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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  • wizardprang

    "and when you want to defer an item to later--you fumble."

    Or, if you use gmail, you boomerang it.

  • John

    Loupugliese - appreciate your eagerness, but I think you are off base.  Despite the myths that some folks are attempting to propagate, technology is not magic.  Real things actually do take time and physical resources.  They have created a product of great demand in a huge marketplace and the must throttle the input in order to deliver acceptable service.  They will get to you.  And if it is worth it you will still be there.

  • Loupugliese

    The roll-out of this is brilliant, however watching a 6 digit countdown for a mailbox reservation is just simply untenable. We live in an instantaneous app and HTML world of immediate gratification.  In my view, unless the mobile email client world is severely broken (and many will correctly argue it is) waiting in line for something that is "better" (an unknown until mailbox proves itself) will drive users to continue to use what's "good enough".  This is a lose lose for everyone.

  • John

    First, agree totally with Leslie.  If all you have with this is gmail you don't have anything of value.  The very first thing it has to do is to look like Outlook in accepting and properly handling main from any possible source.

    Second, it will be great if it works, but I will need to touch it and feel it to see if it really works.  I have found that all of the speculating in the world is meaningless until you touch the product and then you know whether it just works.

    Last, if it works, the next thing would be to feed Facebook into it as if Facebook was just another email feed so that I could sort the 90% junk in Facebook just like I sort the 90% junk in email out of my life.

  • Leslie Pappas

    This looks amazing and very useful.

    Very disappointed there's a line of 400,000 folks waiting for this, and it's not even an app I can use on any service provider other than gmail.  I don't use gmail in my business, I use my business email system run through outlook. It will be a long, time, it seems, until I'll benefit from it.

  • Paul H. Burton

    Outlook User: I agree that Outlook has a lot of features most people don't use. That's the nature of all desktop software. Lots of things do. For example, my Subaru Outback has paddle shifters! It was a "standard feature on my model. That doesn't mean my Subaru is a bad car.

    At it's core, QuietSpacing (my time management method) leverages three of the myriad Outlook functions - Open Next, Move to Folder, Flag for Follow up - to allow users to process and manage e-mail much faster and more effectively than the average user. Thus, my point - it's not the technology that's lacking. It's the lack of training on the use of the tool that's causing the issue.

  • Empowernomics

    Is the solution to change or remove features of 1:1 communication, or is it to enable N:N communication?  

    Sure, email can be improved, but like an improved hammer, you still can't tighten bolts very well with it.  

    Our solution to collaboration doesn't eliminate email, but it puts it in its place.  

  • John Frum

    This is a legacy of people who live their entire lives in front of a computer, tablet, or phone screen. It doesn't occur to them that the entirety of an action item doesn't necessarily consist of sending someone an email, or a reply to an email.

    Personally, I prefer my action items to involve interacting with others in the physical realm as much as possible. But that's just me, I guess.

  • Paul H. Burton

    I applaud Mailboxes effort to reinvent e-mail. However, I am compelled to point out that tools like Outlook - since at least version 2003 - have been loaded with very functional features that allow people to quickly sort and queue e-mail. The issue has been a lack of effort on those of us in the training world to exploit those features, along with a lack of commitment by organizations to fund training their people to be more effective with our existing technology. 

    Fortunately, the bar was raised a few weeks ago with the publication by McKinsey & Co of a report titled "Making Time Management the Organization's Priority." E-mail management is a sub-part of time management which, in turn, is a function of process management. The tool used to conduct this effort - Mailbox or Outlook or whatever - is only as good as the person doing the work. 

    Example: My methodology - QuietSpacing (Amazon) - also uses the term "triage" to describe the need to regularly peruse an Inbox to sort e-mail into four types - Trash, Archive, Reference, and Work. The first three are "closed" items and can be dispensed with using the Delete or Move To Folder function in Outlook. The final type of e-mail - Work - is "open" and needs to be queued using the For Follow-up function in Outlook. What's left in the inbox is a date-sorted list of what needs to be done. 

    In one paragraph, I've just described a simple processing architecture and effectively applied it using an existing tool. Teaching and demonstrating this process takes less than an hour.

    So, again, my point is that we need organizations to stop looking for new technical solutions to our processing problems and start leveraging our existing tools by investing in the people using them.

  • Outlook user

    I disagree.  Outlook is the most cumbersome email client out there, packed with useless features and bloated toolbars full of unused buttons.  While other mail apps make it easy to do what you suggest, Outlook requires a lot of wrangling to make it tolerable.  Like most MS apps, Outlook makes managing my inbox more difficult, not easier.

  • Erik Michielsen

    Thank you for referencing the McKinsey Quarterly article "Making Time Management the Organization's Priority."  It was a great read that included very insightful survey data. Thanks!

  • Bruce InternetSubscriptions

    One of the things I really like about Outlook is adding a reminder to a piece of email.

  • Ed Carp

    The music in the video is just distracting.  Why is it that every tech company just has to hire a marketing company to spend gobs of money to do what winds up looking like an ad for a singer instead of something that will inform the viewer without all the unnecessary bling?

  • Darian Edwards

    Hey Ed, I'm Darian one of the designers at Mailbox. Thanks for the feedback on the video. I'm happy to let you that we didn't hire a marketing company or spend gobs of money we produced this video completely in house and we're actually quite proud of our amateur video. 

  • Janette

    I believe what the ed was trying to say that there is not a lot of discription about what's happening, while the video is conveying. Other then that great piece. We also tried making or own for Freight Dragon. I understand the backlash from critics. Goodluck to you!