Mike Isaac

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Simplify: Square’s Hyper-Focused Hack Week, Where Function Meets Fancy



It’s a Wednesday afternoon before everyone leaves for winter break, and I’m sitting inside a San Francisco tech company office, watching an engineer take sandpaper to a banana.

No, it’s not some fruit-centric start-up. This is Square, the micropayments company aimed at changing the way people make transactions. I’ve stopped by in the middle of the company’s semiannual Hack Week.

For one week during December, employees are given free rein to work on whatever they want, payments-related or not. Some take the time to work on Square-centric ideas that they don’t have time to tackle during their packed work week, when they’re hyperfocused on whatever department they may reside in. Intermingling between the departments is encouraged, so folks who don’t normally work together daily get to meet up and collaborate on a project for the week.

There’s a giant board in the center of the office, smattered with rough sketches of ideas and multicolored Post-It notes. It’s a scattered road map of the product direction the company wants to head over the next year or so (a few top-secret ones were taken down off the wall before I arrived). Each idea was stamped with four or five Post-it notes, with every different color representing a different department member.

Some items are purely creative exercises, stretching the proverbial neural muscles. Founder Jack Dorsey, for example, spent the week attempting to rewrite some of Square’s code base using the French programming language OCaml. (Well, maybe not the whole thing.) Other attempts may end up yielding something tangible: In the past, Hack Week projects like wireless receipt printing and political fundraising have ended up in the Square consumer product itself.

And then some Square people, like Justin Shearer, a very nice engineer I met, decided to work on electronic fruit.

It stemmed (ha!) from chatter around the office when Hack Week began, as folks spouted off about the random ideas they considered tackling for the week. On the whole, Square employees are big fans of Reddit, the massive social link-posting site where memes are born (and where productivity goes to die). The banana phone was a meme that rose to prominence on sites like Reddit, so naturally it came up as a potential Hack Week project. No one took it seriously at first. Except for Shearer.

Square_hack_week_2“Challenge accepted,” as he put it, in familiar meme parlance. It’s actually a cheap, prepaid cellular phone straight from the shelves of a Best Buy, taken apart and rewired to fit inside a fabricated banana. And it really works — Shearer sent me a text from it.

I tell you about all this with some sense of whimsy. But hackathons are commonplace these days in the Valley. Companies sponsor them, often in the days before a big tech conference. Google lets its employees take 20 percent of their time and devote it to other projects not specific to their main jobs. Facebook literally has “hacking” written all over its IPO paperwork.

But Dorsey thinks Square’s Hack Week is special. Google’s 20 percent time is too liberal, which could lend employees to lose focus on their tasks at hand. On the other end of the spectrum, companies like Facebook treat every day like a Hack Week, “moving fast and breaking things” on a regular basis.

“Neither of those models can really create proper cohesion,” Dorsey told me.

Indeed, both Facebook and Google treat hack time antithetically to Square’s company model of hyperfocused, rigorous attention to the process, tweaking and refining ideas and products until they come out just so. Square — and Dorsey, in particular — is known in the Valley for the “devil in the details” philosophy of product design, not to mention clocking crazy long hours at the office to get things right. It’s not for the faint of heart.

Square_hack_weekThe Hack Week, then, is a way of blowing off steam, directing attention away from an employee’s particular area of expertise and freeing his or her mind to play with other ideas. “During Hack Week, we prioritize expediency over quality,” said CTO Bob Lee. “We artificially constrain ourselves to spark innovation. Creativity loves constraints.”

But not too much constraint — nor too little. “It’s tough to find the right time medium to do it in,” Dorsey said, as “one to two days aren’t generally enough to get something finished,” but a constant “hack around the clock” culture like other companies may espouse just doesn’t work for the Square model. A week seems to settle it.

Some teams use the time to create systems that make their daily work lives easier. One fellow, whom I’ll dub the hardware property master, created a rudimentary inventory system to keep track of the myriad Android and iOS devices used to test builds of Square’s software. As you might imagine, phones and tablets often have a hard time finding their way back to the lock-up.

Others find a balance between product relevance and straight-up fun. A group of five assembled a functioning, physical odometer to be hung in the center of the office. It keeps a running tally of Square’s daily GPV — or gross payment value — the total sum of transactions processed by Square every moment.

At the end of the week, everyone comes together at Town Square (the weekly companywide meeting) to vote on the winning prototype. It’s a combination of function and fun, and not always a popularity contest.

I haven’t heard who took home the first place trophy. My bet: There’s always money in the banana phone.

(Take a look at this very funny Hack Week video below, produced by a team of Square employees.)

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