Get Better at Creative Self-Evaluation

The most important step is one we often skip

Thirteen years ago, I took a creative methodology class. The teacher — now a friend of mine — broke the creative process down into three simple steps:

1. Plan.

2. Execute.

3. Evaluate.

It’s a system I’ve since enthusiastically adopted in my own life. For any creative project, I’ve found, it works on multiple levels.

On a macro level, planning is when you do all of your research and sketching and ideation, execution is the actual designing and building of the thing, and evaluation is your post-mortem learnings.

On a micro level, every step can be further broken down into sub-steps following the same pattern. Take planning: First, I need to do research on the creative process by googling five different people’s personal processes. Then, I execute on that by searching and taking notes on what I find. Finally, I evaluate what I’ve gathered: Do I have the information I need to move forward? What’s missing? What logical step could come next?

We’ve all grown up planning: making to-do lists, for example, or adding things to our calendars. And we’re all used to executing: Design. Write. Build. Code. Do the work.

But as a general rule, we’re terrible at evaluating. It’s so much easier to move on to the next thing that it is to face that we might be wrong in how we’ve just spent your time.

And the world makes it easy to avoid facing your own work head-on. You give your essays to your teacher to grade. You put your art on the wall for your class to critique. You call our friends to show them what you’re working on to get feedback. You’re set up to let other people do the evaluation for you.

Admittedly, it’s easier to give a project to someone else for their opinion. But in creative work, whether you’re coming up with your next business idea, painting a picture, writing the next Great American Novel, or shooting your film, the process goes faster and the ideas are stronger if you learn to evaluate your work on your own first.

But it’s hard, I know. Self-evaluation is challenging because you’re so close to your work. It’s tricky to separate the inner coach from the player. But I have two strategies to make evaluating your own work easier and less subjective.

The Imaginary Critique

In this method, you walk yourself through the evaluation process by imagining the questions others would have. Answering those questions will inform the next steps you decide to take, and help you plan what you’ll work on the next time you pick up the project. Here’s how to do it:

1. Establish a regular time to critique your work. Maybe it’s every day, or once a week. Maybe it’s the last 10-15 minutes of your work session. (This is the most important step. Make time.)

2. Imagine your audience: Who are you speaking to? Peers? Clients? Partners?

3. On paper, or in a word document, physically write out your defense and your process. What did you work on today, and how did you make it better? What do you still think needs work? What do you still love about the idea? What can you comment on about your process?

4. If you want to take it one step further, imagine you’re speaking to a critic — maybe a demanding former teacher, a relentless colleague, a meticulous client, or a challenging partner. What would they say about the work? What would they pick apart?

Remember, evaluation can be taxing and mentally exhausting. End each session with a moment of gratitude or self-love. What are you proud of accomplishing?

The Great List

This method of evaluation is less about evaluating your own work and more about evaluating what success looks like, so that you can better identify it in your own projects.

1. Choose eight to 10 examples of what you believe are the best pieces of work in the medium of your choice. It could be novels, films, short stories, poems, photographs. (I’ve done it with advertisements, improv scenes, and website bios.)

2. Spend 30 minutes coming up with a list of everything these works have in common. You should aim for about 200 things. If you get stuck, choose two or three works and look for commonalities.

3. “Neighborhood” the list of traits into different categories. For example, “simple,” “easy to understand,” “minimalist,” and “plain” might all go in the same neighborhood. Aim for about eight neighborhoods.

4. Choose one word or phrase to sum up the theme as a title for each neighborhood.

5. Take this one step further and rank the neighborhoods by importance. What does a piece of great work absolutely need to have? And what is common, but not necessary to make it great?

I’ve done The Great List with my students for the last eight years. I’ve done it with improv troupes and workshop attendees. Inevitably, every group comes up with a rough version of the same list. For example, some groups might call one neighborhood “narrative,” while others call it “storytelling” or “relatable.”

I’ve led workshops helping people and teams build their own Great Lists, and I’ve seen the way this list changes conversations. It shifts a subjective argument (“I like this” vs. “Yeah, well I don’t”) into a more objective one. It allows for a more democratic and level evaluation: “I believe all great creative work evokes emotion and I don’t think this is evocative at all. Do you?” And it helps people quickly get better at the step that stumps them the most.

Try it.

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