Category Archives: Featured posts

The Most Important Question(s) in Storytelling and the Ensuing Two Questions That Allow You to Answer

Is it okay if I admit that I love today’s post?  Because I do.

Maybe because I’ve been tinkering with it for weeks. 

I write about things that lurk in all corners of the writing room, some hidden and lurking in the darkest corners, others sitting on desk begging for attention. 

Sometimes they’re subtle.  This one is isn’t.

This one is huge. 

It’s straight out of Writing 101, smack from the middle of Square One, and no matter how far down the road we are, a return to this fundamental persective can empower, resurrect or otherwise save a flagging writing dream.

You have to get this stuff down.  

Whether you do it naturally or you have to staple a note to your forehead, if you write stories you must pay attention to what today’s post is sticking squarely in your face.

Let that process begin, or at least reignite, here and now.


In our last post, I introduced (though I certainly didn’t invent) the notion of boiling your story down to a few simple questions that, in essence, define the very things your readers will want to know.

You have to know them first. 

And then you have to get clever, strategic, even postively Machiavvellian, about teasing them along toward that denouement. 

Readers want to be sucked in, manipulated, double-crossed and then brought back home… they want to take a journey with you… and then they want to be paid off with an ending that delivers the goods.

Even if this sounds obvious at first blush…

… it’s always good to look at things from multiple and even simplified perspectives.  This question-posing technique, in particular, can do everything from conquering writer’s block to putting your story over the top in terms of its dramatic potential effectiveness.

And, just as critically, it might rescue you from a mistake you weren’t even aware you were making.

Here’s they type of questions I’m talking about.

Will your hero reach her or his goal? 

Will he get the girl? 

Will she find love afterall?

Will she survive? 

Will he ever walk again?  See again?  Play the piano again?

Will what needs to happen actually happen in time? 

Will romance ensue?  Or will it flame out? 

Will she get from under her father’s thumb? 

Will he live out from under his family’s name?

Will the antagonist do irreparable harm? 

Will the antagonist be brought to justice?

Will the rules of the game change?   

Will the hero get the job? 

Keep the job? 

Succeed at the job? 

Find a way to work around the boss-from-hell? 

To kill the boss from hell?  Or at least, get her fired?

Will a moral line need to be crossed? 

Will she be forgiven? 

Will others understand? 

Will the cost exceed the benefit? 

Will he get away with it?

Will the inner demon be conquered?

Notice these are, for the most part, yes or no questions.

That’s on purpose. 

Because it forces you to keep your focus on the primary storylines – one, maybe two, with one or maybe two sub-plots– rather than wandering around in a narrative daze, trying to write a story that’s all things to all readers. 

Too many questions can turn your story into something bigger.  Unwieldy big.   Boringly, unfocused big.

You want to write a page turner, not a character-drenched biography full of side-trips and backstory.

Asking the right dramatic question is perhaps the most important part of storytelling.  If you’ve not given it much attention, focusing on details, characterization and the wonder of your linguistic gifts, you may just be missing the point.  Which in this case is synonymous with opportunity.

 Also, notice that these questions aren’t focused on theme. 

They are guiding you toward plot, toward exposition.  The idea isn’t to pose a question such as, “Will love conquer all?” — which is purely thematic — but rather, will the specific characters in your story find love, or not?

Theme is what your readers will take away from the reading experience.  These questions aren’t about that, they’re about what you, the writer, will do within your story to lead them toward that experience.

And now, for my favorite moment in this post:

Notice, too, that the genius of this technique…

… isn’t being able to answer these questions, but rather, to simply ask them.  To propose the right questions and get rid of the wrong ones.  To prioritize.

Read those three sentences (such as they are) again.  They’re huge.

To create a story spine, instead of a slice-of-life with too many problems to solve and cul-de-sacs to navigate.

And because all of the answers are probably yes – and if you’ve noticed that with any degree of impatience, then grab on, because you’re about to get the entire point right here…

… they force you to square off with the next two levels of questions, which are equally powerful and astoundingly brief.

Because for every yes answer you must answer the question of how.

How will you make that “yes” answer happen?  Make it fit?

Make it exciting, dramatic? 

Make it pay off?

How will you get there?  That answer defines whether your story will work, or not.

And if the answer to a dramatic question happens to be no, then the next question, instead of how?, becomes why?

Which in either case leads you to the next most important storytelling question of all.

Because without this one, those first level of dramatic questions won’t matter. 

Your job as a storyteller is to make things interesting.  Make them meaningful.  Deep.  Seductive.  Compelling.  Frightening.  Illuminating.  Interesting.  Gripping.  Memorable.  Relevant.  Challenging.  Engaging. 


Asking those first-level dramatic questions doesn’t do that, it merely points you toward a means of doing all that.  It gives you clarity, and from that clarity comes the opportunity to really create something fresh and worthwhile.

It forces you to ask… how?

And your answer to that question is the stuff of stellar storytelling.

Because anybody can write a love story, a mystery, a thriller.  Just completing a manuscript and qualifying for membership within a niche isn’t the point.

Making it sizzle… that’s the point. 

Making it stand out.  Making it work in a way that, even if it’s slightly familiar (and aren’t all mysteries and thrillers and romances slightly familiar to some extent, and isn’t that the point?), satisfies and lingers.

You have to have a killer answer ready every time you ask how.

And for that – to answer the most important questions in storytelling – you need the most powerful question in storytelling.

The two most magical words in all of literary creation:

What if… ?

The moment you think of those two words as a tool – as a means of answering the question of how?” – rather than a cliché, your writing will turn a corner.

Because right here is where even the most skeptical of organic writers and painstakingly anal of story planners arrive at an identical point in the creative journey.

You don’t have to settle

You can dream as big, as outrageously, or as cleverly subtle, as you choose in selecting and crafting answers to the how? question with a series of genius what if…? propositions.

But only if how have the right high level dramatic question at the story level preceding it.

When you can answer all these questions, at all three levels – the basic dramatic questions that define your story… how you’ll get there… and the best what if? questions you can come up to make that journey compelling – you’ll have everything in your tool chest that you need to write the best story you have in you.

Think of your favorite stories… can you state the dramatic questions that reside at the heart of it?  Let’s hear from you on that. 

So many stories… so many questions.


Filed under Featured posts

Shades of Gray: A Somewhat Liberating Spin on Story Structure

If you’ve been challenged by the notion – or if you’re in complete denial – that effective stories can and should be broken down into sequential parts, that each of these parts has a unique contextual mission to fulfill, and that each segment is separated by a critical milestone that must accomplish certain storytelling feats… 

… if this is you, then get ready for some very good news.

Because the storytelling world isn’t really quite as black and white as I’ve made it out to be. 

If you’re a screenwriter, you’re still absolutely stuck with specific targets for the plot points in your stories.  But if you’re a novelist, you will be delighted to hear that what screenwriters must regard as a set of rules really function more like a set of principles where you’re concerned.

These principles are like traffic.  Consistently disregard them and chances are you won’t get a professional chauffer’s license.  But exceeding a few speed limits or cheating a stop sign now and then, that doesn’t mean you’ll end up in jail.  Or dead.  Or become the cause of someone else being dead.

It just means you got away with it.  Which, when it comes to writing fiction, may be perfectly fine.  This doesn’t negate the principle, it just serves your creative needs at the time.

Principles, like a moral code, still require a general sense of discipline and homage.  At least if you want to coexist in the society in which they prosper.

Or with writing, at least if you want to publish your work.

The Case of the Wandering Plot Point

Yesterday I used a five hour airplane ride to read a highly regarded thriller by a writer who lives in a neighboring zip code.  As usual, I found myself deconstructing the story as I went along, making sure the requisite plot points appear within their narrowly-defined range of locale, and that the four sequential parts did their generically-prescribed contextual job.

That’s the downside of studying story structure.  Every novel you read and every movie you see becomes a bit of a clinic.  Last time I just sat back and got lost in a story was when the Swiss Family Robinson was turning a confluence of vines into a foyer.

In my advocacy of story structure I encourage this deconstruction process as a means of understanding what the four parts of a story are intended to do, and how the milestones that separate them are the stuff of dramatic tension, pacing and character arc. 

So there I am, sitting in 24A somewhere between Honolulu and Seattle, waiting for the first plot point to appear where it should.  And waiting.  And waiting.  Past the prescribed 20th percentile.  Past the 25th.  Getting nervous as we zip through the 3oth.

The first plot point in this New York Times bestseller finally showed up on page 118 in a 356 page novel.  Do the math, that’s not supposed to happen.

Got me to thinking.  I need to take my musings on story structure a step further.

A plot point may not be what you think it is.

The definition of a first plot point is a change in the story that defines the hero’s quest and need going forward, and does so in the face of an antagonistic force that the reader suddenly understands to an extent that empathy and emotion are evoked, while creating obstacles to the hero’s quest, and thus creating stakes that depend on the hero’s ability to overcome those obstacles.

A mouthful.  Chew it carefully, because it will nourish your story.  Or kill it if you don’t swallow it all.

Because that is always what a first plot point does.

If you look closely, though, the essence of that definition is the grasping of what the plot point means, rather than what it is. 

Read that again.  It’s subtle, and it’s critical.

A husband suddenly dying of an accident may seem like a plot point, if nothing else than by the sheer magnitude of how it changes the widow’s life.  But, if the story is about how she is supposed to deal with the fact that the husband has left all the insurance money to a heretofore unknown mistress, it is the moment when that fact is revealed that becomes the plot point, rather than the death itself.

As you look for plot points in the work of others, don’t be seduced by magnitude.  Look for the narrative moment at which the story clarifies, when the hero’s quest truly begins an informed forward motion. 

When the story switches from set-up mode into reaction mode.

It’s the stakes that the first plot point creates that counts, not the size of the explosion.

A plot point may not appear precisely where it should.

I’ve said (as has Syd Field) that the first plot point should occur at a point between the 20th and 25th percentile in the story.

If you’ve perceived that to be a rule, that’s good, because it is the optimal range.  But you, the novelist, have the latitude to cheat that on either side, depending on the nature of the preceding set-up sequence (the very definition of Part 1). 

If you delay the first plot point past the 25th percentile, then you’ll need several twists and a deepening of the stakes prior to that point.  Without them the set-up will take too long and you’ll lose the reader.

If you’re Big Bang plot point comes much earlier, then make sure you put another twist – one that deepens the stakes of the story – at about the 25th percentile, making sure that it changes the course of the hero’s quest from what it was.

A plot point may be a sequence of scenes, versus a specific moment.

Sometimes the first plot point isn’t a sudden moment at all.  It can also be the consequence of a sequence of scenes or story points, all condensed around the prescribed vicinity where the plot point should occur.

Sometimes when it’s tough to nail down a plot point in a story we are reading or a movie we are seeing, it’s because several things happen that could be the plot point.  For instance, using the example from above…

The husband is seen cheating.  The husband dies.  The wife is told by the lawyer that the insurance policy doesn’t bear her name.  The mistress shows up at her house demanding the jewelry – including her wedding ring – that the dead husband has just left her in his will.

Obviously, the widow has a new quest and need, and she’s in reaction mode.  A plot point has definitely occurred.

But where?  Which moment defines the point plot? 

A plot point may occur as a sequence of scenes that occur from the 20th to 28th percentile of the story.  Each scene changes the nature of the widow’s quest, spinning the story in a new direction, but only after they’re all on the table do we fully understand what it means.

So which scene is the plot point itself?

Answer: it doesn’t matter.  At least not for the reader when the sequence is regarded as a whole.  The writer knows – my money is on the lawyer’s revelation that the mistress is the beneficiary – but post-execution it is the effect of the scenes, rather than the mission, that counts.

Relax.  Tell your story. 

But do so from within the context of understanding how and where story structure comes into play.  This will keep you safe and keep the story moving forward.

Just like a musician can’t go off riffing a solo until they understand the underlying melody.  Just like an athlete can’t successfully freelance a play until they understand where the rest of the team will be on the field. 

Don’t sweat the percentages.  Sweat the stakes, the dramatic tension and reader empathy.  If you’re simply in the neighborhood, story architecture will protect you.

But if you disregard its principles, be aware that this is a tough neighborhood, indeed.  Once lost, you may never be found.

At least, your story won’t be found in a bookstore, that is.




Filed under Featured posts, Story Structure Series