. How does the writer make you feel that way? What is the emotional journey you go on throughout the story? What emotions do you want your audience to feel? At the beginning of your presentation? In the middle? At the end?

Focus on your start and your ending. As Jenifer Hixson from The Moth says, “The takeoff and landing are considered the most dangerous parts of a flight. And so it goes with stories.” Think carefully about your opening. How will you bring your audience into your story. What is your engaging hook? What are the stakes? How can you get them invested straight away, without a lot of unnecessary windup. Likewise, how will you bring things to a compelling close without feeling like the story just trails off with no fulfillment or closure.

Telling a story might mean slowly revealing something to your audience. What are you holding back? What suspense are you building? What keeps them on the edges of their seats, waiting for the payoff? What is the secret to be shared at the end? Foreshadowed, hinted at, teased, and withheld, then brought forth dramatically to reward their patience? Is some sleight of hand required to gently fool them a bit along the way?

When I was working on my talk, 10x Not 10%, I wanted the talk itself to feel like it was building exponentially.

Good storytelling also requires repetition. Good storytelling requires repetition. You’ve heard the old adage, “Tell ‘em what you’re going to tell ‘em, tell ‘em, then tell ‘em what you told ‘em.” Hammer home your primary theme over and over. Say it in different ways. Reinforce it. Say it again. In my 10x talk, you’ll notice I repeated the phrase, “10x Not 10%” numerous times throughout the talk.

Don’t worry about your slides. Seriously. Begin with your story. What are you trying to say? And how do you want your audience to feel? Start there. (By the way, I appreciate that storytelling is much more than just giving presentations, but I’m including what I’ve learned about presenting here as well.)

Once you have the narrative arc, start loose storyboarding. I recommend sketching on paper. Make a bunch of boxes. Aim to have a new slide every 15-30 seconds for an animated, captivating talk. Lay out a set of blank boxes next to your narrative. Walk through your talk, and for each 15-30-second section, write one or two words in the box that match that part of the script.

For example, if you’re saying, “For decades, manufacturers struggled to personally visit each and every turbo encabulator to measure the humidity levels of their cardinal grammeters.” You might write down, “struggled.” Verbs are often good words to pull from your script. The theme you want to get across with this slide is how difficult things were for the poor manufacturers. (We’re in the Challenges part of the Hero’s Journey here. Presumably, the manufacturer is the hero in our story, and our product is the revelation that is going to save them.)

Then, you might look for a nice image to capture this. Perhaps a photograph of a sweaty operator lying on their back, cramped under a turbo encabulator, or a zoomed-out diagram of a map showing the thousands of locations the typical manufacturer had to visit in an average month, with lines between them, demonstrating the hopeless impossibility of the traveling salesperson’s problem. Notice how you don’t even need words to accompany this part of your script.

Your slides don’t need to do much. My philosophy is that suitable storytelling slides should never stand alone. They are backdrops to the talk itself. They’re primarily visual, full of lovely big full-bleed photographs and images. Very few words, and when words do appear, they are massive, huge, fat fonts, a minimum of 25 pixels, preferably much, much bigger.

As an aside, it’s for this reason that I refuse to share the slides after my talks – they end up taking on a life of their own, and because without the talk track, they are meaningless. Instead, I prefer to publish my talk in essay form with the slides weaved in as illustrations. Or better yet, an entire video of the talk was posted online. People might get grumpy when you say no when they say, “Can you email me the slides?” but I find that responding with, “I’ve found that they aren’t very useful on their own. I plan to share an essay version of the talk and I’ll be happy to share that with you when it’s available,” usually satisfies them.

Practice, practice, practice. If you’re giving an important talk that will be in front of a significant audience, such as a conference keynote, YC Demo Day, or a VC pitch, you’ll need to practice a lot. I practiced my keynote talks for at least 100 hours. The shorter the talk, the more you’ll need to practice it. I’ve done Ignite Talks before (here’s an example) and I run through those hundreds of times before I go on stage. The more you practice it, the more natural it will become.

Tap into all of the senses. Show, don’t tell. Use visual imagery as much as possible. Vary your voice. Get louder when necessary. Drop to a whisper when required. Shout. Laugh. Use arm gestures, stomp around the stage, get down on all fours. Crawl? Use music and sound effects. Get tactile. Throw something into the audience. Can you use smell? I’m sure you’ll find a way.

Use humor if it comes naturally. If you’re a funny person, be funny. It will flow. Don’t try to be funny if it doesn’t come naturally. It will feel stilted and forced. Great storytelling doesn’t require endless, raucous laughter. You can captivate your audience without inserting an awkward joke every few minutes.

Which brings me to the most important, and final point…

Find your own voice. Don’t try to copy someone else. Don’t try to do a TED Talk. And for the love of all that is holy, don’t try to be Steve Jobs. Be authentic, tell anecdotes from your own life, and let the audience into your world. The more real you are, the more the audience will want to know you. To root for you. The more your stories will resonate. It sucks to watch someone go on stage and pretend to be someone else. Practice for a close friend or family member and ask them to give you honest feedback. Tell them you want to come through as a real, authentic human being. They’ll keep you honest. Be you.

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Here are some other storytelling resources I’ve collected over the years:

• Joseph Campbell’s Hero’s Journey
• The Hero with a Thousand Faces by Joseph Campbell
• Pixar Storytelling: Rules for Effective Storytelling Based on Pixar’s Greatest Films
• Storyworthy: Engage, Teach, Persuade, and Change Your Life through the Power of Storytelling
• The Moth Podcast is the absolute GOAT for storytelling. They also offer workshops. We hosted one for portfolio founders at GV way back in the day, and it was fantastic.
• Lenny’s Podcast: How to tell better stories: Matthew Dicks from Storyworthy and Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks

One of my all-time favorite resources is Pixar’s 22 Rules of Storytelling. I’ve kept them in my notes app for years. I’ll usually read through them when constructing a talk. Most of them won’t apply, but a few will inevitably jog something loose in my brain that will cause me to improve my talk significantly.

Pixar’s 22 Rules of Storytelling

1. You admire a character for trying more than for their successes
2. You gotta keep in mind what’s interesting to you as an audience, not what’s fun to do as a writer. They can be very different.
3. Trying for theme is important, but you won’t see what the story is actually about until you’re at the end of it. Now rewrite.
4. One upon a time there was __. Every day, __. One day __. Because of that, __. Because of that, __. Until finally, __.
5. Simplify. Focus. Combine characters. Hop over detours. You’ll feel like you’re losing valuable stuff but it sets you free.
6. What is your character good at, comfortable with? Throw the polar opposite at them. Challenge them. How do they deal?
7. Come up with your ending before you figure out your middle. Seriously. Endings are hard, get yours working up front.
8. Finish your story, let go even if it’s not perfect. In an ideal world you have both, but move on. Do better next time.
9. When you’re stuck, make a list of what WOULDN’T happen next. Lots of times the material to get you unstuck will show up.
10. Pull apart the stories you like. What you like in them is a part of you; you’ve got to recognize it before you can use it.
11. Putting it on paper lets you start fixing it. If it stays in your head, a perfect idea, you’ll never share it with anyone.
12. Discount the 1st thing that comes to mind. And the 2nd, 3rd, 4th, 5th – get the obvious out of the way. Surprise yourself.
13. Give your characters opinions. Passive/malleable might seem likable to you as you write, but it’s poison to the audience.
14. Why must you tell THIS story? What’s the belief burning within you that your story feeds off? That’s the heart of it.
15. If you were your character, in this situation, how would you feel? Honestly lends credibility to unbelievable situations.
16. What are the stakes? Give us reason to root for the character. What happens if they don’t succeed? Stack the odds against.
17. No work is ever wasted. If it’s not working, let go and move on – it’ll come back around to be useful later.
18. You have to know yourself: the difference between doing your best and fussing. Story is testing, not refining.
19. Coincidences to get characters into trouble are great, coincidences to get them out of it are cheating.
20. Exercise: take the building blocks of a movie you dislike. How would you rearrange them into what you DO like?
21. You gotta identify with your situation/characters, can’t just write ‘cool.’ What would make YOU act that way?
22. What’s the essence of your story? Most economical telling of it? If you know that, you can build out from there.

1. I’ve been a Dungeons & Dragons DM since 1981, playing regularly to this day. It has probably been the #1 biggest contributor to my improvisational storytelling abilities. ↩