When I joined Sesame as founding designer in Oct 2018, we had a big goal — launch our web app in three (3) months. Yep, you read right. About 90 days. No pressure to launch a two-sided healthcare marketplace from scratch that didn't yet exist in Kansas City from New York City.
Simple, right?
I'd just spent 5+ years working at Fjord where user/customer research was more formalized — scheduled interviews, vetted processes, and statements of work (SOWs). At Sesame, we didn't have time for formal anything.
So I proposed that every other Friday afternoon, we'd take three (3) $20 Amazon gift cards and head downstairs to the WeWork common area in Brooklyn Heights. Then, approach random people working on laptops or eating and ask if they had 45 minutes to look at something we were building.
The conversations I remember
There was the guy who clicked through our first set of Figma wireframes and said, "I don't get it. Why can’t I use the map to search?” Okay. Fair.
Or the woman who spent 10 min looking for doctor ratings and reviews. Partly, it ended up being an issue having to do with touch target size, poor color contrast, and buried under too many clicks. We thought it was clear. But it wasn't.
And the programmer who was all in on the Hotel Tonight concept but got confused during the signup flow, asking, "Wait, am I done?"
These weren’t polished research sessions, by no means. We’d scribble out paper sketches. Once, we taped one to each of our phones. We scraped together minimal Figma prototypes. Sometimes, we were talking through ideas with a static PDF.
We structured our work around biweekly sprint cycles, incorporating regular guerrilla interviews and testing (a $20 Amazon gift card bought us 30-45 minutes of goodwill) to quickly validate ideas.
What actually mattered
Our director of product, Priya, and co-founder Mike would join the sessions after the third week. Watching people struggle with the date picker we’d been working on for weeks was painful but got us to fix it. We ripped it apart and rebuilt it from the ground-up. Not because I told them about it later, but because they saw it and heard it themselves.
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The conversations weren't necessarily revealing earth-shattering insights. They were preventing obvious mistakes. The kind of mistakes you make when you assume people think like you do, when you build and test everything inside your office bubble without ever venturing out.
We'd capture what we learned immediately — right after each conversation, writing down what surprised us, what confirmed our thinking, and what we needed to change. Nothing fancy. Just a shared doc that grew to 35 tests by launch.
Looking back
Most teams I work with now have way more resources than we did. Bigger budgets, research teams, proper tools. But they talk to customers less frequently than we did with gift cards and a laptop in a co-working space.
I can't figure out why the barrier still feels so high. We were desperate and had no choice. Maybe that's what it takes — running out of time to do research "properly" so you just start talking to people.
Something else to consider
“There are no facts inside your building, so get outside.”
Blank, creator of the customer development methodology, captured our WeWork approach perfectly. Even if we didn’t realize it at the time.
Our conversations were the literal embodiment of his principle. When you're pressed for time and resources, sometimes the most direct path outside your building is just down the stairwell.
Five conversations a month. Start there. The perfect research plan you never execute isn't better than the imperfect conversations that actually happen.
What's your team's excuse for not talking to customers this week?
I’m sure I’ve heard it before.
Until next time,
Skipper Chong Warson
Making product strategy and design work more human — and impactful
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