Three Stupid Questions
Don't scoff. They can yank open the door to effective storytelling.
One brief musing about storytelling per day (or, more likely, as frequently as I can muster).
Jan. 5, 2026
IF YOU KNOW ME, you know that for the past two decades I’ve been pushing fellow storytellers to ask three important questions when embarking on a project. These questions are absurdly simple and obvious — almost to the point of being outright stupid. I even occasionally get made fun of when I try to encourage them.
Sometimes, though, the biggest answers lie in the obvious stuff we tend to ignore. And as we have been told over and over in our era of institutional empathy, there’s no such thing as a stupid question.
Here are the questions. They’re basic. Don’t say I didn’t warn you.
What is this story really about?
How should this story be told?
What is your audience — or, more accurately, your audiences — expecting from this story?
As a former editor of mine used to say: Well, duh. (He was a far more effective editor than this sentence might indicate. And at least he was succinct.)
Why are these questions important? Lots of reasons, but one that I identify above all: They prevent us from going into autopilot mode.
Autopilot is not a bad thing sometimes. In my line of work, which is often breaking news, going into autopilot means effective reactions tested over time. When something explodes, you need to know what to do — and do it immediately. Get moving. Get the facts. Get the news out.
But autopilot can cripple us, too. It says that “because we’ve always done it this way, we’re doing to do it this way again, and we don’t really have to think about it much.” At its worst, it creates the conditions for one-dimensional, mechanical storytelling that doesn’t stand out.
Enter the Questions Three (no unladen swallows in this exercise).
“What is this story really about” speaks to theme. It frees you to go past the obvious and tell the story you need to tell. For example, a story about a runner’s years-long quest to win the New York Marathon is interesting — but becomes far more compelling if you learn that she has spent most of her life training on an island two miles wide. Or maybe you’re doing a profile of a family-owned chocolate shop and its struggle to stay afloat in its fourth generation of business. That story changes fundamentally when you learn that the great-grandson who now leads the company is diabetic and can’t eat what his business makes. Asking this question and contemplating it gives you an opportunity for elevation that might not reveal itself otherwise.
“How should this story be told” helps subvert what another old editor of mine used to call the “mushy middle” — creeping dullness, in other words. Basically, this is a question that leads you to what comes out the other end. What’s the best way to express the material you have? A Q&A? A series of photos with captions? A short TikTok video? A podcast? A poem, even? While your job, or your platform, obviously may restrict you some — working journalists likely won’t make many editor friends if they file a poem about the planning commission meeting to the desk unannounced — thinking about the story form and doing so consciously is crucial. Don’t just default to your comfort zone when you can deploy something more appropriate (or more interesting!) for the moment at hand.
Finally, that question is inseparable from “What is your audience expecting from this story,” which helps align what you put out with what the people receiving the tale want to take in. Telling a story about the same topic for AARP Magazine and for TikTok can produce remarkably different outcomes with the same subject matter and source material. If you don’t at least think about connecting with your audience, you risk swinging at the ball and whiffing completely. This question is particularly useful when you’re doing multiple stories around a single topic and want to differentiate them. Too often I have seen several stories in a package that look much the same, and it’s hard to understand why I should read or watch all of them. This question points you back to Questions One and Two, where you may make different choices if you’re considering audience effectively.
In short, then, these questions give storytellers more control. They open up the toolbox and show you the tools at your disposal. Whether you choose to use them or not is your business, but knowing what you have access to — what might be done if the possibilities are contemplated — is a fundamental first step to creating stories that echo.
To Ponder
Which of these three questions resonates most with you? Why is that, and what might it say about your approach to storytelling?
Do you think this approach is feasible in your storytelling neck of the woods? If not, what would make it so?
Think of times you’ve asked these questions in the past. What have the results been?
Sometimes in our rush to tell a story we forget to answer those three basic questions and this is a timely reminder Ted
Another question to consider: Who is my audience?