How Celebrating Mistakes Leads to Better Performance, in Improv and in Product Management

Jen Liu
Jen Liu
Aug 1, 2018 · 5 min read

Improvisational theatre and product management have well-documented parallels: they both involve thinking on your feet, dealing with heavy uncertainty, and saying “Yes, and…”.

Six months into my PM career, I signed up for an improv class hoping to build these skills. Yes, I walked out feeling more comfortable improvising at work, and I learned an important lesson: celebrating mistakes makes you a better performer.

From Day 1, our instructor, Diana, began training us to be OK with screwing up. To warm up, we played a game called Pass the Clap: each person claps in sync with the person next to them in succession, sending the clap around a circle. Pretty simple— until you speed up and introduce the option to reverse directions. You have to maintain focus after you “pass the clap” in case the clap gets passed back to you.

Pass the Clap is a warm-up game that gets progressively faster and harder to keep up with.

At one point, someone failed to accept the clap back, and Diana threw up her hands, exclaiming wildly, “YEEAAAHHH!! CELEBRATE!!!” The class stared at her in confusion, but then she gestured for us to follow suit, and soon we were all clapping and cheering loudly. This felt silly— Billy just goofed; why are we celebrating?

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Each time someone broke the flow, we followed Diana’s cues and broke out into a raucous cheer. Break the rules of the game? CELEBRATE! Call someone the wrong name? CELEBRATE! Freeze in the middle of a scene? CELEBRATE!

I made my own mistakes — and with each fumble, it became easier to laugh. All my life, I’ve dreaded public speaking. At first, improv scenes were no different — what if I stuttered? What if I couldn’t think of anything funny to say? What if I made a fool of myself? By the third class, these feelings dissipated. I realized there was nothing to be afraid of. Worst case, I’d stutter and everyone would cheer for me.

Without us realizing, Diana had fostered a supportive environment where mistakes were not just okay, they were encouraged. “Mistakes are gifts,” she said. In one scene, a British student pronounced “Segway” as if the “g” were a “j.” Everyone giggled initially, but the scene didn’t stop — in fact it it evolved into a brilliant scene where “Sedgeway” was a hot new beauty product on the market. By getting us in the habit of celebrating mistakes when the stakes were low, Diana made us more comfortable blundering in high-pressure scenarios.

As product managers, we can apply the same strategy with our teams. When my new team kicked off, we filled a basket with embarrassing facts about ourselves and guessed who wrote each one. We got a good laugh with this exercise, as well as a reminder that we’re all human. Shedding a positive light on embarrassing moments from the get-go makes it easier to celebrate mistakes later on.

Why celebrate mistakes in the workplace? Well, everyone makes mistakes, especially if they’re moving fast — and moving fast is paramount in high-growth tech companies. (As Miles Davis said, “If you’re not making a mistake, it’s a mistake.”) If we don’t celebrate or at least acknowledge them, we miss out on the “gifts” — the learnings they bring us. Worse, if we shame each other when we make mistakes, we’ll be afraid to make them in the first place. As a result, we’ll move more slowly or hide mistakes — and related learnings.

“If you’re not making a mistake, it’s a mistake.” — Miles Davis

Celebrating mistakes doesn’t need to take the form of raucous cheering as it does in beginner improv. In the workplace, it can be as simple as acknowledging that you made a mistake. The enduring value, however, lies in reflecting upon and sharing the learnings. Here are some ways we celebrate mistakes at Quizlet:

  • Blameless post-mortems that emphasize process over people when something goes wrong. An engineer once deployed a change that broke the site right before heading out on vacation, and no one was in the office. After that, he compiled and circulated a document breaking down what happened, the “5 whys,” and proposed action items to prevent similar incidents from happening in the future. Now engineers are more cognizant about when they deploy, considering who will be on deck to react first.
  • Sprint retrospectives for reflecting on what could have gone better and designating action items to make that reality. We realized we kept running out of time in our ticket estimation meetings. In our sprint retro, we reflected on estimation meetings that had gone well in the past — they’d gone well because we shared tickets with engineers prior to the meeting. Action item for PMs: Do this every time.
  • Visualization of experiments to improve estimation of Impact vs. Cost. We have a giant poster board with experiments along a 2 x 2 matrix of Impact vs Cost. For every experiment, we place one Post-it on the board at the relative location of the predicted (cost, impact) value and one for the actual result. We use learnings from previous experiments to inform new predictions. Over time, our estimates should get closer.
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Matrix of experiments. Each experiment is represented by two Post-its, one blue (predicted) and one red (actual). Goal: get the orange dotted line between the Post-its to be as short as possible.

It’s not easy to admit to making a mistake, let alone to broadcast it widely. It helps when you’re not the only one making a mistake, and if your team supports you when you do. As PMs, we set the precedent for acknowledging and celebrating mistakes. When we create this culture early on, debacles become much less daunting. And if we document mistakes appropriately, we help not only ourselves but also our future teammates. In addition to teaching them not to make the same mistakes, an archive of mistakes can inspire newcomers to make their own mistakes. Like any cultural norm, celebrating mistakes scales with the organization.

Since taking improv, I’ve felt more comfortable not only making mistakes, but with the idea of making mistakes. With a mindset that mistakes are gifts that merit celebration, I feel empowered to have bolder ideas and execute upon them — because what’s the worst that could happen? Maybe my team won’t be clapping with smiles in a circle around me, but we’ll talk about the learnings and move on, stronger. And making light of the situation makes us all better performers, whether on stage or in the workplace.

Shoutouts: to Theresa and Natalie for introducing fun ways to celebrate mistakes to Quizlet, and to Dean and Ranna for celebrating grammatical mistakes in my original post 😘.

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