May 26, 2020 / Esther Choy

sharing stories in conversations

You know leadership storytelling is powerful. You’ve figured out how to choose the right stories to tell. Just one small problem. For many leaders, sharing stories in everyday conversation feels awkward. As a participant in one recent Leadership Story Lab workshop put it, “How do we incorporate stories professionally so it doesn’t seem so ‘off’ and ‘weird’?”

Here’s a four-step checklist for making storytelling come naturally in every conversation.

Step 1: Create a story library.

The best way to incorporate a natural-sounding story is to have a lot of stories to choose from. That way, you’re not forcing a story to fit the occasion, you have a story at your fingertips that actually applies!

Get organized. Start a storytelling spreadsheet.

  • In column A, create a list of experiences you think a lot of people probably share. For instance, being a middle child, having a non-traditional path through school, being in the military, or taking a gap year that turned into five years. Brainstorm as many shared experiences as you can.

  • In column B, develop examples of these shared experiences from your own life.

  • In column C, consider what these examples tell other people about your character.

  • In column D, dig into the meaning behind your examples.

Now you are ready to share more stories in your conversations.

Step 2: Identify your most natural transitional phrases.

It can be easy to tell stories when conversation is already flowing easily, the way it does between friends. It’s much harder when you’re at a networking event, meeting someone for the first time.

Having a good segue helps. Never start telling a story by saying, “let me tell you a story.” This isn’t a hard-and-fast rule, but it is definitely one of my pet peeves. Not only is it awkward, it’s also sure to make a business audience defensive. In ten years of leadership storytelling coaching, training and consulting, I’ve found that people love hearing stories, but they don’t always know they love hearing stories. Because of that, in business settings, it works much better to avoid announcing that you’re about to launch into a story. 
Try these transitional phrases instead:
  • “Oh, that reminds me of….”
  • “I remember when….”
  • “That’s just like this one time…”
Being able to transition into stories requires keeping your ears open for opportunities to insert a story. It requires active, empathetic listening so that you tell a story that is truly a good fit for the situation.
Even with the best transition, however, sharing a story requires risk and may feel awkward at first.
Tina Peters, Senior Learner Experience Manager at Wiley Education Services, worked one-on-one with me recently to find and refine stories. She remembers me telling her, “you have to practice.” So she decided to share a polished, practiced story with her mentor. Even though Tina shared it exactly as she had practiced it, she knew the story was personal. And she knew sharing a personal story required risk—because although she and her mentor had a wonderful collegial relationship, Tina had not shared much personal information with her. Nevertheless, Tina decided to go for it. And as she shared the story, tears welled up in her mentor’s eyes. 
Seeing her listener’s tears, Tina realized the power of what she was playing with when she told stories. “It rattled me,” said Tina. There was a real connection. It was scary, Tina felt, because it worked! 

Taking the risk and sharing a story that was personal (but not private) paid off. Not only did it forge a stronger connection, it also led her mentor to seek Tina’s advice about storytelling when she had to give an important presentation. This also took their relationship to a new level. Because Tina took the risk of telling a story, they became collaborators.

Step 3: Practice.

In business environments, people often feel that stories are a luxury. But far from being an extravagance, stories help listeners process information better and make information up to 20 times more memorable. Even when we know that, it can be difficult to interrupt a fast-paced, efficient meeting to interject a story. (This is especially the case during video meetings, where it can be especially difficult to get others’ attention and time always seems crunched.)

The key is to make sure the story is as concise as possible. It has to move. Most importantly, it has to have a concise, intriguing beginning so that people will want you to keep telling your story. Seeing their body language should help affirm that you should keep going.

Don’t share your first draft. Don’t share an unprepared story. Practice it and share it with others before you attempt to share it in a meeting where you hope to be efficient.

In a recent workshop, one participant shared a first draft that needed shaping. It didn’t have a plot. It was more like throat clearing, and in a short meeting with a lot of participants, you don’t want to use everyone’s collective time for throat clearing.

However, I was thrilled that this participant told such a story! A workshop was exactly the right place for this kind of experimentation. Together, we shaped it and made it better, so that when he tells the story again it will be more concise and efficient.

Step 4: Cultivate a storytelling culture.

Incorporating stories professionally becomes less “off” or “weird” the more our organizations make storytelling expected and routine.
Some companies already have a storytelling mandate. At others, employees find themselves needing to make the case for incorporating more storytelling. 
My client Danielle found herself in this situation a few years ago. Presentations at her company—like those at many others—tended to be very fact based: “This is where we are, this is where we’re going, here’s the takeaway.” Every presentation made a data-grounded case for how the project will succeed. 
“When you copy the same format and structure as every other presentation in your company, you think you are playing it safe,” says Danielle, “but it’s actually a very risky move. It’s risky because your presentation will blend in with everything else. It becomes unmemorable.”
Throughout her career, Danielle noticed the toll that “data only” takes on an audience. “People’s eyes glass over,” she says. When the audience’s attention drifts, the message itself gets lost. The ideas die because no one hears them, and no one becomes inspired to act on your message.
So Danielle decided to go straight to the C-suite at her organization to ask them to change the status quo for presentations, including sharing stories. She modeled how to tell good stories—and she paved the way for a culture where telling stories became more comfortable, and even expected. 
If going to the C-suite is not possible for you at your organization, you can still change the culture. Use storytelling within your own presentations to show how powerful it is. You may even have people come up to you to ask for storytelling advice, like Tina’s mentor did. Change the culture organically so that storytelling is the expectation, not the “weird” exception.
A checklist for sharing stories

Opportunities for sharing stories in the workplace are abundant. But because we’re not used to doing it, initially it might feel awkward, just like those few first times starting to exercise at the gym. But once you get used to it, it’ll actually feel strange when you’re not inserting stories all the time.

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We’d love to help you become a pro at sharing stories in your conversations more naturally. We’ll help you choose and shape the right stories for the right opportunity. Start the conversation!

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This article originally appeared on

Esther Choy

Esther Choy founded Leadership Story Lab in 2010 to help others leverage the art of storytelling to create extraordinary opportunities.
Karla Trotman and Robert Pasin

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  1. Robert on July 19, 2020 at 9:09 am

    Esther, I’ve done something similar with interviews. And this has helped me a lot. Sometimes just being able to references those initial transition phrases is all your need to get going in your story.

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