Dead Bear GroupAs the Windsor-Essex Playwriting Contest enters its fifth year, more local writers than ever before have expressed interest in entering their scripts. So, Post Productions thought it might help to round up and summarize advice judges wished they could give writers in previous years. Knowing these secrets might help you make your script a strong contender.

This seems obvious when it’s bluntly stated, but the most fundamental thing judges are looking for in this contest is a story. That’s step one. Step two is that the story needs to be interesting. After all, they’re going to spend hours reading, re-reading, discussing, and writing feedback on your script. Please don’t bore them. Consider this, too: the winning script has to be interesting enough for a team of people to spend hundreds of hours and thousands of dollars working to bring it to life on stage – and for patrons to spend money to see it.


A great story convinces the judges that people will want to invest time and money into staging and experiencing it. What do I mean by a “story”? I mean, really, that there’s at least one character who wants something and tries to get it.

To make that interesting you need other ingredients: characters and obstacles to get in the way, problems to solve, choices to make, consequences of choices made, at least a rudimentary structure (beginning, middle, end), something to motivate your protagonist to get started and keep going. These are just basics, but they matter. Without these there’s no drama, comedy, or interest.

Some people believe characters must be likable. They really don’t. They need to be engaging, flawed, people with opinions and desires and motivations and hopes and dreams. In a nutshell: they need to be people. Your audience doesn’t need to like them, but they should be able to understand and care about what happens to them.

Over the years we’ve found that the problem that most hurts the odds of a script moving on to round 2 is that the characters are cardboard cut-outs with indiscernible personalities, implausibly inconsistent personalities, or no personalities at all. That makes sense, doesn’t it? The characters are the reasons people care about the story. Their choices – and the consequences of those choices – propel the story from start to finish.

Ultimately, a good story and engaging characters are inextricable. You can’t have one without the other. The good news is, if you have one, you’ll probably be able to develop the other.

A problem that nearly all writers face, especially when starting out, is that they imitate the writers they like – or the writers they think they’re supposed to like – so their work sounds and feels like fan fiction. Work at refining your script until it sounds like only you could have written it. Your ideas, your sentences, your insights – the more of you there is in your script the more fresh, original, and interesting it will be to the judges. To get started on this, review your script to identify and replace all cliches. If your script belongs to a standard genre (fantasy, romance, sci fi, horror, etc.) it’s nearly impossible to avoid tropes, because genres are defined by them. Instead, ensure that you’re doing something uniquely you with every trope you use. Your script will be stronger as a result.

Assume the people who read your play (and the audience who will eventually see it) are intelligent people who can grasp and appreciate subtlety, nuance, and subtext. In practice, this means cutting out unnecessary exposition and not belaboring your theme. Actually, when it comes to theme, it’s best if you’re not certain exactly what you’re trying to say, thematically, as long as you aren’t contradicting yourself. A theme that’s too obvious or spelled out without subtlety is usually grating. Let your audience infer it from what happens in the story.

Entries in the Windsor-Essex Playwriting Contest are supposed to be full-length plays, which means around 90-120 minutes when produced. Although it’s true that shorter plays have won in the past, they had to be extremely strong in other respects to make it to the second round of competition. Scripts that aren’t full-length aren’t taken as seriously by the judges as full-length plays for one simple reason: the winning script has to be produced as part of Post Productions’ next season. Tickets to a Post show cost $25; some patrons feel cheated when they’ve paid full price to see what feels like half of a play. That’s it. It’s important for patrons to feel as though they’re getting value for their money.

Once you’ve worked out your story and characters – the most important parts of any script – step back before you submit to make sure you’ve paid attention to smaller details, such as submission requirements. Getting these right shows the judges that you’re an attentive, serious contender who can at bare minimum consider the needs of their audience. Ignoring them can make you seem sloppy, indifferent, even arrogant. That’s definitely not how you want judges to think of you when they’re reading your script.
For example, does your script start with a cover page that includes all the essential information? Are you submitting it as a PDF? Have you numbered your pages? Details like these may seem trivial compared to story and character (they are), yet they affect the readability of your entry… which means they affect how judges feel while reading it.

The winning script will be produced by Post Productions at the Shadowbox Theatre. Ask yourself: could this script be produced at a reasonable budget at this venue? A script that would be expensive to produce is less likely to win. A script that requires an enormous stage, or multiple intricate sets, or state of the art special effects, or live tigers is going to be inappropriate for the venue, expensive, and maybe dangerous (tigers don’t come cheap). So, it’s unlikely to make it to the second round of competition and even less likely to win. For the same reason, it’s a good idea to consider the realities of live theatre. If your script requires sudden changes of location, it will probably have to be produced as a minimalist, black-box show, in which case, detailed descriptions of the set and a long list of props are going to make it a headache to produce. And if your script contains a character who only appears briefly in one scene toward the end, actors won’t want to play that character – unless they can also play other characters. This means they’ll need time to change costumes and the multiple characters they’d be playing probably can’t appear in the same scene. Of course, clever playwrights have worked around these problems for years by making the problems an intentional part of the script (this works particularly well in comedy). That requires a detailed knowledge of theatre. Which brings us to the next point.

The judges can tell when a writer hasn’t read many (or any) plays, and even when someone hasn’t experienced a lot of live theatre as a patron. Developing your abilities as a playwright requires you to become familiar with how plays are written, how they can be staged, how they can look and sound and feel. To grow you need to read plays. Especially good plays. Most especially, maybe: read plays you enjoy. Get recommendations from others. Read plays that get produced a lot. Read plays that win awards. And go experience as much live theatre – in a variety of styles and genres – as you can. Your sense of what works – as well as your imagination of what is possible – will grow accordingly.

The judges spend many, many hours reading, discussing, and writing about plays for this contest – as volunteers. They’re people who love plays. They want your play to be good (it’s a lot more fun to read good plays). But they also get tired and bored and frustrated so, respect the time they’re devoting to your work by showing them a good time. That doesn’t mean taking them out for drinks (well, it shouldn’t). It means submitting the most interesting, original, engrossing script you can write.

If you follow this advice and combine it with the insights in our blog post, “So You’re Writing A Play” ( your script should be a strong contender – strong enough, I hope, to at least make it to the second round. The worst thing that can happen? A team of keen people read your script and give you constructive feedback. Good luck!

The deadline for the 2022 Windsor-Essex Playwriting Contest is March 31st. For full details about this year’s contest:

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