Some lessons are taught. The best ones are lived through story

I’ve watched the same thing happen in leadership workshops many times.

A framework gets explained, discussed and carefully written down. Weeks later, much of the detail has faded.

But the story someone told during the session stays with people. It might have been about a mistake they made or a moment that changed how they approached something. Months later, someone brings it up again.

There’s something important in that about how people learn, but also about how leaders bring people with them.

Storytelling is a leadership practice

Clear communication matters in leadership. We need to explain what’s happening and help people understand what’s expected of them.

Stories add another layer.

When you hear about a real experience, you can picture the situation and recognise something of yourself in it. An idea becomes connected to a moment, which gives it meaning beyond the meeting or workshop where you first heard it.

I see this in learning environments all the time. People may not remember every element of a model, but they remember the experience that helped the model make sense. This is why I was interested in a recent IDEO U conversation with Catherine Connors, former Head of Content at Disney Interactive and founder of storytelling consultancy StoryQuo.

Their discussion explores storytelling as a leadership practice, particularly for leaders trying to bring people along and create change. That framing really resonates with me.

Start with the experience of your audience

One of the ideas Catherine discusses is experience-centred storytelling.

For leaders, that means thinking about the people receiving the story. What are they feeling? What are they experiencing? Where are they emotionally when you begin the conversation?

Imagine you’re talking to a team facing significant change. People may already be carrying uncertainty into the room. That context should shape the story you choose and how you tell it.

Before choosing your story, ask:

• What are people experiencing right now?
• What matters to them in this moment?
• What do I want them to feel as they hear this?

These questions make storytelling more intentional. They also encourage us to pay attention to the human experience behind whatever change, challenge or idea we’re communicating.

The best stories get carried forward

Another idea from the conversation stayed with me: stories become powerful when people make them their own.

You might notice it when:

• Someone brings the story into another meeting.
• A manager shares it with their own team.
• Someone adapts the story to help make sense of something they’re experiencing.

Once that happens, the story has travelled beyond the original conversation.

I think that’s particularly relevant for leaders trying to influence culture or lead change. You can’t personally be in every conversation across an organisation. The ideas that spread are often the ones people can understand, remember and use themselves.

A story that gets retold has become useful.

What makes a story worth telling?

Of course, putting a story into a presentation doesn’t automatically make it meaningful.

The stories I’ve seen people remember tend to have something real at their centre. When I’m thinking about whether a story is worth sharing, I look for a few things:

• A specific moment. A decision that didn’t go as expected, a conversation that changed someone’s thinking or an experience that challenged an assumption.
• Enough detail to picture it. Give people something tangible that brings the experience to life. They can visualise the details in their mind. (…but not too many details!)
• A clear purpose. Know why this particular story belongs in this particular conversation.

We’ve all sat through stories where, several minutes in, we’re still wondering where they’re going.

A useful story earns its place because it helps people understand something that matters.

Why leaders sometimes hold back their best stories

Some of the most useful leadership stories are also the hardest to share.

Senior leaders have plenty of stories about achievements. A lot of their richest experiences come from moments when they didn’t know exactly what to do, made a decision they later reconsidered or learned something about themselves.

Those moments can feel uncomfortable to talk about. Leadership brings an expectation that you should have answers, and sharing an experience where you struggled can feel exposing. Yet when I hear a leader talk openly about something they got wrong and what they learned from it, I tend to listen more closely. There’s a humanity to it.

It gives other people permission to reflect on their own experiences with the same openness. In a leadership workshop, that can change the quality of the conversation in the room.

Tell stories with intention

Before sharing a story, ask yourself why you’re telling it. What do you want the people listening to understand or experience? That question keeps the audience at the centre and helps you choose an experience that belongs in the conversation.

Leadership storytelling isn’t about becoming a polished performer. Your experiences are already there. The skill is learning to recognise which ones might help someone understand an idea, connect with a change or see a situation differently.

For me, the real test comes afterwards.

If someone remembers your story, makes sense of it through their own experience and carries it into another conversation, it has done something valuable.

And that’s when storytelling becomes more than something a leader does well. It becomes part of how leadership travels.