Three storytelling skills for business that you need


Let's face it, most presentations aren't on stage

If you think about how many times you try to convince your co-workers of something, or how many times you're presenting a decision to your boss, or how many times you are trying to get coworkers to join you on a project or cause—most of your presentations don't happen on stage.

We tend to think about storytelling as something you do when you're on a stage, PowerPoint presentation behind you, and you're speaking to a large crowd. If that's not the default context for storytelling, then you may think about it as you at the head of the table, PowerPoint presentation behind you, and you speaking to a table-full of people.

But that's not your default. That's not the norm.

When you're trying to pitch, to sell, to convince, or to challenge a decision, most of the time you find yourself sitting next to someone, standing with them in the kitchen, or talking with them via Skype.

And that's really when you need storytelling skills for business.

Three storytelling skills for business that you need

The first skill you need is the need to be interesting.

People are busy. They're distracted. They're in a rush. And you can't force them to pay attention to you.

The only way you get their attention is by commanding it, and that's not something you command. It's an invitation.

People who find your stories interesting commit their time to hearing it to the end. People who find your opening interesting invest their time with you and kill their own distractions to hear you.

And that's why it's your job, when getting someone to consider your pitch or position, to get them interested in what you're saying. On where you're going.

A couple of months ago, I was asked a question about marketing and branding at a tech conference. My response started with, “In 1983 Microsoft was a tiny upstart at the Comdex conference in Las Vegas….”

It wasn't the direct answer. But for the most part, it got people leaning in. Paying attention. Investing their time to hear where this was going.

And when I ended the story, the answer to the question was obvious.

The second skill you need is the need to be illuminating.

Your stories need to help people see something they haven't seen before. They need to point a light onto a spot that was previously opaque.

Let's say you want to make the case for the company promoting you. Everyone makes the same case, “Please promote me. Please pay me more money. I'm ready for a new challenge.”

That's not only a boring story because it's so common, it's also not compelling.

When a story reveals something that no one knew, it's more interesting. More compelling.

I once had an employee share her story with me. Three sentences. And it illuminated something I didn't know about here.

She was a writer who helped us create the release notes for our software.

One day she said, “I bet you don't know what I did this summer. I took a SQL class and passed it. My hope is that it will help my writing.”

Do you know what a manager thinks when they hear that? My own three sentence story passed thru my head, “Oh man, I love that initiative. I had no idea she knew more than writing. I don't want her wasting her time on release notes.”

But you can be illuminating even when you don't need or want a raise. You can make your case by sharing the insights others have already experienced. Learning the stories of others is a powerful way to shape how people see the current situation you're in.

The third skill you need is the need to be a little indirect.

People think that everyone likes a straight-shooter. But when we're talking about storytelling skills in business, you need to embrace the fact that if people know where you're going, they have enough time to bring their walls up.

In the business world, you don't just have to make a good case. Sometimes you have to be good at making your case. And those are two different things. Getting past the early and quick rejections takes planning and preparation.

That's why I say you need to come at your arguments from slightly indirect positions.

A masterclass in interesting, illuminating & indirectness

I've never paid much attention to Rachel Maddow until the last few weeks. And not because of politics. Instead, I caught an episode that was pure genius when it comes to storytelling. And today she did it again.

If you don't know who she is, she runs a show on MSNBC. I can't tell you much about it because I've only seen a few episodes / clips and mostly on YouTube. What I love about the episodes I've watched is how well she tackles all three aspects I've written about.

She says, “I also think when you're telling a good story, it sinks in more.”  (source: cbsnews)

When you watch this, you'll notice that she's doing the exact opposite of what you expect of TV today. She's not getting to her point. You don't know where she's going until you've discovered that the story she's telling is interesting, and when she hits you with the illumination, it's a bit surprising. She invests almost half the episode being indirect.

Here's what I mean.

  1. She spends almost four minutes talking about Seattle Airport, Tacoma, and a wacky bridge.
  2. At the 3:55 mark, she introduces us to Bechtel and all the things they've built.
  3. It's not until the 6 minute mark that she mentions Bechtel and Azerbaijan and the high price of building highways.
  4. By 9 minutes in, you finally know that someone else was hired to build it for 3x the price.

Only then does she tell you that if a financial deal doesn't make sense on the surface, it likely makes sense below the surface. She takes 10 minutes to get there. And if you don't like where she's going, she still likely has kept your curiosity and engaged you.

If she had started with a slam on the President, half the country would change the channel. I'm sure half the country doesn't even watch her.

But if you find yourself in a business context where you need to engage your audience, you could stand to learn these lessons from her, regardless of your take on politics.


Maybe the last thing I'd say about storytelling skills in a corporate setting is that you should learn from anyone who does it well. If you notice someone regularly making their case in meetings and getting people to agree (without positional authority), you should learn as much as you can from them.

I don't care if I learn storytelling tricks from politicians, lawyers, the dentist, my mom, or someone who works for me. What I know is that there's always more to learn about telling a good story.

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Chris Lema
Chris Lema has been working with WordPress since 2005. Over the years he's been a blogger, a speaker at WordCamps, a coach for WordPress product companies, and the founder of the conference for WordPress business owners, called CaboPress. Today he's the VP of Products at Liquid Web, where he manages the world's first managed platform for WooCommerce stores.