When we design things - ask how can this go wrong?

It's not the most robust critique on its own. The question "how can this go wrong" is more of a prompt to generate questions, points of view to wonder about, recall things you meant to come back to but haven't yet.

I like to add this question to all sorts of creative and collaborative settings. In my workshops and talks in recent years I add a section near the later part asking this question.

Here are four general steps to create useful responses to asking "how can this go wrong". Each step has a starter set of questions. Be sure to also generate your own along the way because your questions may lead to more interesting insights for your situation.

1. Ask open questions

Take an open prompt and see what comes to mind.

• The classics to get you started, the open ended list of who, what, when, where, how, and why.
• Even with "How can this go wrong?" you might have hunches and thoughts that come to mind, write those down.

2. Points of view questions

Practice perspective taking, revisiting people you learned about in the process of making this.

• How do you feel about learning from your audience? Did you interview people in the early stages and later stages too? How did it go? What did you learn about them and their situation?
• Have you included who you are making this for enough to learn about them in order to represent them well in decisions when you make this?
• Are there any audiences you'd consider vulnerable to harm by this thing existing? How have you worked to give them more safety?
• Power and exchange of value: who benefits from this thing existing and doing what it was made to do?
• How do you feel about the exchange of value?
• Is this creation something that extracts more than it gives?

3. Stuff you thought of and set aside

Reflecting on how you started with this thing you made:

• Past-you has thoughts for now-you, what do you think past you would notice about this and why?
• What did you set aside to get to this point in your project?
• Does your reason still hold up?
• What did you learn along the way and how did it inform changes in what you made?
• Future you, looking back on this thing you made or were part of making, how do they feel about it?

4. Take the what you gathered and make sense of it.

Any useful stuff emerge from the exercise?

Theme and group the ideas and notes and see what takes shape.

Then ask how can I tell this in a relatable way?

Telling people who do your role, who fund your work, and who are in your audience are three useful groups to write relatable messages about how this could go wrong.

Constructive critical thinking.

What I hope to convey: this is a constructive and caring exercise. You might find mistakes. You might find you're doing work as a way to keep food on the table that is a bridge to other work you will prefer to be part of making. This kind of thinking is far from devil's advocate. I see devil's advocate as a way to convey negativity without perspective taking. Here you're purposefully trying to generate ideas to double check your taking of others points of view.

Thinking about people, including them, caring about not causing harm, that's useful to feed into how you critique what you make. Useful to feed this into future iterations of the work, useful if you teach about it.

How can this go wrong is a way to practice perspective taking and thinking critically about how you can keep improving at what you make.