How to tell a great story

I’ve told the story of starting Robin’s Cafe with no experience and selling it on Craigslist hundreds of times.

What’s funny is I’m actually most proud of the culture we built behind the counter, the amount of learning I went through in learning to operate the cafe, and the role the cafe played in creating community in that neighborhood.

But when I mention selling a restaurant on Craigslist, I invariably get a laugh. “Craigslist?” People ask, incredulous.

Stories are the reason people buy from us – our ideas, our services, even our avocado toast. In order to sell, you need to tell a great story.

Everything is storytelling

You are already telling stories all the time.

  • Hiring requires telling a story about your company.
  • Deciding what movie to watch with friends requires telling a story about your point of view.
  • Persuading your kid to eat their broccoli means telling a story about that oh-so-delicious vegetable.

The stories we tell ourselves become how we think of ourselves and the stories we tell others define those relationships.

The first step to telling a good story is to recognize that you already are.


Take note of a story you’ve told recently. I like to do this during my morning journaling. Take two minutes to note down a story that you told someone yesterday.

See What Sticks

The parts of a story that matter the most to you aren’t necessarily the things that matter to your audience.

When it comes to Robin’s Cafe, I’m more proud of having opened up a restaurant in 3 weeks, but that tends to fall flat. I’m proud of the culture we had behind the counter, but without experiencing it, that’s not of great interest to the listener. The moment I get a chuckle is when I share that I sold the cafe on Craigslist.

You aren’t telling a story for yourself, but for the person you are talking to.


Look for reactions. Aspects of your story will land and other parts won’t. That’s useful information! Save the parts that illicit a reaction for your next telling.

Notice What Stories You Already Tell

In 2020, I moved into a house in the woods with my partner. Within a couple of weeks, my partner was parroting back to me a handful of stories that – apparently – I told all the time on Zoom. I hadn’t realized that I was repeating so many of the same stories on different calls!

Even if you aren’t aware of it yet, you are telling other people stories all the time. Pay attention to those stories, and use them as fodder as you refine your narrative.


When you are beginning to sell something new – as sophisticated as a new business or as simple as asking a friend to lunch – write down a list of possible stories that might help you accomplish your goal.

Refine and Hone Your Stories

We take for granted that a comic has to practice their jokes, or an athlete their sport, thousands of times for every single performance. It is less obvious that that storytelling, too, is a craft.

Every time you tell a story is a chance to iterate and improve your storytelling craft.


Try telling a story in a subtly different way. Add a new variation or detail, and notice how your audience reacts.

Emotion > Rationality

When we foster connection with another person, we create the opportunity for change.

Facts and figures are great, but they don’t accomplish much without the wrapper of a good story. To get someone even just to listen to your data, you have to form an emotional connection.

We like to tell ourselves that we are rational, but most of our behaviors come down to emotion.


As you head into your next meeting or difficult conversation with your spouse, ask yourself how you want them to feel.

We don’t get to control another person’s emotions, but just considering how you’d like for them to feel will influence how you show up and the course of the interaction.

A good story doesn’t guarantee in a successful sale, but without a good story your attempt to sell probably won’t work. Storytelling is necessary, but not sufficient.

Hone your storytelling skills, by noticing and improving the stories that you already tell, and you’ll be better able to move your audience – and your objectives – forward.

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