4 Mistakes Leaders Make Telling Stories: What’s the Point?

Part of an ongoing 4-part series on common storytelling mistakes I’ve seen leaders make in corporate storytelling spaces.

Long story short. Many leaders fail to tell compelling stories because they don’t know what point they are really trying to make.

There are many, many ways to tell any one story. You could start or end the story in different places each time. You could emphasize certain details over others. You could expand or contract the story. And all these choices depend on one question: What’s the point?

Especially in stories where you’re hoping to persuade someone of something, being crystal clear on your purpose in telling the story is paramount. I often encourage the leaders I coach to think of their story’s purpose as the gatekeeper of the story’s content: it should decide what gets in and what doesn’t. In other words, with a clear purpose or point in mind, you can ask yourself, “Does the audience need to know this in order to make sense of the point I’m trying to make?” If not, then you probably should cut it.

I often encourage the leaders I coach to think of their story’s purpose as the gatekeeper of the story’s content: it should decide what gets in and what doesn’t.

For example, remember the origin story I wrote about back in December? The one about hearing my dad tell really rough stories at his health clinic and not having a clue what to do with them? I could tell a variation of that story for a prompt about coming of age, or about something unexpected. I could use it to emphasize the challenges of rural health care, or talk about the importance of alternative spring breaks, or explore father-son dynamics. And depending on what the primary focus is, I’ll shift the content. I won’t need all the same details in each of those versions.

A helpful preparation practice can actually be to write out, “I’m telling you this story because…” I like the discipline of writing my story’s point down in a single sentence. It keeps it simple and ensures I know precisely what I’m up to. You don’t have to include this sentence explicitly in your story—though there are times when doing just that can actually significantly strengthen the story. The practice of writing it out, though, will focus your process of crafting the story. Every sentence you choose to use in the story, then, can strategically guide your listeners swiftly and surely toward the takeaway you have in store.

What happens when you don’t get clear on your story’s point? Well, then your story starts to sound meandering, wordy, and confusing. Your audience either begins to glaze over because they can’t keep the story straight, or they begin focusing on the “wrong” themes or threads in the story. The impact you were hoping for just withers and dies before your very eyes.

Well, that’s a touch dramatic—but you get the point.

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4 Mistakes Leaders Make Telling Stories: No Vulnerability