Failing fast, getting back to the whiteboard, and starting over

Failing fast, getting back to the whiteboard, and starting over
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Me (left) with my Bootcamp teammates from PRX, The New York Times, and the AP

The McClatchy team’s journey with Matter was quite a bit different from the other partners taking part in the 5-month innovation program that mirrors the one Matter offers to startups. Our team from The Kansas City Star won a company-wide contest to propose a new product idea, then refine it using design thinking, and pitch it at a Demo Day in New York City. We were granted the opportunity to take a leave from our normal day-to-day jobs to focus on this full-time.


The Matter partner program began with a weeklong bootcamp at the Associated Press’ New York City headquarters where we were placed in teams with staff from other partner organizations. It took the form of a design thinking sprint challenging us to develop completely new products that had nothing to do with our own companies. We used guerrilla, out-on-the-street interviews, Lego blocks and a lot of sweat to come up with ideas that stretched our imagination and creativity. These skills became our toolkit as we moved forward.

We embraced and then embodied “the drunken walk of the entrepreneur,” working both on our own and at the monthly Design Reviews held at Matter’s offices during the partner parallel program.

Product #1

After bootcamp, we began using design thinking full-time to refine our prototype, which was a rough outline for a multipurpose app. Absolutely everything was about uncovering desirability. As we interviewed potential users, we gained insights into their behavior that we realize now are even deeper than we thought at the time (primarily that people don’t find devising workarounds on their phone to be inconvenient, as we’d once imagined).

Our product grew and morphed into a consensus-building and scheduling tool. Our intended user was a female millennial who wanted to arrange a social activity with friends. The one that stuck the most from user interviews was Melissa, the prototypal decision-maker in her group. The second was
Molly, the new college grad with big plans and big decisions to make,
but few specifics.

Then we did a design workshop, synthesized a bunch of interviews and worked through some role-play. That was when we realized we were trying to solve a problem that didn’t really exist, and that asking “would you use this?” had been the wrong question. Groups were already successfully using a mixture of screenshots and instant messaging to figure out plans. They didn’t need a new tool. On top of that, we saw our solution was a Swiss Army knife that had been made unnecessarily complicated from all the feedback we tried to integrate. The user was too specific, the product too unspecific. It was time to pivot.

Product #2

We started over. At first I felt ambivalent about having to go back to the drawing board, but ultimately it was energizing. We held a brainstorm to “flare” and “focus” on a new user, an underserved reader who isn’t engaging with traditional newspapers. We decided to focus on the young adult facing a massive number of important real-life decisions as she’s getting started in the whole business of adulting. We conducted dozens and dozens of new empathy interviews to understand her point of view.

Low-resolution prototyping aplenty ensued. We tested concepts from an online video series (working title: “Small Change”), to virtual reality games, to educational materials for the classroom. We even hired actors to stage a personal finance improv theater happy hour at a local bar to create real world scenarios young people could interact with (no joke — that really happened).

But we ultimately found we’d hit a brick wall. We saw that the market was simultaneously both vast and saturated, and that we couldn’t offer anything novel. We learned from speaking to these young adults that they did have access to plenty of helpful financial information, but that they would only ever look it up in a crisis. Our educational tool was redundant.

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At Design Review 2, testing out the concept of “Small Change,” financial planning for millennials

Product #3

That brought us to our next pivot, and back to an iteration on our original idea. The principal thing people had liked about the direction they thought we were going in back then was the “happy hour tab” — the possibility of a mobile solution that focused just on finding happy hours. One of our key insights had been that in making plans with friends, people cobble together their own solutions from Google, Yelp and social media, but those workarounds still don’t help in finding happy hours while they are going on. Most data on happy hour locations was literally six years out of date. So after our dead end with personal finance, that was the light bulb that went off, and we knew we had to be laser-focused.

That led us to Sipsy — a free and accurate happy hour finder based on a frequently refreshed events database we had at the Kansas City Star. We’re currently in alpha, with a working model ready to deploy in the city’s vibrant Crossroads Arts District. We’re also gathering contact info from people who want in once we launch. After we prove the business model in our pilot neighborhood, Sipsy will expand throughout the metro area.

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KCStar’s Jennifer Hack pitching Sipsy at Matter’s Partner Demo Day in NYC


Even though it isn’t part of my daily work, design thinking with Matter gave me a whole new way of thinking about product development. First of all, as Matter’s Managing Partner Corey Ford says, you need to realize going into the process that all your ideas are probably going to be terrible, and that you can’t hold on to them. The concept of failing fast and failing forward was integral, especially with our abandoned young-adult user. We didn’t spend undue time on any single solution, but instead kept things moving, and sometimes even a little crazy. That’s key to not falling in love with a misguided product. Secondly, we realized that if you don’t uncover desirability in your user, you’re likely wasting your time.

Our drunken walk led to a few hangovers along the way, but it was an exciting and liberating experience, one we won’t likely get the chance to repeat in our careers. I know that from now on I’ll be able to incorporate what I learned from design thinking into my daily work, and will be taking a user-first approach to every business problem I’m faced with.