How To Tell A Story In Conversation (15 Storyteller Tips)

“When I try to tell my friends a story, I can see their eyes drifting. Sometimes, no one reacts to my stories at all, which is embarrassing. How can I become a better storyteller?”

It’s awkward when you tell a story only to receive little or no response. In this article, you’ll learn how to keep everyone’s attention and turn everyday events into interesting stories.

1. Tell stories that match the mood and setting

You should only tell stories that match the current topic and tone of a conversation. In other words, tell happy stories if you’re having a positive conversation with someone, sad stories if the mood is more somber, and so on. No matter how good a story is, it will feel a bit off if it isn’t related to the situation or the mood.

Follow the flow of the conversation. If the conversation moves on and people start talking about another topic, don’t try to change the subject just so you can tell your story. This strategy might occasionally work in a one-on-one interaction, but almost never in a group conversation.

2. Pick the right story for your audience

As a general rule, if your audience has been in a similar situation, they will probably appreciate the story. If they have, they will think the story is a lot funnier because they can relate to it.

Take your audience’s knowledge and background into account. For example, if you are a programmer and want to tell a story about something funny that happened to you at work, don’t use jargon or specialist terms unless your listeners have a basic understanding of your job role and industry.

You also need to think about the kind of topics and humor your audience will and won’t enjoy. For example, your grandparents might not be keen to hear about what you did when you got very drunk at a party, but the story might work well in an informal gathering of friends.

3. Avoid one-upping others’ stories

If someone tells a story and everyone loves it, it’s tempting to start thinking about similar stories we can tell. We instinctively want to get a similarly positive reaction like that other person just got.

But if we instantly start talking about our own experience, the other person will feel one-upped or de-throned. We steal their spot in the limelight.

So, if someone shares a funny thing that happened when they were in Guatemala, it’s often better to avoid talking about an even funnier thing that happened when you were in Venezuela.

This is as true for one-on-ones as it is for group conversations.

Always give the other person their deserved attention, ask follow-up questions, laugh with everyone and enjoy the moment. THEN, you can tell your story.

4. Avoid stories where you are the hero

A story about a struggle is almost always more interesting than a story of victory. In most cases, success becomes interesting first when it comes after a struggle. This is why “rags to riches” stories are popular in movies, shows, and books.

You can still speak positively about yourself. There’s no need to be constantly self-deprecating. But your audience probably won’t be entertained by a story that centers around your positive qualities or achievements.

A story is more valuable in a social setting if it makes people feel good about themselves. Avoid stories that make others feel inferior.

Read more: How to gain the respect of people around you.

5. Do not start a story by giving away the ending

In a scientific report, the most important finding comes first. For example, “Scientists discover cure for Alzheimer’s.” After the main message, the background and context are explained for readers who want more detail.

This “top-down” approach is great for getting key information across, but it’s a boring way to tell a story.

Good stories are bottom-up. First, you get the context and the background. Then you share more details to hold your listener’s interest before finally revealing the punchline at the end.

Here’s an example of a top-down story:

“I wore my shirt inside-out to a big meeting today. I only realized afterward when I looked in the bathroom mirror. My boss gave me a few weird looks, and a couple of the interns giggled when I got up to give my presentation. I think I put the shirt on the wrong way around because I was in such a hurry this morning.”

Telling the story top-down like this isn’t entertaining. It comes off as complaining instead of funny. The storyteller gives the most important piece away first: “I wore my shirt inside-out to a big meeting.”

In a good story, we want to go bottom-up. First, we set the context. For this story, it would be something like, “I was in a hurry this morning because I had a big meeting at work today.”

Let the punchline come last. For example, “When I went to the bathroom afterward, I looked in the mirror and saw that I was wearing my shirt inside-out.”

Preface your story with a hook

Instead of jumping straight into a story, you can begin with a hook. A hook doesn’t give away what happens in your story, but it tells the audience to expect a memorable anecdote. You should still tell the story bottom-up; the hook should leave listeners wanting more, but it shouldn’t reveal the ending.

For example:

  • [In a lighthearted conversation about vacations that go wrong]: “Speaking of bad travel experiences, did I ever tell you about the time I got stranded on a tropical island?”
  • [In a conversation about strange things burglars do when they break in]: “A burglar did something seriously weird to my kitchen once.”

6. Give enough detail to set the scene

You probably know people who can babble on about the finer details of a story for a long time and never get to the point. This makes their listeners lose interest. You need to add context to set the scene without giving too much detail.

At the same time, when people give too little context, it’s hard to understand the point of the story.

For example, if you’re telling a story about something funny that happened to you in the morning because you overslept, talking about what you did the night before would be irrelevant and probably not very engaging. But if you didn’t make it clear to your listeners that your story took place in the morning, they would be confused.

7. Use vivid descriptions

Overdoing vivid descriptions can make you seem overdramatic, but sprinkling one or two in your story can be a great way to hold your audience’s attention.

Try using the following:

Similes: A direct comparison between two things. E.g., “The spider was kind of cute, like a fluffy black pom-pom with legs.”

Metaphors: A non-literal description. E.g., “The new boss looked grumpy and scary, but really he was a soft, friendly bear.”

Analogies: A comparison between two things that serves as an explanation. E.g., “Her mood was like a yoyo, always up and down.”

8. Use a logical story structure

To make sense, a story needs to have a clear beginning, middle, and end. As a general rule, the whole story shouldn’t last longer than a couple of minutes.

If you forget a detail, don’t return to an earlier part of the story unless it’s absolutely essential. If someone interrupts and asks an irrelevant or distracting question, say, “Hold that thought, that’s a whole other story!” and carry on.

9. Make eye contact with your listeners

Popular wisdom says that if someone is truthful, they will be able to look you directly in the eye when talking. This isn’t always true, but many people believe that if someone is struggling to make eye contact, they may be hiding something.[1]

Learning how to use appropriate eye contact may make you come across as more reliable, engaging, and honest. See our guide on how to be comfortable making eye contact during a conversation for practical tips.

10. Use your voice to make the story come alive

Good storytellers use their voices to keep their listeners engaged. Experiment with varying the volume, pitch, and tone of your voice.

For example, you can:

  • Speak faster to give a sense of energy and urgency when describing exciting moments in your story
  • Raise the volume of your voice to highlight key points or twists in the story
  • Give each person in your story a separate “voice.” Be careful because this requires sensitivity. You want to make each character distinct without mocking them or turning them into a caricature.

Don’t overdo any of these techniques, or you’ll distract your audience from the narrative.

If you tend to speak in a monotone voice, your listeners might struggle to pay attention to your story, even if it’s funny. See this guide on how to fix a monotone voice for tips on how to make your voice more interesting.

11. Use pauses for dramatic effect

Short pauses can break up the flow of your story, build suspense, and emphasize important points.

For example, you can use a brief pause:

  • Just before revealing a key piece of information

Example: So she finally comes down the stairs and says, ”I don’t know how to tell you this, but… [Brief pause] there’s a snake in your bath.”

  • When you want to give your audience time to build an entertaining mental picture

Example: “So there we were, three managers all dressed up in banana costumes. Just picture that for a second… [Brief pause] Then…”

  • Just before the story’s punchline

Example: “Then I finally realized why I didn’t understand a single word the professor said… [Brief pause] I’d been in the wrong class for half an hour.”

Use pauses sparingly because they will annoy your listeners and become less effective if you use them too often.

12. Use gestures to illustrate your story

Gestures add a visual element to your storytelling. They can help your audience to imagine what happened. Gestures also convey energy, so they can make you a more engaging speaker.

Here are a few examples of gestures you can use when telling a story:

  • Move your hands apart or closer together when describing distance or the size of an object.
  • With your palm facing downwards, raise or lower your hand to describe the height of a person or object.
  • Shrug and turn both palms upwards to indicate despair or resignation.
  • If you want to list people, items, or key points, use your fingers as you do so. Put one finger up for the first item on the list, raise two fingers for the second, and so on, keeping your palm facing toward your audience.

13. Use your facial expressions to convey emotion

By using your face to show how you felt in a situation, you may make your story more engaging. If you aren’t naturally expressive, it may help to try out different expressions in front of a mirror, so you know what they feel like.

This video for actors has some useful tips on conveying emotion to an audience. Don’t overdo it, or you’ll come across as fake or overdramatic.

14. Don’t aim for 100% accuracy

Telling stories is about entertaining your listeners. Although it’s not a good idea to make things up or tell outrageous lies, you don’t need to be completely accurate. For example, you don’t have to replicate every line of dialogue word-for-word precisely as it was spoken. Getting hung up on accuracy can make you appear hesitant and interrupt the flow of a story.

Putting it all together: an example of an effective story

Here’s an example of a story that shows some of these principles in action:

“So, I wake up to this important day full of exams and appointments. Almost immediately, I feel this rising wave of panic when I realize that I’ve slept through my alarm. I’m feeling totally exhausted, but I start preparing myself for the day anyway.

I take a quick shower and shave. But I just can’t stop feeling tired, and I’m actually throwing up a little on my way to the bathroom. The situation is freaking me out at this point, but I still prepare breakfast and get dressed. I stare at my porridge, but I can’t eat and want to throw up again.

So I grab my phone to cancel my meetings – and that’s when I see it’s 1:30 AM.”

Let’s review why this story works:

  • The opening sets the scene and gives context. It’s a bottom-up story. We can see why the situation is meaningful; the storyteller has a big day ahead of them, and if something went wrong, there would be significant consequences.
  • It’s relatable. Most of us have slept through an alarm at some point and become stressed out.
  • It doesn’t show the storyteller as a hero, and it isn’t an opportunity for the storyteller to brag.
  • It contains enough detail to paint a vivid picture for the audience, but it’s not long-winded.
  • It follows a logical structure and timeline.
  • It has a strong punchline.

This story also shows that you don’t need to experience amazing things or lead a remarkable life to be good at telling stories.

Should you ask, “guess what happened next?”

You may have read that one way to keep an audience engaged is to pause before revealing the next part of the story before asking, “Guess what happened next?”

For example:

“I was driving to my friend’s house, and suddenly I heard this weird sound behind me, kind of like a roar. I looked over my shoulder; guess what it was?”

When used occasionally, this technique can make your audience feel more invested in the story. But it only works well if:

  • Your listeners feel comfortable enough to offer their opinion; some people may not want to make themselves look silly by “getting it wrong.” Others might feel annoyed if you ask them to take an active role because they just want to listen.
  • The next part of your story is likely to be more interesting than your listeners’ guesses; if their answers are creative and exciting, the next part of your story might look dull by comparison.

How to get more experience as a storyteller

1. Learn from other people

You may also find it helpful to watch and listen to storytellers at The Moth. Listen to a few of the short stories and decide what makes them effective or boring. You might pick up some tips on how to hold a listener’s attention.

The Speak Up Storytelling podcast is another useful resource. You can listen to stories plus critique and commentary that explores why they do (or don’t) work.

2. Practice writing stories

Some people find that creative writing helps them learn how to structure a good story. However, be aware that when you tell an anecdote, you also need to use your voice and body language, which can’t be practiced by writing a story.

3. Practice telling your stories

Have two or three stories you can use for social occasions. Rehearsing them line-by-line and trying to recite them word-for-word may make you come across as stiff, but practicing them by yourself or with a friend can make you feel more confident when telling them to other people.

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  1. ah luckily I no longer have this issue as I’m now a novel writer and I’ve learnt the art for ages. I actually came here to see if the tips would be any good for writing books, too XD.

    Reply
  2. It’s true that some people have natural good storytelling skills. But others can learn it too, through practice and by following a few tips. As you have mentioned, it is very important to tell stories that are related to discussion topic or mood of the gathering. If you start telling a story that is not related to the topic being discussed, it is very likely that people with not listen to you and they may even get annoyed.

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  3. If I followed all your advice I’d be trying to remember 157 different principles. Just perfect for someone who overthinks. Do you actually see the flaw in your advice?

    Reply
    • In the program that this extract is taken from, you get exercises for how to internalize the advice before you go into a social setting by practicing this form of storytelling on your own.

      That way, you don’t have to deal with overwhelm.

      If you want to focus on only one thing, I would recommend rule number 6.

      Reply

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