Storytelling lessons I’ve learned on my journey…

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Storytelling lessons I’ve learned on my journey…

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I’m of the mind that Storytelling is THE communication imperative for today’s most effective leaders. But the question is always—

  • What does Storytelling “look like?”

  • How do I start the Storytelling path?

  • And, how do I become a great Storyteller?

And, while I don’t profess to be a “professional” Storyteller, I have become a solid Storyteller over the years, so this article is intended to share some of my learnings.

Stories are found, not made

You have to first become an active observer of your surroundings. You have to pay attention and, dare I say it, write things down. This is why I’m such an avid proponent of journaling. And by journaling, I mean old-fashioned paper and pen journaling. Jerry Weinberg wrote a book called Weinberg on Writing, where he shared his fieldstones technique for gathering story nuggets (fieldstones) that you later piece together into effective stories. The wonderful thing about this idea is you can “reuse” your stones. 

Find your own style

In other words, don’t try to be someone else or don’t overtly copy others. And I think it takes some time to find your storytelling style. Now I’m not saying don’t study others. Viewing TED talks is a wonderful way to gain insights into effective storytelling practices and style. But, don’t copy others. Instead, develop your own style. 


In order to become a great storyteller, you must practice. Practice a lot! Makes sense, doesn’t it? Practice in the mirror or even in your mind. Go through the arc of your story over and over again, fine-tuning it. If you’re fortunate to have colleagues to practice with (Dojo triads) then do that. And it can be incredibly useful to record your stories, then play them back for critique and adjustments.

Story ARC

I think of stories as having a beginning (opening moves), a middle (middle game), and an end (endgame). In other words, they have an ARC to them. You spend much more time in the middle game than you do the opening moves or endgame. Planning your storytelling with this arc in mind can be a helpful metaphor to leverage.

Target your audience

I try to create a persona of my audience and target that in my storytelling. As part of the persona, I try to hit the middle of it—reaching for the middle 80% and not trying to communicate with everyone. Often, I’ll visualize a person that represents the persona, so I’m speaking to a virtual person if you will.

Make eye contact; manage your presence

I like to walk around, reading the audience, and making eye contact when I tell stories. It helps me to sense the energy in the room and determine how my story is resonating and landing with everyone. If it’s not, I try to make real-time adjustments. I know this is harder when you’re telling your stories virtually but try. For example, ask everyone to turn on their cameras and pan through your audience. Also, be present by focusing on the connection over the content.

Create a visual journey

As much as possible you want your story to paint a picture for the listeners. Take the time to connect to common themes. Take them on a journey and take the time to build and share visuals with them. And it’s not just the visual channel. You can share sounds and smells as well to activate all of their senses.

Dramatic License

One of the things I’ve learned is that it’s perfectly fine to embellish, exaggerate, and otherwise build up your stories. No, I’m not telling you to lie. But I am encouraging you to exaggerate your key points and not to be afraid to be overly dramatic.

Less is More

Focus on making a singular point. In other words, don’t try to communicate too many items, points, complex scenarios in a single story. It just adds complexity and prevents connection and understanding. Simply put—less is more!

The Power of the Pause

All of us, or at least I am, are uncomfortable with silence. But silence or a pause, carefully crafted in a story can be incredibly powerful. And you can artificially inject them by asking a question or taking a drink or looking around the room. Silence can make your stories remarkable.

Land it!

Create a drop the mic moment in each of your stories. It’s incredibly important to land with your point—whether it’s directly made, implied, or emerged. You’ve got to land it.

I use a Steve Jobs video in my Certified Agile Leadership classes when I’m discussing storytelling techniques. I’ve found his Stanford Commencement address to be a masterclass in effective storytelling and we usually talk about it for 30 minutes or more—mining it for tactics, techniques, approaches, and strategies.

For example, you can truly see the ARC of his storytelling throughout. Here are a few video talks that I highly recommend—

As great examples for your storytelling learning and growth.

As I stated at the beginning, storytelling has become the very best way to communicate. Period.

That being said, most of us suck at communications in general and storytelling in particular. I strongly encourage you to “embrace your suck” in this area and begin to work on your storytelling skills and repertoire of stories.

I guarantee it will make a difference in your professional journey.

Stay agile my friends,



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