Pilar Alessandra is the director of the instructional writing program On The Page,® host of the On the Page Podcast and a highly sought-after speaker and script consultant who’s taught at Disney Animation, DreamWorks, ABC, the AFM and around the world. She is also the author of The Coffee Break Screenwriter and The Coffee Break Screenwriter Breaks the Rules.  Her students and clients are working writers and producers who have written for Homeland, The 100, Dear White People, Grey’s Anatomy, Silicon Valley, The Chi and more. They’ve sold features and pitches to Warner Bros., DreamWorks, Disney and Sony and have won the prestigious Nicholl Fellowship and Austin Screenwriting Competition.

Can you pinpoint the moment when you knew teaching screenwriting was what you wanted to do?

That first writer “lightbulb moment” was enough to make me realize how creative and stimulating teaching can be. There is nothing more rewarding then helping a writer develop their idea into a story and seeing that story grow and nuance until it’s artful and entertaining.

We receive a lot of questions from writers on how to get started and what to prioritize in their writing process, how do they get past the challenges of starting their first script?

I’ve seen so many writers analyze their work, tear it down and assume audiences and the industry will hate it … before ever writing page one. The first step is to commit to your good idea and your unique point of view. It’s good! Write it.

What adjacent disciplines do you believe would help writers the most?

Stand-up comedy for word choice and editing. Improv for spontaneity and imagination. Travel to introduce yourself to characters beyond yourself.

The Coffee Break Screenwriter is fundamentally based on asking the readers questions, to flesh out their story into a full script. Can you walk us through your stream of consciousness and the first 3 questions you ask writers when an idea pops into their head?

What’s the hook?  Where’s the fun? What’s the surprise?

Acts 1 and 3 are usually busy, in the sense that a lot of information simply must be shared with the viewer. Act 2 is more relaxed, and this is where a lot of screenwriters struggle because there are fewer structural guard-rails. What are some good questions to ask for navigating Act 2? What are good prompts to get yourself unstuck?

The best question to ask is “what can I pay off that was already set-up in the first half of the movie.” We get to know characters in the act of doing things in Act 1.  And in Act 2A (first half of act 2), they’re learning as they try out a new experience, figure out who their friends and enemies are, try out new skills and learn the rules of the world. In Act 2B (second half of act 2) all of those things are paid off. Antagonists push back. Skills are tested. Characters help or hinder. Same goes for Act 3. Your solution often lies in what was planted very early on.

Are there any signals that an idea won’t work, at least not in the present form?

Be open to the fact that your movie may actually be better as a television pilot and vice versa. A movie usually commits to a mission or problem that needs to be completed. A TV show is all about world and characters. If you just want to dig into environment and people, think about your idea as a series.

In your latest book, The Coffee Break Screenwriter Breaks the Rules: A Guide for the Rebel Writer, you give writers permission to break just about every screenwriting rule you’ve heard of, with examples of movies and shows that did it successfully. Can you list some examples in practice?  

Too much to list! Just think about your favorite binge-able TV shows or recent Academy Award-nominated movies. Now ask yourself what they would have been like if they’d followed rules like  “no voice-over,” “ no flashback” or “no non-linear writing.”

What piece of craft advice have you changed your opinion about?

I believe there was a time that I fell into age-ist ideas about who should be a lead character. I have definitely changed my mind about that. People over 40 have lived interesting, complicated lives and we need to see more of them on screen. And that’s not just because I’m over 40. Well … maybe a little.

What common piece of craft advice do you consider to actually be counterproductive?

Your character must be likable. Really? How is your character going to have room to learn? How are we supposed to relate to them? And what exactly is “likable?” (Not surprisingly this note is most often given to female characters.)

In some of the online communities, we sometimes see writers express feelings of anxiety or inadequacy. What would be your advice to writers struggling with those feelings?

Why not you?  Why just them? Why only those stories? Why not yours?

Are there any things you’d wish amateurs would stop saying?

“But Tarantino does it!”

Are there any things do you wish professionals would stop saying?

“No period pieces.”

What do you think is good advice to give before the commencement of a first draft?

Don’t over-outline.  Figure out what your tent-pole act markers are and use that as a guide. Put deadlines on the calendar for pages 1-25, 1-50, 1-75 and the full draft and stick to them.  Try spacing these deadlines out every three weeks. You’ll be amazed at how quickly you move through your first draft.

What piece of otherwise good advice do you think is bad to give before the first draft?

“You must research.”  Um … not yet. First, follow your gut. Imagine. Invent. Stretch the story. Then find the research to back up your scenes and make them feel authentic. Googling before you’ve hit page one will only take you down a rabbit hole.

Finally, are there any questions you wish people would ask more?

“What new job can I give this character that we’ve never seen on screen before?”  The world is filled with much more than cops, doctors, and strippers.

Other interview: John Warren On The Process Of Story