Technical leaders make these 3 common storytelling mistakes

Here are practical ways to make your pitches, conversations, and stories more engaging

Wes Kao
Wes Kao
Sep 29, 2018 · 4 min read
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Photo of the webinar, “Storytelling for Technical Founders” for Backstage Capital

I recently had the privilege of giving a talk for Backstage Capital and their amazing early-stage portfolio companies. My talk was called “Storytelling for Technical Founders” and I shared how technical leaders can tell better stories.

Here are a few common mistakes and takeaways:

1. Over-reliance on technical details

Real-life is non-linear, but stories are linear. Therefore, stories are always a simplification.

You definitely want to tell the truth, but don’t feel guilty for leaving out details in order to prioritize your overall narrative arc. I’ve coached plenty of founders who were afraid their audience would call them out for speaking in broad strokes. The paranoia of getting called out is real.

Your audience doesn’t mind. They want to be wooed, entertained, and taken on a journey — in addition to learning about your product and story. What about the subject matter experts who might have a specific question about your technology? They’ll ask. And you’ll be ready to answer and impress them with your substance.

Anytime you feel the urge to say, “Well, technically…,” you are about to kill a good story.

Remember: What gets someone on the door isn’t necessarily what gets them to stay.

For example, think about J.Crew stores. They show colorful window displays and front tables with a rainbow assortment of t-shirts in salmon pink, lemon yellow, neon orange, and cerulean blue.

Nine times out of ten, I walk in and end up buying a basic color (white, black, navy, grey). Most customers do this — that’s why retailers plan the inventory accordingly and have stockrooms full of basic SKUs.

But if they put only the most basic stuff on display, you would probably keep walking and never enter the store.

Hook your audience with a story, so you get them in the door. You likely won’t close the sale in one pitch anyway. If your audience has a positive impression, you’ll earn the opportunity to share more details and build trust with drip emails, 1-on-1 conversations, sales decks, content, and more ways to tell your story.

Ask yourself,

“Can I simplify my story to make it even more powerful?”

“Can I remove tangential comments, so I can focus on getting my main point across?”

“Am I spending precious time describing something I could share later?”

2. Trying to remember too many tactics

When you are in the moment, don’t try to remember a giant list of storytelling tips and strategies. It’s more likely to make you anxious and worsen your performance than anything.

By all means, practice your pitch and set of stories. Most professionals don’t wing it because they know how hard it is to make things look effortless. But once you practice, when you’re out in the field (in front of a live audience of venture capitalists, prospective customers, at a networking event), let go of the laundry list of things you learned in preparation for telling your story.

Instead, just stay present and focus on eliciting emotion: “How can I make this person’s eyes light up?”

(I call it “ELU” for short.)

ELU is the moment when your audience gets emotionally invested. We all know when people are listening to us to be polite. And you can tell when someone suddenly wakes up during the conversation and wants to hear more.

It’s hard to anticipate what will resonate with your audiences, so experiment with your stories — and look for that spark.

Ask yourself,

“How can I stay present, enjoy telling this story, and look for moments when my audience leans in with excitement?”

3. Too much backstory

If you’re telling a story about your camping trip, don’t start when you were brainstorming options for tents and carpooling. Start right before you almost get eaten by a bear on a 13.2-mile hike.

I constantly remind myself to cut backstory in conversational settings too and am usually glad for it. Backstory can easily take up the majority of the time you have during an introductory call or a pitch, so be mindful of avoiding “backstory scope creep.”

Ask yourself:

“Can I cut out more of the backstory?”

“Does my audience really need it?”

“What’s the bare minimum I need to set the context, so I can spend time on the juicy stuff?”

As usual, it’s not complicated — it’s just hard. There are hundreds of permutations and combinations of ways to tell your story, so it’s part art and part science. If it feels unnatural for you at first, it’s totally normal. Developing your muscle memory with storytelling is part of the process.


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Wes Kao

Written by

Wes Kao

Marketing | Product | Strategy | Prev: altMBA, Seth Godin HQ, Flite (acq by Snapchat), Gap Inc. @wes_kao | weskao.com

The Startup

Medium's largest active publication, followed by +682K people. Follow to join our community.

Wes Kao

Written by

Wes Kao

Marketing | Product | Strategy | Prev: altMBA, Seth Godin HQ, Flite (acq by Snapchat), Gap Inc. @wes_kao | weskao.com

The Startup

Medium's largest active publication, followed by +682K people. Follow to join our community.

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