A book about listening, learning, and leading

Jon Bell

Jul 20, 2018·75 min read

Download an epub version here.

Preface

Five years ago, I published a book of design essays. When I was done, I thought I had nothing else to say. It turns out I was wrong. I kept writing and eventually I had a stack of new things to publish.

While editing, I realised that everything could fit into three topics: Listen, Learn, and Lead. But that was a lousy name for the book, so I went with Reasonable Defaults instead. Naming things is hard!

Now I’m done and I have nothing else to say. Again. For now.

Chapter One: Listen

Table of contents:

• Getting To “It Depends”
• Be Still
• A Better Design Critique
• Ugly Babies
• Some of the Many Times Steve Jobs Fell Short
• Open Letter to People Who Send Feature Requests to Product Team Members
• How to Write Design Documentation
• The New Table Stakes

Getting To “It Depends”

I love learning from people who know they don’t know anything about a topic. Their opinions aren’t sophisticated, but they’re pure. They’re not necessarily right, but they’re great at listening and absorbing new information with an open mind.

I love learning from people who are masters of their field. They have a lot of hard-won experience. Their intuition is pretty solid. And most importantly, they know enough to know they still have a lot to learn. They say things like “it depends” a lot. And that’s the goal. Learning enough to see shades of grey.

It’s that middle space where many of us struggle. It’s really easy to learn a few things, lose our humility, and fall for the illusion that we know more than we do. From that place, it’s almost impossible to listen well. Things seem obvious to us, and we have a difficult time understanding how people might see things any different.

But even then, there are always things we don’t know. When I’m feeling like things are black and white, I try to dive into something I don’t know. I make all my best progress when I have an open mind. Not just as a designer, but as a person.

Be Still

When AirPods were announced, the reaction was immediate and boilerplate: Too expensive. Short battery life. They look stupid. They’re nothing new. Apple has forgotten how to innovate. But the specifics jumped out at me. A lot of people declared on Twitter that they’d fall out of your ears constantly.

So I went to an Apple Store and asked for a demo. I did everything I could to make the AirPods fall out. I jogged in place, I thrashed my head around, and I opened and closed my jaw. They didn’t fall out a single time, which felt like magic since every other pair of headphones do. I had always assumed I have defective ears.

The next time I went on a run, I paid attention to the black wire connecting my standard headphones to my phone. I was constantly looping the wire around my fingers, and being careful that my phone didn’t extend too far away. I hadn’t considered it before, but do you know the single greatest cause for headphones flinging themselves out of your ear?

1. A wire.
2. Connecting your headphones to a heavy weight.
3. Dangling across your arms.
4. While you’re pumping your arms during a run.

Which, of course, wireless headphones avoid altogether. It’s funny how the number one criticism levelled at the AirPods is actually its greatest strength. But you’d have no way of knowing that by looking at an image on Twitter. It’s something you have to actually experience for yourself.

There’s a lesson here. When you’re presented with something new, be still. Slow down. Learn about it. Try it. Form your own opinion. Don’t measure yourself or your design ability by how quickly you can shoot down an idea. Instead, try measuring yourself by how well you give the benefit of the doubt, do original research, and listen.

A Better Design Critique

I believe tech and design culture are in an intensely cynical and self-defeating place. It seems as if we’re celebrating the most mean spirited and shallow critiques and glossing over analysis that encourages us to think deeper. It’s easier to retweet an angry headline to your followers than to spent time really considering the nuances of a topic. And even if you do put in the time to do some research, how are you going to get Twitter famous with slow, considered, nuanced material? Information is speeding up every day, and we’ve got quotas to hit, people!

As I’ve gotten older, I’ve gotten to meet people who are more interested in the nuance. They’re less likely to be on Twitter, and they’re less likely to think things have quick and targeted solutions. They use phrases like “wicked problems,” a term used to define complex issues like climate change or poverty. But that same advanced level of thinking can be used anywhere, from software to governmental policy. And when you do, you realise a few things. Like the fact that your first opinion about a topic is incomplete, and usually wrong.

Think about your field, or your job, or your hometown, or your country. Now think about an article you’ve seen written about it. If you’re like most people, the article probably disappointed you. Sure, it had some commonly understood facts you can find on Wikipedia. And the article probably wasn’t lying outright. But it’s likely it was written without the depth of understanding that you personally have about it. Chances are, it missed the real story in favour of a shallow one.

Years ago, I started writing a series called Design Explosions. It was a new kind of software design critique based on these principles:

1. The team that built this product is full of smart people.
2. There are many things we can’t know without joining the team.
3. You can’t judge and learn at the same time.

Every time I revisit these principles, I believe in them a little more. Especially when I’m upset about something. The product or policy that’s annoying me? It’s easy to assume the people who came up with it are all awful, greedy, and stupid. But what if they’re smart? What if they care as much as I do? What if they’re working as hard as I am? What if there are details I’m not aware of? That requires a new mode of thinking. A better one. And it leads to richer, more full answers. With the right frame, the world becomes slightly more clear.

Instead of assuming I know every tech company’s motivation, I like reminding myself that I’m just guessing from the outside. There are always more details than appeasing Wall Street. Most people don’t know that, meaning they’re stick with a freshman’s understanding of the world. Take it from someone who’s been on the inside and fighting like hell, there’s more to it than “it’s all doomed” or “they must be corrupt.”

And that brings us to judging versus learning. I think the design critique world is under a collective delusion that what the world needs is less common ground and more demonisation. We need to call bullshit more! We need to listen less! That’s what we seem to believe right now, but we have it fully backwards.

A closed question, such as “How could you think these colours are acceptable” will only make people defensive. You won’t learn a thing. But an open question, like “Can you tell me more about your process for picking these colours?” sets judgement aside, which allows you to learn something. We should always be trying to learn things and make things better for people. If you aren’t, I’m not sure design is the right career for you.

Ugly Babies

There we were, a squad of fancy designers dispatched from our proud design firm. We were about to have an introductory dinner with our new clients. Before we ordered drinks, our most important stakeholder told us “Our baby is ugly.”

What a great thing to lead with!

Notice how succinctly he was able to state a universal client truth:

• We are very passionate about this (it’s our baby)
• … but we know it needs work. (it’s ugly)

All product work starts with an ugly baby. Without the belief that changes need to be made and the passion to get it done, there’s no product brief or budget. Ugly Babies are why product designers have jobs! But…

Don’t Insult the Baby

This client did us a big favour. He signalled that he was open to change, but also reminded us to keep it civil. And that’s easy to overlook. Sometimes we’re so focused on explaining how to improve things that we forget that every decision was made by someone who was doing their best. Maybe they’re the client, or your co-worker. They’re often sitting in the room while you call their baby ugly.

I’ve worked with designers who swoop into a new job and lecture everyone about how poorly run the design studio is and how they can do it better. I’ve worked with product managers who introduce themselves by saying all their co-workers are bad at their jobs. I’ve worked with engineers who seem to have two settings: “I agree with this idea“ or “this idea is stupid.”

None of these approaches work. What does work is moving past the ugly baby and into the next stage, where you explain what you’re going to do.

Explain What’s Next

You don’t need to say “This flow is a catastrophe,” you can say “I wonder if we can make successful task completion 50% faster.” You don’t need to say “I can’t believe how dated this looks,” you can say “We were thinking of aligning with Material design and explorations kicked off yesterday.” Don’t bother saying “this is so bad,” just jump straight to the standard and much more engaging “what are the problems we’re trying to solve?”

It makes all the difference.

Study How You Make People Feel

Sometimes hiring managers reach out to me to ask about my experience working with a particular designer. When they do, I don’t remember how quickly they could churn out art boards. Sometimes I don’t have any idea if they use Photoshop or Sketch. Even their talent level is sort of a wash . I know a bunch of “good designers,” so that’s not a very significant metric.

The only thing I consider when I’m asked to give feedback on a designer is “how did they make me feel?” Were they able to disagree without being disagreeable? Were they able to listen? Do they take feedback? Do I like them? If I answer no to any of these questions, they don’t get my reference.

There are a lot of designers in the world. There are a lot of good designers in the world. But I’m only interested in good designers who are kind. How do I find them? I pay attention to how they talk about clients and their ugly babies.

Some of the Many Times Steve Jobs Fell Short

One of the most important lessons in design is that there is no such thing as perfect. There are only tradeoffs, and it’s your job to balance them.

So your phone has a big, beautiful screen? Takes more battery than a small one. The fastest car on the road? No one can afford it. Really tiny file sizes for movies streamed over the internet? Then it won’t be as crisp as one at full resolution. A sweater that keeps you warm outside? It’s probably too hot when you’re riding on a bus with heating. Absolutely everything is a tradeoff.

What sets good designers apart from bad designers isn’t how close they get to perfection. It’s how well they find balance. Early Steve Jobs designs often failed because he picked incorrectly. The story of Steve Jobs is how he learned to hone his approach and eventually find success. But it took decades!

Lisa

The team wanted to have a graphical user interface, accurately believing it to be the future of computing. It cost about $25,000 in 2016 dollars. It failed.

Macintosh

The team wanted a cheaper (and more beautiful) version of the Lisa. They got the price down to around $5700 in 2016 dollars. It did better, and inspired the industry, but it was still too expensive and had reliability issues. It failed.

NeXT

The team wanted to make a high end workstation with cutting edge technology and features. They spent tons of money on the hardware design, the branding, and some truly amazing software. The world wide web was invented on a NeXT machine! Still too niche, still too expensive. It failed.

Bondi Blue iMac

The team wanted to remind the world that Apple still existed and still had the ability to inspire. The result was an inspiring product that was inferior in almost every way (limited software selection, sluggish specs, a mouse people didn’t like, no restart button, and no disk drive, more expensive). This was one of the first times Jobs actually used design successfully. That iconic blue case saved Apple.

G4 Cube

Riding Apple’s resurgence, the team decided to take a standard tower configuration, make it much smaller, prettier, harder to upgrade, and more prone to overheating, and sell it for almost the same price as a real tower. Inspiring to look at, but it failed.

iPod

The team wanted to make the best music player in the world. And they eventually got there. But history has forgotten those first three years. The device was far too expensive, the screens scratched too easily, they only worked on Macs, and the addition of capacitive buttons was usability nightmare. It was a great product in some ways, but it took a while to find mainstream acceptance.

iPod Shuffle

The team wanted the shuffle to be cheap. So they were ok with any tradeoff they needed to get there. So they removed the screen. Later, they even tried making a version that required you to control it with your voice.

Apple TV

The team wanted a drop-dead simple interface, so that’s what they did. The tradeoff was that it couldn’t do much while still being much more expensive than its competitors.

iPhone

After ten years, we understand iPhone was a massive success. But it was rough for those first few years. There were no apps for it at first. It was far more expensive than anything else. It was on a slow wireless standard and had slow software. It could barely make successful phone calls, and it was only on one carrier. It wasn’t even close to perfect, but it did change the world.

Removable Media, Ports, Standards

When the Macbook Air launched, Apple removed the DVD player to save some space and weight. People hated it at first, but over the years no one missed it. The same happened with the headphone jack, USB, MagSafe, Firewire, serial, SCSI, and plenty of other standards. Not to mention the move from OS 9 to OS X, which required a whole new operating system, with completely new apps and drivers. Or the much from PowerPC to Intel chips, another enormous tech migration.

What’s Going On Here?

The designs made by Steve Jobs and Apple are famous for their imperfections. And yet they make some of the best rated, best loved, highest valued designs in the world. How can this be? How can a company seemingly uninterested in perfect continually make things that people love so much? I have a theory.

When you try to make something perfect, you become timid because you can’t bear to fail. But when you understand your job is to try again and again, you do. The more you try, the more you improve. The more you fall short, the further along you get.

What Jobs Thought of The Past

I love this story. The original Macintosh team was in crunch mode back in 1984, trying to ship the first Macintosh, and someone asked Jobs about typewriter-specific documentation. Had he considered making a migration guide for people used to typewriters who wanted to buy a Macintosh? He thought about it and reportedly said something like this:

“People will figure it out. And the others will die off.”

That’s a big part of his design philosophy, and by extension, Apple’s. They always try to make the best thing they can, based on the things they deem most important. But to celebrate the things they want to go do, they’re going to have to be sub-standard at other things. The product may be the most beautiful, but it’ll be the most expensive. The technology may be years ahead, but it’ll only work on Macs, or only on AT&T. The phone may be slimmer than anything else, but you may drop a call if you grip it wrong. Think that’s crazy? Steve has an answer for you.

“You know what? Some mistakes will be made along the way. That’s good. Because at least some decisions are being made. We’ll find the mistakes … and we’ll fix them!”

That’s why he eventually succeeded. He didn’t believe in perfect. He believed in working hard, doing your best, seeing what people thought of the result, and trying again. And again. And again. It’s not easy, but it is simple. Anyone can do it once focus more on iteration than perfection.

Open Letter to People Who Send Feature Requests to Product Team Members

To Whom It May Concern,

Thank you so much for taking the time to write. Everyone wants to feel they’re having an impact, so emails, tweets, private messages, and hallway conversations at conferences remind us that people care about our work. That’s huge.

I’m sorry I can’t say much more than that. I can’t tell you if your feature is in progress, or if we’ve decided never to do it, or if it’s brand new to us and we’re all throwing a party in your honour of your stellar idea. Why? For legal, competitive, and intra-personal reasons. We haven’t come up with any way to signal “thanks!” without breaking our contract or causing trouble.

For example, let’s say I want to do feature X. But my product manager really does not want to do feature X. We’re doing a delicate dance every day where we’re working out the best overall answer as partners. But if you tweet at me and say “do feature X!” and I say “working on it!” or retweet it, or tap the heart icon, I’m doing three things wrong.

First, I may be breaking my NDA. Second, I’m publicly disagreeing with my team. Third, and worst of all, I’m making it seem like I get to make decisions unilaterally. That’s not how software works unless you’re a one person team.

So, again, please keep the feedback coming. Please know that we read all of it, and yes, the feedback often finds its way into our internal discussions. But it’s not really a good idea for us to respond. We’re sorry about the silence.

Sincerely,
Someone on a product team who has signed an NDA

How to Write Design Documentation

What if your team had an actual history book explaining the tradeoffs that led to the feature or product you’re being asked to work on? Imagine if you joined the team working on Powerpoint for Android at Microsoft, and on your first day you were handed a book titled Powerpoint: A Design History.

Typically a book like this is filled with glossy marketing photos that focus on what shipped, which is of limited value. Instead, what if this book described every notable change to the product’s UX over its whole life, with detailed explanations for why each product decision was made? Helpful, right?

So I’ve been working on writing docs just like these for a few years. I call them DHRs, for “Design & History Rationale” documents. Here are some tips our teams found when we adopted them.

Cultivate a neutral tone

It’s important to explain each decision in good faith while explaining why changes were made. Writing “We did this dumb thing because the lead was a jerk, but then he quit and that’s why the product got better” doesn’t help much. On the other hand, “we believed we could get more x if we sacrificed some y. After launch, we decided we had lost too much y, so our follow-up version aimed to address that.” does. The more you can define the tradeoffs, the better people can learn.

Speak in layers

Decisions are multi-layered. There’s no one diagram or chapter that can explain everything. You have to work in layers to isolate each topic from others.

For example, if I was writing the design history of Powerpoint, I’d spend time explaining the evolution of the navigational structure from menus to the ribbon to the simplified ribbon that came when Surface got popular. But the key would be going beyond screenshots and embracing instead the meaty discussion about the pros and the cons of everything that led to it.

With that overview established, you could then turn to more detailed topics. A section on design decisions around animation. Another for presenter mode. Another for composition and editing of content. Eventually you’d have to explain differences with the Mac and how the design direction was reconciled with the Windows, web, or Android versions. It wouldn’t be a quick read, and that’s the point. This stuff is worth documenting clearly and comprehensively.

Explain what happened to understand what might be next

Things that are in the middle of being designed require a format that’s more similar to a diary or a journal. Link to meeting notes, research papers, sketches, images of whiteboards, everything.

Things that recently shipped should start to add more rationale to go alongside the history you’ve already written. Ideally you can hit a point where the documentation is done and packaged up. Then the later versions can simply build on the previous ones, like episodes of a television show.

The more you document your past, the easier it is to make a roadmap for the future. If you know where you’ve come from, and what tradeoffs got you here, it’s easier to know where you want to go next, and how to best proceed.

Invest the time

The companies that document better have better documentation. There are no shortcuts; you simply need to invest time and resources to make it happen. If you don’t, your competition will. I remind myself of this when I’m trying to get motivation to keep my documentation clear and up-to-date!

The New Table Stakes

Software companies often use the phrase “table stakes” to describe something that users expect. For example, you might have heard Microsoft executives say in 2010 “Windows needs an App Store, that’s just table stakes now.”

But if you dial the clock back a year or two, you’d see the same Microsoft leadership explaining why Apple’s App Store was too strictly controlled. This isn’t unique to Microsoft, of course. Apple wrote off the two-button mouse for years, or the importance of gaming, or VR, or a million other things. User expectations have a funny way of inflating over time, and the key is evolving your product offerings to address user needs.

Here are some features I consider to be table stakes as of September 2017. These are not all things that are being actively requested by users. But they are things that make your product, platform, or service compare unfavourably if you don’t include them. I suspect over time these items will become more and more obvious, to the point where it was odd I ever had to write these down.

End-to-end encryption

Some apps have encryption, others don’t. If you’re making a messaging app in 2017 that hackers and governments can spy on, why would someone choose you over your competition?

Identity theft safeguards

We keep seeing data breaches where personal information like social security numbers, credit cards, addresses, phone numbers, and even passwords are all stored together for easy theft. This is bonkers.

There are better, more secure ways to handle data. Your customers won’t ask about this, but they will eagerly join a class action lawsuit against you if their information ends up being stolen.

Polite email notifications

Customers will put up with some emails from your company. And if you work hard, they might even look forward to the emails the way some people look forward to Medium’s Digests.

But most people’s email boxes are completely jammed full and they don’t want more junk. Some companies understand and respect this by using email sparingly and featuring a one-click way to unsubscribe. If a company can’t run their business in 2017 without spamming customers, they won’t be around long.

Respect of platform conventions

Material Design, designed by Google, should be followed on Android. Apple’s design language, designed by Apple, should be followed on iOS. There’s always some wiggle room, but copy/pasting iOS patterns to Android or vice-versa causes all kinds of issues down the line.

A trustworthy app store

There used to be a time where you could install software that could ruin your computer. With the arrival of the App Store, we were able to trust that the software you installed would usually run correctly without malicious side effects. Sometimes bad software gets through, of course. But it’s not nearly as bad as it used to be. This is no longer an optional feature. Good.

No invasive tracking

People understand that apps are going to track user data to help improve their product. And they’ve resigned themselves to the idea that the Googles and Facebooks of the world track them around the web.

But a product that can explain exactly what data it wants access to, and why, and give them easy and transparent ways to disable it, will be in a better position than ones who don’t. There was a time when seatbelts were seen as too expensive. Then companies like Volvo made it a big part of their brand. We’re see the same with companies that don’t track you, and I expect we’ll see even more of it.

Graceful offline mode handling

Your SMS, email, calendar, and phone app don’t fall apart with a series of confused error messages when the internet isn’t available. They just do the best job they can without an internet connection, then they reconnect when they can. Every app should handle the internet this gracefully.

After all, most people don’t experience a fast, cheap, or reliable internet. They experience spotty connections that work for a bit, then lose connection, then come back again, then get slow, then drop out, then back again. “Offline Mode” isn’t binary. It’s an approach to design that means you understand the internet isn’t reliable for anyone, no matter how much money you have.

Low impact data

If your app uses fifty meg of data per day, and your competitor finds a way to provide a similar experience for only one meg, they’ll have the advantage. People expect apps to be careful with their data.

Low impact storage

The same applies to how much space your app uses. If you’re using a gig of space on the phone and your competitor can provide a similar experience at ten meg, you’re the first to get deleted when a user needs more space.

And to be clear: almost everyone needs more space on their phone. It’s more intense in poorer countries, but it’s a nearly universal issue across the world.

Graceful “out of space” handling

People run out of space on their phone all the time. If your app can’t help people in those situations, it will lose to the ones who can. Google brilliantly highlighted this difference between Google Photos and Photos.app in their famous ad campaign. Expect to see more of this sort of messaging.

Actual customer support

Customer support is better and worse than its ever been. There are some pioneers who have built great reputations around their superior customer support, and they’ve been rewarded for it. Good!

On the other hand, most tech companies try to dodge customer support costs entirely. A relationship with a user is a privilege, not a right. If you wish you didn’t have to deal with customer’s requests quickly and fairly, you might soon get your wish. They’ll move to your a competitor who treats them better.

Access to files from anywhere

People expect to be able to have files where they need them, when they want them. This is easy to say, but extremely difficult to actually pull off. Apps need to be able to communicate across different platforms and screen sizes, then store data in the cloud, then synchronise everything correctly without dreaded merge conflicts. It’s devilishly complex to get right, and the people who make it look easy are going to run away with the market.

Simple backup/restore

People don’t like to back up their data, even if they know they should. But when disaster strikes, they want to be able to get the files they lost as simply as possible.

Years of security upgrades

Hackers are constantly finding ways to attack devices. Software updates (For example on iOS and Android) as well as carrier updates are the only way for devices to stay ahead of the curve and keep customers as safe as possible. No one actively asks about this feature in the store, but the lack of it will provide a demonstrably worse experience in the long run.

Leadership people can respect

There are still plenty of people with questionable morals running companies. But the PR damage from being sexist, racist, homophobic, or just plain mean has never been greater. In the modern era, an increasing number of people expect to give their money to people and businesses they can respect. Or at least not actively hate.

Accessibility

Some products and features work well if you have a disability or just prefer a more usable interface. Most don’t. This is no longer a low priority, constantly-delayed feature, because some companies have made it a priority and shown the world how it can be done.

A clear and consistent abuse policy

For many years, there were two beliefs that made abuse on the internet worse. One was the idea that simple is always better, meaning an interface shouldn’t be cluttered with user controls like block, mute, and report.

The other mistaken belief was that you could just throw everyone’s words into a giant pile on the internet and the best, most true, most trustworthy, and most noble content would magically win and rise to the top. Free Speech! This led to a disastrous hands-off policy of hoping everything would get better even as it was proved it there was no limit to how awful people could be to each other on the internet.

People expect companies to notice that abuse and harassment is a real problem. They expect terms of service that are clear and followed consistently. People expect that they have a right to say what they want, but also that they have a right to not be attacked just for existing.

People talk a lot about the future. Are we going to be commuting via self-driving tube shuttles? Are we going to use VR and AR to experience a new layer of reality on top of the one we already know? Are we going to use nanotechnology to wage war and cure diseases? Will we move to a system of wearables and leave our traditional phones at home? I’m not sure.

All that is really fuzzy to me. I don’t know, and I can’t get too excited about trying to predict the specifics of what’s going to happen. But I do know that trust, privacy, and respect are evergreen concepts that mattered one hundred years ago and will still matter in the next one hundred. People aren’t thinking about a specific technology, they’re thinking of completing tasks that matter to them. If they can trust that a tool will complete their task in the right way, respecting them and their privacy, and work in any context, that tool will win.

Conversely, if the tool can’t gain trust then it’ll have a tough time. You might not trust that the app will work right because it’s poorly designed. You might think the views of the CEO are abhorrent, and as a result not trust the company’s whole mission. You might not trust that the company isn’t going to invade (or leak) your personal data. None of these are easy things to paper over or fix.

The future, like the past, will come down to trust. To me, that’s the central goal every tech company needs to work towards. In a world with a lot of options and not a lot of trust, how can you act in a way that makes people want to support you? It’s not just up to engineering, or design, or marketing, or PR. It’s a question of morality and ethics. And that’s not something tech companies have been great at.

Which means there’s an opening. And that’s exciting.

Chapter Two: Learn

Table of contents:

• “I Thought You Were Born With It”
• The Triangle Epiphany
• Jim Morrison vs No Man’s Sky
• The Graph That Changed Me
• First, Best, Free
• “Shipping the Org Chart” and Omelettes
• Deiter Rams Could Not Have Foreseen Dick Pics
• What the Orange Badges Taught Me
• Leaning Out
• Four Tricks
• Seeking vs Flow
• I No Longer Trust Notification Badges
• Some Stories About Designing for Voice
• Robots Are Replacing Designers

“I Thought You Were Born With It”

Imagine a man in the corner of a large design studio, pacing in tight circles, pulling at his sleeves, muttering to himself. “Hi everyone, today we’re going to- no. Damn it. Product design is about tradeoffs, so- fuck. Hi, today I want to talk about design tradeoffs, because without them… gaaaaah. No.”

Another designer approaches and says, “This is good to see, Jon.”

“What, your design lead pacing around and talking like a crazy person?”

“It’s good to see you practice. I thought you were born with it.”

Wow. No. I was absolutely not born with it. And that’s when I realised I need to make this much more clear. If you think some people are naturally good at certain skills, it follows that most people aren’t. And if that’s the case, why bother trying at something? Why not just leave it up to gifted people?

Years ago, I worked at frog design. I tried to keep my head down and do good work. I was intimidated by the other designers, and I was not known for my speaking abilities.

So you can imagine my surprise when I was asked to speak to the entire studio as part of our “Third Thursday” speaker series. Someone else had dropped out and a fellow designer decided I’d be a good replacement. I was hard at work when she wheeled her chair over to mine. I scooted away. She scooted again, and I scooted away again.

“You’re doing Third Thursday,” she informed me.

“What? No thank you,” I deflected.

“You’re doing it,” she said, and wheeled away before I could stop her.

I had a talk lying around. It was a presentation I had used once on university students. I figured I could re-work it for my designer co-workers. Maybe. They were used to seeing really talented designers, but instead they were going to get me. So I set out to make my presentation as good as possible.

For the next 20 days or so I practiced my talk 2 or 3 times a night. I recorded myself on camera and studied the tape to see what parts worked and what parts didn’t. I timed myself again and again to make sure nothing lagged. I poured extra attention on the intro and the conclusion.

Later, Dawn’s husband explained his theory about how much I practice. “You’re terrified it won’t go well,” he said, and he’s right. It’s not because I’m a naturally gifted speaker, or I read an inspiring book about public speaking, or I’m trying to hone my craft. Nope. I’m terrified, so I practice. That pretty much sums it up.

The deadline arrived, as it always does. I was terrified, as I always am. So I did my best. When I was done, the head of the studio barely waited for the crowd to stop clapping before saying, “That was good. That was really good. You should … do that always. I’m serious. Like, you need to submit that to SXSW or something.”

I started working on other talks and I got to experience life of a speaker. Green rooms. A/V checks. Q&A. Hotel and airfare paid for. The speaker’s dinner. People recognising you at the breakfast bar from the day before. And in time, I did end up speaking at SXSW. But it was a slow road. Paved with lots of practice.

And that was right around the time my direct report said he thought I was born with it. I wish I was! When I do well, it’s not because of raw talent, it’s because I’ve practiced more than anyone says you should. Anyone can do that. Some people do, and those are the ones that are mistaken for having natural ability. But anyone can do it.

The Triangle Epiphany

In the thirty years since we’d spoken, he had been to war several times. I squinted and tried to reconcile the enormous man before me — fingers so large he couldn’t use a smartphone! — with the four year old I remembered.

We talked about a lot of things. At one point he said “You’re thinking in a spectrum from left to right. But that’s one-dimensional.” He held his two fingers together in a plane. “But, see, there’s a whole other world over here.” And he rotated his fingers to form a triangle with his thumbs.

That was the triangle epiphany. It’s stuck with me ever since.

I lean on this framing technique all the time when I’m designing. When I’m helping a team to the best of my ability, it’s because I’m facilitating and coordinating and helping reconcile a million different incentives and goals across lots of different people.

My best work, the stuff for the trophy case, never comes down to the pixels. It’s when I’ve been able to see the spectrum of ideas from A to Z, but I’ve somehow been able to turn the entire spectrum of thinking on its side in order to add a third dimension to it.

Jim Morrison vs No Man’s Sky

Jim Morrison wrote a poem that asks “Did you have a good world when you died? Enough to base a movie on?” It’s an exciting premise. Travel to interesting places, meet and fall in love with amazing people, do great things, rack up the life experiences, leave behind a lot of great memories. Enough to base a movie on.

I briefly had a manager that had a similar worldview. He sketched it all out on a whiteboard while I watched silently. “I want to retire in ten years. It takes two years to make anything great. I have five shots left to be great. That’s it.”

I thought about his working style. He was confident and brash, and people found it really hard to work with him. Many people quit because of him, including me. I remember thinking “This is a deeply unhappy man,” and it felt like the reason why might have been scrawled on that whiteboard, a dead-end screenplay masquerading as something more noble.

No Man’s Sky is easy to describe. It’s a video game where you can fly through the galaxy and discover new planets and the lifeforms on them. There’s practically no plot, character development, or conflict. First you’re on a planet. You see things. Then you fly to another planet and see different things. You just keep doing that. It’s more meditation than task completion. It’s more Thoreau than Tolkien. Thoreau wasn’t interested in goals. So you do well in school to get a good job to afford a house to … what? What comes next?

Games like No Man’s Sky put that question front and centre. There’s no princess to save, no dragon to slay, no mid-career slump. You’re on a planet. You’re alone. There’s a strange creature over there. Now what? What can you come up with all by yourself? I’ve learned, slowly and haltingly, and over my entire life, to love that feeling.

One of my favourite essays is called Solitude and Leadership. His points about hoop jumping really resonated with me.

I know what it’s like for you guys now. It’s an endless series of hoops that you have to jump through, starting from way back, maybe as early as junior high school. Classes, standardised tests, extracurriculars in school, extracurriculars outside of school. […] what I saw around me were great kids who had been trained to be world-class hoop jumpers. Any goal you set them, they could achieve. Any test you gave them, they could pass with flying colours. They were, as one of them put it herself, “excellent sheep.” […] What gets you [up the career ladder] is a talent for manoeuvring. Kissing up to the people above you, kicking down to the people below you. […] Being whatever other people want you to be, so that it finally comes to seem that, like the manager of the Central Station, you have nothing inside you at all. Not taking stupid risks like trying to change how things are done or question why they’re done. Just keeping the routine going.

I meet a lot of Jim Morrisons in tech, each trying to make their life a movie. They want to be on the team developing the coolest features, with the smartest people, eating only the best food, drinking the best drinks, and getting the most credit from the widest range of people. Some succeed, but they tend to have a reputation for being hard to work with. I think a lot of it stems from learning how to be a hoop jumper, then running out of hoops.

My career increasingly reminds me of No Man’s Sky. If I look at it one way, it’s all the same thing with slightly different textures or colours. There might be a trillion design projects, but if you squint, they all pretty much work the same. And that can feel stale and stifling if you’re trying to make a highlight reel. But if you’re just trying to learn and stay curious as long as possible, wow, the possibilities can feel vast, confusing, and exciting. Let’s go exploring!

The Graph That Changed Me

I worked at RealNetworks in 2000. At that time, it was a proud internet pioneer. But then the dot-com bust hit, and the company made a lot of user-hostile decisions. And over time people learned not to trust the company anymore.

As employees, we weren’t proud of our business tactics, and we griped about them frequently. The topic came up at company meetings, round table conversations with executives, and through a lot of water cooler conversation over email, during lunch, and across the foosball table.

One day my manager showed me a graph. It was pretty simple: the graph was steady, then it dropped straight down, then after a short period, the line shot straight back up and stayed level again. It looked like a cup, or the Big Dipper.

“That’s what happens when we do the right thing”, he said while pointing at the drop, “and that’s how much money we lose. We tried it just to see how bad it was for our bottom line. And this is what the data tells us.”

“Wow,” I said. My employer clearly had two options: “do the right thing” or “be profitable”. That was the position they had manoeuvred themselves into through a series of bad management decisions.

My manager then said, “More than half the company would have to lose their job in order for us to stop these tactics … so are you volunteering to be one of them?” I learned a lot that day.

Once people become wary of your products or your business ethics, it’s game over. You can’t sustain for long, because you won’t keep your customers much longer. Not to mention your employees.

First, Best, Free

I read an article a while back that talked about three ways for a product to win in a category, especially software: be first, be best, or be free.

For example, there have been smartphones for a long time. You could argue that Blackberry was first successful one, and iOS did it better, and Android did it free. We can debate if iOS is still best, or if Android is really free, but the point still stands: there are multiple ways to set yourself apart.

Most items in the The Internet of Things are currently the “first” category. A lot of early adopters are having trouble getting their smart lights, smart speakers, and smart thermostats to talk nicely to each other, or even work well by themselves. These products are relying on a single marketing point: “now you can do this!” And that’s fine for people who want to help beta test new computing interaction paradigms. They make a reasonable size of the market.

But the fun part for me is when someone makes something that’s actually good, not just novel. The marketing shifts from “hey nerds, are you ready to do something complicated and new?” to “this is useful and you don’t need to be good with technology to make it work.” That’s when I like to get involved. Not only as a designer, but also a consumer. Although sometimes I forget and get involved too early.

Case in point: I recently bought some remote control cars for my son that are powered by your smartphone or tablet. You can even race against a computer opponent that controls the second car via Bluetooth. Sounds fun! Sounds novel! So I bought them.

And they’re ok. But the handling is really bad, and they go really fast. Meaning you spend most of the time unable to control your car and hitting walls at high speed. After the geeky novelty of “cars that can talk to each other in real time” wore off, we asked ourselves if we were having fun. We weren’t. Into a drawer they went, like most firsts.

It’s a good reminder for your own product. History tells us that “first” success is fleeting, but the product perceived to be “best” gets to live on. And there’s hardly ever any overlap between the two. Plan accordingly.

“Shipping the Org Chart” and Omelettes

From Walt Mosberg’s review of the Samsung Galaxy S7:

Out of the box, there are two email apps, two music services, two photo-viewing apps, two messaging apps, and, except on Verizon, two browsers and dueling wireless payment services. (Samsung says Verizon barred including Samsung’s browser and Samsung Pay out of the box.) And Verizon builds in a third messaging app.

The setup process also guided me to using Verizon’s messaging app rather than Samsung’s and a Verizon backup service. It even warned me I might lose important stuff if I didn’t sign up for the Verizon service.

That’s called shipping the org chart. Or in this case, the org chart of three separate companies. It also happens within single companies. Each division pushes for their own goals, meaning the user experience is left to suffer.

Imagine making an omelette where you had to deal with the egg team, the mushroom team, the butter team, and the tomato team, where each had made a team goal of increasing their usage by 20% quarter over quarter.

You’d make a bad omelette, and that’s called shipping the org chart.

What you really need to do is use the correct amount of each team’s output to make the best overall experience, even if it means some teams don’t get to shine quite as bright. That’s good management and should result in good product design. I think all of us in tech can nod our head at this assessment. Yes. Design is good. Experience is important. Companies should get their act together and prove they care about people using their products! Huzzah!

Not so fast. It turns out breaking things into little pieces and then hoping it’ll all come together can’t be blamed just on giant multi-national corporations because designers do it to themselves. Don’t believe me? Find any designer’s website and if it could talk, it’d say

“Hi. My name is John Doe, and I like perfect pixels and strong coffee. Here are six different links to learn more: LinkedIn, Behance, Dribbble, Twitter, Instagram, PDF of my resume, and my email. Good luck.”

So then you click through each of the links to learn more. LinkedIn gives you a sense of what they’ve done in their career. Behance shows their creative work in a safe, gridded, vanilla portfolio format. Dribbble shows their creative work in a series of thumbnails. Twitter shows the last time they were annoyed at an airline delay. Instagram shows the sunsets and brunches they enjoyed last weekend. And that’s all ok. But it’s not great product design.

To use our omelette metaphor, designers are basically putting a bunch of ingredients on the counter and walking away. It’s not a good omelette or even a bad omelette. It’s just an indication that you didn’t feel much like cooking. And if you’re trying to get a job as a chef, that’s probably not the message you’re looking to send.

Deiter Rams Could Not Have Foreseen Dick Pics

Dieter Rams famously wrote Ten Principles for Good Design that states that good design:

• is innovative
• makes a product useful
• is aesthetic
• makes a product understandable
• is unobtrusive
• is honest
• is long-lasting
• thorough down to the last detail
• is environmentally friendly
• is as little design as possible

These points all sound fine because they don’t have to grapple with any tradeoffs or real world scenarios. They’re as uncontroversial as saying that puppies are cute, or that cake tastes good. And I’ve learned over time that this simplistic, platitude-driven approach to evaluating design actually results in worse, more harmful, less human designs. Let’s use dick pics as a case study.

In 2016, Ash Huang went to her Instagram messages and saw an inappropriate photo waiting for her. She long-pressed on it, swiped at it, tapped around for some sort of edit button, or mute, or block. Something. Nothing was there to help her with this scenario. The feature was designed to communicate, with no answer for when people communicated in an offensive way.

She eventually found a way to report the guy. But she had some insights about the experience that I think are important for every product designer to think about and be aware of.

It feels like everyone got busy on something else and then forgot to finish this feature. They implemented the simplest solution and then never went back to it. Sorry, Dieter. Simple is not always better. Sometimes simple is way, way worse.

The more “simple” a social product is, the more trouble it can cause. No one taught me that in art school. Maybe we should start.

I’m sick of living in a graveyard of V1’s that never get fixed and ultimately become confusing places to get lost in, or worse, backdoors for abuse from the badly behaved.

When Rams wrote his guidelines, “simple” meant clean, minimalistic, and pure. But things have changed. These days, the word simple just means you didn’t think through the edge-cases. It strongly implies that it only works in English, chews through people’s data plans, only works on modern phones, is not accessible, and has no answer for handling online abuse.

Anyone can make something simple. But the people practicing great design are on a whole other wavelength. They’re building things that are thoughtful instead. And they’ll be richly rewarded for it.

What the Orange Badges Taught Me

One day at work they gave everyone orange badges to hang on the doorknobs of our offices that said something like “Warning: there may be content unsuitable for children being viewed behind this door. Please be advised.” We had signed a deal with Playboy, and that started one of the most odd projects I’ve ever worked on.

Insight #1: You can get used to anything

One day I needed to work on an audio/visual bug with my co-worker. I went to her cubicle and we tried to reproduce the issue. That’s how we ended up with a graphic sex scene playing, in a loop, while we worked to troubleshoot the issue. Eventually we figured it out, I wrote some stuff on a whiteboard, we agreed on next steps, we stopped the video, and I went back to my desk. No big deal.

Insight #2: We go with our personal taste more than we think

Our VP was a woman, and most of our engineers were men. At one point we were in a meeting and the female VP asserted what porn genre was best to put at the top of the page. I disagreed, but didn’t want to say anything.

If we’re discussing the design of anything other than porn, it’s my job to have an opinion, express it, listen to others, and then work together to move forward. But when the topic is porn, everything changes. Suddenly I have to decide if I want to tell a co-worker that I disagree with their taste in porn. No thanks.

Situations like this happened a lot, and they acted as a great lesson. The things we feel strongest about are often wielded as fact, when in reality they’re opinion. Even if you’re a VP.

Insight #3: Power dynamics are everywhere

I’m typically confident in meetings. I have opinions. I never have to wonder if someone disagreed with me because of bias against my gender, race, or nationality. But once I had to frame my design decisions through the lens of sex, I immediately got more shy. Which meant I wasn’t designing to the best of my ability. There was an invisible power dynamic at play, and I immediately saw the corrosive results in my work. I lost half my impact.

So that’s what I learned from the orange badges. That project gave me a deeper understanding of how the status quo is designed to benefit people like me the most. Whenever I see an under-represented person holding back in a meeting, I don’t blame them. I relate a little more than I might have ten years ago. Sometimes the culture isn’t designed for everyone to speak up the same way and the product suffers as a result.

Leaning Out

Sometimes I can’t stop talking. I tell very long stories and I tend to turn two-sided conversations into one-sided lectures. The irony is I would much prefer to stay quiet and listen. But sometimes it’s a compulsion. I can’t stop talking.

I’ve had many female friends and co-workers describe the other side of this. Not just working with me, but most men. When a person won’t stop talking, it’s hard to wrest control of the conversation. Most women I knew end up thinking “Ok, I guess I’ll just be taking notes in this meeting.” Sometimes that’s easier than finding a way to get a word in edgewise.

Women are often told to “lean in” when faced with these situations. But to date, I’ve never had a conversation with a man about “leaning out.” Going out of your way in a meeting to say less than last time. Looking for opportunities to hear a statement you agree with to then amplify it. Trusting that not every topic needs you to weigh in, and knowing that the more you lean out, the more space you’re leaving for others to fill.

I still talk too much. I haven’t suddenly gotten great at saying less. But it’s something I’m working on, slowly. And the results have been fascinating. It’s not as if I’ve disappeared from the radar. I’m still working just as hard. I’m still contributing just as much. But our discussions have gotten richer as more people have gotten comfortable talking. And that’s always a good thing.

Four Tricks

1. Scientists learned that talking about doing something actually releases happy chemicals in your head. And that makes you less likely to actually do it. So if I say “I’m going to write a novel!” I’m actually robbing myself of some of the chemical motivation. So, step one: stop talking about it.
2. The human mind likes to grow and succeed. (The three key words are mastery, autonomy, and purpose — you want to get better, control your destiny, and feel like it matters.) So you can set up little games for yourself. My favourite is making “chains” and then trying not to break them. Each day I write. Then I keep a log of my hot streak. As of today, I’m up to day 38, a record! So, step two: make things into a game.
3. Inspiration is misunderstood and overrated. Imagine 100 people are reading this essay, and 90 are inspired to go create something. How many do you think actually turn that into a tangible result? Probably five or less. And that adds up. Those 5% are the ones getting the good jobs, breaking through writer’s block, and finding meaning. So, step three: get to work. There’s no trick, there’s no secret. It’s just work. Be one of the 5% or someone else will. Go!
4. Now, you’ve probably read this kind of self-help essay a million times, right? What can you learn from this? Maybe reading isn’t helping. Maybe you don’t need any more lofty talk. Maybe you don’t need to passively look on the internet or in books for inspiration. That brings us to step four: don’t read so much. You want time to seek, but also time to flow.

Seeking vs Flow

Flow is that fascinating, productive, magical state where you’re focusing so intently that time can melt away. You might discover it playing music, writing comics late at night, or knitting.

Then there’s another state called seeking. It’s how you feel when you’re foraging for new content, new information, or new ideas. You’re seeking right now. And you’re in the same mode when you scroll through a timeline, or put together a mood board, or when people-watch at the park.

I’ve been thinking about these modes a lot. I’m always either seeking or I’m flowing. Seeking is metaphorically sitting on the couch, watching TV, and daydreaming about your next move. It’s your default state, it’s easy, and it’s perfectly healthy in moderate amounts. On the other hand, Flow is going to the gym. It’s hard, but it’s good for you. It makes you feel better. And even an hour here and there is worth a lot, if only you can get the motivation.

But the key — and this is really important — is you can only do one at a time. You’re reading this article right now, meaning you’re not making anything. And while you’re making things, you don’t have time to absorb other people’s thoughts. Seeking and flow are mutually exclusive. So go forth and seek, but don’t forget to flow. That’s what works for me.

I No Longer Trust Notification Badges

Many social apps started out with a simple pattern: one tab for global stuff, one tab for stuff that has to do with you. It was usually called Notifications, and people learned to place higher importance on it. It’s similar to how you care more about a personal letter than a generic advertisement sent to everyone in your neighbourhood. For a while, the “unread notification” badge was special.

Then things changed. Companies realised they could put all sorts of stuff in there, even general advertising, and people would look. Or “engage,” as we say in the biz. Each time people “engage” with a feature, someone in the company gets closer to reaching their metrics. Which makes money. Which means promotions. Hurray for capitalism!

But I don’t trust notification badges anymore, and I bet I’m not alone. We’ve been trained over time by companies like Facebook that the red badge can’t be trusted anymore. Which makes us engage less. Meaning someone is reading a spreadsheet somewhere inside Facebook and freaking out. There’s an important lesson here.

It’s easy to boost numbers in the short term with design decisions like these. But the gains are often temporary, and it’s incredibly hard to win that trust back. But “trust” is such a squishy word. Let’s use real dollars.

Let’s say your company is making $10 per user, then you mortgage long term trust for short term gain by putting spam in notifications. That boosts the number to $11 per user. That’s a 10% increase! Wall Street rejoices!

But as time goes on, people like me learn to ignore the badge. And whoops, now your per user value goes back to $10, then to $9. What does the company do? How can it reverse this slide? How can it please Wall Street?

Most designers would like to believe we could revert to the old non-spam pattern. But nope, that would mean the numbers could drop another 10%, which will make the money problem worse. They’re stuck.

And what about accountability? The person or team that originally made the change are probably on another team or even another company by then.

So the spam sticks around with no easy fix, and with no one taking responsibility for addressing it or causing the problem in the first place. The experience gets worse, meaning the product is worse, meaning the company makes less money. And the downward spiral continues.

John Gruber has a great insight on this phenomenon for everyone at a product-making company, from CEO to designer to engineer to product manager to CFO. As an industry, we should all take note:

Once you’re backed into a corner like this, where your users’ happiness and satisfaction are no longer aligned with your revenue, you’ve already lost. It’s like the dark side of the Force — you should never even start down that path, or you’ll be corrupted.

You can convert trust to impact for a while, but not forever. Don’t even try.

Some Stories About Designing for Voice

In 2007, I worked at a voice recognition startup. You’d call a phone number, speak to the service, and we’d send you a transcript via email. Because it was done with human assistance, you didn’t need to be as careful with your speech, or get frustrated nearly as often.

A year later, Apple announced an official SDK for writing iPhone apps. I lobbied my CEO and CTO to give me budget for hiring someone who could make an iPhone app. I got the budget, then designed and PM’d the release. It went live on day one of the App Store, hit #1 in Productivity, got featured by Apple in print media, and eventually the company was bought out by Nuance. But before all that was the meeting with Steve Job’s friend, a venture capitalist in Seattle.

We arrived at his office and showed him a beta of our app. He gave us some good feedback, then said “Steve is obsessed with audio input. And he always has been. Remember the 1984 Mac?” Over several minutes, this man impressed on us very clearly that Steve believed the future of computing, or at least a big part of it, would be voice controlled.

“We’ve got this iPhone, a big sheet of glass, and you can fit, what, five navigational items across the bottom? And a few actions on the top?” This guy knew, back in 2008, that we’d soon ask our phones to do nearly everything we ask of desktop operating systems, with far fewer pixels to work with.

Then he asked about the elephant in the room. To really do voice right, it would need to be done at a system level. You wouldn’t want to launch an app before asking it for a weather forecast, or telling it to call Betsy. You’d want to tell the phone, meaning it would be controlled by Apple, not our tiny start-up.

Back in the office, the CEO and CTO quizzed me about what the VC had said. I agreed wholeheartedly that Steve Jobs has historically been obsessed with audio input and output. I agreed wholeheartedly that Apple would add something like this at the OS level. And I agreed wholeheartedly that a dictation scenario was a sliver of the overall audio strategy for Apple. This was bad news.

“There’s got to be some hook into the OS we can get via the SDK,” they said. “There’s got to be some workaround for being the app that Steve is looking for across the entire phone.”

“Maybe,” I said. I hated breaking the bad news to them. “But Apple believes in owning the whole widget. If they think it’s a big deal, they’re going to build it themselves. At the OS level.”

Within a year, the startup had been bought by a leading voice recognition company called Nuance. Two years after that, Siri launched as an OS-level voice assistant powered by Nuance. It was exactly what his VC friend had told us, and exactly what Steve had been aiming Apple towards since 1984. His company had finally kicked off his long-dreamed about voice assistant.

Steve Jobs died the day after Siri was announced to the world.

Six months prior to Siri’s beta release, I was a lead designer on Windows Phone’s Apps team. We built first party apps for the device such as Mail, Calendar, SMS, and Internet Explorer.

We had been working on an idea called “Capture” which sprung from the insight that jotting down quick notes via voice, scribble, or text is really important. I was fond of saying that our main competition for this scenario was the simple sticky note. Software is slow, sticky notes are fast. We racked our brains trying to figure out a way to address this scenario.

Capture got killed off multiple times to make room for other features. We kept bringing it back by looking for new ways to justify the investment in the feature. At one point, I remembered what Steve’s VC friend had told us years earlier about voice input. And I remembered about a vague rumour floating around amongst the Apple faithful, that Apple was working on an “assistant” for iOS.

iPhone and Windows Phone already had a rudimentary voice-to-text feature, but “assistant” sounded like a bigger bet. It sounded like it might be Steve’s voice dream coming true. So I put together a PowerPoint presentation explaining that I thought the future of “Capture” was not just a single feature idea. I thought the concept of easily capturing any audio, text, or doodle and performing actions with it had big implications. I predicted it’d soon become a “table stakes” feature.

Which isn’t to say Cortana was kicked off because of my PowerPoint, because it wasn’t. There were a million moving parts and I was just some designer trying to argue for a feature he believed in.

But however it happened, Siri launched and then the Cortana team was created soon afterwards. Many of the designers were my friends, and they sat right next to me, so I got to listen in and share thinking through the early stages.

I remember one of the key things I was concerned about was the idea of Cortana being too much of a “black box.” What if you don’t care for Taylor Swift but somehow the computer has decided you love her? What if your entire search and entertainment experience gets corrupted by this bad assumption? And worse, what if there’s no way to see the bad assumption? And worse still, what if there’s no way to correct it?

These discussion led to Cortana Notebook, a place to see the assumptions Cortana is making about you and train her when she gets something wrong. When things are stored in black and white, you can correct mistakes and even input important insights to allow Cortana to help in far more intelligent ways than a black box assistant might.

We’re at an interesting point in software design. When product designers were asked to transition our software from big monitors to small mobile devices, we found ourselves cutting back all but a few features to fit on the screen. That was a tough transition. But moving from mobile app designs to voice will be even harder. When designers can’t rely on any visual design to communicate a product’s feature-set, status, or error states, much of what we’ve learned will go out the window. I’m looking forward to it.

Robots Are Replacing Designers

Art is subjective, product design is not. You can prefer a certain typeface, colour, layout, design pattern, composition, set of icons, or visual trend. But if it makes the company less money, and results in less engagement, and causes confusion amongst more people, it’s an objectively worse design.

I learned this the hard way in 2005. I was asked to rank 5 banner ads based on how I thought they’d perform. We ran the objective results against my subjective art school training, and I was 100% wrong. The ads I liked the most did the worst. The ads I thought were the worst, the grossest, the ugliest, the ones lacking class performed the best. By far.

I was looking at the ads through the lens of art school, a common mistake for young designers. I was trained to look for beauty, tight Swiss grids, and pleasing colour choices. But that’s not how people choose to click on ads. Sometimes they click on the garish, blinking, awful ads the most. That’s why they’re used. They work.

The biggest myth in art school is that fine taste somehow overrides the objective facts of what non-artists want. They don’t. Increasingly, the data is proving that art school sensibility is out of touch and quaint when compared to the rigour and objectivity of machine learning.

This isn’t an issue for the future, either. Already there are huge bot ad networks that collage together thousands of variations of advertising in real time. They can see which ads are getting the most attention, and algorithmically make new versions on the fly. It’s fast, it’s effective, and it doesn’t care how intelligent you think your design is: these Darwin-born ads will always win. They’re millions of times faster, get provably better results, and work for free. The robots are already putting designers out of work, and fancy art school degrees won’t stop it. If anything, they might accelerate the trend.

As designers, we can sit on the sidelines and grumble about it. Or we can figure out how to harness the power of these robots and put them in our creative toolkit and processes. And the first step to doing that is embracing the reality of these tools. They work, they matter, and designers that resist them will be replaced by designers who learn to leverage them well.

Personally, I’m excited by the challenge. Designers have always been hired problem solvers whose results are judged against clear metrics. It always been our job to make the numbers go up. The higher they go, the better the design and the better the designer. Objectively speaking.

Chapter Three: Lead

Table of contents:

• The Ideal Speech for a New Lead
• Pick a Lane
• Bury, Bloat, or Kill
• The $1000 Birthday Bonus
• Slow or Choppy? A Litmus Test
• Speed
• Getting Stuck in the Gobi Desert
• Solo, Paired, Grouped
• Puppy Features
• Hire the Settings Designer
• All the Things That Don’t Matter
• My Big Pink Watch and Dorky Headphones
• Machine Learning Is Indistinguishable from Magic
• Surviving Information Warfare

The Ideal Speech For a New Lead

Let’s say you got hired to spearhead a cool new product at Google. Imagine that the team had been operating for about a year before you showed up, but the previous head stepped down for some reason, and now it’s your first day. What would you say? What’s the ideal speech for a new design lead?

1. Make it about them, not you

Maybe I’m alone here, but I don’t really care much where the person came from and what they did. Either they’re so impressive that I know them already, or we’re going to waste a few minutes letting the person brag about themselves while we escape into our phone.

When I’m the audience, I want to know how things will change. Is a re-org coming? Is my project going to be canceled? Am I going to be able to work with you? Trust you? Do you listen well?

2. Skip the boilerplate high level stuff

It’s not your job to say we’re going to shoot for excellence, it’s your job to explain how we’re going to get there. “Let’s go hit a home run!” is not a particularly inspiring message in sports or product design.

3. Don’t imply that you’re saving them

I see this mistake all the time. People start a pitch by saying “We all know that feature X really sucks, so my proposal is going to finally make it great.” Or “It’s been a tough road until now, but if we work together we can really do something great.” I don’t care how true you think it is, it’s rude.

People are ready to accept new ideas, but not if you frame everything in a “it’s a good thing I’m here” kind of way. So maybe don’t do that.

Here’s a talk I’d lead with:

Hi everyone! Thanks for that nice introduction. I’m really looking forward to jumping in and learning more, and that’s exactly what I want to talk about today. I’m going to talk for about two quick minutes, and then we’re going to open up for discussion. Sound good? Here goes.

Any designer knows that you need to understand the problem you’re trying to solve. Which means humility and listening. So, to that end, it’s my job in these first few weeks to listen. The better I listen, the better I’ll be able to lend a hand. So that’s what I’ll be doing, before anything else.

I’ve sat through this kind of meeting many times. Some new person shows up, brags about how they’re going to do such a great job, probably does a re-org, things don’t get much better, then after not too long, they leave. Right? Too harsh? Maybe. But I see it a lot. I think we all have.

Here’s the thing. I have ideas, obviously. Otherwise I had no right to take a job as important as this one. But my ideas mean nothing if I don’t listen well right from day one. I don’t want to shoot from the hip or drastically change direction, I want to help accelerate whatever’s already working. Which means less talking from me and more feedback from you.

So! That’s my piece. Now I’d like to open it up for Q&A, or even better, just straight feedback. If you want to tell me about a thing you think is going well, or not going well, or anything else, please do! Because the more honest we can be right now, while I’m still learning, the better it is for all of us. So, does anyone want to be the brave person to go first? Gold star to the first one who says something. Which is pretty hypocritical of me to say because I’d rather die than ask the first question.

Ah ha! First question! Very brave. Please take my mic.

Pick a Lane

When people tell me they love taking the time to get it right, I mentally calculate in my head “high quality work, but has trouble hitting deadlines.” If they say the reverse, something about how “done is the engine of more,” I think “fond of MVP releases, might not be as good at polish, user delight, and long term brand strategy.” Both are perfectly valid approaches. The problem is when you refuse to believe there’s a tradeoff to make at all.

Here’s an example I see often: when design teams say that reusing components in a design language is important for UX consistency, I agree. Strongly. That’s my default design philosophy and it’d take a unique client, product, or scenario for me to not default to it.

But componentised work, for all the benefit, has downsides as well. Some feature ideas just aren’t possible with standard components. Meaning new work often takes much longer, with lower morale, because teams have to wait for the design system team to bless a new interaction model, or for the platform to provide it. There’s no magic bullet, only tradeoffs.

This is why it’s helpful if teams don’t just use the happy words (consistent, user-focused, delightful, simple, clean, fast, awesome) but factored in the scary words too. For example, instead of “Quality first,” it should be “We’re comfortable shipping late in order to make sure the feature is as good as possible.” Don’t say “MVP” if you’re not willing to say “We’re ok with a product that could negatively affect our brand because we think the lessons we learn will be worth it.”

Pick a lane. Don’t tell me how great it’s going to be, tell me what you’re willing to make less great in order to get there. That’s where the real conversations happen. That’s where the real work is done. The rest is just talk.

Bury, Bloat, or Kill

Apps are always adding new features. Features demand screen space. Mobile devices have a limited amount of space available. Something has to budge.

When faced with this tradeoff, you have three options: bury, bloat, or kill.

Bury is the dismissive term for putting a button a few taps away, behind a “long press,” or in a hamburger menu. The argument against burying is that engagement goes down if it’s not on the front screen. This is a very good point. But it’s not a veto card. Not everything gets to be one tap away.

Bloat is the dismissive term for putting the button on the main screen. Maybe your app starts with five buttons at first. Then you roll out a new feature and need a new button. Then your sales team signs a deal and it requires a new button. Over time, people say your app is bloated and they’re right.

How do you get around the choice between bury and bloat? You kill. But good luck with that. Removing features once people rely on them in software is extraordinarily dangerous to the health of the business. It’s easy for a designer to mock up at a whiteboard, but it’s very hard to explain to paying customers or customers why they lost their favourite feature. Not to mention why they should trust you anymore.

So what’s the answer? As with anything else in software design, the answer is “it depends.” But don’t go into these debating thinking it’s easy. Don’t think if someone buried they’re a bad designer anymore than someone who bloated is a bad designer. And don’t assume just because someone managed a kill that makes them a good designer. Product design requires a lot more from its practitioners than one-size-fits-all answers. If it didn’t, it wouldn’t be so fun!

The $1000 Birthday Bonus

Everything seems obvious in hindsight. Of course Steve Jobs’ product genius would save Apple. Of course the electric car was destined to happen. Of course Google’s search engine would make the company a lot of money as we moved from boxed software to internet delivery. But none of those were a given, and few of us would have made those bets back when they were new ideas.

At first, new ideas look unprepared, disheveled, and dangerous. It’s easy to see their flaws, hard to see their potential, and most of the time we’re right to be sceptical. Most ideas are not good. But as they prove themselves, and time passes, we tell ourselves the ending was always clear. But it wasn’t. Spotting potential amongst the silly ideas is the fun part.

Imagine the two of us start a company together. We have a product, we have a name, we and now we’re trying to figure out how to hire people and grow the business from scratch. What if I said “Hey, I think at our company we should give everyone $1000 on their birthday?” If you’re like most people, it’s easier to see the downsides than the advantages. Imagine how you’d respond.

You might think the idea is interesting, but wonder if that’s really a high priority task. After all, we need to get office space, and buy equipment, and find clients, and a million other things. Do we really have the luxury of thinking about interesting perks when we don’t even have a staff? If you’re like most people, you’d move on to the next item on the list.

Imagine it’s a year later. The company has grown and you’re hiring as fast as you can. One promising hire turns down an offer to work at your company to work at a competitor across town. You hear that they give everyone $1000 on their birthday. Wait, we had that idea! Maybe it’s time to revisit it. Maybe there’s more merit to it than you first thought?

Can the company afford it? Well, sure. It’s just $1000, and you have 20 employees. That’s $20,000 versus payroll which is over two million dollars. If you’re really struggling, you can always pay everyone $1000 less of a salary to offset the bonus. In fact, you can even make it a marketing or recruiting expense. You can make it work.

But it sure is a lot easier when someone else proves the idea first, and it starts affecting your competitive standing. Going from zero to one takes guts. But being a “fast follower” is easy. It’s just good business. Imagine a year goes by, and suddenly everyone in town is offering $1000 birthday bonuses. It’s gone from a novel idea, one that brings prestige to the first ones to adopt it, to part of the expectations landscape. Now all you can do is provide larger birthday bonuses, but that won’t have the same impact as when the idea was new.

This happens again and again. A lot of new ideas are crazy until they’re expected. I saw this happen with Silicon Valley benefits step by step. It used to be crazy for work to pay for your lunch, or provide free yoga classes. Now if you can’t keep up, you’re not part of the conversation.

We’re seeing this in all sorts of fields and trends, and we’ll continue to. The question is not whether or not new ideas will seem crazy at first, because they always will. The question is which ones are actually good, and how long will it take for other people to notice?

Slow or Choppy? A Litmus Test

On Twitter, Dustin Senos asked the following question:

Which do you ship? A screen that:

A: takes 10–15 seconds to load, scrolls smoothly

B: loads instantly, incredibly choppy scrolling

51% picked A and 49% picked B, which is great. But I was more interested in the ways people tried to get additional context on the question. These were the most frequent ones.

“It Depends”

26% of his responses asked for more information. This is how designers are trained to approach problems, so this is a good start. But it quickly leads into something designers struggle with, which is …

“Neither”

… refusing the premise outright. Sure, there’s nothing in the real world that would force cause you to make this exact decision. There’s always going to be additional context.

But refusing to go with the premise, in a dumb little Twitter poll, is a red flag for me. It’s not a sign of mental strength to be unable to decide. It’s a sign you have a fixed mindset and trouble making decisions. This isn’t a good answer.

“Both, then test it”

I’m torn on this one. It’s refusing to answer the question, which isn’t great. But it’s also pointing to an emerging reality in software design: computers know more. Ad companies literally generate a few thousand different visual layouts via code, then find the one that tests best. It always tests better than the one the designer made by hand, which is a sobering fact that designers should understand and accept. I have to give some credit to that thought process.

“Both, then let the server determine the right path”

One person said this, and it’s an evolved version of the previous answer. All software design requires context. Change the brightness when the room is dark. Change the layout when the language reads right to left. Play different sounds based on whether or not the phone has been set to vibrate. Show different content behind China’s firewall. Show the full version on desktop but load smaller assets on mobile. And so forth.

So this answer isn’t just saying “ship it and track the results,” it’s implying that a lot of the design happens via smart algorithms in the background. This is a Real World way of thinking about the problem, so whatever points are docked for not following directions are added back on for seeing where a lot of the design work of the future will live: in the algorithms powering the rendering of the eventual experience. Good design is contextual.

Slow load

Those who chose option A are dooming their users to a 15 second wait, which is an eternity. Some people said they’d get around it with informative or cute loading screens, and only if it didn’t happen frequently. With that context, I’m ok with it. But otherwise, no. A 15 second delay without an extraordinary amount of user messaging is not an acceptable design, no matter how buttery smooth the app is once it’s loaded.

I sometimes call these “load-bearing animations,” meaning the whole thing comes crashing down if you don’t get the animation and messaging just right. It’s easier said than done.

Choppy

The remaining folks chose choppy and used the same rationale I would: sure, a choppy UI is unacceptable, but loading immediately is more important that smoothness, if you have to pick one. And without additional context to understand what kind of experience we’re designing, we should default to fast loading speed.

What these answers say about you

Yes, always gather data. But you’re going to hit a point, even after prototyping and researching, where you have to take a leap of faith. And people on your team may be divided. Embrace those situations. Make your best guess, learn from the data quickly, and wherever possible, let the computer help frame the context and gather result data for you. There’s always a way forward, and it’s your job to find it. Not reject the premise on its face. Where’s the fun in that?

Speed

My friend recently posted this quote on Twitter.

“Indifference towards people and the reality in which they live is actually the one and only cardinal sin in design” — Dieter Rams

Which immediately reminded me of this quote.

‘It is difficult to get a man to understand something, when his salary depends on his not understanding it.’ — Upton Sinclair

The first quote, while perhaps true, is a feel-good motivational speech that leaves everyone feeling like winner. Designers skim it, say “Yup!” and feel like great designers since they agree with the mightily respected Dieter Rams. There are no designers who read that quote and think “Oh. I wonder if I do that.” Because of course not. That would mean they’re not awesome.

The second quote explains why most apps and websites are too slow. The very things we know to recognise in a “good design” (massive hero images, 2x retina graphics, custom fonts, customised and specialised controls, Disneyified motion design, and three megs of Javascript tracking scripts that the business requires) are the things that are slowing software down more year over year.

Now, no one’s arguing that we should change the web to a purely text medium, but the ballooning size of apps and websites has gone from notable to incredible to a mockery of basic design tenets. And it’s getting worse.

“#notalldesigners,” you might be thinking. “#yesallconsumers,” I say.

I was once in a design review. There were two teams present, one that was trying to make a splashy new feature, and my team, who was trying to help the feature work in bandwidth constrained/expensive networks like India and Brazil.

This conversation happened:

Me: “This looks great. Have you considered using some of our tools that help your feature’s images degrade gracefully in places like India?”

Team: “We don’t have time to redesign this for every country.”

Me: “Understood. But if you just use our framework, you won’t have to redesign anything. It just means we’ll automatically compress your images when we detect a slow connection.”

Team: “The design is solid. Besides, India will eventually get broadband.”

This is a team incentivised to ship something “great.” But thinking about slow connection speeds, scenarios where internet is expensive, or the fact that almost no one in the world has a reliably fast connection contradicted those incentives. It would mean their graphics couldn’t be as slick. It would mean they couldn’t ship as quickly as possible. It would make their design less great, according to their narrow, high speed, skyscraper, San Francisco, designer-oriented definition of great.

Let’s read those quotes again.

Indifference towards people and the reality in which they live is actually the one and only cardinal sin in design.

and

It is difficult to get a man to understand something when his salary depends on his not understanding it.

And there’s your problem. Designers won’t fix this problem because they’re not incentivised to think about it. They think they’re empathetic, and they are. As long as they don’t have to change anything they’re used to. That’s not empathy. And that’s not good design.

Postscript: it’s worth pointing out that even on wifi, even on LTE in San Francisco, even with a high end phone with no data cap or memory problems, bloated design is still a big problem. These issues are not limited to someone on a feature phone in rural Africa, as is often implied. Speeding an experience by a single second, on any network, leads to direct financial and user experience gains. Speed matters, every time, everywhere, always.

Getting Stuck in the Gobi Desert

My elementary school did “writer’s workshop,” time set aside for kids to learn creative writing. Somewhere along the way, I began writing an epic story. I invented a new society and a new race with their own customs and rituals. I even went into detail about the special kinds of caves they built, and set the story in a real place, the Gobi Desert.

My teachers were charmed and thrilled. I was only in second grade, but I had charted a bold trajectory across an entire trilogy of epic-length books. My enormous project was a novelty around school. I was sent to other classrooms to show it off, like a traveling roadshow.

Here’s the problem. The story was all talk. I only ever wrote a single chapter. There were lots of discussions, some sketches, and my roadshow. But when it came to the actual work, it was one lonely little chapter. It turned into a thing to talk about, not a thing to actually do. It took me days just to settle on a location. That’s nuts, but it looked on the outside like hard work. It was actually fear.

At the XOXO conference a few years ago, I spotted one of my early web heroes. I love his writing style, so I struck up a conversation with him. I asked how his novel was coming along. Soon it was clear he was stuck in the Gobi Desert.

“Well the thing about writing an epic novel is first you have to define the history, which takes some time. Then you need to layer in the culture, and then-” and I tuned him out like the Peanuts listening to the droning teacher. “Oh my,” I thought. He is never going to write this book. Unfortunately, I was right. It’s such a common story. How can we prevent it from happening to us?

Here’s what I do. Imagine every single piece of writing or design in the entire world, all lined up like they’re in a horse race. Imagine you can see how far along they are, from conception to being released into the world. From 0% to 100%. How would the dots animate over a year? How would the dots move towards their respective finish lines?

You’d see one in a billion that just seems to fly along the track, from start to finish, again and again over the course of months. That’s Stephen King. Hi Stephen King! That guy is in his own league. Ignore him.

But the other thing you’d notice is how few most of the dots ever move. They flicker into life at the starting line, and maybe lurch forward 1% or 5%. And then they stop. And fade away. That’s their entire lifespan.

That’s how my Gobi Desert epic died. That’s how my web hero’s story died. That’s happening, again and again, across the entire creative universe, every day. That’s how creative works are born and die too young, over and over, making it by far the most common ending. It happens to me, it happens to you, it happens to everyone. But it doesn’t have to.

Aim for the space between Stephen King and letting your projects die out. Do it by doing a little bit, over and over, and one day you’ll be done. And then you’re in good shape, because done is the engine of more.

Solo, Paired, Grouped

I learned this trick from Quiet, a book about introverts. Instead of running a brainstorm the standard way, where everyone groups themselves together, try going solo, then paired, then grouped.

Imagine you’re asking the room to collect insights about your team’s current product. First get everyone to write ideas on sticky notes. As many as possible. Then, instead of going straight to the big discussion where you group sticky notes and rank them, like most sessions do, you pair up.

In the pair, nothing gets lost. It’s two people talking, regardless of circumstance. Even if they’re introverted. Even if they’re in the throes of impostor syndrome. Even if they think their ideas aren’t as important, or won’t be popular, or a million other little doubts that get in the way. It’s just two people sharing their thoughts as efficiently as possible.

A Venn Diagram appears. There are ideas that person A has, but person B does not. Then the reverse. Then ideas they both have. All three circles have valuable information. Document them. Then it’s time to jump into the broader discussion, the standard brainstorm. You’ll find they run much better when you ease into them. Which means better teams, designs, and products.

Puppy Features

People often fall in love with a silly, adorable, floppy-eared, brand new puppy. Then time passes, the puppy becomes a dog, and the owner realises dogs are a lot of work. As a result, city shelters are full of animals that weren’t properly cared for after the novelty wore off.

It’s sad, but it’s human nature. New things are fun, sustaining things over time is hard. It applies to everything. Pets, relationships, jobs, and especially software features.

I’ve worked at a lot of companies. I’ve been on a lot of teams. I’ve worked on lots and lots of features. But I can categorise all the work I’ve ever witnessed into to clear buckets: Puppy Features and Other.

Everyone wants the Puppy Features. A bold new bet! “Blue sky” thinking! Discovery! A way to not mess up like all the other dumb features that came before it. Sometimes they even make a whole new team for it. And it’s hard not to fall in love . Everything is exciting and new, and the amount of maintenance and long-term responsibility required is close to zero.

That’s not to say shipping a feature like this is easy, but there’s no question it’s easier than version five. Just like your first move in chess is a big deal, but it’s nothing compared to the complexity of move five. Or move twenty-five.

When version one ships and grows up, you then have to take care of it. But that’s not as fun. It’s harder to find people who want to work on it. It’s harder to prioritise it. You have to support users, which costs more time and money than you planned for. And as technology marches forward, aspects of the code or design patterns become outdated. Taking the time to get it feeling bright and fresh feels like a waste of time. After all, there are new puppies coming in every day. Shouldn’t we focus on them instead?

It’s hard to fight human nature and not fall in love with the puppy features. But it’s the old things that need the craftsmanship. It’s the boring foundational stuff that needs your best designers and engineers. And if your “best” are bored by that work, I question your definition of best. They might just love puppies, and that’s not a particularly hard trait to replace.

Puppy Features don’t make for great design. They’re novel, original, and fun. But great design that solves real-world problems effectively doesn’t happen until after version one, if ever. Invest your design resources accordingly.

Hire the Settings Designer

I’ve seen this play out several times on multiple teams. Everyone wants to captain the fancy new features, the sorts of things that might appear on billboards and commercials. But no one asks to work below deck, in the app’s version of the boiler room: the settings screens.

Not only are settings extremely boring, they’re also much harder than almost every other screen in the app. There’s little room for animations, or delight, or even visual design. But it’s where legal requirements collide with business objectives. It’s where what you want the app to do runs headlong into how people are actually using it. It’s where you want to be concise and clear but end up having to fit in a paragraph of explanation text because the feature is just too complicated to explain otherwise.

You spend a lot of time pondering the merits of clumsy, inelegant design patterns such as “don’t show me this again” checkboxes, and after exhausting every other option, you sigh and go with them because there’s just no other way. The life of a designer deep in the bowels of settings is disappointing and ugly. And the older an app, the more settings there are, because toggles and switches never die. They’re the living embodiment of the design debt built up from hundreds of tough design calls deferred.

But it’s great training. There’s no better antidote to Diva Sickness. There’s no quicker way to understand that compromise is not a dirty word. It’s a swift kick in the gut for young designers who have been misled about what software design really entails. If I could choose between a person who only worked above deck on user-facing features or below deck on settings, I’d go with the settings designer every single time.

All The Things That Don’t Matter

In 2011 or 2012, I pulled aside two friends at work and asked if they wanted to work on a new side project. Over the next few weeks we followed a standard design process to discuss insights, experiment with some directions, and put together a little movie and a PDF to help explain the idea to others.

We called it Project Fuzzy. The big insight was something we hadn’t seen anywhere else: messaging bots that help users get things done, notably around group calendaring. Now it’s been the better part of a decade and this is a direction that’s seen lots and lots of investment.

This is where a lot of designers go wrong. We get sad and think “That could have been me!” or if our product shipped we say “Yeah, but we shipped it first.” But that attitude isn’t just defeatist, it misses the point.

The fact is, if you give 100 design teams the same set of insights and the same problem to solve, they’ll come up with ~90% the same solutions. Not because they’re lazy, but because there are finite ways to solve problems well. This is tremendously exciting.

A design process is more scientific, structured, and reproducible than most people realise. Great design doesn’t run on magic, muse, and talent. It’s just a process. One that can be taught, learned, and improved on. It’s not any different from learning any other skill, like woodworking or accounting.

But you wouldn’t know this by how the tech press talks about design. When a new product is announced, everyone rushes to write stories about how it’s imitating another product. Or how someone else had that idea first. Or how the team’s talent pre-destined them to find that design solution.

These are all the things that don’t matter. What matters is taking some insights, running them through a design process, and then asking yourself if you solved the problem you set out to solve. Then you do it again. That’s what matters in software. Anyone can do it, and they do.

My Big Pink Watch and Dorky Headphones

A few days ago I decided to put my phone in my bag and see if my cellular-enabled Apple Watch Series 3 could get the job done by itself.

I popped in some AirPods and they chimed in anticipation. I held my Watch up to my face. It was 7:10am, I had a meeting at 8:00am, and I had 100% battery life. I tapped the Music complication I had placed for quick access and saw some albums that had automatically synced overnight. The second option was Kendrick Lamar. Sure, let’s do it, K-Dot.

I usually skip the first song, so I brought the Watch up. The software was still on the Music app. This is notable because the first edition always went back to the standard watch face. It was nice not having to hunt and peck for the app.

I know where my bus stop is, but I was curious how directions work. I tapped my AirPods twice and said “Hey Siri, directions to work.” My Watch buzzed with a response. I had expected the directions to play over the headphones, but I realised it was confirming the results on the watch face. It took me some hunting to find the way to change directions from car to transit. Turns out it was behind Force Touch.

On the bus, I realised the first big loss of my phoneless existence. Books. I can delay most of my phone tasks while I’m on the bus and I feel like I’m living a more virtuous life. But going without books seems like a step backwards.

At work, I worked. That means I had access to a full keyboard, the Mac version of iMessage, and a full email client with lots of bells and whistles. Then work was over and I got ready to head home. I didn’t miss my phone all day.

The evening commute was the same as the morning commute. I read a book while listening to music. Sometimes I had a text to respond to, and I did. A few times I needed to do other things like look up a friend on Find My Friends or look up an old photo, and I could. There were two exceptions. The sun was reflecting off a building in a beautiful way, but I couldn’t take a picture. Later I wanted to listen to a podcast, but Apple Watch doesn’t support them yet. So I settled for Music.

Later that night, I had to move some boxes around. I never realised what a pain wired headphones are, but now that they’re gone, I feel it. I spent hours exerting myself and the headphones popped out zero times. With traditional headphones, I’d give up on listening to music after accidentally hooking them on furniture for the second or third time. It makes a huge difference for me, something I confirmed when I went on a run.

So that’s how it’s been so far. It reminds me of the iPod review I wrote after buying one the first week it was on sale:

The most noticeable thing about owning such a gadget is how boring it is. I opened the case, peeled off the sticker on the faceplate that said “don’t steal music” in 5 languages, and plugged it into my computer.

With no fanfare, it started to swallow my entire MP3 collection, and about 8 minutes later, it was done downloading.

[…]

After the 30 second learning curve, all that’s left to do now is buy some new music. Anyone have music recommendations?

That’s how the Apple Watch Series 3 is working for me. It’s just doing what I want it to do, and there’s not a lot more to say. Leaving the iPhone at home no longer feels like a radical five year vision. If you have access to a computer during the day, and perhaps a paperback book or two, and can go without podcasts, going phoneless is starting to become feasible.

Maybe it’s not for you, and maybe it never will be. But for those looking for a little less tech in our life, that day may be getting closer. It took three years for the iPod to start to find mainstream success. I suspect this shift will go even faster.

Machine Learning Is Indistinguishable from Magic

Machine Learning and Artificial Intelligence have gotten a lot of press over the last few decades, and for good reason. In 1997, we witnessed a robot beating the best chess master in the world. It was a landmark moment, because it foreshadowed a day where machines could perhaps outthink humans.

(Historical note: some disagreed with this conclusion, because chess isn’t as nuanced a game as the ancient Chinese game of Go. But twenty years later a robot beat a human Go master. And so progress marches on.)

I’ve seen a worrying trend in tech circles over the last few years. Machine Learning, or “ML,” has turned into a shorthand for “magic.” For example, you might say “We could use ML to make sure your phone automatically gets set to silent when you walk into a movie theatre.” Or “We could use ML to make sure you never see abusive comments on the internet.” Sounds great, like everything that comes from a magic wand.

But it doesn’t happen as easily as magic. All of this delight needs to be designed for, which means we need some guidelines. Here’s what I’ve learned designing for ML-powered experiences over the years:

1. Don’t draw attention if you don’t need to
2. Obvious always wins
3. Explain the implications
4. Provide opportunities to teach the system

1. Don’t Draw Attention

When Google auto-fills search results, they don’t need to say “brought to you by Machine Learning.” They just auto-fill search results.

When your car notices that you’re skidding and goes into a specially designed skid algorithm, it lets you believe you are still braking while it silently gets the job done.

When your phone knows you always check your email at 7:02 in the morning, then tap Twitter, then tap Facebook, it can learn to pre-load all those requests one minute earlier. It doesn’t need to provide a setting for it, and it doesn’t need to explain it’s doing it.

Obvious Always Wins

Sometimes people miss important things on Facebook because its algorithms buried something they cared about. This leads to a loss of trust. Even if the algorithm is right 99% of the time, our brains are designed to feel anxiety about that 1% that the robot is getting wrong, and to overstate how often it happens.

The answer is not to forego all ranking and sorting, just to spot and neutralise situations that could lead to a drop in trust. For example, you can provide messaging that explains how things are sorted, and provide ways to see how the timeline would look without any ranking at all.

Explain the Implications

Gmail has an option that says “never show me spam like this again.” And then it will show you all the similar messages that would be affected by your new filter. This way you can see exactly what assumptions the product will be trying to make on your behalf, which increases the quality and the trust level.

If you’ve decided you need to tell the user about some gee-whiz ML feature, then you’ve signed up for clearly explaining the implications of their actions. And you also need to…

Provide Opportunities to Teach the System

Spam filtering can guide us here as well. Sometimes the robot gets a bit over-zealous with its filter and suddenly your birthday greeting from Aunt Gretta is banished to the spam folder. But when you find it, no problem, you can tell the system “never mark this sender as spam.”

This is a great pattern for a few reasons.

1. You are able to see the implications of the incorrect decision
2. Failures don’t lose data, they move into a special folder
3. You’re able to train the system to do better next time

These steps make the system smarter while increasing trust. Win-win.

If you’re working on products as part of a team, and someone refers to Machine Learning, here’s what you do. First, you should appreciate that they’re thinking boldly. That’s a good start. But then you should get to a whiteboard with this person as soon as possible to hash out the specifics. The seeds of success or failure are sown in those first discussions. What is the problem we’re trying to solve? Where do we want to take the user?

Do you ever wonder why Steve Jobs was so unsuccessful early in his career and so successful later on? This lesson:

“One of the things I’ve always found is that — you’ve got to start with the customer experience and work backwards to the technology. You can’t start with the technology and try to figure out where you’re going to try to sell it. And I’ve made this mistake probably more than anybody else in this room. And I’ve got the scar tissue to prove it. And I know that it’s the case.

And as we have tried to come up with a strategy, and a vision for Apple, um, it started with … what incredible benefits can we give to the customer? Where can we take the customer? Not starting with — let’s sit down with the engineers and figure out what awesome technology we have, and then how are we going to market that. And I think that’s the right path to take.”

And that’s where we are with ML. As powerful as it is, it can’t change the reality that the human mind hates mysterious and inconsistent black box design. Humans hate it when the robot makes the wrong decision, hates it when the machine won’t allow the user to undo incorrect assumptions, and hates over-hyped and underwhelming products.

These concerns collide against Machine Learning’s default state, which is to powerfully guess, with no human input, and no clear rationale or documentation that explains how or why it performed an action. In other words, magic. When it works, it’s amazing. When it doesn’t, it’s far worse than any software we’ve seen until now. So it’s up to us to be careful, listen well, and work hard.

The best design of the Machine Learning era won’t take place in pixels or algorithms. It’ll all be in the messaging. That’s where the differentiation will be.

Surviving Information Warfare

Zen, meditation, living in the moment, being present, learning to do nothing, solitude retreats, deep breaths, finding your centre, listening to your inner child, following your bliss, you’ve probably read those articles before. I’m here to tell you that things have gotten a lot more real over the last few years. And I have some media training suggestions I hope you take to heart.

1. Understand you’re being manipulated

Nearly everything you see, read, or hear is trying to get you to buy into something. And there’s nothing inherently wrong with that. If a company makes a product, and you want to buy that product, there’s nothing sinister going on.

But you need to understand that you’re outgunned. They have a lot of money to spend on making you feel like you need to buy more things. Your gut feeling about a product is extremely easy to manipulate.

The biggest mistake you can make is believing your instincts are operating cleanly, with no outside interference. You’re being manipulated every day. Just being aware of that can help a lot.

2. Reconsider how much news you really need

Older generations taught us that good citizens keep up with the news. And I think that used to be true. But the volume and velocity of news has increased to a point where there are some serious downsides to trying to keep up.

And if it were a bunch of respectable news organisations duking it out, it wouldn’t be so bad. Because facts are stubborn things, and you’d find yourself reading pretty much the same story everywhere. So that’s not so bad.

But information has been weaponised. And I don’t use that word lightly. I mean, literally, people are attacking you with disinformation. It’s part of a broader plan, and its much more effective and widespread than people know.

You don’t actually need to read the news every day. You don’t need to follow news sources on Twitter or Facebook. You think you do, to be an informed citizen. But it’s backfiring. You’re getting more overwhelmed, your moral compass is getting randomised, and you feel like you’re drowning in news. That’s by design. Reconsider how much news you really need.

3. Leave Twitter

The stated design goal and business plan of Twitter is to tell you what’s happening in the world, but there are no safeguards against disinformation. Twitter is how you mainline disinformation, fear, anger, and division straight into your mental process. Twitter’s drawbacks outweigh its benefits.

4. Demote Facebook

Keeping up with friends and family is important, and that’s where Facebook is strong. On the other hand, those tight bonds are even more damaging when they’re used for disinformation. Hang tight to your friends, but understand the longer you spend on your timeline the worse off you’ll be.

This goes for other social networks as well. Do a search for a video called This Video Will Make You Angry and it will tell you everything you need to know.

5. Audit your time

I’m going to say something controversial. You’ll probably disagree with me at first. Ready?

You might have too much free time.

I know, I know. Everyone’s busy. Everyone’s balancing a million things. We’re stressed and harried and there’s never enough time and and and-

But hear me out. If you couldn’t check any social media at all throughout the day, meaning no Twitter, Facebook, Instagram, or Snapchat, how would your life change? And what if you went a step further and decided you weren’t allowed to look at any news at all? If you’re like me or most people I know, an interesting thing would happen.

You’d have more time, and your schedule would reshape itself in odd ways. It’s a bit like putting coins in a jar for a year and then discovering you have $100. When I cut out news, I regained 2 minutes here, or 5 minutes there. I wasn’t getting hours back, but my day started to have more daylight. That made me want to fill it up with better things.

When I didn’t have the built-in distractions, I found myself get bored more often. When faced with a choice to be bored or get my work done faster, I found myself preferring productivity. Which did leave me with more time. I filled it with books and writing.

This took time and effort. I didn’t figure this all out in a day. It was a multi-year process, and I’m still working at it. But it all started by auditing my time. When it occurred to me that reading news and opinion online was the single biggest obstacle to a healthier mind, the choice was clear.

Notes

Published in July 2018
ISBN: 978–0–692–15847–0

Licensed under the Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 United States License. You are allowed to quote, send, translate, and reuse as much of this as you’d like as long as you kindly respect these two wishes:

First, you must give me credit. Second, you cannot make money off this work. Email me at reasonabledefaults@lot23.com if you have any questions or comments. Thanks for reading!