Category: Technology

One year at Microsoft

Last week marked one year at Microsoft for me, and what an unexpected adventure it’s been! I thought I was coming in to lead a a stable of popular, but well-trodden web properties, and I ended up getting to work on a whole lot more, including Windows, Bing Chat, and the company’s biggest bet in years: Copilot.

Microsoft Copilot Logo
“The Handshake” — Designed with Love, in Puget Sound

I usually write a lot about the companies I work at but have held off until now because we haven’t been hiring. Well now we are! We’re specifically looking for Designers and UX Engineers to work on our design system for Copilot. Some of these positions are on my team and based where we have offices (Puget Sound, the Bay Area, Atlanta, New York, Vancouver, Barcelona, Hyderabad, Beijing, and Suzhou) and some are on adjacent teams and can accommodate fully remote work. If you are a Designer or UX Engineer with a passion for design systems and AI, we’d love to chat.

Our deisgn team in Beijing
A recent visit to our team in Beijing… I had never been!

So what has year one been like? The good and the “needs improvement”. 🙂 👇

One of the reasons I decided to join Microsoft was I missed the joy of in-person product-making. I know not everyone feels the same way so I’m not trying to make any broad statements about local vs. remote work, but for me, it has been even more refreshing than I expected. I usually come in 3-4 days a week, while others on the team are anywhere from 0 to 5.

It’s funny, sometimes I will wake up on a Monday and think to myself “ahhhh, this is going to be a chill work-from-home day” and by the end of the day, I realize I’ve been staring into a screen on video calls for almost the entire day and how much that slowly saps my energy. Meanwhile, in-person days are filled with walks, whiteboarding, and energizing sessions with some of my favorite teammates I’ve ever had. I realize not everyone feels this way about being in the office from time-to-time, but I do. Even our fierce, interdepartmental karaoke battle helped bring a bunch of teams together who had never met before.

Mojin killin’ it at design karaoke

The other great thing about lucking out and joining when I did is that we are embarking on one of the rare paradigm shifts that occurs in technology maybe once a decade. The 1980s were about personal computers. The 1990s were about the internet. The 2000s were about smartphones. The 2010s were about the cloud. And the 2020s will be about AI. The really powerful thing about all of these developments is that they don’t replace each other, but rather they build on each other. AI is the result of everything that came before it. If you got into design to help shape the culture of the world around you, these are the moments you treasure.

These turning points are also wonderful because they give you a chance to reawaken to your Beginner’s Mind. I have learned more in my first year here than at almost any other time in my career. Not only does the pace of technological change in AI force you to build skills as you go, but there are so many amazing engineers, designers, researchers, writers, marketers and other creative people to learn from, that it happens almost automatically.

When I was interviewing here, not even my prospective new boss told me about any of what was behind the curtain. Only during my first week did I find out all we are working on to empower every person and every organization on the planet to achieve more. That is Microsoft’s mission statement, if you hadn’t heard it before. It’s an uncommonly good filter with which we can all ask ourselves every day “does this project actually do that?” It’s quite freeing as it gives you license to question projects at every stage of development.

Ask questions as early as possible
Don’t sleep on these pillows

Another thing I’ve loved about my first year here is that I joined a group that has figured out how to ship very quickly. That also has its downsides, as we have plenty of craft problems to solve, but it’s great working for one of the largest and most established companies in tech and being able to ship within weeks of designing something.

One more thing that’s blown me away is the Inclusive Tech Lab, where we work on new technologies to make our products inclusive to people all of abilities and walks of life. No one experiences technology the same way, and teammates like Dave Dame and Bryce Johnson do a ton of great work to make sure that’s top of mind for everyone.

Finally, one of the unsung benefits of working for a native Seattle company again is that Seahawks stuff is all over the place. Presentations, charity auctions, everyday office attire… you name it. It’s nice to not be the only one with good taste in football teams.

Seahawks art on campus
There are actual seahawks on campus

I am no corporate shill, however, so I must also be honest about some of the things that need improvement over here.

At the top of my list is that Microsoft has not yet fully embraced the role design plays at most other tech companies. We were engineering-driven in 1975 and we are squarely engineering-driven in 2023. The world, meanwhile, has changed in that time. It is no longer sufficient for complex things to work. They must also shed their complexity. People expect the products and services they spend their time and money on to delight. To overdeliver. To give them superpowers. Those sorts of qualities only materialize when you have supergroups building products.

In music, a supergroup is when a singer, a guitarist, a bassist, a drummer, a keyboardist (and so on) who are all at the top of their game come together to create an album. In tech, a supergroup is a researcher, a couple of designers, a product manager, and a Volkswagen Bus or two full of engineers. Up until a decade or so ago, a lot of tech companies followed the model of packing projects with as many smart engineers as they could find and only sprinkled in things like design and research as necessary. I still see some of this thinking in pockets over here. I’m trying to influence things, but it’s a delicate dance, especially when the company has had such enormous success by doing so many other things very well.

I think there are plenty of people here who still feel like being engineering-led is unequivocally good, but to those people I would say that in a modern tech company, design is engineering. It’s no better or worse, but it does have very different leverage in the building of a product.

A diagram of a cross-functional team
Mess up the green or the yellow, and all the blue work can be wasted

On the plus side, Microsoft has never had as much design and research talent as it has right now, and we are increasingly looked to by the executive leadership team as lighters of the path. When we go into high-stakes meetings, we always go in with pixels and prototypes, which are uniquely good at cutting through bullshit and ambiguity. As a wise person once said, a prototype is worth a thousand meetings.

There are a ton of amazing designers and researchers who have been here for 10 and even 20+ years whose hard work has led to this moment of evolution for the company, and every day I am in awe of their perseverance.

Temple of the Dog concert photo
Temple of the Dog: Seattle’s greatest supergroup

Next on my list is how often we get in our own way with “procedural goo”. I’ve worked in plenty of large companies including Twitter, Disney, and MSNBC, and have never seen the level of approvals, paperwork, and rules that get in the way of speed and autonomy here. Just transferring someone from within my own org to a slightly different role within my own org took a dizzying amount of effort. At most companies, this would have been about 10 minutes of work: one minute from me and nine from someone in HR trying to navigate to the right screen in Workday.

Then we have acronyms. My GOD do we have acronyms. I actually liked acronyms before I got here! I usually think they are cute. After seeing a new one almost every single day since getting here, I have resolved to never use them either inside or outside of work. I even say “Cyan Magenta Yellow Black” out loud if I have to!

cf2gs logo
When I think of bad acronyms, I always remember cf2gs: an excellent, but unfortunately named ad agency from Seattle’s past

Finally, the last thing on my list — and this is where you come in — is dedication to craft. It is so tempting to try and “science” your way into viable products these days. Build the beginnings of a customer base through rudimentary product-market fit, and then fastidiously optimize your funnel, your game mechanics, your viral loops, your push notifications, and so on and so forth. These gains are not always easy to come by, but they are rooted in ruthless experimentation and allegiance to short-term data. Our north star is at least pretty pure — Daily Active Users — and that metric is usually a good indicator that you’ve made something people like, but doctrinaire allegiance to almost any singular metric can quickly make people forget why we are in this profession to begin with: to improve lives. Or to put it squarely in Microsoft parlance again: to help every person and organization on the planet achieve more.

If you ever find yourself asking the question “how can we increase Daily Active Users?” instead of “how can we make our product better for people?”, you’ve already lost. Metrics are trailing indicators of qualitative improvements or degradations you’ve made for your customers… they are not the point of the work.

Recently, we’ve made some excellent strides in prioritizing qualitative product improvements even when they fly in the face of metrics we care about, and it’s really gratifying to see. It reminds everyone that a product is the collision of thousands of details, and the crafting of these details requires taste.

Edwin Land and his magic Polaroid camera
The Polaroid SX-70 camera: a triumph of design, engineering, and dedication to craft.

Designers are often looked to as “owners of craft and taste”, but craft is very much a team sport. It’s not just how things look and feel but also how they work. I very much like how Nick Jones (channeling Patrick Collison) at Stripe put it in this video:

What we put out there should quite plausibly be the best version of that thing on the internet“.

To do this takes an unbroken chain of excellence:

  1. An idea that can improve lives if executed well.
  2. Foundational research to light the path before design and coding begin.
  3. Rich design explorations and prototyping to make the experience palpable.
  4. Buy-in to build it at a level of quality that makes the team proud.
  5. Impeccable UX engineering and UX writing to make sure every detail is dialed.
  6. Well-conceived server-side engineering to make it scalable and maintainable.
  7. Creative marketing to prime people for the experience.
  8. … and finally, maybe more important that anything else on this list, the will to keep refining relentlessly after the experience is launched. This part is so often neglected as companies rush to build more things.

Some people would look at this list and think “yep, makes sense”. Others would look at it and think “sounds slow and not very agile”. The trick to balancing this level of quality with speed of development is realizing that it’s often more efficient to experiment in step 3 than it is in step 6. This is why so many modern tech companies realize that hiring more designers and researchers doesn’t waste time and money… it saves time and money. With less than a week of one designer’s time, we can produce a wide variety of prototypes to test with real people. Just recently, we created an entire GPT-powered research application without even bothering a single engineer.

Design is engineering.

Finally, a brief note about prototyping. I would argue that the most impactful innovation in the craft of product development over the last 20 years has been the rise of rapid design prototyping. Prototypes that demonstrate an experience are useful not just in usability testing, but also in selling ideas up and across the organization. Engineers hate working on things that haven’t been thought through or “appropriately politicked” yet, and if you can bring them a working prototype that has already been vetted with users and various stakeholders across the company, they will love you for it and work hand-in-hand with you to get every detail right.

Design prototypes are the currency of a high-craft, high-speed product development organization, and they are increasingly the currency of our team.

Alright, back to the hiring. I plan to hire against the entire growing list of products our team is responsible for: Copilot, Windows, Edge, Bing, Start, Skype, SwiftKey, and so much more… but for now, this is a concerted hiring effort centered around Designers and UX Engineers to help build out the emerging design system for Copilot and our suite of AI-powered products.

If this is you, please have a look at the following roles we’ve just posted:

We’d love to work with you on the future of design systems at Microsoft!

I’m Joining Microsoft!

Despite living in Seattle for almost all of my adult life, I haven’t actually worked for a local company in almost ten years. Remote work is great in so many ways, but in-person collaboration is what gives me life.

In confident pursuit of that feeling, I’m thrilled to be joining Microsoft to run Design & Research for their Web Experiences organization.

I was Microsoft-adjacent 10 years ago at MSNBC.com in Building 25, but this will be my first time as a blue badge, so to speak. I’m also thrilled to be joining Liz Danzico and John Maeda, who have also started at Microsoft in the last several months. I’ve known them both for a long time and have wanted to work with them forever.

There are several things which drew me to this opportunity, but at the top of the list is the people. Not just Liz and John, but the thousands of teammates in Seattle, Vancouver, Hyderabad, Barcelona, Beijing, and many other cities. There are certainly some great solo efforts in tech, but almost all of the best work I’ve been around has been the result of getting the right people jammin’ with each other. In my first several days here, I’ve already met so many of those people, and I can’t wait to continue the momentum Albert Shum created by carrying the torch for one of the best Design & Research teams in the Pacific Northwest.

The second thing I’m super excited about is the scale of the work. I’ve worked on the largest sports site in the world and one of the largest social networks in the world, but the properties in this group reach well over a billion people. Between the (refreshingly fast!) Edge browser, MSN, Bing, and several other products, Microsoft has quietly built up one of the top five properties in the world in terms of traffic and reach. They’ve also done it with humility, knowing how far they are from being perfect. I also love that so many of these products can and will be so much more as we begin to use some of the technology that’s emerging within Microsoft. In my first two weeks, I’m already overflowing with ideas.

Finally, the other thing I’m most excited about is getting back into the office in a flexible hybrid environment. I’ve worked in-person for most of my career and remotely for the last four years, and where I’ve landed is that everyone’s preferences are different, and it’s just tradeoffs all the way down. Where you land depends on a mix of your personality, your life outside of work, and what type of job you have. For me personally, I very much like being around people and feel like I do better work when I am… but I also like getting back my commute time a couple of days a week and making daily jogging more convenient. Also, Henry (pictured above) enjoys the extra lap time. Microsoft’s hybrid policy is a nice balance, and it sounds like exactly the right setup for someone like me.

Speaking of the exactly right, this also feels — for me at least — like exactly the right time to join Microsoft. The company has been through several distinct eras over the decades, but this feels like the era of re-commitment to the planet. To customers delightful experiences, to employees a great environment, and to the natural world, a smaller and eventually negative carbon footprint.

It’s a new year, and I couldn’t be any more here for it!

How to Automatically Post your Tweets to Mastodon

Over the last several weeks, I’ve gotten in the habit of trying to move all of my Twitter activity over to Mastodon instead. I signed up for Mastodon several years ago, but only now are there enough people using it for it to replace a lot of what you might use Twitter for. Some of your friends are there, some of your favorite bots are there, and some news sources are there. What more do you need in life, really?

I’ve been using Pinafore (along with a user stylesheet I created… feel free to grab it for yourself) to use Mastodon on the web, and a combination of Ivory and Metatext on my iPhone. Ivory looks a bit nicer but Metatext has a Notifications tab that acts more you’re used to it working on Twitter.

If you want to move all of your activity over wholesale, go to town. If, however, you want to keep publishing Tweets on Twitter and have them automatically publish to your Mastodon account as well, this short guide is for you. The entire process should take around five minutes. It’s mostly just clicking around on a couple of websites.

Important: If you do this, the goal should not be just replicate your Tweets and never visit or engage on Mastodon. The goal should be to help you build your Mastodon presence and save you from having to manually double-post. Ideally you quickly get to the point where Mastodon becomes your primary crib.

Step 1: Open a Mastodon account

If you’ve already done this, great. If you haven’t, head to any server you want — like mastodon.social, for instance — and set up your account. You can always switch your server (along with any followers you accrue) later, so don’t stress about the server you choose.

Read more…

Here Lies Flash

In just a few short days, on December 31, 2020, we will say our final goodbyes to one of the most important internet technologies that ever lived: Flash.

I remember vividly the first time I saw Flash on a computer screen. It was 1997, I was finishing up college, and I had managed to teach myself enough HTML to think about pivoting from print design to interactive design as a career.

Web design, at the time, was a clumsy beast. Most web sites were essentially Times New Roman black text on a grey background with an occasional low-quality image here and there. The “design” part was often just figuring out how to best organize information hierarchies so users could feel their way around.

Once we got bored of basic HTML (there was no CSS at the time), we started doing unholy things with images. We’d set entire pages in Photoshop, slice our layouts into grids of smaller images, and then reassemble everything into a clickable mess. These were dark times.

My college, having invented PINE, was considered “on the front edge” of the internet at the time. Here’s is what our site looked like back then:

University of Washington Home Page in 1997

Even the most beautifully designed sites felt a bit lifeless, and once someone came up with a new layout that worked well, everyone would just ape it. To make matters worse, every new advancement in methods required more convoluted hacking to display correctly across Netscape, Internet Explorer, and every other fringe browser in use at the time. It was a total mess.

Here is the first version of Zeldman.com I could find, from 1998. Amazing for the era, and holds up impressively in a nostalgic, cyber-Americana sort of way, but you can see how limited we were by screen widths, color palettes, and layout technologies.

Then one day in 1997, I clicked on a link to Kanwa Nagafuji’s Image Dive site and the whole trajectory of web design changed for me. It looked like nothing I had ever seen in a web browser. A beautiful, dynamic interface, driven by anti-aliased Helvetica type and buttery smooth vector animation? And the whole thing loaded instantly on a dial-up connection with nothing suspicious to install? What was this sorcery? Sadly, I can’t find any representation of the site online anymore, but imagine the difference in going not just from black-and-white TV to color TV, but from newspaper to television.

Nagafuji’s work was such a huge, unexpected leap from everything that came before it that I had to figure out how it was done. A quick View Source later revealed an object/embed tag pointing to a file that ended in “.swf”. A few AltaVista searches later led me to the website of Macromedia, makers of ShockWave Flash (“SWF”), the technology that powered this amazing site.

I downloaded a trial version and was blown away at the editing interface. Instead of a shotgun marriage of Photoshop, HTML, browser hacks, and a bunch of other stuff that felt more like assembly than design, here was a single interface to lay out text, shapes, images, and buttons, and animate everything together into an interactive experience! It was magic.

After mucking around in the Flash editor (version 2 at the time) for a few hours, I did what every self-respecting web designer would do and immediately set out to find other cool stuff to copy. Over the course of the next several months and years I would find such gems as:

Yugop from Yugo Nakamura
Once Upon a Forest and Praystation from Joshua Davis
Nose Pilot by Alex Sacui
Natzke.com by Eric Natzke
Presstube by James Paterson
Gabocorp from Gabo Mendoza
John Mark Sorum by WDDG
2Advanced by Eric Jordan
NRG Design by Peter Van Den Wyngaert
The Hoover Vacuum Site by Fred Flade

… and of course, everything by Hillman Curtis (Rest in Peace)

(Sadly, much of this work is hard to relive due to Flash already being disabled in many browsers. I’ve tried to point to video demos where possible, but you can also try your luck with the Ruffle plug-in.)

From there, a bunch of us new designers set out to learn more about animation, type, scripting, and everything else that put you at the vanguard of the profession in those days. Flash was the first technology that showed us we could be great.

My initial effort was mdavidson.com, a rudimentary personal site that was the precursor to Mike Industries:

From there, I would move on to design Flash sites and features for ESPN, Disney, K2, The New York Rangers, and dozens of other organizations, never matching the quality of the masters listed above, but always breaking new ground in one way or another.

K2 Skates site

Other fun projects I collaborated on with my friend Danny Mavromatis included a virtual observation deck for the Space Needle, an interactive on-demand SportsCenter, and a Disney movies-on-demand service fully 20 years ahead of Disney+! All in Flash.

Perhaps the thing that gives me the most joy though is something we built and gave away for free: sIFR. What started as our brute-force attempt to use Akzidenz Grotesk for headlines on the front page of ESPN, turned into a more elegant implementation by Shaun Inman, which then turned into a scalable solution by Mark Wubben and me. We poured hundreds of hours into sIFR not to make any money but just to advance the state of typography on the web.

Over the next several years, sIFR was used to display rich type on tens of thousands of web sites. Although it relied on Flash, it was standards-compliant and accessible in its implementation, so it was the preferred choice for rich type until Typekit came along in 2009 and obviated the need for it.

All of this is to say, the role Flash played in helping transition the web from its awkward teenage years to a more mature adulthood is one I will always appreciate. And we haven’t even talked about its role in game development.

When discussing the life and death of Flash, people often point to Steve Jobs’ “Thoughts on Flash” as the moment things turned south for it. Worse yet, the idea that “Steve Jobs killed Flash”. I don’t think either of those things is actually true.

Flash, from the very beginning, was a transitional technology. It was a language that compiled into a binary executable. This made it consistent and performant, but was in conflict with how most of the web works. It was designed for a desktop world which wasn’t compatible with the emerging mobile web. Perhaps most importantly, it was developed by a single company. This allowed it to evolve more quickly for awhile, but goes against the very spirit of the entire internet. Long-term, we never want single companies — no matter who they may be — controlling the very building blocks of the web. The internet is a marketplace of technologies loosely tied together, each living and dying in rhythm with the utility it provides.

Most technology is transitional if your window is long enough. Cassette tapes showed us that taking our music with us was possible. Tapes served their purpose until compact discs and then MP3s came along. Then they took their rightful place in history alongside other evolutionary technologies. Flash showed us where we could go, without ever promising that it would be the long-term solution once we got there.

So here lies Flash. Granddaddy of the rich, interactive internet. Inspiration for tens of thousands of careers in design and gaming. Loved by fans, reviled by enemies, but forever remembered for pushing us further down this windy road of interactive design, lighting the path for generations to come.

RIP Flash. 1996-2020.

If you feel so moved, pour one out for our old friend in the comment section below.

Machine Learning and Cover Songs

There’s nothing like a great cover.

You’re rekindling angst at a Pearl Jam show and without any warning they go right into a Beatles song. You recognize some David Bowie lyrics on Spotify, and you discover it’s an unrecognizable version of Let’s Dance by M. Ward. You listen to Tiny Cities by Sun Kil Moon several times before you even realize it’s an entire album of beautifully fermented Modest Mouse songs.

How often have you thought to yourself, I would love to hear this person sing this other band’s song in their own style? For instance, I wish I could listen to Mike Doughty sing just about anything.

Over the past year or two, we’ve started to see artificial intelligence begin to approximate that dream (or nightmare, depending on your perspective). First it was eye-opening deep fake videos of past presidents appearing to say things they never said, but now it’s moved on to much more creative and cool endeavors like OpenAI Jukebox. You should read the full description on the site, but essentially they are training models to identify everything that goes into a song: instruments, lyrics, musical style, and a whole lot more. The models are primitive for now, but even at this early stage, they can start recombining things in interesting ways like having Ella Fitzgerald sing a Prince song but in the style of folk rock.

I spent a good part of the weekend messing around in Jukebox, and it’s mesmerizing. It really feels like the beginning of something big, and just as excitingly, something that could get orders of magnitude better within only a few years.

When you listen to it, it almost feels like the first words of a child… or if you prefer, the first song from Jimmy Page.

A lot of the stuff in the library is pretty rough, but here are some of the most interesting ones I found:

Everything feels very Frankensteiny right now, but imagine a few years from now when these techniques are improved and expanded. We may reach a point where there is a virtually unlimited universe of concert-quality covers you can create with just a few taps. As a music lover, this is super intriguing, but on the other hand, I wonder how musicians will feel about it. And will their opinions change based on whether we can find a way to monetize it generously for them? I could see some artists rejecting this sort of thing outright because it’s not real music in the traditional sense, and I wouldn’t blame them. But what if you told them that every time their voice was mixed into another song, they made a royalty off of it? That might change some opinions.

This is going to be a really fun space to watch closely over the next few years. Until then, I leave you with another great cover: Metallica’s Orion — by Rodrigo y Gabriela. Incidentally, the header image for this page is from their Masonic Auditorium show in 2015. Pure luck but probably the best photo I’ve ever taken.

Minimum Viable Connectivity

I remember about 15 years ago — before the launch of the iPhone — thinking quite resolutely that internet-connected phones were just a really unexciting transition phase between the desktop internet and immersive technologies like contact lenses and brain implants. We knew where we already were: amazing high bandwidth experiences on the desktop, and it seemed pretty clear where we were going in a couple of decades: even better experiences with no visible hardware whatsoever.

The new class of experiences on mobile phones at the time, however, was uninspiring. Palm Treos with barely functional browsers on them. Blackberries that handled email but little else well. T9 keyboards that were a pain to use. Barely any designers wanted to work on this stuff. It wasn’t very fun to create, use, or even tell anyone you worked on.

When the iPhone came along in 2007, it was the first mobile device that was fun to design for and fun to use for a wide variety of things. As it grew more and more useful, I began to think of internet-connected phones as quite a bit more exciting but still ultimately a transition state to full cyborg land. It seems inconceivable that in 10 or 20 years, we will still be staring down at these glass rectangles instead of directly at the world with whatever augmented reality experiences we choose in between.

As phones have gotten more comically large and the services on them more tragically addictive over the past few years, I’ve found myself wondering if there is more value in letting some of this connectivity go. Clearly smartphones provide a lot of value for us, but what is the true cost of all this convenience? Being able to receive a text from your spouse while you’re at the supermarket is valuable, but the same device that delivers you that text can deliver a social network notification while you’re driving that ends up killing you or others.

Attempting to quantify the large and small harm caused by smartphone use is a big project better suited to places like Tristan Harris’ Center for Humane Technology, but you don’t need to quantify it to admit it’s doing you some amount of harm.

There is no shortage of advice about how to make your phone less addictive. Turn off a bunch of notifications. Flip on Do Not Disturb. Use Black & White mode. Delete social networking apps. It’s all good advice, but for me, having that giant, heavy glass brick in my pocket is a constant reminder of what’s at my fingertips.

What I’ve really grown to want is less at my fingertips.

Minimum viable connectivity.

Wherever I happen to be, I want the least amount of potential digital distractions and appholes around me. It’s no different than the concept of eating healthier. When you want to lose weight, you don’t keep a bunch of junk food in your pockets and just promise to never open it. You remove junk food from your house completely.

Until recently, there was no great way to stop carrying your smartphone with you without giving up a ton of benefits. Over the past two weeks, however, I’ve begun using an Apple Watch without a phone almost all day long, and it’s been great. It’s introduced exactly the amount of digital friction I need in my life and I don’t imagine going back to hyper-connected smartphone world anytime soon.

“The best way to guarantee success is by preemptively engineering systems to reduce friction for positive habits, and increase friction for negative ones.” — Craig Mod, from the great piece I linked to above

I love that I am still generally reachable by phone or text when I wear it. I love that I can still navigate with maps. I love that I can track my runs without third party services and listen to podcasts along the way. I love that I can see when it’s about to rain.

And I love that that’s about all I can do. I don’t mind that texts are a little harder to send. I don’t even mind that there’s no camera. If I’m on vacation in an interesting place, I will surely take my phone, but do I really need to be taking more photos around town? Probably not. This is the point many people will break with me on this whole strategy, but try it. You may be surprised.

In terms of things I don’t like about about this experiment so far, it really just comes down to a couple of flaws with the watch itself: the LTE radio is pretty spotty and the Apple Podcast app is a usability disaster, both on the phone and the watch. Because the radio is weak, you really need to make sure anything you want to listen to is downloaded already, and because the apps are so bad, it’s very hard to ensure that actually happens. You’ll generally have some podcasts downloaded and ready to listen to but they just aren’t always the ones you expected. ¯\_(ツ)_/¯

Even with those problems, I still feel great about this less-connected road I’m going down. Somewhat surprisingly, I don’t even feel like I’m missing out on anything.

The hyper-connected future will probably still happen, but the form it will take doesn’t feel so inevitable to me anymore. I’ve learned in these two weeks alone that I don’t actually want every distracting digital experience in the world at my fingertips. I only want what is helpful and stays out of the way.

The last time I wore a watch was in high school, and I distinctly remember how excited I was to finally get a cell phone my junior year.

27 years later, I’m just as excited now to do the opposite.

Superhuman’s Superficial Privacy Fixes Do Not Prevent It From Spying on You

Last week was a good week for privacy. Or was it?

It took an article I almost didn’t publish and tens of thousands of people saying they were creeped out, but Superhuman admitted they were wrong and reduced the danger that their surveillance pixels introduce. Good on Rahul Vohra and team for that.

I will say, however, that I’m a little surprised how quickly some people are rolling over and giving Superhuman credit for fixing a problem that they didn’t actually fix. From tech press articles implying that the company quickly closed all of its privacy issues, to friends sending me nice notes, I don’t think people are paying close enough attention here. This is not “Mission Accomplished” for ethical product design or privacy — at all.

I noticed two people — Walt Mossberg and Josh Constine — who spoke out immediately with the exact thoughts I had in my head.

Let’s take a look at how Superhuman explains their changes. Rahul correctly lays out four of the criticisms leveled at Superhuman’s read receipts:

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Superhuman is Spying on You

Over the past 25 years, email has weaved itself into the daily fabric of life. Our inboxes contain everything from very personal letters, to work correspondence, to unsolicited inbound sales pitches. In many ways, they are an extension of our homes: private places where we are free to deal with what life throws at us in whatever way we see fit. Have an inbox zero policy? That’s up to you. Let your inbox build into the thousands and only deal with what you can stay on top of? That’s your business too.

It is disappointing then that one of the most hyped new email clients, Superhuman, has decided to embed hidden tracking pixels inside of the emails its customers send out. Superhuman calls this feature “Read Receipts” and turns it on by default for its customers, without the consent of its recipients. You’ve heard the term “Read Receipts” before, so you have most likely been conditioned to believe it’s a simple “Read/Unread” status that people can opt out of. With Superhuman, it is not. If I send you an email using Superhuman (no matter what email client you use), and you open it 9 times, this is what I see:

A log of every time someone has opened your email and what location they opened it from.

That’s right. A running log of every single time you have opened my email, including your location when you opened it. Before we continue, ask yourself if you expect this information to be collected on you and relayed back to your parent, your child, your spouse, your co-worker, a salesperson, an ex, a random stranger, or a stalker every time you read an email. Although some one-to-many email blasting software has used similar technologies to track open rates, the answer is no; most people don’t expect this. People reasonably expect that when — and especially where — they read their email is their own business.

When I initially tweeted about this last week, the tweet was faved by a wide variety of people, including current and former employees and CEOs of companies ranging from Facebook, to Apple, to Twitter:

It was also met critically by several Superhuman users, as well as some Superhuman investors (who never disclosed that they were investors, even in past, private conversations with me). I want to talk about this issue because I think it’s instructive to how we build products and companies with a sense of ethics and responsibility. I think what Superhuman is doing here demonstrates a lack of regard for both.

First, a few caveats:

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Design-Driven Companies. Are We There Yet?

It’s fashionable these days for companies to proclaim their commitment to great design.

You may hear things like “Design is very important to us” or “Design has a seat at the table” or even “We’re a design-driven organization”. As a designer evaluating job opportunities, should you take statements like this at face value or might you be able to get a clearer picture by asking questions, reviewing a company’s products, and other investigative means?

Throughout my 20 years in design, I’ve worked in everything from design-hostile to design-driven environments, and I can tell you that succeeding (and being happy) within each requires a different mindset going in.

Before discussing strategies, let’s describe several types of organizations along the design spectrum so as to identify what they look like. Importantly, when I say things like “design-driven”, I don’t necessarily mean Design-ER driven. In other words, it doesn’t mean that designers call all the shots. It just means that great care goes into every detail of the user experience of a company’s products. That level of detail could come from engineers, researchers, execs, or any number of other people (and often does!), but it also tends to correlate with designers playing key roles at the company.

The Spectrum of Design Drivenness

Design Hostile

CRMster is a 20-person startup that develops Customer Relationship Management software. There are 10 salespeople, 8 engineers, 1 CEO, and one contract designer. Most product decisions are made by the CEO and one salesperson. The rest of the team just builds whatever they are told to build. If a designer or engineer brings up concerns about a product feature, they are told to just stick to the program and produce what the CEO asked for as quickly as possible.

Design Ignorant

GitBusy is a 5-person startup building a new way to sync files across computers. All five team members are back-end engineers and they have spent their first year building out core functionality. The product is a bear to use, but it’s starting to work reliably. They keep making minor usability improvements but they’ve never thought to hire someone full-time who specializes in user experience.

Design Agnostic

MegaloBank is a Fortune 100 financial institution that employs over 10,000 people. They employ plenty of designers and design-minded people around the company, but mainly as support for other teams. If you asked the CEO of the company what his or her designers did, the response would be something like “I think they make our logos and business cards.” Important product design work does get done at Design Agnostic companies, but the people who do it just aren’t looked at as core talent the same way as sales, engineering, or marketing might be. Their compensation unfortunately reflects this.

Design Interested

CellYou is a 20-year old wireless carrier, employing over 10,000 people. They are feeling the heat from their competitors and have just embarked on a high-profile effort to redesign their product line so it is much easier to use. They don’t have all the right people in place yet, they aren’t walking the walk in terms of a user-centered product development process, and they still pay their designers a lot less than PMs and engineers, but they are starting to talk about things in the right way and starting to recognize the value of design. It may take a few years, but they are moving in the right direction. A lot of companies who say they are Design Driven are actually in this category instead.

Design Driven

HyperBowl is a 500 person company that makes a versatile kitchen appliance which can cook hundreds of different foods. It started as one chef and one engineer, but even from the very beginning, there was a relentless focus on building product prototypes and iterating them rigorously based on how they performed with users. New products are developed only when they can perform important jobs for users. At HyperBowl, there are 10 full-time designers but everyone in the company considers user experience to be one of their most important job functions. Many decisions are made with data and research, but there’s room for subjectivity, taste, and long-term vision as well.

Those are the five archetypes you’ll generally run across in the market today.

The Challenges of Each

As a designer, you may immediately think to yourself “I only want to work for a Design Driven organization!” If your goal is to join an environment that immediately affords you the ability to practice great design, then this is a natural choice. Take Apple, for instance. Whether you are fresh out of school or a 20-year design veteran, as a new employee at Apple, you won’t need to spend any of your time convincing anyone of the value of design. You will be paid roughly on par with engineers, expected to help lead the product development process, and likely do some of the best work of your career. I have a bunch of friends who have worked at Apple, and one of them summed it up best: it’s like career rocket fuel. You may find the work/life balance unsustainable in the long term, but your time there will be unencumbered by any fights about the value of design.

A lot of companies (even some of the largest and most successful in the world) will tell you they are Design Driven, but they are actually one level away, in the Design Interested category. You should always maintain a healthy suspicion about this, in fact. Like our cellular carrier above, they are in the midst of a positive transformation, but they just aren’t there yet. What this means for you as a designer (or researcher, or front-end engineer) is that not that you won’t be respected to listened to, but rather that part of your job will be to move the company from its old way of doing things to a new way of doing things. This involves a lot more than just your technical skills. It involves the patience to work in suboptimal conditions and the willingness to help lead the process of becoming more Design Driven. Thankfully since the company is already Design Interested, the “what”, “when”, and “why” have already been taken care of for you, but the “who” and “how” are still open questions. You are part of the who that will help determine the how!

A large number of companies in the world fit into the next category: Design Agnostic. These companies have found a way to turn a profit without paying as much attention to user experience as they could or should. Sometimes when you find a market need that is strong enough, you can get away with selling a “merely adequate” solution. Other times, your business is specifically aimed at gathering the most profit for the least amount of work possible. Joining a company like this requires you to be cool with one of two things. Either you are content to produce “good enough” work in a system that doesn’t value you as core talent, or you are interested in taking on the much larger challenge of turning your company into more of a Design Driven organization. To be clear, thousands of designers have no problem with the former, and I have no problem with that career choice. In fact, sometimes it’s all that exists, depending on geography, experience, economy health and other factors. The latter, however, is one of the hardest and most substantial things you could ever accomplish in your career. Imagine being the person (or small group of people in this case) who got Google to care about design? If you find yourself thinking about joining one of the many Design Agnostic companies in the world today, don’t think of it necessarily as “settling”. Think of it as an opportunity to redesign the entire product development factory within. If you succeed, they’ll carry you around on a rickshaw.

The next category, Design Ignorant companies, are actually a bit easier to make an impact in than Design Agnostic companies. That is because Design Ignorant companies haven’t normalized the role of design yet. They simply haven’t experienced it yet. In fact, you may even be treated more as a hero upon your arrival at a Design Ignorant company than a Design Driven company. Going back to our example above with the file-syncing startup, imagine how much immediate impact you’ll make when you optimize the sign-up flow, improve the product copy, and flatten the navigation. If you do your job well, you’ll be appreciated right from the start. Unfortunately, you probably won’t be paid well, but Design Driven companies are usually the only companies that pay designers what they are worth at this point. This is changing for the better, but it is a multi-year process.

Finally, at the end of the spectrum, are Design Hostile companies. Think of the challenges and rewards here much the same as Design Agnostic companies except these companies have already decided that your craft is but a necessary evil for them. This by far the least desirable company type for people in our field to work at, but hey, there are plenty of cases of these sorts of companies turning around eventually. In fact, I would venture to say that using my definitions here, there are plenty of Design Agnostic companies today that ten years ago may have been Design Hostile. If you find yourself entertaining an offer from a company like this, you really need to determine how pliable they are with regard to how they view design and whether you’re ok with that.

Strategies to Know What You’re Getting Into

There are four ways to determine what sort of company you’re thinking about working at: looking, listening, asking, and verifying. You should do all four.

Looking

Thinking about working for that popular, growing auto insurance company in town? Start looking at their products. Does their visual identity seem professionally executed? How usable is their app or website? Go ahead and actually sign up if you can. Was the process reasonably well designed? Nothing is ever perfect, but often times, just spending an hour or two with a company’s product will give you a feel for how much they care about details. And when I say “details”, I don’t just mean how buttery smooth is the animation but also how smooth is the “Forgot Password” process?

Take notes as you go, in case you end up interviewing there. It’s always good to have firsthand knowledge and constructive criticism ready for when someone asks you what changes you’d make to their product (do this tactfully though, as you don’t know what factors went into a given product decision).

Make sure to also look at competitors’ offerings. While the auto insurance site may not be as modern as your favorite social networking site, maybe it’s head and shoulders better designed than all other auto insurance sites. In an industry that perhaps moves slowly in terms of technology upgrades, maybe this company is moving 10x faster than its competitors. That would be a pretty good sign.

Listening

When recruiters or employees of the auto insurance company try to pitch their company to you, they will usually do so in a way that portrays their company in as positive of a light as possible. In other words, although it does happen, you’ll rarely hear a prospective employer tell you “design is an absolute mess here”, even though it very well might be. Instead, listen for coded language. Things like:

“Over the last year, design has become a real priority.” Why? What happened before that?

“Design has a seat at the table now.” Cool, why now? What problems occurred before that?

“We’re looking to bring some fresh design blood into the company.” What are you doing with all of this blood? What problems with the current staff are you trying to solve?

Every statement should be examined for possible hidden meaning. By the way, these people are just doing their jobs. When I recruit designers, I also try to accentuate the positive. It’s your job as a candidate though, to dig deeper. Especially since your prospective employer will be digging deeply into your work as well.

Asking

In addition to responding to statements like the coded ones above, there are some good universal questions you can ask on your own:

“What is the attrition rate of designers at your company?” This should ideally be low.

“Are designers paid on par with engineers and PMs? If not, how close are they?” Pay should ideally be close or equal. Don’t be surprised if you get some bad answers or non-answers here, depending on company.

“Who does the Head of Design report to?” The CEO is always the best answer, but a great COO, CTO, CPO, GM is fine too.

“When someone needs to break a rule here, what is the process?” If they need help, perhaps give an example of a rule you’ve needed to break in the past, and ask how they’d handle it.

“What is the one negative or challenging thing about working here that no one is telling me right now and I will only find out after I start?” It’s a bad sign if they don’t have an answer.

“When someone has an idea for something they want to build, what is the process of getting approval and then building it?” Ask for a lot of detail here, right down to prototyping, user testing, and release.

“How do decisions get made when Design, Engineering, and PM can’t agree on something?” You’ll have to judge for yourself whether you like the answer.

“Tell me about a time when a product design was made subjectively or in the face of opposing data.” You might need to ask a particular person to get a good answer here, but if the answer is “never”, that’s indicative of an overly rigid decision making process.

“How are designers judged and promoted here? Is it different than Engineering and PM?” Ideally there is a thoughtful, well-articulated process in place that rewards behaviors and not just outcomes. If you’re judged solely on the metrics you move, that’s a bad sign.

It’s up to you to ask these questions with tact and at the appropriate times, but you are well within your rights to ask them. In fact, it’s a bit reckless not to.

Verifying

Do you know anyone who has worked for this company, past or present? If so, ask to get coffee with them. Depending on how secret your candidacy is, you may need to keep your questions general, but there is a lot to be gleaned from employees who aren’t trying to pitch you on anything. Start by asking what their overall experience was like. Would they recommend the company to a friend as a good place to work? Dig, if you can, into some of the things the recruiter or hiring manager told you.

“I’ve heard the decision making process is pretty egalitarian. Design, PM, and Eng all take part in that process.”

To which you might hear:

“Yep. It’s a great system. I always felt like an equal partner.”

Or:

“Haha. I am dying of laughter right now. If you’re in the room at all, it will just be to tell you what decision has been made without you.”

Importantly, when you hear things like this, you need to get a feel for whether those conditions still exist. Did this employee work there three months ago or three years ago? Is the person who enacted that decision-making process still even there? Because of the passage of time, you may get both false positive and false negative results from ex-employees. It’s ok though… it’s just a data point for you.

Also, at massive, sprawling companies, you may get different answers depending on which department’s employees you talk to. Maybe the auto insurance company’s consumer product is built in San Francisco and its broker product is built in Seattle. Maybe the working environment in San Francisco sucks but it’s great in Seattle.

So… by looking, listening, asking, and verifying, you can get a pretty accurate idea of what sort of company you are thinking about joining.

Fixing the Product Development Process, One Company at a Time

One of the reasons I wrote this piece was that I read a Tweet from a well-followed person in San Francisco talking about how the best companies in the world are all design-driven now. I get what he was trying to say, and I think that directionally, more companies are design-driven now than ever, but the vast majority of boots-on-the-ground designers in the world know how much work is still left to do. They also know that just because some high-profile companies have figured out that design is important, that doesn’t mean their own company in Seattle, or Omaha, or Bangalore has. A rising tide lifts all boats, but this is more of a slow motion wave you need to stay upright long enough to ride.

Finally, I also think it’s important to highlight the value of helping upgrade your own company’s product development processes. Designers love talking about the actual product design work they’ve done in the form of visual artifacts and launched services. Just as valuable, however, is the work that went into reshaping the processes that made these products possible. PMs make their own PM-centric contributions to what product development processes look like, and engineers do the same with their own lens. By adding your own perspective as a designer and improving the product development process at your own company, you’re accomplishing something you may not even get to accomplish at a place like Apple… and that, is something to be proud of.

(This post also available on Medium.)

An Epitaph for Newsvine

Today, the creation I am most proud to have brought into the world disappeared from the internet.

After 11 years and 7 months in service, Newsvine, a participatory news site I launched with four friends on March 1st, 2006 was officially sunsetted by NBCNews.

Although I’ve been away from the company and the service for five years now, today brings back a rush of memories and some perspective on how the problems Newsvine set out to solve over a decade ago are actually the opposite of the problems that most need solving today.

In 2005, I found myself five years into a stint at Disney, wondering what was next for news. We owned ESPN, ABCNews, and several other media properties, but most of the fresh new takes on news seemed to be coming from non-traditional sources. Neither Twitter nor the iPhone had been invented yet, and Facebook was still just a campus dating site, but blogs were sprouting up by the thousands and sites like Digg and Slashdot were becoming popular destinations.

There seemed to be this growing bifurcation between mainstream media and citizen journalism. Mainstream newsrooms didn’t want to share their platform with amateur writers, and a lot of amateur writers grew more distrustful of mainstream media. Our big idea with Newsvine was to license the same Associated Press feed of professional reporting that made up the majority of what you’d see on a site like CNN.com, publish it faster than any other site in the world, and enlist citizens from around the world to create original, paid journalism around and alongside it… and open up every single piece of content for threaded discussion as well.

In other words:

CNN = AP Wire stories + Professional Journalism
Newsvine = AP Wire stories + Citizen Journalism + Discussion

… and we could do it all with a staff of under 10 people.

We didn’t know for sure if it was going to work, but the day we decided we’d be happy to have tried it even if it failed was the day we ended up quitting our jobs (incidentally, if you are thinking about leaving your job for a new risky thing, this is the acid test I recommend).

We spent about 6 months getting the company off the ground and the service into public beta, and it wasn’t long until extraordinary acts of journalism began appearing. Chris Thomas, one of our most prolific users, broke news of the Virginia Tech shootings on Newsvine before it appeared anywhere else. Jerry Firman, a 70 year old Newsviner from Ohio, got his name on the ballot for Congress and documented the process of running for office. Corey Spring, a student at Ohio State, scored an original interview with Dave Chappelle.

The design, tech, and operational work associated with growing Newsvine were fairly straightforward, but the one thing that seemed to get more and more difficult as the site grew was moderating and cultivating the community. Your first 1000 users are easy. People are just happy to be there. Then when you get to 10,000 you have a few fights here and there but nothing unmanageable. Even at 100,000, a small team of thoughtful people can stay on top of things. But when you hit 1 million, 10 million, and beyond, the community becomes much less intimate and more volatile.

Such was the case when we were acquired in 2007 by MSNBC.com (now NBCNews.com). Our site was already decently big but MSNBC’s was many times bigger… about 45 million people at the time. The post-acquisition work was twofold: 1) continue growing Newsvine as a standalone property, 2) use our technology to add registration, profiles, discussion threads, and other features to MSNBC.com. We also ended up powering all of the company’s blogs and some other things.

I ended up staying at MSNBC for about five years, and I would say the results of the experiment were mixed overall. On the upside, we provided technology that helped launch new editorial brands quickly and connect journalists to their audiences, but on the downside, “community” at that scale can be very messy. Additionally, with the eventual rise of Twitter and Facebook, Newsvine never grew to those usage levels. MSNBC.com was a great parent throughout though, and I have nothing but love for the people I worked with.

It’s interesting to compare Newsvine (and sites like it) to the now wildly successful fortunes of Facebook and Twitter. Newsvine at its core was a news site with a social network wrapped around it. Facebook at its core is a social network with news (and photos, and events, etc) wrapped around it. Twitter is probably structured more like Facebook in this regard as well, but its biggest challenge, in my opinion, has always been a lack of commitment to building those real-life social connections into the service.

When we look at how the average person’s news and media diet has changed over the last decade or so, we can trace it directly back to the way these and other modern organizations have begun feeding us our news. Up until 10 or 15 years ago, we essentially drank a protein shake full of news. A good amount of fruits and vegetables, some grains, some dairy, some tofu, and then a little bit of sugar, all blended together. Maybe it wasn’t the tastiest thing in the world but it kept us healthy and reasonably informed. Then, with cable news we created a fruit-only shake for half the population and a vegetable-only shake for the other half. Then with internet news, we deconstructed the shake entirely and let you pick your ingredients, often to your own detriment. And finally, with peer-reinforced, social news networks, we’ve given you the illusion of a balanced diet, but it’s often packed with sugar, carcinogens, and other harmful substances without you ever knowing. And it all tastes great!

As someone who has created Newsvine, worked at Twitter, and had many discussions with people at Facebook, I can tell you that this sort of effect was never “part of the business plan”. However, maximizing engagement was and still is, and that has led to a world in which what appears on people’s screens is what is most likely to keep one’s attention, as opposed to what is actually most important to know and understand.

The solutions to these problems will not come easy. They aren’t as simple as banning some jerk from Twitter or improving bot detection on Facebook. We’ve trained people to get their news and information from the cookie jar, and since we now know exactly what that world looks like, we must begin the job of untraining them… or at least engineering a healthy cookie.

We probably got a lot of things wrong at Newsvine, but one thing I still feel we got absolutely right is our longstanding tagline:

Get Smarter Here.

That’s really the only promise we ever wanted the service to fulfill.

After 800,000 articles, 65 million comments, 11+ years, thousands of new friendships, and at least one marriage and child from the site that I’m aware of, I’m confident it has fulfilled its mission for at least some who roamed its jungles.

(Special thanks to the entire Newsvine community. Without the dedicated efforts of all of you, we would have never had this special corner of the internet to write, meet new people, and have our perspectives changed. Thanks also to my partners Calvin, Mark, Lance, Josh, Tom, Tyler, Sally, Luke, Todd, Bobby, Dave, Arun, Jim, Mike, Brenda, Carl, Charlie, Rex, and everyone else at MSNBC.com for making this all possible. Also, extra special thanks to Nick, one of our investors, for introducing me to my wife, who I would have never met were it not for this little chance we took. And finally, thanks to my wife who helped get me through everything back then and since.)

(This post also available on Medium.)

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