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Brand Storytelling Lessons From a Successful Screenwriting Instructor

smiling woman-paper-covered table
Pilar Alessandra, photographed by Kevin Scanlon

If “content strategy” is one of the most overused and abused phrases in marketing, then “storytelling” can’t be far behind. Trendy brands are jostling to tell brand stories and catchphrase-savvy marketers are adding “storytelling” to their LinkedIn profiles at a breakneck pace.

The big problem is that just because storytelling is becoming more popular doesn’t mean it’s always being done well. In truth, effective storytelling is deceptively difficult, requiring dedication, focus, and ongoing practice (talent plays a bit part, as well).

Few people know more about crafting a successful story than Pilar Alessandra, a popular and respected Hollywood script consultant. She has worked as a script reader and story analyst for top studios, including Amblin Entertainment, DreamWorks, and Robert Zemeckis’ company ImageMovers, and has consulted for The Robert Evans Company, Saturday Night Live Studios, Interscope Communications, and Radar Pictures, among others.

She is also a skilled content creator on her own behalf: Her long-running podcast “On the Page” offers a consistently fresh take on the craft and business of screenwriting, and has catapulted Alessandra to international fame. She now teaches writing workshops all over the globe, guiding aspiring storytellers on the best ways to get ideas out of their heads and onto the page.

I recently caught up with Alessandra to ask her to translate some of her story expertise into a content marketing context. What follows are some of her insights and recommendations on visual content, marketing, and what brands can do to tell better stories.

Buddy Scalera: Tell me a little about who you are and what you do. And don’t hold back. This is a new audience, and I think it’s fair that they know that you’ve got a lot of unique and interesting things in your professional portfolio.

Pilar Alessandra: I’m a screenwriting instructor, the author of the book The Coffee Break Screenwriter, and the proud director of a studio for writers called On the Page. The in-person and online classes at On the Page cover all things script-related, from breaking story to rewriting. As a speaker, I’ve had the honor of traveling the world teaching screenwriting and have done so in places as far away as Vietnam and Poland. I also host the popular “On the Page” podcast which interviews writers, producers, actors, and authors who have something valuable to say about the script-writing process.

Scalera: Let’s start with a pretty basic question that’s probably going to have a somewhat complicated answer. What is “story”?

Alessandra: Believe it or not, I don’t think anyone has ever asked me that before! For me, story is action plus emotion. It’s a series of interesting choices strung together, incited by emotion, or resulting in emotional consequences.

Scalera: We’ve all grown up reading and seeing and hearing stories, so why is it so hard to write a decent story?

Alessandra: It’s just hard to be both inventive with your story beats and artful with your execution. Most writers are good at one, but it takes work to get both (the plot and the craft) working at the same time.

Scalera: I was amazed at how much discipline it takes to write a succinct story that really touches people. In fact, [when I took] your class, I discovered that the “story” I was trying to tell was really just the universe I wanted my characters to exist in. Your class and your podcast made me dig deeper and really find the story. So first, what’s really the difference between a concept and a plot and a story, and how do people find that inner story?

Alessandra: Concept = idea. Plot = the events that express that idea. Story = concept + plot + emotion.

Scalera: In your class and on the podcast, you talk a lot about character development. Again, we all know people. Many of us are actual people. Why is it so difficult for us to nail down characters? 

Alessandra: You bring up two things here: character development and nailing down characters.   One is about change; the other is about voice and personality.

Developing your character means tracking the changes your character goes through as he or she becomes more involved in the story. Remember that your character came into the story with a desire. But that desire was probably altered as your character became attached to other characters, or discovered new information. By the end of the story, your character now desires something else; something bigger or more important than what it was that he or she wanted on page one. That’s character development: paying attention to the changes in your character and demonstrating to the audience when and where those changes occur.

As for “nailing down characters,” it’s funny, but one of the biggest mistake writers seem to make these days is in stealing personalities from movies rather than from real life. I read so many action movies, for example, where the hero sounds like… well… an action star. He delivers cliché lines, makes predictable choices, etc. Even when the writer tries to add some kind of back-story, it’s one we know by heart.

So, the first thing to do is to play against that type. Make the opposite choice. Change the motive. Create a habit we’ve never seen before. Challenge the genre convention.

Scalera: What makes writing for the screen unique and special, perhaps compared to other forms of story?

Alessandra: You have to show it. A book allows you to go inside of the mind of a character and enjoy the inner monologue as he or she makes a choice, weighs the pros and cons, analyzes the moment, and dreads the consequences.

On-screen stories don’t allow for that. Instead, you have to show characters making choices through activity. If they weigh pros and cons, you need to visually bring home what those are. If they dread the consequences, it’s because we’ve witnessed what’s at stake. We aren’t just hearing about it — we’re seeing it and experiencing it for ourselves. 

Scalera: You’ve talked about writing for a visual medium, so you’re often on the topic of the visual action versus the spoken dialogue. So many writers use dialogue to express what the audience can see. I’m framing the question to get to the heart of visual content as a means of storytelling, so let’s start with the basic concept: What’s the best way to write for a visual medium? 

Alessandra: Turn down the sound. Don’t let your characters speak… yet. Now, what pictures do you see that effectively tell your story?

Scalera: Related to this, how do you coach writers to get the most out of the dialogue and the visuals?

Alessandra: I remind screenwriters that they have the benefit of capturing small details and facial expressions. Those small moments of behavior often tell more of the story than the words do. So, writers have to remember to “show” as they “tell.” 

Scalera: Let’s shift gears into an area that is going to be of great interest to my readers: marketing stories.

Storytelling has long been part of advertising and marketing, but the internet has made it possible for marketers to tell much more unique and compelling and interesting stories. Brand marketers want to tell their brand’s story. I wonder if that’s what we should be doing. Should we be telling stories about “The Brand”? Or should we be focusing on what that brand means to the people who might want to buy or use it? You don’t have to agree or disagree with either of those questions, since you’re the expert here. Essentially, I want to know your thoughts on brand storytelling.

Alessandra: Years back there was this wonderful commercial that always made me cry. In it, a grandfather affectionately holds his arms out to his granddaughter. She toddles toward him… then passes right through him. It was an anti-smoking ad. And it made its point by telling the story of a smoker who’d missed out on his life.

To me, that’s when brands make their point best — by telling us stories. Rather than showcase the brand, tell a story about the need for or effect of a brand, and your audience will pay attention.

Scalera: What should content marketers be thinking about as they try to craft that story? What really matters when you’re trying to tell a story that is going to motivate someone to buy or use a brand?

Alessandra: I can’t claim to be an expert on branding; but I do believe that there’s so much power in making an audience feel emotion. Whether they’re genuinely worried for a character or laughing out loud about a choice that’s being made, triggering an emotion is the first step towards connecting your audience with that brand.

Scalera: Websites were once compared to a “choose your own adventure” book because you can pretty much land anywhere in the story and then select where you want to go next. What sorts of things can brand storytellers learn from screenwriters? 

Alessandra: Actually, these days I think that screenwriters can learn a lot from brand storytellers! There’s a desire to connect with audience that’s exciting on the web. Well-crafted online stories start big and get even bigger. Its characters shock a bit more, and its moments push the envelope.

In order to get noticed, you have to do something different. Screenwriters and TV writers need to think this way, as well. What can they show that the audience has never seen before, or can see in an entirely new way?

Scalera: If every asset you create for your brand is part of a complete and holistic story, but everyone jumps on at a unique starting point, how can you grab people so that they want to continue? I mean, this is definitely something that serial storytelling grapples with because people don’t always start with Season 1, Episode 1 and watch loyally through every minute.

Alessandra: I’d look to TV to give this answer. While some of the best TV out there is serialized in its overarching storyline, its character choices are so unique and interesting, that one can jump into an episode and still be caught up.

Scalera: There’s always a certain amount of exposition that writers grapple with. As brand storytellers, what can we learn from screenwriters about incorporating exposition in a compelling way?

Alessandra: Talk around the idea. Force a listener to pay better attention by trying to determine what is being discussed.

In class, I have my students write a scene where they have to convey that two sisters have just left their mother’s funeral. But, the writers aren’t allowed to give the sisters dialogue that uses the words “funeral” “mother” or “death.”

Scalera: Related to this, I know that Hollywood writers are trying to find ways to extend the story across multiple media, including comics, webisodes, second-screen interactions. What kinds of interesting things do you see happening out there that extend the storytelling experience? If you have an example that impressed you, please share it.

Alessandra: Online stories allow a writer to pluck a character out of her big-screen story and focus on her private life. It allows a minor subplot in a TV show to play out as a series of its own.  It encourages docu-style viral videos that make an audience actually think they’re experiencing an event before they see it fictionalized in a movie theater. In this way, the stories keep living and writers increase their opportunities.

I’ve been pleased to see several of my clients, who work so hard as writers, finally get their “big break” when they post online content. Producers want to see that writers can make an immediate connection with an audience. The web is terrific for showcasing those skills.

Scalera: Now, let’s really talk about visual storytelling. I am trying to get to some existential truths about telling a visual story. You spend most of your time talking about the page, which will be translated to the screen, but I know you are an avid viewer, too. What do we see in other humans that makes us keep watching the story?

Alessandra: We see windows into secrets. We’re such detectives when it comes to watching people — especially on-screen characters.

We think, “What did she mean by that?” “Why is he looking that way?” “What are they hiding?”  These visual cues make us want to turn the page or keep watching.

Scalera: How much (and what kind) of storytelling is told through the body language and proximity to other characters?

Alessandra: Think about a “tell” in poker. We look for cues to a player’s cards in his body language or facial expressions.

On screen, we’re looking for the same thing. For writers, then, it’s always good to think about the “tell” of your scene. What visual cue are you providing that tells the audience what’s really going on?

Scalera: Brand marketers are hiring storytellers, including established screenwriters and producers, to tell brand stories. It’s becoming a hot thing to hire storytellers to craft content for YouTube. What should brand marketers know about screenwriters if they are going to bring them into a project? How can we best prepare to have a trained storyteller in the room?

Alessandra: Get a sense of the “big picture” the writer is going for. They may not be showcasing your brand front and center, but they’re conveying the themes and message that you want your brand to represent.

Scalera: How can we incorporate the core concepts of good storytelling into brand storytelling? And by this I mean, can we still tell a story without a three-act structure? Can we do it without conflict and tension? Or — going back to my early realization that I was telling a setup for a story and not an actual story — do we still need to tell a story?

Alessandra: It’s always best to remember that we tend to naturally tell stories with a beginning, middle and end. Conflict arises organically. There’s no need to impose a structure on it that feels false or untrue to your story.

Scalera: We’re nearing the finish line. Where can people find you?

Alessandra: They can listen to the On the Page Podcast on iTunes (we just hit 350 episodes), go to, email me directly at [email protected], or follow me on Twitter @onthepage.

Your unique brand story is one of the five core elements for running successful, scalable content marketing operations. Read our 2016 Content Marketing Framework: 5 Building Blocks for Profitable, Scalable Operations for an overview of the full strategic blueprint.