Try this.

Find a picture of something. It can be anything, though a line drawing might be easiest. Then get a some paper and a pencil. Try copying the picture. Do your best.

Done? Okay. Now, turn the picture upside down. Try copying the picture again.

Compare your drawings. My guess? The second drawing is a lot better than the first one. It might not be perfect, but if you look especially at the areas of detail and complexity, I'm confident the upside-down drawing is more accurate than your first attempt.

This is an exercise from Betty Edwards' classic Drawing on the Right Side of the Brain. Edwards explains that when we flip the picture upside down, our brains process it differently. When we look at the image the right way up, we see don’t interpret it as just contours or lines. Instead, our brains interpret what we see as an eye, or a wheel, or a car. When we try to copy the picture, our brain pushes us to draw those symbols rather than what’s actually in the original. It’s very hard to break out of those patterns.

But, there’s one trick that seems to work. When we flip the image upside down, it disrupts our sense of those symbols. Instead, we focus on the lines themselves. We don't draw a face. We focus on how lines converge and diverge, and draw abstract shapes—what we actually see—instead of gestalt objects.

Familiarity contributes to conventional thinking

I like this exercise because it helps demonstrate the power of de-patterning. Typically, when we encounter a situation or an idea, our impulse is to fit it into an existing category in our mind. We try to make it familiar to us, so that we can more efficiently repsond and react.

In many situations, that's fine. But when we're thinking about complex issues, this kind of thinking is dangerous.

It can lead us to over-emphasize similarities between things, and to not think enough about the differences. This can make us think that we understand the problem, though we may be glossing over critical details that can make our break our decision-making process. We jump to the most available conclusion or solution rather than working to discover the best one.

In organizations, we do this all the time. We often feel a strong pull toward the practices and patterns that are most familiar to us. After all, when something's familiar, it feels comfortable and safe. It's reliable. At least, it can feel that way.

But if we want to create new knowledge and insights, or come up with innovative solutions, we need to break free of comfortable modes of thought. We need to be able to find new vantage point from which we can look at things anew, from a perspective that's uncluttered by our biases and that's more open to possibility, opportunity, and experimentation.

Alien nation

We need to turn our ideas upside down. We need to flip problems, disrupt our assumptions, and overcome our existing paradigms of thought.

In Modernist theater, playwrights like Bertolt Brecht provoked their audiences into reconsidering their interpretation through something called the alienation effect. In Brecht's plays, for example, actors stepped out of character, and set designs exposed the artifice of the stage to remind audiences that they were watching a production. This reminded viewers that they weren't watching real people in real situations. Brecht believed that this forced his audience to think more critically about what they were seeing, on stage and off. It broke their emotional connection to the characters and forced them to think about things in a different way.

When problem-solving, we need to adopt similar tools and techniques. We must resist the temptation to fit problems into familiar categories and treat them as familiar. We need to be able to make our ideas alien to ourselves.

To do that, we need processes and techniques that defamiliarize problems and first look at each situation as a novel set of circumstances.

There are different ways of we can flip the problem space. Here are some possibilities—but there are many more.

  1. Spend more time articulating the problem. Problem solving starts with problem definition. Often, we're so eager to come up with a good solution that we don't spend enough time clearly articulating the problem. In many cases, we unconsciously (or consciously!) imply the solution with the way we frame the problem. Think of as many ways to articulate your problem to solve as you can.

  2. Zoom out. Move to a higher level of abstraction. Use the "five whys" technique to expand your problem space before you begin to converge. What is the broader context of your problem space? What would happen if you didn't do anything?

  3. Flip your scripts. Collect a list of your assumptions, and imagine the reverse of each one was true. What opportunities would that create? How would you approach the situation differently?

  4. Try an analogy. Groups solving problems were more likely to come up with a solution when they were asked to consider an analogous situation from outside of their typical domain. Look to adjacent or even distant industries or spaces to broaden your perspective on the opportunities and solutions available to you.

  5. Come up with bad ideas. A lot of them. What is the worst thing you could do? What’s the most ridiculous thing you could do? Then, flip your bad idea around. What is the inverse of your bad idea? It should be a pretty good idea.

  6. Perform a pre-mortem. Imagine you've made your decision. Then, think ahead two years and imagine that it has gone as poorly as you can possibly imagine. Where did you go wrong? Why did it fail?

  7. Ensure that you have a diverse team. This doesn't mean only people who represent a broad range of experiences and backgrounds, but also people who represent diverse ways of thinking. Researchers have found that teams that are cognitively diverse—that is, they represent a variety of perspectives and information processing styles—solved problems more quickly than teams that were not.

  8. Engage in more debate. When brainstorming, teams that discussed and debated their ideas have been found to be more creative and effective than those who were instructed to not critique one another's thinking. Debate and dissent forces us to find ways to better articulate and defend or thoughts, and provide feedback loops that help us to reassess and adapt our view points.

Ultimately, our brains are too powerful to recognize situations in which our conventional thinking is holding us back. These techniques, and others, can force us to think about things in new ways. When we abstract and disarticulate ideas, we make it possible to creatively recombine our insights and create new networks of thought.