Remote Team

Drive by comments, or likes, while working remotely

In a quick conversation this morning with Davide Casali, who is a founding member of our new Design Ops team led by Alison Rand, he brought up a phrase I often hear while working remotely of a “drive by” comment. On the one hand that can sound a bit macabre like in the case of how it’s often used in the media involving shootings.

But if we consider it in more of a “pop” way, we end up on a YT music video with close to 150MM views called “Drive By” — referring to driving by a potential love interest and missing out on love. In other words, it’s about being non-committal.

That’s the spirit with which Davide described a phenomenon where one can post design work within a remote organization hoping for substantive commentary, and instead just get a drive by. What does he mean by that? I think it’s one of three things:

  • A “like” — which is as useful as a wet tissue when you’ve just sneezed.
  • One positive word, such as “Awesome!” — which beats a “like” by 5%.
  • One negative word, such as “Awful!” — which does a ton of damage.

Any of these three options lack commitment and fall into the category of being marginally more useful or more damaging than saying nothing at all. I think for that reason remote cultures can easily degrade to going silent.

Why? Because sharing a longer comment that is more substantive can break the flow of your day while working async. You may say the wrong thing, and then somebody will appear out of nowhere and start to argue with you. And if you don’t respond to them (because everyone’s watching to and waiting to see what happens) then you’re a bad person. Hey, that sounds like … the Internet (smile). 

As drive by comments and likes go, if you’re curious about my own method when working with my team it is:

  1. I use a “like” to signify to someone that I’ve read what they posted. It doesn’t have to mean I agree with it.
  2. I use a comment to share an opinion I might have. But I don’t expect anyone to change their mind — my goal is to drive the overall direction, but not to actually micro-direct. 
  3. I use a comment to ask a question that I’d love to know the answer around — or at least I’d like to be sure that the person has asked the question themselves. Ultimately I don’t need the answer.

Okay, this is kind of a drive by blog post as I need to get back to work. I hope it’s useful to you. It was useful to me to write this, so let’s hope for win-win! —JM

Photo by anja. on Unsplash

Remote Team

2016 Curious Minds podcast on design

I was curious to try out WordPress developer and guru Helen Hou-Sandí’s new Simple Podcasting plugin for Gutenberg. 

CM_062: John_Maeda on Great Design

Wow! That was so easy! —JM

Remote Team

Getting on the same page in an all-remote team

Update for 2020

Since sharing this post, I’ve joined Publicis Sapient as Chief Experience Officer in 2019 to bring a computational mindset to established companies so they can become more “AI Ready.” You can learn more about our approach to remote work and also about our rapid response teams at our evolving microsite.

Although the variety of tools available to fully distributed teams is staggering — everything from virtual stand-ups, sit-downs, async, sync, todo, not-todo, audio plus screen, all video, post-it shares, partial video, full video, AR, VR, and so forth — it’s not an easy to thing to connect 1-to-many. 

However connecting 1:1 is easy because there’s no ambiguity with respect to who’s communicating. That goes for all-remote or all-premise the same way. Direct, unfiltered communication is super powerful.

But when you’re in a group larger than two, then all-remote degrades much quicker than all-premise. I believe it’s because of the following reasons:

  1. Spatial cues vanish and it gets hard to coordinate a shared view of everyone in the same space. The left, right, back, front of a room aren’t usable as orienting devices. You can’t use your eyes to look to someone and they know you’re looking at them — so gaze doesn’t matter. In theory VR- and AR-based systems will help to solve this.
  2. Everyone isn’t comfortable with their video on and/or their audio on. When working remotely there may be a background noise so you need to turn the mike on mute; you or the room your in may not look great, so you turn the camera off. It’s hard to gauge the attention level of the room so misunderstanding forms more easily.
  3. Async is the norm, so being in sync mode feels extra constraining and slow. Over time when you are working all-remote, you come to get used to communicating async and get the benefits of being able to manage multiple streams of communication. So being in sync mode can feel slow and cumbersome.

These detractions aside, sync space can be useful for getting on the same page because it’s a significant investment by everyone in being co-present. It’s the closest thing to a handshake in an all-distributed environment to just show up in the same sector of spacetime.

As a small courtesy the 2019 #DesignInTech Report PDF link and the 2018 #DesignInTech Report PDF link will be sent to you soon after you sign up! —@johnmaeda

When working in sync-time, the importance of timezone inclusivity comes to the foreground. This was an early suggestion made by my Automattic colleague Paolo Belcastro — that I’m forever grateful he gave me. I tried running in three timezones a while for my all-hands as an experiment, but over time I realized that two worked fine. So whenever I run an all-hands in design, I run it twice with identical content: one in US/EMEA and another in APAC/US.

Looking back to my early days (a year ago 😉 ) I realize that I overdid my sync time asks in the beginning, and so I scaled them back because it didn’t fit the overall culture. But I’ve kept some regular sync time, and I keep experimenting with how to make async 1-to-many exchanges as impactful as sync exchanges can be. How? I try to keep listening to my constituents, and I am iterating as I blog! —JM

Remote Team

Data, Inclusion, Craft Principles at Automattic Design

Originally published on

We’ve spent the last half year at Automattic Design finding our design principles. That might sound easy to do when so much has been written out there about design. But we’re the world’s largest all-remote design team, so we felt there was a need to brew our own.

  1. Start from curiosity. Welcome and seek out difference.
  2. Intuition is grounded in interpretation through iteration.
  3. Search for and tell stories about people, not just data.
  4. Consistency builds trust. Speed builds trust. Simplicity builds trust.

The design team has gone through many iterations, and will likely go through many more. In essence, our design principles are all about people. And they’re essentially about our constant need to understand people who are unlike ourselves in order to design better products and services for the entire world. How do we go about serving these people best? We need to listen to them.

So we’re now understanding our customers through “organically-farmed” customer research practices that have been a pleasure to get to watch grow and set root within our design community. In addition, we’re all fans of Rochelle King and her mantra to be “data aware.” And Kat Holmes joined Automattic’s Board of Advisors last year — we’re super proud to have her tutelage on the inclusive design front.

I’ve enjoyed seeing the four principles of Automattic Design emerge because it’s how I’ve tried to serve my own customers: namely, the designers of Automattic. Let me use the principles in the context of explaining how they apply.

Start from curiosity. Welcome and seek out difference.

From day one of my arrival, I’ve espoused the importance of Kim Scott’s radical candor concept. I use it in the context about the feedback I give, but it’s often more about the feedback I look to receive. The designers of Automattic have grown to be super candid with me about their difference in opinions about directions I’ve taken. It’s so much easier to serve one’s constituents when you hear immediate and direct feedback with candor. Because I can take it in and immediately decide how to course correct, if necessary. And it’s often needed (wink) — I’m not at all perfect.

Intuition is grounded in interpretation through iteration.

I’ve often had an idea set in my mind when working with someone on my team, and then it’s been completely changed after actually working with them. It’s a process of learning to work with someone else — and it goes in both directions as they learn me. Being hypersensitive to how it goes well with someone, or how it doesn’t go well, isn’t a matter of trying just one time. You need to try over and over again until the connection forms. Iteration is truly everything — and intuition becomes an end result that is crafted, instead of just something you use on the front end and never bother to correct or reshape. That’s called guessing!

Search for and tell stories about people, not just data.

I find that the more senior that you get, the more you like to throw down numbers. Numbers sound awesome when you’re trying to make a point. And then it happens — you forget that the numbers connect with real people. It’s so easy to get caught in the ego of rationality. I’ve been lucky to have many mentors who’ve always cautioned me to not “go numerical” even when my most mathy-ness tries to take over my brain. It’s always paid dividends for me to focus on the people first; and the numerical data is a great special sauce to add to the overall mix.

Consistency builds trust. Speed builds trust. Simplicity builds trust.

In my book The Laws of Simplicity, my favorite law has always been the Law of Trust.

> Excerpted from Page 1 of my book, The Laws of Simplicity

Imagine an electronic device with only one unlabeled button on its surface. Pressing the button would complete your immediate task. Do you want to write a letter to Aunt Mabel? Go ahead and press the button. Click. A letter has been sent. You know with absolute certainty that it went out and expressed exactly what you needed. That’s simplicity. And we are not far from that reality.

Every day the computer becomes increasingly smarter. It already knows your name, address, and credit card number. Knowing where Aunt Mabel lives and having watched you write a letter to her before, the computer can send a fair approximation of a kindly email to her from you. Just click a button and the deed could be done—finito. Whether the message is coherent and keeps you on dear Aunt Mabel’s Christmas list is another story, but that is the price of not having to think. In simplicity we trust.

Why? Because trust is all that matters when people are involved. And when people use your digital products, you (= your products) need to be trustworthy.

Okay! My blogging break is over. Thanks for reading! —JM

Remote Team

Many illustrators design and work remotely

Liz Meyer / Shauna Lynn / Grace Sandford / Alleanna Harris / Megan Piontkowski / Jade Johnson

A few links I clicked on from Dan’s list …

I was happy to see a call by Dan Mall for illustrators out there, and the discussion thread has a bunch of talented folks to impart a heightened sense of humanity to any digital project out there in remotelandia.

Illustration is a field where working remotely is quite common. And many writers do the same as well. So it means there’s an incredible amount of talent to tap into out there for remote design teams with respect to imagery and content — what are you waiting for? —JM

Remote Team

Remote work in the 2018 #DesignInTech Report

42% of designers surveyed work most only on premise. The rest work blended (41%) or all-remote (16%).

2018 Design in Tech Report
Remote Team

25+ insights from remote design team members

This is a set of tips we’ve gathered at Automattic Design from less than a year ago. Enjoy! —JM

Getting Started for Remote Designers

Design Processes for Remote Designers

Customer and User Research for Remote Designers

Teamwork and Leadership for Remote Designers

Environment and IRL Hacks for Remote Designers

Addressing Isolation Challenges for Remote Designers

Toolkits and Systems for Remote Designers

Remote Team

Thoughts on leading a remote team

Update for 2020

Since sharing this post, I’ve joined Publicis Sapient as Chief Experience Officer in 2019 to bring a computational mindset to established companies so they can become more “AI Ready.” You can learn more about our approach to remote work and also about our rapid response teams at our evolving microsite.

I thought I’d take advantage of Gutenberg‘s imminent release to use it as often as I can for what it was designed for: writing. But I’ve been wondering what to write about …

On a recent visit to Silicon Valley, I noted how there are more than a few major technology companies that are wondering how to make a fully distributed (aka “remote”) design team work well. They were all asking me how it’s done at Automattic. The ? went off in my head.

I feel so fortunate to have stepped deep into the territory of all-distributed teams by joining the Automattic universe 22 months ago, and I have enjoyed every minute of it. But I haven’t had time to really write about the experience. So let me start!

First of all I’m using a cool “WP LinkedIn Auto Publish” plugin so I can connect to an audience I have over there automatically. I had wanted to connect in my Medium account but unfortunately they haven’t updated the plugin … but I guess I can just copy and paste stuff directly over there.

Secondly, I should start out by finding what folks would like to know about remote design teams. Let me start with a rough framework like: 1/ How does it work? 2/ How it doesn’t work? 3/ How do you make it work better? If I really get going I’ll open a TypeForm to gather more information.

How does it work?

Automattic is a 700-person all-remote company with one key secret to how we work well in an all-distributed fashion: it’s got to work. In other words, it all works well because it’s the only way that we operate. We have no headquarters to rely upon, so we figure out how to make-do without one.

A few years ago our CEO Matt Mullenweg shared this key thought:

“While it’s possible to work remotely, there’s a bonding and a familiarity that develops when you’re in person together that’s irreplaceable.”


And that’s the second secret to Automattic: we get together IRL (In Real Life) throughout the year. We gather in all kinds of places all around the world in small groups and across teams — and what makes it cost effective is that we don’t have a physical infrastructure to pay for or any other large capital outlay. Cool, huh?

As a small courtesy the 2019 #DesignInTech Report PDF link and the 2018 #DesignInTech Report PDF link will be sent to you soon after you sign up! —@johnmaeda

Lastly, the third secret to Automattic is the people. We’ve got great people who are passionate about making the Web a better place. The idea of safeguarding the Internet’s global, distributed nature is sacrosanct for us — so our values overlap perfectly with how we operate.

Thanks for visiting, and I’ll try to keep this up so I can get through all three pieces of my rough framework. So next up: How it doesn’t work? —JM