I often not only think about ideas, but also think about thinking about ideas, especially in a collaborative setting. A lot of what we do is riff on ideas with potential founders and investors, but how do you make the most of it? How do you draw the best ideas out of people? How do you avoid sucking the creative air out of a room?
I was fortunate to chat with my friend and accomplished screenwriter Karen Struck about these questions. Karen was most recently a writer and co-producer on 50 Cent’s For Life, which just aired its first season on ABC, and has worked with some of the biggest names in television, such as David Shore (House, Law & Order) and David Kelley (Boston Legal, Big Little Lies, Monday Mornings).
No stranger to thinking creatively, Karen has reinvented her career three times, from being a nurse, to a risk management consultant, to now being an acclaimed screenwriter. And, as a screenwriter, she has collectively spent years in a writers’ room, planning out a show’s story arc, character development, and plot twists. The writers’ room quite literally runs on ideas, so I thought who better to help me out.
When to think quickly and when to incubate
When it comes to how people generate ideas, Karen puts people in two groups: those who think quickly on the fly and those who need to incubate. “I once worked with a woman we used to call Idea Factory. No matter what the topic was, she could come out with ideas so fast and think on her feet. She didn’t need to do what most writers do, which is called incubation, where you step away from the process.”
She then described what it was like to work with a rockstar incubator. “I worked with another writer who, every day, would go away and come back the next day, saying ‘I thought about what we worked on yesterday and where we got stuck. What if this and this happened…?’ And you’d go, ‘Of course! How could we have spent 6 hours on this idea and never have thought of that?’ That’s what incubation allows.”
In startups and, specifically, in product, I think both modes of thinking are super important. I’ve seen two types of scenarios, often used together, like planning out a new feature, or riffing on improving existing features:
Quick thinkers seed the field, then incubators develop and improve, or
Incubators take time to develop an idea (usually in more detail), then quick thinkers offer ideas to fill gaps or improve
Knowing which scenario to shoot for depends on the topic. I think #1 is most often helpful when starting with something big, like a new business or a new marketing strategy. You want to generate as many ideas as possible (quick thinking) to narrow down to what works or refine (incubating).
I’ve found #2 is most helpful when the bigger idea is settled, but it now needs to be fleshed out and stress-tested. For example, working through the user experience of a specific idea or feature.
Ultimately, though, I think you need both types. A brainstorm of just incubators would be no brainstorm at all and a brainstorm of just quick thinkers may leave ideas on the table by not allowing time and space to ruminate. Fortunately, I think people inherently jump between both modes depending on the topic.
Make it safe to think
Ideas are fragile and a lot of people are pretty vulnerable, too, when throwing out ideas. (This topic is especially, especially near and dear since we started reading this book to our son.) It doesn’t take much to stifle creativity and squash idea generation, which is probably why Karen and Google agree: psychological safety is a big deal.
“For people to really expose themselves and get raw means that it has to be a safe zone,” says Karen. To achieve that safety, there are some ground rules: not (consistently) interrupting, tolerating failure, and being open.
Interrupting is a double-edged sword in that it can stifle sharing and feel disrespectful, but can also build on others’ ideas and lead to better ideas when done well. “If the room functions really well and everybody’s really developed respect, then there is a way you can interrupt because it’s launched somebody into having a good idea. You don’t want them to hold it for fear that they’ll forget it or we’ll spend an hour in the wrong direction without it,” explains Karen. “There’s a proper way to interrupt. Say ‘Wait a minute, we’re kind of just going off that…’ or ‘You said something that was really, really terrific and it propelled me to the next level.’ It makes it very polite.”
But policing interruptions is critical. “It’s really clear when people continuously say, ‘Oh, that just made me think of such and such.’ Someone (typically the executive producers) will take them aside pretty quickly and say, ‘You really need to let people finish and not interrupt.’” We’ve all been in seemingly collaborative settings where you can’t get a complete thought out before someone cuts you off and we’ve all likely been the offender at some point (I know I have).
Confrontation like that can be awkward, but it helps maintain the culture of the group and ensures psychological safety continues.
A huge aspect of safety is feeling safe to look or sound dumb, or to fail. “You have to allow everybody to say ideas that might flop because you never know what idea is going to turn into a fantastic idea,” says Karen. “Writers tend to be very insecure and remember the failures with amazing accuracy. You still hear hugely successful writers talk about their insecurities and how they remember every failure. So it helps if there’s a certain amount of commiserating, like ‘It’s okay, you tried, you came up with something that was better than nothing’ or ‘Everybody has a bad day,” Karen continues.
At a macro level, it’s relatively well known that part of Silicon Valley’s magic is its ability to absorb and celebrate failure. But on a micro level, it can be hard to develop a culture where that ability is reinforced on a daily basis. As Annie Duke wrote about in her book, Thinking in Bets, you don’t want to be guilty of resulting: focusing on the outcome and neglecting the process that produced the outcome.
Riffing, brainstorming, whatever you call it, is the process and it will necessarily involve a lot of failure and a lot of dead end ideas. It’s healthy. If you recognize that, then bouncing back from failure becomes second nature: brush it off — you’re bound to swing and miss every now and then.
Above all, you want to be open and to not become the place where ideas go to die. “Openness is one of the foundations of creativity. Without being open, the process doesn’t flourish,” states Karen. “In rooms where people don’t encourage energy towards at least test driving an idea, imagination is undermined; a writers’ room needs to be the opposite. That usually has to do with someone shooting ideas down too quickly and saying, ‘I don’t like that idea. Move on,’ instead of exploring it. When somebody who stifles the process isn’t in the room, the room functions and feels better.”
How do you encourage the free flow of ideas? “You can respond with, ‘That idea might not work like that, but does anybody have a take that might work?’ or ‘The idea as a whole doesn’t work, but I like this aspect of it…,’” offers Karen. You can often find kernels of a good idea even in a lackluster idea, which then helps others build on top of it.
Grab the crazy stick
When ideas just don’t seem to be working, or when you need to prime the room, sometimes you just have to grab the crazy stick. “Sometimes, it’s just not working. So somebody wants to take an idea and flip it completely and say, ‘Okay, look, let me take the crazy stick and just imagine….’ Sometimes, you land on something that really works. It’s just about giving it a completely fresh slant,” explains Karen.
You know The Crazy Stick™. It sometimes comes up as “this is out of left field, but…” or “go with me for a minute.” It’s a prefix that lets everyone know: don’t rush to judgment — sit back and hear this idea out. It’s something Karen is intimately familiar with.
One of Karen’s favorite episodes she wrote was an episode of ABC’s The Good Doctor which centered on an emotionally tortured pedophile who didn’t act on his impulses because he knew they were wrong. He landed in the hospital after attempting a self-castration. Karen asked, “You think of people in medicine generally being compassionate, but what if the doctors hated the patient? And people think of pedophiles as trying to live close to schools and lying in wait all day, but what if he was a nerdy, very Boy Next Door type? And what if there was a way to make him a sympathetic pedophile?”
Karen then did research to better understand, of all things, pedophiles, so she spent some time lurking in the dark corners of the web where these people tend to congregate. “When I did the research, I learned most pedophiles don’t act on it — they just hate themselves, self-isolate, self-mutilate, and all kinds of other things so they won’t act on it. Very few people act on it. So I said, ‘Alright, let’s talk about a sympathetic pedophile’ and that’s just something you don’t normally think about.”
She knew the idea was working because of the response in the writers’ room. “[An idea that works] generates buzz in the room. If you can deliver, you know that enthusiasm will translate to viewers at home. And it did.” Karen’s episode ended up critically acclaimed, while tackling the show’s “thorniest storytelling challenge,” as Indiewire reported. As Karen says, “I think in television...the best thing a writer [can] hear [is]: ‘I didn’t see that coming.’”
Users are more and more demanding delightful software experiences. As entrepreneurs and builders, we have to balance existing experience and design patterns, while also introducing sheer moments of delight and surprise. Sometimes we just have to grab the crazy stick and go for it.
Huge thanks to Karen for being up to talk to me about all things writers’ room. You can check out her latest show, For Life, on ABC.