In general, there are two ways to be good at something. You can be born with it (be “a natural”), or you can learn how to get good at it. The mistake I see a lot of people make when they want to get good at something is to find “a natural” and ask them for advice. The problem with that is naturals typically can’t actually tell you how to get good at something if you are not, because by definition, they were never not good at the thing they’re good at.
In that vein, I am not a creative person. I consider myself a pretty solid engineer, manager, and occasional product person, and have generally excelled at tasks that require logic or other structured thinking. Creativity, on the other hand, has always been a struggle for me. I’ve always looked on with admiration (and envy) at friends and colleagues who were naturally creative, but I had been able to get by without being creative.
But as my career has progressed, I’ve found that creativity has become more and more important, especially as I started leading teams. In particular, I needed creativity to solve problems effectively. More complex problems required more creativity.
So here’s my list of how to generate creativity if you’re not a naturally creative person. There’s a common theme, which I’ll get to at the end, but first, let’s talk about the tactics.
- Ask multiple people to solve it independently. You and your team agree that you will go off and independently try to solve the problem, then regroup1. Force people to write down their thoughts. Have two or three people write design docs before you implement a system.
- Ask multiple people to solve it together. You and your team do a “brainstorming session”. Initially, you cast the net wide: any idea is fair game, and no one can shoot down an idea no matter how crazy it sounds. Then you can start to narrow down the space of possible solutions.
- Constrain the problem. How would you solve the problem if you only had one day to solve it? How would you solve it if you wanted to do it without any additional cost or head-count? If you didn’t have to worry about existing product and technical debt?
- Un-constrain the problem. How would you solve the problem if you had effectively endless time, money, and people to throw at it?
- Invert the problem. Supposed You Wanted to Kill a Lot of Pilots. What if you wanted to achieve the opposite of your intended solution? Does that generate a set of solutions to avoid, or a set of solutions that might be adjacent to them? Are your perceived fears not as bad as you thought?
- Change your surroundings. To break out of a mental pattern, sometimes you have to break out of a physical one. Travel can help, but even things like spending time in nature or just in a high-ceiling environment can alter your thinking enough to generate creativity.
- Move. Exercise or walk.
- Sleep on it. Sometimes a problem just needs more time, and often, when you disconnect and stop actively thinking about a problem, you give your subconscious enough room to interject a solution or your conscious enough time to forget whatever parts of the problem are causing a mental block. Take a long shower. Sleep on it.
- Ask people who have solved similar problems. How did they solve them? What other solutions did they consider? What did they learn? Is your circumstance similar to theirs?
- Ask people who have solved un-similar problems. Especially in other domains. Just choose a random person who has solved problems successfully in other domains, give them a little bit of context, and see what they say.
Why they work
Ultimately, creativity involves two competing forces—generating solutions and choosing solutions. System 1 dueling with System 2, or the elephant sparring with the rider, or even just “right-brain” vs “left-brain”. Part of your mind evolved to form abstractions, trying to simplify the world around you to efficiently generate conclusions, while part of your mind evolved to think, ideate, ruminate, and even obsess (it’s what makes us human).
The abstraction-forming part of your brain constantly constrains the world and the set of possible solutions to any problem and tries to minimize your intellectual effort. This can hinder creativity. Solutions are eliminated prematurely, and most of the time, that part of your brain is right. But creativity requires a little delay to that process. Ideas that your brain may not consider at all due to preconceived notions, or ideas that your brain would shoot down right away might require a little nurturing before they’re ready to be sized up.
You can also view this through a probability/statistics lens. For example, having multiple independent brains work on a problem, is, in a sense, increasing variance (since the input variables are more independent), and with creativity, you want more variance. On the other hand, while brainstorming together makes the input variables more dependent, it can also increase variance if it creates room for interactions (often non-linear) between the input variables (ie people building on each others’ ideas).
Do it iteratively
Conventional wisdom is often to do the broad, un-constraining activities first, then work to constrain and limit. I find it’s better to do it iteratively. You can still start with un-constraining activities, but it’s not a funnel, it’s a loop or a ping pong match.
- As an example, my company recently parted ways with a marketing agency because they weren’t delivering results, but we still had to generate marketing phrases for our product. We staged a friendly, inter-company competition. Everyone came up with an idea for a phrase, and we tested them in ads. The best-performing ad variation performed significantly better compared to our ex-agency’s best performing ads.
But you need to be careful with this one. You don’t want a destructive intra-team competitive dynamic about who’s better at coming up with solutions. Your team needs to have a high amount of trust and you need to reinforce that even when brainstorming independently, the goal is to come up with the best solution as a team.
Somehow Manage 