How to build the storytelling habit

Posted by  Shawn Callahan —December 11, 2014
Filed in Business storytelling

Business people love structure. When I ask people after our storytelling workshops what they found most valuable, more often than not they will say they loved the story patterns. These are a few different story structures we teach that are great for changing minds, or for answering the question ‘Why?’

Story patterns are good set pieces, but they only account for a tiny percentage of day-to-day business storytelling. The majority of the time we spend sharing a business story, we are simply trying to make a point. So rather than focusing on how to use story patterns, we should be developing our ability to find the right story to make a business point. We should also be practising the art of succinctly making our point at the start of a story, which, as I recently explained, doubles the audience recall.


Now to be an effective business storyteller, you have to do two things simultaneously. You have to build both your story repertoire and the storytelling habit.

Building your story repertoire

Building your story repertoire is a process of discovery. It starts with fine-tuning your ability to spot stories. Because the best stories are the ones that evoke an emotion, you want to keep an ear out for anything that sends a chill up your spine, brings tears to your eyes, or sets the hairs on your arms on end – stories that make you feel something and which you think you can use to make a business point. (The good news here is that you can make a business point with any evocative story.)

Now you need to tell these stories to remember them. Here are a couple of reminders about how to make stories stick in your memory.

This process of finding stories, working out what they mean to you and then telling them is how you build your story repertoire.

Building the habit of storytelling

In the past few years there’s been a flurry of new books on how habits are formed, including The Power of Habit by Charles Duhigg, Making Habits, Breaking Habits by Jeremy Dean, and Hooked by Nir Eyal. All of them point out that habit formation requires effort and time for the behaviour to become automatic. Let’s use Eyal’s four-stage model of trigger, action, reward and investment as a guide to forming the storytelling habit.

It all starts with a trigger. External triggers are things like getting up in the morning, having a shower or sitting down at your desk. Internal triggers are things you think or feel, such as feeling hungry or thinking to yourself, ‘I need to make a point’. We can use this last internal trigger to build our storytelling habit. Whenever you need to make a point at work, state it and then tell a story that illustrates it. Aim to do this at least once a day. Get the Lift habit-forming app for your iPhone to help you.

The action is telling the story. Nothing more needs to be said.

The most effective reward for habit formation is a variable one; that is, one where you can’t predict the intensity of the reward before you get it. This is why poker machines and email are so addictive. The reward you get when you tell a story is the impact it has on your listener, and this is always variable. But you need to look out for it, to consciously watch for a reaction. You can also ask your audience what they are thinking and feeling: What are they planning to do now? Has the story inspired them to action? Often, the impact of a story is not immediately apparent, so pay attention to what happens over the next few days. See if your listeners retell the story – this is the ultimate reward for storytelling.

Finally, remember that by building your story repertoire through jotting down stories, then seeing them have an impact, you are making an investment in storytelling. When we have invested in something, we want to continue using it. We don’t want our investment to go to waste.

Stick at it

Habits don’t form over a few weeks. In fact, you’ll need to stick at this for months. But you don’t have to be regimented to be successful. On the contrary, try and have fun with it. Look out for times you can make a point at work, tell a story, and collect your reward from the faces of the people around you. Eventually, it will just come naturally. And when it does, you can then start thinking about how to make your stories even better.

About  Shawn Callahan

Shawn, author of Putting Stories to Work, is one of the world's leading business storytelling consultants. He helps executive teams find and tell the story of their strategy. When he is not working on strategy communication, Shawn is helping leaders find and tell business stories to engage, to influence and to inspire. Shawn works with Global 1000 companies including Shell, IBM, SAP, Bayer, Microsoft & Danone. Connect with Shawn on:


  1. Shawn, good article. I agree filling the story with the right content is key, and doing it economically.

    It’s just like as you develop your sense of humor, things start to strike you as funny. For this to happen, you need to be aware. Great humor, I believe, is also often very insightful. I feel the same way with stories. They are like a ray of light on the darkness that customers are not seeing. The added benefit of telling insightful stories is that they will never be boring.

Comments are closed.