The making of FiftyThree’s beloved Paper app for the iPhone

By John Paul Titlow

This article originally appeared on Fast Company and is reprinted with permission.

FiftyThree could have launched its new iPhone app three years ago and quickly amassed millions of users. But the New York-based company decided to take the scenic, more thoughtful route. Instead of shrinking down Paper—the sketching app chosen by Apple as its iPad App of the Year in 2012—and cramming it onto the iPhone, they reinvented it entirely. That process, as you might imagine, posed no shortage of challenges amidst what CEO and cofounder Georg Petschnigg says were the “thousands of decisions” that needed to be made. No wonder it took so damn long.Slideshow-322271

“There are super feature-heavy products,” says Petschnigg. “And then there are super-pared-down, simple products. We felt there wasn’t a good balance in between. We wanted something that’s simple, fast, and beautiful.”

Paper’s iPhone app, which finally launched last week, does feature the familiar functionality of its tablet-based predecessor: ultra-smooth digital sketching, painting, and coloring tools packed into a delightful-to-use, thoughtfully designed interface. But it also takes a step back and considers how people prefer to capture ideas using their smartphones, as opposed to tablets. The resulting app combines drawing and diagramming tools with photo capture, and then layers on text entry that dares to rethink how people have worked with words on screens for decades.

If that sounds audacious, it’s worth remembering the company’s roots: Petschnigg and FiftyThree’s three cofounders came from Microsoft, where they worked on products like PowerPoint, Word, and OneNote, and helped reimagine the ubiquitous Office suite of productivity software for tablets. After launching its inaugural iPad app to massive fanfare in 2012, FiftyThree has gone on to ship a stylus (whose name was recently, uh, borrowed by Apple), launch a sketch-sharing community called Mix, and even bridge the analog-digital divide with Book, a print-on-demand Moleskin notebook of your Paper-produced sketches. Along the way, they’ve raised $45.1 million in three rounds of funding from well-known investors.

So wait. With all that tech industry street cred, why not just push an iPhonified version of the Paper app out the door?

“Three years ago, a phone product would have been a small version of Paper,” says Petschnigg. “We ran it. And we were like, ‘That’s cute.’ But it wasn’t the right thing.” Instead, Petschnigg and his team wanted something that considered not just the disparity in screen size, but the wildly different contexts in which people use these devices: Tablets are lean-back-and-relax gadgets that we usually leave at home. Our phones are always with us, always connected. And they’re already being used to take notes and capture ideas—Paper’s iPhone app didn’t want to be a mini-sketching app, but rather what the team likes to refer to as an “idea processor.”

“We realized, whoa, we’re not where people are developing their ideas,” Petschnigg says. “We must figure out how the phone fits into this. How can the phone become a creative tool?”

To do Paper’s mission justice on the iPhone, the team would have to rethink the entire concept, investors and impatient users be damned.

“At that point, we knew we were opening the entire patient again,” says Petschnigg. “That’s uncomfortable because it means the development timeline could be longer. It means there’s a lot of risk that’s being introduced. People can perceive the product very differently. You already knew there were thousands of decisions you had to make. Now there are even more.”

To get a better idea of how people already use their phones to record ideas and other notes, FiftyThree used a platform called Ask Your Target Market to quickly conduct market research into people’s mobile note-taking behaviors by polling thousands of smartphone users. As it turned out, most people record reminders and ideas on their phones using photos and other images. “That’s a huge behavior change,” says Petschnigg, who recalls the days of working closely with the OneNote team at Microsoft, which focused almost entirely on text input.

Armed with this insight, the team decided to make their first major departure from Paper’s beloved tablet interface: Paper for iPhone would bring the camera front and center (literally, it’s right in the middle of the app’s three-option navigation), making it dead simple to take photos, highlight important parts, and annotate them using Paper’s virtual drawing and coloring tools.

Rethinking Text

When we’re not making note of things by snapping photos with our phones, we’re launching an app like Apple’s virtual notepad or Evernote to tap them out the old fashioned way: with words. To account for this, the FiftyThree team decided to incorporate text into its new app in a prominent way. The only question—a huge one—was how. They wanted to let users format text, for instance, without turning Paper into a full-blown word processor littered with buttons and drop-down menus. The coders on the team pushed for Markdown, the text formatting schema popular with many developers and bloggers. But was that too geeky? Designers played with different layout options and type treatments. Paper’s approach to text input and formatting soon became a topic of internal debate.

“My contribution to that was that I kept my mouth shut,” says Petschnigg, who was eager to ship a long-overdue product and placate impatient investors. “Let’s please just get two lines of text in there!”

Finally, a breakthrough happened. Ian Curry, a visual designer at FiftyThree, blurted out: “Why don’t we visually format the text?” After some back and forth, the team settled on what they now call swipe-to-style, a way of formatting text using gestures instead of interface buttons. Over the next 48 hours, a developer coded up a prototype called Text Trial, an internal app that would allow them to test out different methods of formatting text with touch gestures. The possibilities here were practically endless: You could rotate your fingers to change the typeface, swipe this way or that to make text bold, italicized, or underlined.

In the interest of simplicity, the team finally settled on two key gestures: Swipe left to turn a line of text into a bold subheading. Right to turn it into a bulleted list item. Reasoning that the most popular use case for text entry would be the creation of shopping lists and other to-do lists, they chose these two gestures to start with. Users can also hold their finger down on an item to “grab” it and change the order of the list, eliminating the need for traditional (and far more tedious on a touchscreen) copy-and-paste functionality. Other gestural formatting, they figured, could come in time, once people were used to the new gestural formatting paradigm. It is, after all, an admittedly ballsy move to tinker with how people have worked with text since the dawn of personal computing.

“If you know how something works, you need to present something that’s 10 times better because people will be like, ‘Hey, why are you making me learn something new?’” Petschnigg explains. Adding functionality that requires users to relearn behaviors is a tall order, not just because it asks the user to do something new, but because it forces the product to interject new points of friction up front, usually by adding some kind of explanatory onboarding process. User experience designers know that even the most innocuous-seeming extra step can turn off some users, who may close the app and never return. “We decided to take the risk on swipe-to-style,” Petschnigg says.

When Moving Forward Means Axing Features

Porting an app like Paper from tablets to a smaller form factor is as much about axing features as it is about adding them. In this case, the team was forced to reconsider some popular elements of its interface, a bold move when your app has piled up the accolades that Paper has.

On the iPad, Paper relied on the skeuomorphic notebook-style interface, wherein each collection of drawings quite literally resembles a digital Moleskin. But on the iPhone, which is smaller than a standard notebook, this paradigm didn’t make as much sense. Instead, it uses the sticky note for what Petschnigg calls the app’s “spiritual guiding post.” Indeed, using Paper for iPhone feels very much like using some kind of newfangled, digital sticky note with photos and state-of-the-art doodling tools built right in. In the new version of the app, notes are stored in stacks instead of in virtual notebooks. This new interface worked so well on iPhone that they decided to use it on the iPad as well.

“We literally tore up the book,” says Petschnigg. “We just removed one of our signature UI elements.”

While some users will be sad to see the virtual notebook concept get tossed, others will appreciate that its death is simply a casualty of the sometimes messy evolutionary process of product development.

We’re not lean startup people. But we’re also not chubby. We really just want to get it right.

In other cases, the team was forced to ax features before they even saw the light of day. At one point, a multifinger twisting gesture was used to “rewind” to the previous state—a modern, multitouch take on the”undo” button. Clever as this was, it didn’t meet one of the team’s user experience requirements for the smartphone version of Paper: Every key action should be possible with one hand. It’s for this reason that the main navigation controls were moved to the bottom of the interface (the bigger iPhones require too far of a stretch for one’s thumb to reach the top of the screen). On that navigation bar, you’ll notice that one of the buttons features an old-school “rewind” button. That’s the “undo” function that the team had to settle on after scrapping the original gesture. “I’m still sad about the fact that rewind is not in the product as it used to be,” says Petschnigg.

“Sometimes we work on things for two or three months and then we have to throw it away,” says Petschnigg. “And that’s okay. It’s better that we did that because it allowed us to hone in on the other solution.”

How FiftyThree Tests And Prototypes

As you might guess, FiftyThree’s product development process is packed with with extensive sketching, prototyping, and testing. From whiteboards and paper sketches to digital renderings and one-off prototype apps developed in-house (the Text Trial app used to refine Paper’s text formatting features is just one example), no tool is off-limits when it comes to prototyping and mocking things up. At FiftyThree, prototyping is an intensive, cross-discipline process that relies heavily on tools like Interface Builder and Scout, the prototyping engine used by the team’s designers, coders, and product managers.

“You want to use different tools,” says Petschnigg. “You want to talk to many people. That’s why we started this company in New York City. It’s much easier to have a diverse set of customers around you here.”

That diverse, decidedly non-Silicon Valley population came in handy as the product started to get more polished and ready for real-world beta testing. In addition to in-the-flesh app testers, the team relied on a service called UserTesting.com, which automates and distributes the process of conducting usability tests for apps and websites. It was through this process that they learned which details still needed some polish. The instructional onboarding video, added to help users get the hang of Paper’s new text formatting features, was confusing some users because it lacked audio. In trial after trial, beta testers would try to adjust their phone’s volume when the video started playing. So they added some ambient-sounding music to the onboarding videos. A tiny detail, but one that’s very easy to miss without a rigorous testing process.

“We’re not lean startup people,” says Petschnigg. ” But we’re also not chubby. We really just want to get it right.”

[Photos & Illustrations: courtesy of Fifty-Three]

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