Most founders suck at storytelling

I was one of them. Here’s how I got better.

If I had to name the top three skills a venture-backed founder CEO needs, storytelling would be on that list.

I was a bad storyteller and a terrible public speaker early in my career. I didn’t realize how important storytelling is to a CEO’s success. That was a big mistake. I should have invested in getting better at it earlier.

Fundraising. Hiring. Closing and retaining customers. Retaining your best people. Buying companies. Selling your company. All of that comes down to your ability to tell a compelling story. It’s not enough to have the best product or fastest growth. You need that, but you also need a good story and the ability to convey it in different formats, through various channels, and to a wide range of audiences.

Here’s what I’ve learned about where storytelling shows up in business, why most CEOs and founders struggle with it, and how to get better.

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Table of contents:

• Storytelling touches every part of the business

• Why most founders struggle with storytelling

• How to build storytelling skills as a CEO

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Storytelling touches every part of the business

Storytelling includes the words you use, but it also includes your slides, your imagery, your body language, and the mediums you choose. All of it is part of the story you’re telling, and it shows up everywhere.

Fundraising

Investors are mandated to find the next generational company. They’re looking for ideas that will return their fund multiple times over. Most of those companies don’t look like generational companies when they first meet with investors.

As the CEO, you need to paint a picture of a future world and how your business is going to play a pivotal part in it. None of it is true today. But you have to tell a story about how you arrived at this idea and why you truly believe it’s such a big opportunity.

You need to show them the pain the world will face without your product and ultimately, how your product is the painkiller, the solution. And the story needs to be compelling enough that someone hands you millions of dollars to pursue it. That’s storytelling.

People are not good at pitching. And so investors do the worst thing possible – they give you less time, which makes the pitch worse. Your job is to be good enough that investors want more time with you. – Mark Dannenberg, Executive Coach. Read the article here.

Acquiring customers

The biggest companies in the world still send their CEO to close major deals. There’s a reason for that, and it’s because they’re often the most qualified to tell the story in a way that draws in the customer.

I had a CIO tell me once that he chose a vendor with an inferior product over the market leader. Why? The market leader sent a sales rep who walked him through their feature list. The other vendor sent their founder CEO, who told them their vision for the future.

The CEO delivered the story and vision so well that the CIO felt excited about the idea of going on that journey with them. The story, vision, and direction of an up-and-coming product inspired them more than the market leader.

A compelling story from a CEO who really knows how to deliver it goes a long way.

Retaining customers

How do you tell a story to a customer who’s been with you for years, in a market with hundreds of new competitors, where AI is changing everything? How do you make them want to renew over and over again?

There are tons of competitors out there. New ones are actively building, and they’re coming for your customers. You need your existing customers to be so bought into your vision that they never have a reason to leave. That means telling a story that makes them believe you understand their problem better than anyone else, that you have a plan to solve it, and that you’re the one they should bet on to deliver.

Hiring

People make roughly six career moves throughout their lives. When someone joins your company, you’re asking them to spend one of those chapters with you. That’s not a small ask. They’re betting their career on you.

You have to tell a story that makes them believe this is the place where they’ll do their best work, that they have the opportunity to have a career-defining experience with your company, and, therefore, this is the company they should spend the next several years with.

Retaining top employees

You can’t afford to lose your top employees. Many times, even at large companies, the CEO is the one who’s going to maintain those relationships and retain those really top people.

If you’re telling a compelling story consistently, this gets easier because your best people already believe in where you’re going. Money alone won’t pull them away because they’re bought into your vision. But competing offers still happen. And when they do, they need to know your company is better. Not better on paper, but better for them.

For my best people, I’d meet with them one-on-one a couple of times throughout the year and map out where I thought their career could go within our company. I’d share with them how their role could evolve and what they could become in the future. I wouldn’t promise a specific timeline, but I’d make sure they could visualize the return on their investment of time with us.

Those are the types of stories that keep your best people from leaving.

Selling the company

Acquirers need to believe an acquisition will change the course of their company. They need to feel like the market is still early, and that they didn’t miss it. They need to believe you have things or know things that they don’t, and that together, you can unlock something neither of you can do alone.

Some of the biggest acquisitions happen because the founder told a compelling story. Not just any story, but one tailored specifically to that acquirer’s future with and without the acquisition.

Building a brand

Storytelling is the foundation of a brand. Many people think brand is about making the best logo, website, and ad campaign. But increasingly, people are buying from people. They find companies through their CEO’s thought leadership posts and general online and offline presence. LinkedIn has never been a more powerful distribution channel, and the founders who understand that are winning.

Every post you write, podcast you appear on, and every time you show up publicly and tell your story strengthens your brand. The CEOs who are known in their market got there by showing up consistently and telling a story worth following, even when it’s uncomfortable for them.

Why most founders struggle with storytelling

I’ve found that storytelling doesn’t come naturally for most founders. But you can build the muscle. I know, because I did.

Some founders are the exception, like the Adam Neumanns and Elizabeth Holmeses. They were so gifted at painting a vision and telling a story that their stories outran reality. They have a natural gift for grandiose visions and an endless supply of confidence. But they went too far. We could all use a little more audacity, just not that much.

For the rest of us, there are three reasons storytelling skills don’t come easy.

Most people aren’t taught storytelling skills

Unless you had a background in creative writing, public speaking, or journalism, chances are no one ever taught you how to tell a story. It’s just assumed you’ll figure it out. Most people don’t.

Operational founders are wired differently

Some founders are real operators. They’re good at execution, they’re in the weeds, and they’re focused on the reality of the business. But it’s hard to take a step back and paint a bigger picture when your brain is wired to deal with what’s in front of you.

And in many cases, you’re scared to tell a big story when your current business can’t fully back it up yet. A lot of founders won’t share a billion-dollar vision because they don’t know yet if it’s actually going to happen. They think being “honorable” is safer than selling something they can’t fully back up.

That was the case for me. Even if I knew we’d be launching a feature, I was only comfortable talking about things that were already fully baked into the product.

Putting yourself out there is uncomfortable

It can feel really uncomfortable and cringy. You wonder why anyone would want to hear what you have to say. That’s imposter syndrome, and it’s telling you that your take on the world isn’t widely shared and others will judge you for putting it out there.

I really struggled with this. I was scared of public speaking, and I was reluctant to write on LinkedIn. And those fears slowed me down. They were real disadvantages.

How to build storytelling skills as a CEO

You can build storytelling skills, but it takes serious time and commitment. Here’s what worked for me:

Accept the responsibility

This was my turning point. I’m the CEO. Whether I like public speaking or not, and whether I’m good at storytelling or not, if I want the company to succeed, I have to do this. If it’s cringey, too bad. I chose to be a founder, so it’s time to lean in even if it’s uncomfortable at first.

Spend time crafting the story

I see people do this all the time: they take six different decks, copy and paste slides together, and call it a pitch. It shows. Crafting a story takes time, and you need to be very deliberate about it.

The words, the slides, the flow, and the structure all have to be built deliberately. AI can help, but it needs your voice to be usable. There are no shortcuts here. Craft your story, deliver it, and iterate.

Get reps

There is no substitute. You need real audiences to get a feedback loop. The problem is most people avoid reps because they’re scared or not good at it yet. You just need to get started. Practice with family, your most trusted employee, a small group of customers, and/or your closest investor. Get the feedback you need to become better.

Make it yours

I like having slides as a visual aid when storytelling. I also like a fast build. That’s what feels natural to me. A CMO once built out my slides in their own style and handed them to me. I felt uncomfortable presenting them because it wasn’t mine.

Whatever your style is, it has to be authentically yours because if it isn’t, it won’t land.

Bring energy

Your body language and tone of voice matter more than the words. I told a CEO recently that I thought he hated his company. He was giving me a flat, monotone pitch for what was genuinely his life’s work.

That hurts you more than doing nothing at all. People match your energy. And they associate your entire brand with how you convey yourself and tell your story.

Jimmy Buffett probably sang Margaritaville 100 thousand times, but if you’re out in Cocktail Cove and you heard him singing that song live, he’s going to put a spin on it that makes it feel like it’s his first time singing it. – Scott Voigt, Founder and CEO of FullStory. Watch the podcast episode here.

Before any important storytelling moment (a pitch, sales meeting, hiring conversation), amp yourself up so you can set the right tone and bring the necessary energy.

Use real stories

Abstractions don’t land. Real stories do. When I’m talking to a prospective customer, I tell them a story about another customer. When I’m talking to a candidate, I tell them a story about another employee who stayed and what it unlocked for their career.

When I’m pitching investors, I tell stories about companies that came before us with similar traits. I use real examples that let people see themselves in the story. That way, they become the main character.

Realize everyone else is doing this

VCs have people pitching them billion-dollar visions all day. They’re all selling futures. Analysts are seeing fully polished prototypes of products that don’t exist yet. If you walk in and tell them only what’s true today, you think you’re being honorable, but you’re actually just at a disadvantage.

When that clicked for me, storytelling got a lot easier.

Stop memorizing

Find a flow state instead. Memorization backfires. If you miss one beat, the whole thing falls apart. The goal is to internalize the story so deeply that it flows naturally. And even though you’re going to be presenting this story hundreds, maybe thousands of times, you need it to feel natural, not forced.

Storytelling is part of the job

I have watched great founders who built real products and genuinely cared about their customers fail. They couldn’t fundraise when they needed to. They couldn’t get the right people in the door to build a strong team. And they couldn’t hold onto the great team members they had. The product was there, but the story wasn’t.

Learn storytelling skills, or you’ll lose to a competitor who did.

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Key takeaways

• Storytelling skills are a requirement for any venture-backed founder/CEO.

• Storytelling shows up everywhere: fundraising, hiring, closing customers, retaining your best people, and selling the company.

• Most founder/CEOs lack storytelling skills because nobody ever taught them, and they’re wired to work operationally, not selling the future.

• The best business storytellers don’t make themselves the hero. They make the other person (the customer, the employee, the investor) the hero.