Yes, And: What an Improv Stage Can Teach You About Leading Cross-Cultural Teams in Tokyo | TokyoDev

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Image:<br>Amanda Yanagawa

The Senior Vice President from AXA wanted a demo. Right now, in this meeting room, with little warning.

I was Head of Product at Asken Diet at the time, and this was one of those meetings that gets whispered about in Slack beforehand. AXA was exploring our diet app as an employee health benefit for their workforce.

Landing a partner that size would have been more than a revenue bump: it would have raised the ceiling on what my small company believed it could become. So we had over-prepared the deck and the talking points, even designating who would speak in what order.

What we had not prepared was food.

It was 2017 and we had just shipped photo recognition, built with Sony: point the camera at your plate, the app names the food, and the work of logging a meal drops from a dozen taps to a few effortless seconds. The SVP wanted to see our diet app work, including the newly-released (beta) photo recognition. But no one from my team thought to bring in dishes of real food to demo that function.

I scanned the room and saw the bookshelf. Cookbooks. We were a nutrition company, so naturally someone had filled a shelf with them as decor. I pulled one down, found a glossy full-page shot of a meal, and slid it across the table. “Try it on this,” I said.

That’s how a Senior Vice President ended up taking a photo of a photo of food.

The app completely misidentified the dish.

There is a specific feeling I know well from twenty years of improv comedy: the half second after something goes wrong on stage, when the audience is watching you to see whether this is a disaster or the best part of the show. The answer is almost always up to you.

So, I did what I do every month in front of a paying audience. I accepted the new reality and built on it. I explained, half knowing and half guessing out loud, that the model was reading printing dots and page glare instead of the depth and texture of real food, which is why it does better on an actual plate.

Then I turned the failure into the point. This was the system in its worst case, a photo of a photo, and it still returned a structured guess in seconds.

The rest of the meeting was pivots and reactions—reading his face, adjusting the pitch live, handing moments to the right colleague. It felt less like a business meeting than an improv scene where the stakes were a corporate partnership.

We got the deal.

Walking out of that room, I understood something I had somehow missed for two decades.

I don’t have a day job in tech and an improv hobby. I have one job, managing uncertainty in front of other people, and I happen to do it wearing two different hats.

My 20-year double life

The two hats thing might need some explaining.

I moved to Japan in 2005, a punk music fan from Minnesota who has spent 20 years trying to convince Japanese friends that Minnesota is a real American state worth visiting. (Success rate to date: low.) I landed in Osaka, and that same year I founded an improv group called the Pirates of the Dotombori.

In 2010 I moved to Tokyo and founded the Pirates of Tokyo Bay, an English and Japanese improv comedy group that has performed monthly ever since, currently at What the Dickens! pub in Ebisu. In 2012 the Pirates and I appeared at TED@Tokyo, TED’s talent search event, with a talk called “Why You Won’t Die On Stage.”

I didn’t invent that title as a metaphor. Dying on stage is the fear nearly everyone brings to their first improv class: I’ll freeze, the audience will watch me fail, I will die up there. The talk was about why it never actually happens, and about what performing unscripted comedy in two languages, for audiences that rarely share a first language, teaches you about failure that no book ever managed to teach me.

By day, those same 20 years were spent in the Japanese tech industry. Product at Asken, the diet app. Then conversational commerce at Zeals. Now I’m at Peatix, the event and ticketing platform, where I lead product. My working hours are filled with specs, roadmaps, KPIs, sprint planning, and stakeholder reviews, almost all of it on mixed Japanese and international teams, where the hardest problems are rarely technical.

For a long time I kept the two lives strictly separated, partly out of a vague fear that “improv guy” would undercut “product guy” in a Japanese business context. The AXA meeting collapsed that wall. Since then, I have taught versions of this material on GLOBIS Unlimited, the online arm of Japan’s largest business school, and in corporate workshops for organizations from Google Japan to the US Embassy in Tokyo.

But the honest laboratory is still the monthly show, where I test in real time whether these skills hold up under pressure. They do, and they are trainable.

What follows are the four habits I lean on most as a foreign product manager in Tokyo, each one...