#54 The Single Most Important Skill Every Storyteller needs to be Great

And two essential tools for a storyteller’s arsenal

I consider myself a professional question asker. In all of my roles, asking the right questions has led to greater impact and better solutions. In my storytelling it allows for me to dive deeper into the motivations of my characters, or customers, or subjects as I work to bring a story with nuance and depth to life.

I’ve written about the value and impact of curiosity in storytelling before. But the step after that is action to relieve that curiosity. Usually that means asking a question whether you ask a person or you ask google—I encourage you to ask people when you can, because usually the answer is a story you can learn from.

I want you to commit to becoming a professional question asker in addition to what you also currently do for a living (there is no pay, but a lot of fulfillment). Asking questions clarifies the problem at hand (if there is one), opens you up to new possibilities, and creates deeper and more honest connections between the askers and answerers.

But being a professional question asker requires another important skill. Really it’s an essential device in the storyteller’s toolbox. Without it, really, your stories will lack the humanity and vulnerability required to make them good. It’s also something that needs to be cultivated over time and through practice. That wonderful tool is humility, specifically the ability to let go of your ego and acknowledge that while you probably know a lot of things, there are an equal amount of things out there that you don’t know. And that’s okay. In fact, it’s exciting—so much to discover.

“Curiosity is a superpower of mine that I want everyone who reads this newsletter to develop.”

And that is the magic of storytelling—through stories you get to share what you know and receive what others know. Because ideally when you ask a question, you’ll get the answer in the form of a story. But you have to be in a place where you’re comfortable with admitting you don’t know something, or you don’t know all of something and need help understanding. My favourite question as a journalist, researcher, and strategist is “help me understand.” Because people may give you answers that make you uncomfortable. Whether because it enrages you, confuses you, or something else the true magic comes when rather than going on the attack or being dismissive you get curious, you get humble and you ask for them to come to where you are and walk you along the path to where they are.

It gives them the ability to become the teacher and the storyteller and it allows room for understanding and connection between you both. Another good one is, “tell me more.” I use this when someone says something that excites me, but I want to be sure I understand exactly what they mean by it.

“I believe dinosaurs still roam the earth.” Tell me more!

You may still leave the conversation unconvinced of their view or confused about it, but you will certainly leave with a new perspective to consider and that is something you can use and infuse into the stories you share in the future. (It’s also an approach that can help you connect with folks who perhaps hold different and/or opposing views to yours, which I think is especially valuable in the increasingly ideologically divided world we currently occupy).

So get out there, ask questions, and see how the understanding and/or perspective that comes with it starts to help you tell better, more interesting, and more nuanced stories. If you’re stuck with where to start, go with the classics: Who? What? Where? When? Why (this is my personal favourite of the group)? And How? You won’t go wrong and who knows what you’ll learn along the way.


A Story Well Told

As you all know, I believe very strongly that storytellers work across different mediums—we’re not just writers and marketers, though a lot of us end up in those fields. One storyteller whose work I’ve been obsessed with for over a decade is a visual artist. Alex McLeod creates these sumptuous, surreal digital landscapes that I just want to dive into and explore. The stories they tell for me are endless and rich. He’s only gotten better (and more famous) over the years since I was first introduced to his work as a young reporter covering art prize winners. His pieces just absorb me. I encourage you to explore the works on his website and if you ever get the chance, check out his pieces IRL. They’re… something special—at least to me they are.

Do you have artists who just absorb you with their work? What mediums do they work in and what stories come to life for you in their work? Share any favourites in the comments (I’m always looking for new artists to enjoy).


Sharing and subscribing are the two best ways to help me continue to share my own adventure in storytelling. If you know someone who has a story to tell and may need some help crafting it, please share this newsletter with them and encourage them to subscribe.

Have a question? Something you’d like me to cover in a future letter—an element of your storytelling you may be struggling with? Just ask. Leave a comment on the website or reply to the email. I’m here to help.

You can follow me on Twitter here, and Instagram here. And you can always reach me through my website. If you’d like to work with me, reach out here.

Thanks for reading and I’ll “see” you next week. Whatever the world may bring, there will always be important stories that need you to tell them. I’ll be here to help.

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