Once Upon a Time

Once upon a time, I had a coworker named Bob who, when he needed help, would start the conversation in the middle and work to both ends. My phone would ring, and the first thing I heard was: “Hey, so, we need the spreadsheets on Tuesday so that Information Security can have them back to us in time for the estimates.”

Spreadsheets? Estimates? Bob and I had never discussed either. As I had been “discouraged” from responding with “What the hell are you talking about now?” I spent the next 10 minutes of every Bob call trying to tease out the context of his proclamations.

Clearly, Bob needed help—and not just with spreadsheets.

Then there was Susan. When Susan wanted help, she gave me the entire life story of a project in the most polite, professional language possible. An email from Susan might go like this:

Good morning,

I’m working on the Super Bananas project, which we started three weeks ago and have been slowly working on since. We began with persona writing, then did some scenarios, and discussed a survey.

[Insert two more paragraphs of the history of the project]

I’m hoping—if you have the opportunity (due to your previous experience with [insert four of my last projects in chronological order])—you may be able to share a content-inventory template that would be appropriate for this project. If it isn’t too much trouble, when you get a chance, could you forward me the template at your earliest convenience?

Thank you in advance for your cooperation,


An email that said, “Hey do you have a content-inventory template I could use on the Super Bananas Project?” would have sufficed, but Susan wanted to be professional. She believed that if I had to ask a question, she had failed to communicate properly. And, of course, that failure would weigh heavy on all our heads.

Bob and Susan were as opposite as the tortoise and the hare, but they shared a common problem. Neither could get over the river and through the woods effectively. Specifically, they were both lousy at establishing context and getting to the point.

We all need the help of others to build effective tools and applications. Communication skills are so critical to that endeavor that we’ve seen article after article after article—not to mention books, training classes, and job postings—stressing the importance of communication skills. Without the ability to communicate, we can neither build things right, nor build the right things, for our clients and our users.

Still, context-setting is a tricky skill to learn. Stray too far toward Bob, and no one knows what we’re talking about. Follow Susan’s example, and people get bored and wander off before we get to the point.

Whether we’re asking a colleague for help or nudging an end user to take action, we want them to respond a certain way. And whether we’re writing a radio ad, publishing a blog post, writing an email, or calling a colleague, we have to set the proper level of context to get the result we want.

The most effective technique I’ve found for beginners is a process I call “Once Upon a Time.”

Fairy tales? Seriously?

Fairy tales are one of our oldest forms of folklore, with evidence indicating that they may stretch back to the Roman Empire. The prelude “Once upon a time” dates to 1380 BCE, according to the Oxford English Dictionary. Wikipedia lists over 75 language variations of the stock story opener. It’s safe to say that the vast majority of us, regardless of language or culture, have heard our share of fairy tales, from the 1800s-era Brothers Grimm stories to the 1987 musical Into the Woods.

We know how they go:

Once upon a time, there was a [main character] living in [this situation] who [had this problem]. [Some person] knows of this need and sends the [main character] out to [complete these steps]. They [do things] but it’s really hard because [insert challenges]. They overcome [list of challenges], and everyone lives happily ever after.

Fairy tales are effective oral storytelling techniques precisely because they follow a standard structure that always provides enough context to understand the story. Almost everything we do can be described with this structure.

Once upon a time Anne lacked an ice cream sandwich. This forced her to get off the couch and go to the freezer, where food stayed amazingly cold. She was forced to put her hands in the icy freezer to dig the ice cream sandwich box out of the back. She overcame the cold and was rewarded with a tasty ice cream sandwich! And they all lived happily ever after.

The structure of a fairy tale’s beginning has a lot of similarities to the journalistic Five Ws of basic information gathering: Who? What? When? Where? Why? How?

In our communication construct, we are the main character whose situation and problem need to be succinctly described. We’ve been sent out to do a thing, we’ve hit a challenge, and now we need specific help to overcome the challenge.

How does this help me if I’m a Bob or a Susan?

When Bob wanted to tell his story, he didn’t start with “Once upon a time…” He started halfway through the story. If Bob was Little Red Riding Hood, he would have started by saying, “We need scissors and some rocks.” (Side note: the general lack of knowledge about how surgery works in that particular tale gives me chills.)

When Susan wanted to tell her story, she started before “Once upon a time…” If she was Little Red Riding Hood, she started by telling you how her parents met, how long they dated, and so on, before finally getting around to mentioning that she was trapped in a wolf’s stomach.

When we tell our stories, we have to start at the beginning—not too early, not too late. If we’re Bob, that means making sure we’ve relayed the basic facts: who we are, what our goal is, possibly who sent us, and what our challenge is. If we’re Susan, we need to make sure we limit ourselves to the facts we actually need.

This is where we take the fairy-tale format and put it into the first person. Susan might write:

Once upon a time, the Bananas team asked me to do the content strategy for their project. We made good progress until we had this problem: we don’t have a template for content inventories. Bob suggested I contact you. Do you have a template you can send us?

Bob might say:

Once upon a time, you and I were working on the data mapping of the new Information Security application. Then Information Security asked us to send the mapping to them so they could validate it. This is a problem because we only have until Tuesday to give them the unfinished spreadsheets. Otherwise we’ll hit an even bigger problem: we won’t be able to estimate the project size on Friday without the spreadsheet. Can you help me get the spreadsheet to them on time?

Notice the parallels between the fairy tales and these drafts: we know the main character, their situation, who sent them or triggered their move, and what they need to solve their problem. In Bob’s case, this is much more information than he usually provides. In Susan’s, it’s probably much less. In both cases, we’ve distilled the situation and the request down to the basics. In both cases, the only edit needed is to remove “Once upon a time…” from the first sentence, and it’s ready to go.

But what about…?

Both the Bobs and the Susans I’ve worked with have had questions about this technique, especially since in both cases they thought they were already doing a pretty good job of providing context.

The original Susan had two big concerns that led her to giving out too much information. The first was that she’d sound unprofessional if she didn’t include every last detail and nuance of business etiquette. The second was that if her recipient had questions, they’d consider her amateurish for not providing every bit of information up front.

Susans of the world, let me assure you: clear, concise communication is professional. The message isn’t not to use “please” and “thank you”; it’s that “If it isn’t too much trouble, when you get a chance, could you please consider…” is probably overkill.

Beyond that, no one can anticipate every question another person might have. Clear communication starts a dialogue by covering the basics and inviting questions. It also saves time; you only have to answer the questions your colleague or reader actually have. If you’re not sure whether to keep a piece of information in your story, take it out and see if the tale still makes sense.

Bob was a tougher nut to crack, in part because he frequently didn’t realize he was starting in the middle. Bob was genuinely baffled that colleagues hadn’t read his mind to know what he was talking about. He thought he just needed the answer to one “quick” question. Once he was made aware that he was confusing—and sometimes annoying—coworkers, he could be brought back on track with gentle suggestions. “Okay Bob, let’s start over. Once upon a time you were…?”

Begin at the beginning and stop at the end

Using the age-old format of “Once upon a time…” gives us an incredibly sturdy framework to use for requesting action from people. We provide all of the context they need to understand our request, as well as a clear and concise description of that request.

Clear, concise, contextual communication is professional, efficient, and much less frustrating to everyone involved, so it pays to build good habits, even if the basis of those habits seems a bit corny.

Do you really need to start with “Once upon a time…” to tell a story or communicate a request? Well, it doesn’t hurt. The phrase is really a marker that you’re changing the way you think about your writing, for whom you’re writing it, and what you expect to gain. Soup doesn’t require stones, and business communication doesn’t require “Once upon a time…”

But it does lead to more satisfying endings.

And they all lived happily ever after.

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