Email Is A Universal Plague; Can Mailbox Make It Manageable Again?

A quarter million desperate email haters have signed up for Mailbox, the email-as-to-do app. CEO Gentry Underwood shares his plans to repair our relationship with the inbox.

"Could we build an inbox that gave people a different relationship with their mail?" asks Orchestra CEO Gentry Underwood, referring to everyone's favorite 2.5-hours-a-day communication timesuck. "Mailbox is the beginning of an attempt to do just that."

Judging by the 250,000 people signed up for the app's launch today, the million that have watched the video below, and the enthused writeups of the beta UI, there's plenty of interest in the Palo Alto startup's effort to tame email.

But as Underwood himself has written, the inbox is unruly. Which is why it takes a mind like Underwood's—equal parts social science and software design—to understand what we're complaining about when we complain about email.

Gentry Underwood

Underwood, 36, has spent most of his life seeking social and technical solutions. After studying symbolic systems at Stanford, Underwood worked as a therapist, pursued a PhD in social change at Vanderbilt, and finally ended up in human factors at Ideo. He was at the design-thinking consultancy from 2006 until 2010. There he helped develop "the Tube," the firm's Yammer-anticipating intranet; that turned into a business unit, helping other companies build collaborative networks. But consulting, Underwood says, is like hitting golf balls at a practice range: you never got to make (or miss) the final putt. Then came a career-altering epiphany.

He and Scott Cannon, then iPad operations team leader at Apple, realized that "people use email as a terrible to-do list." With this insight in mind, they left their respective vaunted companies to cofound Orchestra in January 2011.

Their mission: to make tools that people actually want to use as opposed to tools that people are forced to use. Their problem: Everyone had tasks trapped in their inboxes. Their solution: Orchestra To-Do.

The thought was, "What if we built a to-do list with the communication baked right into it?" Underwood says. "Can we skip that email step and help people send tasks more directly? Then people can free themselves of their inboxes."

Launched in September 2011, their initial bid for inbox freedom set off sparks—Jack Dorsey gave it tweet love, Lifehacker named it the best iPhone to-do app, Apple declared it the productivity app of the year—but then fizzled out.

They had high adoption and low retention, as even the most hardcore of users still had tons of tasks trapped in their inboxes. (Underwood recalls when his wife, excited to win an eBay auction, emailed—rather than Orchestra'd—him the listings). They realized that unless the whole world switched to Orchestra and gave up email, people would still be beholden to their inboxes. The inbox-task problem was still unsolved.

Orchestra would need to pivot from to-do.

Same company, blank slate

"What if we took all the emails you got and dumped them into Orchestra?" Underwood remembers asking. It was the kind of crazy proposal you entertain at the beginning of the design process, trusting that counterintuitive ideas will move from divergence to convergence.

"This seemed like an insane idea, building a to-do list that sucked in every email," Underwood says, "and then we realized what we were really talking about was a rethinking of the email client itself."

If they really wanted to solve the problem of email being a terrible to-do list—and not just create another inbox to manage in addition to the original—Orchestra would have to turn their solution on its head.

"Instead of building a to-do list that worked like email," Underwood says, "we needed to transform your inbox, where all those tasks that are trapped in email live."

So how do you do that? By understanding how people actually use email on their phone—and how to improve it.

Email triage

So you have a few minutes between meetings (or drinks). You pull out your phone to check your email. But what are you actually doing?

Underwood sees the mobile email check as triage—like what a doctor does in an ER. You scan your inbound messages for tasks: What requires immediate attention you act on by sending a reply, what you don't care about you archive or delete, what you want to delegate you forward along, and when you want to defer an item to later—you fumble.

As of now, do-it-later is hacked with "mark as unread" or clicking star, but if too many messages arrive in the interim between phone and desk, the message can get away from you, leaving behind an "Am I missing something?" residue. That unfinished to-do buzzes in the back of your mind, an unclosed loop sucking energy from your task at hand—psychologists call it the Zeigarnik Effect.

Task-time organization is one of those signs of productivity prowess—David Allen's Getting Things Done has a whole analog system for it. But that requires developing a suite of discipline skills. Not everyone has those self-management skills, but Mailbox has been designed to.

Mailbox's "snooze" fills that missing deferential piece, allowing you to outsource task management to your phone in the same way you outsourced navigation to Maps. Those unfinished loops can be handed off, Underwood says, waiting until the appropriate time, and the app starts to feel like a trusted assistant, an extension of yourself.

"That's at the heart of this system," he says, "setting up that relationship."

App relationships, like any other, are hard work

Mailbox is an attempt at creating a "euphoric inbox," Underwood says, and that undertaking presents design and technical challenges.

Most mobile email apps are ports of a desktop experience, Underwood says. In contrast, Mailbox is native to mobile and takes advantage of the inborn gestural system. As well, recognizing that long messages are probably going to happen at a desktop or a laptop, the reply system encourages short messages. As well, the cloud extension of the app checks for messages and scrubs them of anything but the new content, making the message chain much lighter.

What tasks are on schedule for Underwood and Orchestra, aside from probable long nights? Right now monetization looks like it'll be the freemium model—if people love the service enough, they'll pay for parts of it, like Evernote or Dropbox. Underwood says that Mailbox is "very much a minimum viable product" and that there's room to create better tools for collaboration and organization. And the inbox itself can be continually improved, from better filtering for relevant info to automatic archival to fine-tuning notifications.

It's a part of the mission that Orchestra was founded on—to create tools that people wanted to use instead of had to use—and the lesson in relationships that prompted the pivot.

"Rather than trying to ask everyone to use a new system," Underwood says, Mailbox aims to "transform the system that everyone is beholden to."

[Image: Flickr user Bryan Costin]

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