The Secrets to Succeeding in The Windsor-Essex Playwriting Contest

Winners of The Windsor-Essex Playwriting Contest 2018-2024

The Windsor-Essex Playwriting Contest is returning for its eighth consecutive year. Founded in 2018 the contest was created by Windsor-based theatre company Post Productions to serve as a vehicle for finding high-quality scripts by local writers – and as a program to help experienced and novice playwrights receive constructive feedback on their work. Each year the winning script earns a spot in the company’s production schedule in the following year, with its playwright receiving 10% of the production’s gross ticket revenue along with the opportunity to participate in the casting and rehearsal processes. That means, obviously, that in order to win the judges must believe your script will attract audiences and provide a solid basis for a provocative and entertaining experience. But since the contest is also intended to be developmental its other goal is to give playwrights the feedback they need to continue refining their work so they’ll eventually be able to win the contest and hopefully attract the attention of other producers, even outside the Windsor-Essex region.

So let’s say you’re a playwright, maybe you’re working on your first script or maybe you’ve had several scripts produced, and you’re thinking of entering a script into the 2025 Windsor-Essex Playwriting Contest (deadline: 20 April 2025). What can you do to maximize your chances of success? That’s what this article is for. We want everyone to succeed so we’re willing to share some behind-the-scenes secrets to help you hone your submission before you send it in. Here are the ten critical secrets to succeeding in the Windsor-Essex Playwriting Contest…

1. Pay close attention to the eligibility requirements. The judges receive a lot of submissions every year. It takes the judges a minimum of twenty hours to read, discuss, and write constructive criticism for each individual submission. There are only 24-hours in a day. This is why the contest has eligibility requirements – to filter out submissions that couldn’t win the contest or don’t fit the contest’s purposes so judges can focus their attention on scripts that have a chance of winning. So if you’re not a Windsor-Essex resident, or you aren’t originally from Windsor-Essex, don’t submit. This contest is only for people who live in or hail from our region. Yes, we will check. Post Productions only produces plays, so the contest isn’t open to musicals or dramatic monologues or other forms of theatre. That doesn’t mean there’s anything wrong with those forms of theatre – we enjoy them as much as anyone else – just that they aren’t the kinds of scripts the company would produce, so they can’t win the contest. There are also requirements for file format, title page, and several other features that you can find at https://www.postproductionswindsor.ca/play-contest.html. Read them carefully and make sure your submission meets all of the eligibility requirements before you send it off. Occasionally we decide to assess a script that doesn’t meet one of the requirements but we’ve always ended up regretting that. Those are hours of our lives we can’t get back. One year someone submitted a script that wasn’t in the proper format and was too short, but we decided to assess it anyway because it was during the pandemic and our schedules were unexpectedly open. That turned out to be a terrible mistake because there was no way for the script to make it to the second round, much less win. That playwright also openly mocked the contest and the company in the script so in the end we felt like suckers for being generous enough to assess it. Don’t mock the people who are spending hours of their lives carefully reading your work. It’s a bad look.

2. Write characters that come across as individual human beings. The best stories are driven by engaging, complex, unique characters. And characters are supposed to be people (sometimes beings of fantasy, but you know what we mean). People are unique. Each person has their own perspective on the world, shaped by their experiences, beliefs, values, desires, fears, and needs. Each person speaks with their own patterns, the kinds of words they select, the way they construct sentences, the expressions and idioms and metaphors they use to communicate. Each character in your script, whether a principal character or minor character, should come across as a unique individual with their own personality and voice. Someone should be able to read what two characters say and distinguish them without even knowing their names. The more well-crafted and individual your characters are, the better your story will be, and the more judges will enjoy reading the script and audiences will enjoy a production using that script. This means, also, that we shouldn’t know everything about your characters. We should wonder what they’re going to do next, based on what we know about them. We should anticipate the range of choices that are possible for that person, given their personality, without being able to predict what they’ll do with one hundred percent accuracy. This makes characters intriguing. This makes us want to learn what happens next, which keeps us reading.

3. Good stories aren’t things that happen to characters, they’re the result of the choices characters make. One of the most common problems we encounter with scripts submitted to the Windsor-Essex Playwriting Contest is a lack of story. Sometimes there’s no story at all – just a succession of scenes connected only by the fact that they share certain characters. A story is more than one scene followed by another scene followed by another scene. It’s a slice of life set in motion because someone wants something. That desire leads them to make a choice. That choice has consequences, which necessitate more choices. A good story is a series of choices and consequences that occurs in the course of someone trying to satisfy a desire. Sure, some things can happen to those characters, things that are out of their control. But it’s important to remember that even in those cases, even when things happen to a character, those are often the consequences of choices made by other characters – or they’re the consequences of the world in which the characters live, features of the environment, or society, in which they live. And even when those kinds of forces are exerted on your characters what matters are the choices they make as a result. Across every genre, across all of the differences that define all the different kinds of stories told, the sequence of choices and consequences is shared by every story that matters.

4. Without conflict you don’t have a story. All stories involve conflict. If a character desires something then gets it without any difficulty whatsoever, you don’t have a story you have an anecdote. Something has to get in the character’s way, something that prevents them from getting what they want. These are conflicts. Sometimes you can also think of them as obstacles or challenges. Conflicts don’t need to be melodramatic life or death situations, although they can be. Think about the daily conflicts that all of us encounter. Let’s say you want to be a chef. Achieving that goal, satisfying that desire, will involve several challenges – all of which are conflicts. Maybe you have to go to culinary school but you don’t yet meet the entrance requirements. You have to convince the powers that be to admit you to culinary school. Resolving that conflict will involve a lot of choices and a lot of consequences. Let’s say you resolve those and you’re now in culinary school, but you find it difficult to keep up with the workload and you find yourself in competition with many other students who are also promising chefs. How do you get through culinary school? How do you stand out? Those questions point to conflicts that need to be resolved through choices. Once you graduate, you need to build your career which will involve (at minimum) landing a job in your field. Again, there are problems to solve, obstacles to overcome, challenges to endure – all of which are conflicts requiring you to make choices. All of those choices will have consequences that will require you to make other choices. You get the point. Even the most normal everyday stories involve conflict.

5. If the events of your story don’t matter to your characters they won’t matter to your audience. Sometimes we get scripts in which there is a story, but the story doesn’t matter because nothing’s at stake. Without stakes your characters lack motivation. Without stakes you’re going to bore your audience. The stakes don’t have to be high, like apocalyptic matters of cosmic significance. Consider what we said earlier about the person who wanted to be a chef. What’s at stake here is that person’s dream, their goal of becoming a chef. If they don’t care about that then there’s no reasonable motivation for them to make the choices that would drive that story. And that means there would be no reason for the audience to care about what happens to that character because the audience needs to be invested in the character’s struggle to remain engaged in the story from beginning to end. We’re often surprised by how frequently we encounter stories in which there are no stakes. A script might involve a conflict, for example, a situation in which several characters are vying for the same thing that only one of them can have. But none of the characters actually seem to want it. The conflict exists only because the writer put it in the script, so it comes across as inauthentic and dull. The characters need to care about that thing so that they’re motivated to act in ways that lead them into conflict. That means they have stakes in the conflict. That’s what makes the story interesting. Most importantly, that’s what keeps the audience holding their breath and trying to anticipate how the conflict will be resolved.

6. Concepts, ideas, moods, emotions, and illnesses are neither stories nor characters. One year we received three scripts about depression. Depression was either the protagonist (the principal character) or the story itself. Except depression is neither a character nor a story; depending on your perspective it’s a mood, an attitude, or a mental illness. As a result, none of those scripts worked. Now, there are lots of stories about characters who experience depression that work. Their secret is simple: depression is something that happens to a character, something they’re afflicted with, but not a substitute for a personality. This gives you something to work with. Think of it this way: if you removed depression from that character what would remain? What remains is their personality, their individuality, all the characteristics that make them a unique person. In storytelling terms maybe their depression is preventing them from acting on their desires, or it’s leading them to make poor choices. Again, that gives you something to work with. Here’s another example. Every year we receive at least one script about the Seven Deadly Sins. But, like depression, the Seven Deadly Sins are neither characters nor a story. You could certainly have characters that embodied the Seven Deadly Sins – but they would need personalities on top of that, and they would need to make choices to drive a story. Sloth, for instance, is just one trait. A character could exhibit Sloth but they would need to do so in a way that made it part of their overall personality along with all of the other characteristics that constitute a personality. And let’s face it the Seven Deadly Sins are a cliché anyway – so if you’re going to use them do it in a way that’s unique or subversive so you don’t end up repeating what’s been done many many times before.

7. A sermon is not a theme. Many playwrights find theme difficult. Exploring and developing themes well truly is difficult. There’s always the temptation to turn a theme into a lesson or sermon, which is what happens on most sitcoms. But although sermons and lessons can deal with themes, or can express themes, they aren’t in themselves themes. A good theme is subtextual. It’s what your story is about. The story is what happens but the theme is what the story makes us think about. It can be tempting to write a script in order to make a point. If you do that the inevitable result is that the story comes across as inauthentic and the characters become vehicles for a sermon you’re delivering to your audience. Some people like that because decades of sitcoms have conditioned us to shun the deep and challenging thinking that a good theme arouses. That’s not what we’re looking for; Post Productions aims to produce intense plays that cause people to think deeply long after the play is over. Subtly and nuance are necessary, as are ambiguity and ambivalence. The audience should wonder and discuss and debate about what the play is saying, precisely what it’s about. If they’re explicitly told what the theme is, or if the characters in the story are just servicing a lesson, the audiences’ minds will be turned off rather than on. To develop a good theme it’s best to go in without a conscious attempt to make a particular point. Then, once your first draft has been written, let it sit for a while. Then come back to it with a fresh mind, read it, and ask yourself what themes are emerging subtextually from what you’ve written. Your subconscious will have laid the foundations of your theme for you. Ask friends to read your script and ask themselves that question as well. Once you’re able to see the themes that are emerging from your draft you’ll be able to revise and edit the script to bring those themes out with nuance and subtlety. Keep in mind that in most good stories, too, different characters and plot points will address the theme in different ways. If your characters are pointing towards different answers to the same questions you’re on the right track.

8. Read and watch good plays. It’s pretty obvious to the judges when a script is written by someone who doesn’t read or watch plays, because plays are a particular artform with particular conventions and standards. If you’re familiar with the conventions and standards of screenplays, teleplays, novels, short stories, poetry, and similar artforms some of those will be relevant to playscripts as well. And as a rule it’s good to be intimately familiar with various forms of writing. But if you’re writing a playscript for a contest intended for playscripts you really do need to understand how plays work. Watching good plays will help; you’ll become acquainted with the ways in which the story moves through scenes, the challenges of transitioning from one location to another, the time needed for actors to change costumes, and other details that won’t come across if you only watch movies and TV shows. Better yet, make sure you also read good plays. Reading good plays from a diverse range of excellent playwrights will help you understand what’s possible, how playscripts are formatted for readability and practicality, and you’ll probably also find yourself inspired in ways that will help you improve your own scripts. Literacy is essential to writing, and literacy degrades if it isn’t used. All writers, not just playwrights, need to read regularly. Since one of the primary goals of this contest is to find a script that Post Productions can produce as part of its next season, it’s especially important to be familiar with the company’s brand of theatre. The more you know about the kinds of plays Post Productions stages the better you’ll be able to craft something we’ll want to produce.

9. Proofread your work – and get a literate critical friend to proofread it as well. Every script contains some errors and typos. They’re inevitable and inescapable to some extent. All of the judges are writers themselves, so we know full well that even if you write multiple drafts, edit carefully, pass your work through a copy editor and a proofreader, there are still going to be some typos and errors in the final product. But we can tell when a script hasn’t been proofread at all. It shows. It’s obvious. You want to present your work in its best possible form, so edit and proofread it very carefully before you submit. And then get a friend who’s very literate and who knows you well enough to feel safe being critical to proofread your work as well. Maybe offer to buy them dinner in exchange for the favour. You’ll be glad you did. So will the judges.

10. Treat the feedback you receive in the spirit in which it’s given. This advice is for people who are hoping for a career in the arts and/or who plan to submit to the contest again. The basic idea is simple: if you want to be an artist of any kind you have to accept feedback graciously. Critique is an inevitable, even ubiquitous, feature of any artist’s life. Often the feedback an artist receives is minimal and meanspirited, but even in those cases successful artists learn to interpret and use the feedback to improve. But the Windsor-Essex Playwriting Contest is different. The judges read your scripts carefully, paying attention to the forest (the big picture) as well as the trees (the small details). They discuss your script at length with each other. Notes are finessed into feedback that is intended to provide insights from five or six intelligent and experienced people who have taken great care to think through every aspect of what you’ve written. The notes are edited into constructive criticism that identifies what’s working, what isn’t working, and what you could do to refine your work so that you can be successful in the future. Because ultimately our hope is that you will use the feedback to refine your work and you will submit a revision of that script next year, or a new script, that will be better. We want you to win. We want everyone to win eventually. But a lot of playwrights, especially novice playwrights, treat constructive criticism as an attack on their value and talent. The result of treating feedback as an attack is that you become immune to understanding it and therefore incapable of using it effectively. And it can lead you to give up. We don’t want you to give up; we want you to persevere and achieve your potential. So please don’t send us hate mail when you receive your decision letter, which contains several pages of constructive criticism. In fact, 2024 was the first year we didn’t receive any hate mail in response to the decision letters we sent – and, oh, what a lovely experience that was.  

There you have it! Those are the ten secrets to succeeding in the Windsor-Essex Playwriting Contest. If you take them to heart, you’ll be able to improve your craft and submit scripts the judges will enjoy reading, scripts that have a solid chance of making it to the second round of the contest, and maybe even winning. You might also find it helpful to take some of the creative writing and playwriting courses offered at The Shadowbox Theatre as part of the Theatre Skills Education Program, where you’ll receive help from experienced and dedicated teachers in applying these tips and lots more. Courses in the next semester of the Theatre Skills Education Program will be announced shortly. I hope we receive a script from you this year – and every year to come!