[Bloganuary] Dream Job

This post is part of my attempt at Bloganuary 2024. Today’s prompt is:

What’s your dream job?

It feels like a bit of a cop-out to say I’m already doing it, but that’s true. Well, mostly (read on and I’ll make a counterpoint!).

Automattic

Dan (wearing a rainbow bandana) waves at the camera; behind him are four work colleagues, and behind that the Colosseum in Rome.
Getting to hang out with my awesome teammates in various locations around the globe is a plus.

I’m incredibly fortunate that my job gets to tick so many of the boxes I’d put on a “dream job wishlist”:

  • I work on things that really matter. Automattic’s products make Web publishing and eCommerce available to the world without “lock-in” or proprietary bullshit. I genuinely believe that Automattic’s work helps to democratise the Internet and acts, in a small way, as a counterbalance to the dominance of the big social media silos.
  • I get to make the world a better place by giving away as much intellectual property as possible. Automattic’s internal policy is basically “you don’t have to ask to open source something; give away anything you like so long as it’s not the passwords”.1 Open Source is one of the most powerful ideas of our generation, and all that.
  • We work in a distributed, asynchronous way. I work from where I want, when I want. I’m given the autonomy to understand what my ideal working environment is and make the most of it. Some mornings I’m just not feeling that coding flow, so I cycle somewhere different and try working the afternoon in a different location. Some weekends I’m struck by inspiration and fire up my work laptop to make the most of it, because, y’know, I’m working on things that really matter and I care about them.
  • I work with amazing people who I learn from and inspire me. Automattic’s home to some incredibly talented people and I love that I’ve managed to find a place that actively pushes me to study new things every day.
  • Automattic’s commitment to diversity & inclusion is very good-to-excellent. As well as getting work work alongside people from a hundred different countries and with amazingly different backgrounds, I love that I get to work in one of the queerest and most queer-affirming environments I’ve ever been paid to be in.

Did I mention that we’re hiring?2

Three Rings

Dan sits at a boardroom table in an airy, bright room. He's wearing an Automattic t-shirt that reads "Let's make the Web a better place." In the background, several other people discuss a pile of post-it notes that have begun to pile up on the table.
I don’t know how I managed to select a photo of my fun-loving kickass volunteers that’s somehow more dry and corporate than the photo of my work colleagues above.

But you know where else ticks all of those boxes? My voluntary work with Three Rings. Let me talk you through that wishlist again:

  • I work on things that really matter. We produce the longest-running volunteer management system in the world3 We produce it as volunteers ourselves, because we believe that volunteering matters and we want to make it as easy as possible for as many people as possible to do as much good as possible, and this allows us to give it away as cheaply as possible: for free, to the smallest and poorest charities.
  • I get to make the world a better place by facilitating the work of suicide helplines, citizens advice bureaus, child support services, environmental charities, community libraries and similar enterprises, museums, theatres,  charity fundraisers, and so many more good works. Back when I used to to helpline volunteering I might do a three hour shift and help one or two people, and I was… okay at it. Now I get to spend those three hours making tools that facilitate many tens of thousands of volunteers to provide services that benefit an even greater number of people across six countries.
  • We work in a distributed, asynchronous way. Mostly I work from home; sometimes we get together and do things as a team (like in the photo above). Either way, I’m trusted with the autonomy to produce awesome things in the way that works best for me, backed with the help and support of a team that care with all their hearts about what we do.
  • I work with amazing people who I learn from and inspire me. I mentioned one of them yesterday. But seriously, I could sing the praises of any one of our two-dozen strong team, whether for their commitment to our goals, their dedication to making the world better, their passion for quality and improvement, their focus when producing things that meet our goals, or their commitment to sticking with us for years or decades, without pay, simply because they know that what we do is important and necessary for so many worthy causes. And my fellow development/devops volunteers continue to introduce me to new things, which scratches my “drive-to-learn” itch.
  • Three Rings’ commitment to diversity & inclusion is very good, and improving. We skew slightly queer and have moderately-diverse gender mix, but I’m especially impressed with our age range these days: there’s at least 50 years between our oldest and youngest volunteers with a reasonably-even spread throughout, which is super cool (and the kind of thing many voluntary organisations dream of!).

The difference

The biggest difference between these two amazing things I get to work on is… only one of them pays me. It’s hard to disregard that.

Sometimes at Automattic, I have to work on something that’s not my favourite project in the world. Or the company’s priorities clash with my own, and I end up implementing something that my gut tells me isn’t the best use of my time from a “make the world a better place” perspective. Occasionally they take a punt on something that really pisses me off.

That’s all okay, of course, because they pay me, and I have a mortgage to settle. That’s fine. That’s part of the deal.

My voluntary work at Three Rings is more… mine. I’m the founder of the project; I 100% believe in what it’s trying to achieve. Even though I’ve worked to undermine the power of my “founder privilege” by entrusting the organisation to a board and exec that I know will push back and challenge me, I feel safe fully trusting that everything I give to Three Rings will be used in the spirit of the original mission. And even though I might sometimes disagree with others on the best way forward, I accept that whatever decision is made comes from a stronger backing than if I’d acted alone.

Three Rings, of course, doesn’t pay me4. That’s why I can only give them a few hours a week of my time. If I could give more, I would, but I have bills to pay so my “day job” is important too: I’m just so incredibly fortunate that that “day job” touches upon many of the same drives that are similarly satisfied by my voluntary work.

If I didn’t have bills to pay, I could happily just volunteer for Three Rings. I’d miss Automattic, of course: there are some amazing folks there whom I love very much, and I love the work. But if they paid me as little as Three Rings did – that is, nothing! – I’d choose Three Rings in a heartbeat.

But man, what a privileged position I’m in that I can be asked what my dream job is and I can answer “well, it’s either this thing that I already do, or this other thing that I already do, depending on whether this hypothetical scenario considers money to be a relevant factor.” I’m a lucky, lucky man.

Footnotes

1 I’m badly-paraphrasing Matt, but you get the gist.

2 Automattic’s not hiring as actively nor voraciously as it has been for the last few years – a recent downtown in the tech sector which you may have seen have heavily affected many tech companies has flooded the market with talent, and we’ve managed to take our fill of them – we’re still always interested to hear from people who believe in what we do and have skills that we can make use of. And because we’re a community with a lot of bloggers, you can find plenty of first-hand experiences of our culture online if you’d like to solicit some opinions before you apply…

3 Disclaimer: Three Rings is the oldest still-running volunteer management system we’re aware of: our nearest surviving “competitor”, which provides similar-but-different features for a price that’s an order of magnitude greater, launched later in the same year we started. But maybe somebody else has been running these last 22 years that we haven’t noticed, yet: you never know!

4 Assuming you don’t count a Christmas dinner each January – yes, really! (it turns out to be cheaper to celebrate Christmas in January) – as payment.

Dan (wearing a rainbow bandana) waves at the camera; behind him are four work colleagues, and behind that the Colosseum in Rome.× Dan sits at a boardroom table in an airy, bright room. He's wearing an Automattic t-shirt that reads "Let's make the Web a better place." In the background, several other people discuss a pile of post-it notes that have begun to pile up on the table.×

Magician Roles

Because I work somewhere hip enough to let people tweak their job titles, mine is “Code Magician”.

Employee directory photocard showing "Dan Q, Code Magician on Fire (Woo), started Oct 18th, 2019".

LinkedIn isn’t as hip as Automattic, though. That’s why they keep emailing me sector updates… for the “Magician” sector… 😅

Email from LinkedIn with the subject "Hiring trends for Magician roles".

Employee directory photocard showing "Dan Q, Code Magician on Fire (Woo), started Oct 18th, 2019".× Email from LinkedIn with the subject "Hiring trends for Magician roles".×

Announcers and Automation

Nowadays if you’re on a railway station and hear an announcement, it’s usually a computer stitching together samples1. But back in the day, there used to be a human with a Tannoy microphone sitting in the back office, telling you about the platform alternations and destinations.

I had a friend who did it as a summer job, once. For years afterwards, he had a party trick that I always quite enjoyed: you’d say the name of a terminus station on a direct line from Preston, e.g. Edinburgh Waverley, and he’d respond in his announcer-voice: “calling at Lancaster, Oxenholme the Lake District, Penrith, Carlisle, Lockerbie, Haymarket, and Edinburgh Waverley”, listing all of the stops on that route. It was a quirky, beautiful, and unusual talent. Amazingly, when he came to re-apply for his job the next summer he didn’t get it, which I always thought was a shame because he clearly deserved it: he could do the job blindfold!

There was a strange transitional period during which we had machines to do these announcements, but they weren’t that bright. Years later I found myself on Haymarket station waiting for the next train after mine had been cancelled, when a robot voice came on to announce a platform alteration: the train to Glasgow would now be departing from platform 2, rather than platform 1. A crowd of people stood up and shuffled their way over the footbridge to the opposite side of the tracks. A minute or so later, a human announcer apologised for the inconvenience but explained that the train would be leaving from platform 1, and to disregard the previous announcement. Between then and the train’s arrival the computer tried twice more to send everybody to the wrong platform, leading to a back-and-forth argument between the machine and the human somewhat reminiscient of the white zone/red zone scene from Airplane! It was funny perhaps only because I wasn’t among the people whose train was in superposition.

Clearly even by then we’d reached the point where the machine was well-established and it was easier to openly argue with it than to dig out the manual and work out how to turn it off. Nowadays it’s probably even moreso, but hopefully they’re less error-prone.

The "Mercado de Abasto" (central wholesale fruit and vegetable market) of Rosario, Argentina, 1931. Horses with carts work alongide automobiles and an omnibus.

When people talk about how technological unemployment, they focus on the big changes, like how a tipping point with self-driving vehicles might one day revolutionise the haulage industry… along with the social upheaval that comes along with forcing a career change on millions of drivers.

But in the real world, automation and technological change comes in salami slices. Horses and carts were seen alongside the automobile for decades. And you still find stations with human announcers. Even the most radically-disruptive developments don’t revolutionise the world overnight. Change is inevitable, but with preparation, we can be ready for it.

Footnotes

1 Like ScotRail’s set, voiced by Alison McKay, which computers can even remix for you over a low-fi hiphop beat if you like.

Automattic Privilege

I’ve been thinking recently about three kinds of geographic privilege I enjoy in my work at Automattic. (See more posts about my experience of working at Automattic.)

1. Timezone Privilege

Take a look at the map below. I’m the pink pin here in Oxfordshire. The green pins are my immediate team – the people I work with on a day-to-day basis – and the blue pins are people outside of my immediate team but in its parent team (Automattic’s org chart is a bit like a fractal).

World map showing the locations of Dan, his immediate team, and its parent team. There's a cluster of nine pins Europe, a few pins further East in Russia and Indonesia, one in Cape Town, two in North America, and one in Central America.
I’m the pink pin; my immediate team are the green pins. People elsewhere in our parent team are the blue pins. Some pins represent multiple people.

Thinking about timezones, there are two big benefits to being where I am:

  1. I’m in the median timezone, which makes times that are suitable-for-everybody pretty convenient for me (I have a lot of lunchtime/early-afternoon meetings where I get to watch the sun rise and set, simultaneously, through my teammates’ windows).
  2. I’m West of the mean timezone, which means that most of my immediate coworkers start their day before me so I’m unlikely to start my day blocked by anything I’m waiting on.

(Of course, this privilege is in itself a side-effect of living close to the meridian, whose arbitrary location owes a lot to British naval and political clout in the 19th century: had France and Latin American countries gotten their way the prime median would have probably cut through the Atlantic or Pacific oceans.)

2. Language Privilege

English is Automattic’s first language (followed perhaps by PHP and Javascript!), not one of the 120 other languages spoken by Automatticians. That’s somewhat a consequence of the first language of its founders and the language in which the keywords of most programming languages occur.

It’s also a side-effect of how widely English is spoken, which in comes from (a) British colonialism and (b) the USA using Hollywood etc. to try to score a cultural victory.

Treemap showing languages spoken by Automatticians: English dominates, followed by Spanish, French, German, Italian, Hindi, Portugese, Mandarin, Russian, Japanese, Polish, Afrikaans, Dutch, Green, Catalan, Cantonese, Romanian, and many others.
Languages self-reportedly spoken by Automatticians, sized proportional to the number of speakers. No interpretation/filtering has been done, so you’ll see multiple dialects of the same root language.

I’ve long been a fan of the concept of an international axillary language but I appreciate that’s an idealistic dream whose war has probably already been lost.

For now, then, I benefit from being able to think, speak, and write in my first language all day, every day, and not have the experience of e.g. my two Indonesian colleagues who routinely speak English to one another rather than their shared tongue, just for the benefit of the rest of us in the room!

3. Passport Privilege

Despite the efforts of my government these last few years to isolate us from the world stage, a British passport holds an incredible amount of power, ranking fifth or sixth in the world depending on whose passport index you follow. Compared to many of my colleagues, I can enjoy visa-free and/or low-effort travel to a wider diversity of destinations.

Normally I might show you a map here, but everything’s a bit screwed by COVID-19, which still bars me from travelling to many places around the globe, but as restrictions start to lift my team have begun talking about our next in-person meetup, something we haven’t done since I first started when I met up with my colleagues in Cape Town and got assaulted by a penguin.

But even looking back to that trip, I recall the difficulties faced by colleagues who e.g. had to travel to a different country in order tom find an embassy just to apply for the visa they’d eventually need to travel to the meetup destination. If you’re not a holder of a privileged passport, international travel can be a lot harder, and I’ve definitely taken that for granted in the past.

I’m going to try to be more conscious of these privileges in my industry.

World map showing the locations of Dan, his immediate team, and its parent team. There's a cluster of nine pins Europe, a few pins further East in Russia and Indonesia, one in Cape Town, two in North America, and one in Central America.× Treemap showing languages spoken by Automatticians: English dominates, followed by Spanish, French, German, Italian, Hindi, Portugese, Mandarin, Russian, Japanese, Polish, Afrikaans, Dutch, Green, Catalan, Cantonese, Romanian, and many others.×

Automattic Retrospective (days 207 to 334)

Last year, I accepted a job offer with Automattic and I’ve been writing about it every 128 days. I’ve talked about my recruitment, induction, and experience of lockdown (which in turn inspired a post about the future of work). I’ve even helped enthuse other new Automatticians! Since my last post I’ve moved house so my home office has changed shape, but I’m still plodding along as always… and fast-approaching my first “Automattic birthday”! (This post ran a little late; the 128-day block was three weeks ago!)

Dan in his home office (links to an interactive 360° panoramic photo with info points).
If you missed it the first time around, click through to explore an interactive panoramic view of my workspace. It’s slightly more “unpacked” now.

As I approach my first full year as an Automattician, I find myself looking back on everything I’ve learned… but also looking around at all the things I still don’t understand! I’m not learning something new every day any more… but I’m still learning something new most weeks.

This summer I’ve been getting up-close and personal with Gutenberg components. I’d mostly managed to avoid learning the React (eww; JSX, bad documentation, and an elephantine payload…) necessary to hack Gutenberg, but in helping to implement new tools for WooCommerce.com I’ve discovered that it’s… not quite as painful as I’d thought. There are even some bits I quite like. But I don’t expect to fall in love with React any time soon. This autumn I’ve been mostly working on search and personalisation, integrating customer analytics data with our marketplace to help understand what people look for on our sites and using that to guide their future experience (and that of others “like” them). There’s always something new.

Alpha project planning meeting via Zoom.
I suppose that by now everybody‘s used to meetings that look like this, but when I first started at Automattic a year ago they were less-commonplace.

My team continues to grow, with two newmatticians this month and a third starting in January. In fact, my team’s planning to fork into two closely-linked subteams; one with a focus on customers and vendors, the other geared towards infrastructure. It’s exciting to see my role grow and change, but I worry about the risk of gradually pigeon-holing myself into an increasingly narrow specialisation. Which wouldn’t suit me: I like to keep a finger in all the pies. Still; my manager’s reassuring that this isn’t likely to be the case and our plans are going in the “right” direction.

Kudos to Dan "for resolving a weeks worth of project issues in one day".
Our “Kudos” system can be used to acknowledge other Automatticians going above and beyond. I was particularly proud of this one.

On the side of my various project work, I’ve occasionally found the opportunity for more-creative things. Last month, I did some data-mining over the company’s “kudos” history of the last five years and ran it through vis.js to try to find a new angle on understanding how Automattic’s staff, teams, and divisions interact with one another. It lead to some interesting results: panning through time, for example, you can see the separate island of Tumblr staff who joined us during the acquisition gradually become more-interconnected with the rest of the organisation over the course of the last year.

Automattic Kudos social graph for September 2020
Automattic as a social graph of kudos given/received during September 2020, colour-coded by team. Were you one of us, you’d be able to zoom in and find yourself. The large “branch” in the bottom right is mostly comprised of Tumblr staff.

The biggest disappointment of my time at Automattic so far was that I’ve not managed to go to a GM! The 2019 one – which looked awesome – took place only a couple of weeks before my contract started (despite my best efforts to wrangle my contract dates with the Bodleian and Automattic to try to work around that), but people reassured me that it was okay because I’d make it to the next one. Well.. 2020 makes fools of us all, I guess, because of course there’s no in-person GM this year. Maybe, hopefully, if and when the world goes back to normal I’ll get to spend time in-person with my colleagues once in a while… but for now, we’re having to suffice with Internet-based socialisation only, just like the rest of the world.

Alpha project planning meeting via Zoom.× Kudos to Dan "for resolving a weeks worth of project issues in one day".× Automattic Kudos social graph for September 2020×

Future Challenges for Remote Working

When the COVID-19 lockdown forced many offices to close and their staff to work remotely, some of us saw what was unfolding as an… opportunity in disguise. Instead of the slow-but-steady decentralisation of work that’s very slowly become possible (technically, administratively, and politically) over the last 50 years, suddenly a torrent of people were discovering that remote working can work.

Man in sci-fi jumpsuit and futuristic AR goggles.
Unfulfilled promises of the world of tomorrow include flying cars, viable fusion power, accessible space travel, post-scarcity economies, and – until recently – widespread teleworking. Still waiting on my holodeck too.

The Future is Now

As much as I hate to be part of the “where’s my flying car?” brigade, I wrote ten years ago about my dissatisfaction that remote working wasn’t yet commonplace, let alone mainstream. I recalled a book I’d read as a child in the 1980s that promised a then-future 2020 of:

  1. near-universal automation of manual labour as machines become capable of an increasing diversity of human endeavours (we’re getting there, but slowly),
  2. a three- or four-day work week becoming typical as efficiency improvements are reinvested in the interests of humans rather than of corporations (we might have lost sight of that goal along the way, although there’s been some fresh interest in it lately), and
  3. widespread “teleworking”/”telecommuting”, as white-collar sectors grow and improvements in computing and telecommunications facilitate the “anywhere office”

Of those three dreams, the third soon seemed like it would become the most-immediate. Revolutionary advances in mobile telephony, miniaturisation of computers, and broadband networking ran way ahead of the developments in AI that might precipitate the first dream… or the sociological shift required for the second. But still… progress was slow.

At eight years old, I genuinely believed that most of my working life would be spent… wherever I happened to be. So far, most of my working life has been spent in an office, despite personally working quite hard for that not to be the case!

Driver's temperature being checked at the roadside by somebody in full protective equipment.
Apply directly to the head! Commuting looks different today than it did last year, but at least the roads are quieter.

I started at Automattic six months ago, an entirely distributed company. And so when friends and colleagues found themselves required to work remotely by the lockdown they came in droves to me for advice about how to do it! I was, of course, happy to help where I could: questions often covered running meetings and projects, maintaining morale, measuring output, and facilitating communication… and usually I think I gave good answers. Sometimes, though, the answer was “If you’re going to make that change, you’re going to need a cultural shift and some infrastructure investment first.” Y’know: “Don’t start from here.” If you received that advice from me: sorry!

(Incidentally, if you have a question I haven’t answered yet, try these clever people first for even better answers!)

More-recently, I was excited to see that many companies have adopted this “new normal” not as a temporary measure, but as a possible shape of things to come. Facebook, Twitter, Shopify, Square, and Spotify have all announced that they’re going to permit or encourage remote work as standard, even after the crisis is over.

Obviously tech companies are leading the way, here: not only are they most-likely to have the infrastructure and culture already in place to support this kind of shift. Also, they’re often competing for the same pool of talent and need to be seen as at-least as progressive as their direct rivals. Matt Mullenweg observes that:

What’s going to be newsworthy by the end of the year is not technology companies saying they’re embracing distributed work, but those that aren’t.

…some employers trapped in the past will force people to go to offices, but the illusion that the office was about work will be shattered forever, and companies that hold on to that legacy will be replaced by companies who embrace the antifragile nature of distributed organizations.

Distributed Work's Five Levels of Autonomy, by Matt Mullenweg.
I’ve shared this before, I know, but it exudes Matt’s enthusiasm for distributed work so well that I’m sharing it again. Plus, some of the challenges I describe below map nicely to the borders between some of

Tomorrow’s Challenges

We’re all acutely familiar with the challenges companies are faced with today as they adapt to a remote-first environment. I’m more interested in the challenges that they might face in the future, as they attempt to continue to use a distributed workforce as the pandemic recedes. It’s easy to make the mistake of assuming that what many people are doing today is a rehearsal for the future of work, but the future will look different.

Some people, of course, prefer to spend some or all of their work hours in an office environment. Of the companies that went remote-first during the lockdown and now plan to stay that way indefinitely, some will lose employees who preferred the “old way”. For this and other reasons, some companies will retain their offices and go remote-optional, allowing flexible teleworking, and this has it’s own pitfalls:

  • Some remote-optional offices have an inherent bias towards in-person staff. In some companies with a mixture of in-person and remote staff, remote workers don’t get included in ad-hoc discussions, or don’t become part of the in-person social circles. They get overlooked for projects or promotions, or treated as second-class citizens. It’s easy to do this completely by accident and create a two-tiered system, which can lead to a cascade effect that eventually collapses the “optional” aspect of remote-optional; nowhere was this more visible that in Yahoo!’s backslide against remote-optional working in 2013.
  • Some remote-optional offices retain an archaic view on presenteeism and “core hours”. Does the routine you keep really matter? Remote-first working demands that productivity is measured by output, not by attendance, but management-by-attendance is (sadly) easier to implement, and some high-profile organisations favour this lazy but less-effective approach. It’s easy, but ineffective, for a remote-optional company to simply extend hours-counting performance metrics to their remote staff. Instead, allowing your staff (insofar as is possible) to work the hours that suit them as individuals opens up your hiring pool to a huge number of groups whom you might not otherwise reach (like single parents, carers, digital nomads, and international applicants) and helps you to get the best out of every one of them, whether they’re an early bird, a night owl, or somebody who’s most-productive after their siesta!
  • Pastoral care doesn’t stop being important after the crisis is over. Many companies that went remote-first for the coronavirus crisis have done an excellent job of being supportive and caring towards their employees (who, of course, are also victims of the crisis: by now, is there anybody whose life hasn’t been impacted?). But when these companies later go remote-optional, it’ll be easy for them to regress to their old patterns. They’ll start monitoring the wellbeing only of those right in front of them. Remote working is already challenging, but it can be made much harder if your company culture makes it hard to take a sick day, seek support on a HR issue, or make small-talk with a colleague.
Teleworker dressed from the waist up.
On the Internet, nobody knows that you’re only properly-dressed from the waist up. No, wait: as of 2020, everybody knows that. Let’s just all collectively own it, ‘k.

These are challenges specifically for companies that go permanently remote-optional following a period of remote-first during the coronavirus crisis.

Towards a Post-Lockdown Remote-Optional Workplace

How you face those challenges will vary for every company and industry, but it seems to me that there are five lessons a company can learn as it adapts to remote-optional work in a post-lockdown world:

  1. Measure impact, not input. You can’t effectively manage a remote team by headcount or closely tracking hours; you need to track outputs (what is produced), not inputs (person-hours). If your outputs aren’t measurable, make them measurable, to paraphrase probably-not-Galileo. Find metrics you can work with and rely on, keep them transparent and open, and re-evaluate often. Use the same metrics for in-office and remote workers.
  2. Level the playing field. Learn to spot the biases you create. Do the in-person attendees do all the talking at your semi-remote meetings? Do your remote workers have to “call in” to access information only stored on-site (including in individual’s heads)? When they’re small, these biases have a huge impact on productivity and morale. If they get big, they collapse your remote-optional environment.
  3. Always think bigger. You’re already committing to a shakeup, dragging your company from the 2020 of the real world into the 2020 we once dreamed of. Can you go further? Can you let your staff pick their own hours? Or workdays? Can your staff work in other countries? Can you switch some of your synchronous communications channels (e.g. meetings) into asynchronous information streams (chat, blogs, etc.)? Which of your telecommunications tools serve you, and which do you serve?
  4. Remember the human. Your remote workers aren’t faceless (pantsless) interchangeable components in your corporate machine. Foster interpersonal relationships and don’t let technology sever the interpersonal links between your staff. Encourage and facilitate (optional, but awesome) opportunities for networking and connection. Don’t forget to get together in-person sometimes: we’re a pack animal, and we form tribes more-easily when we can see one another.
  5. Support people through the change. Remote working requires a particular skillset; provide tools to help your staff adapt to it. Make training and development options available to in-office staff too: encourage as flexible a working environment as your industry permits. Succeed, and your best staff will pay you back in productivity and loyalty. Fail, and your best staff will leave you for your competitors.

I’m less-optimistic than Matt that effective distributed working is the inexorable future of work. But out of the ashes of the coronavirus crisis will come its best chance yet, and I know that there’ll be companies who get left behind in the dust. What are you doing to make sure your company isn’t one of them?

Man in sci-fi jumpsuit and futuristic AR goggles.× Driver's temperature being checked at the roadside by somebody in full protective equipment.× Distributed Work's Five Levels of Autonomy, by Matt Mullenweg.× Teleworker dressed from the waist up.×

Automattic Lockdown (days 79 to 206)

Since I accepted a job offer with Automattic last summer I’ve been writing about my experience on a nice, round 128-day schedule. My first post described my application and recruitment process; my second post covered my induction, my initial two weeks working alongside the Happiness team (tech support), and my first month in my role. This is the third post, running through to the end of six and a half months as an Automattician.

Always Be Deploying

One of the things that’s quite striking about working on many of Automattic’s products, compared to places I’ve worked before, is the velocity. Their continuous integration game is pretty spectacular. We’re not talking “move fast and break things” iteration speeds (thank heavens), but we’re still talking fast.

Graph showing Automattic deployments for a typical week. Two of the 144 deployments on Monday were by Dan.
Deployments-per-day in a reasonably typical week. A minor bug slipped through in the first of the deployments I pushed on the Monday shown, so it was swiftly followed by a second deployment (no external end-users were affected: phew!).

My team tackles a constant stream of improvements in two-week sprints, with every third sprint being a cool-down period to focus on refactoring, technical debt, quick wins, and the like. Periodic HACK weeks – where HACK is (since 2018) a backronym for Helpful Acts in Customer Kindness – facilitate focussed efforts on improving our ecosystem and user experiences.

I’m working in a larger immediate team than I had for most of my pre-Automattic career. I’m working alongside nine other developers, typically in groups of two to four depending on the needs of whatever project I’m on. There’s a great deal of individual autonomy: we’re all part of a greater whole and we’re all pushing in the same direction, but outside of the requirements of the strategic goals of our division, the team’s tactical operations are very-much devolved and consensus-driven. We work out as a team how to solve the gnarly (and fun!) problems, how to make best use of our skills, how to share our knowledge, and how to schedule our priorities.

Dan in front of three monitors and a laptop.
My usual workspace looks pretty much exactly like you’re thinking that it does.

This team-level experience echoes the experience of being an individual at Automattic, too. The level of individual responsibility and autonomy we enjoy is similar to that I’ve seen only after accruing a couple of years of experience and authority at most other places I’ve worked. It’s amazing to see that you can give a large group of people so much self-controlled direction… and somehow get order out of the chaos. More than elsewhere, management is more to do with shepherding people into moving in the same direction than it is about dictating how the ultimate strategic goals might be achieved.

Na na na na na na na na VAT MAN!

Somewhere along the way, I somehow became my team’s live-in expert on tax. You know how it is: you solve a bug with VAT calculation in Europe… then you help roll out changes to support registration with the GST in Australia… and then one day you find yourself reading Mexican digital services tax legislation and you can’t remember where the transition was from being a general full-stack developer to having a specialisation in tax.

An Oxford coworking space.
Before the coronavirus lockdown, though, I’d sometimes find a coworking space (or cafe, or pub!) to chill in while I worked. This one was quiet on the day I took the photo.

Tax isn’t a major part of my work. But it’s definitely reached a point at which I’m a go-to figure. A week or so ago when somebody had a question about the application of sales taxes to purchases on the WooCommerce.com extensions store, their first thought was “I’ll ask Dan!” There’s something I wouldn’t have anticipated, six month ago.

Automattic’s culture lends itself to this kind of selective micro-specialisation. The company actively encourages staff to keep learning new things but mostly without providing a specific direction, and this – along with their tendency to attract folks who, like me, could foster an interest in almost any new topic so long as they’re learning something – means that my colleagues and I always seem to be developing some new skill or other.

Batman, with his costume's logo adapted to be "VAT man".
I ended up posting this picture to my team’s internal workspace, this week, as I looked a VAT-related calculation.

I know off the top of my head who I’d talk to about if I had a question about headless browser automation, or database index performance, or email marketing impact assessment, or queer representation, or getting the best airline fares, or whatever else. And if I didn’t, I could probably find them. None of their job descriptions mention that aspect of their work. They’re just the kind of people who, when they see a problem, try to deepen their understanding of it as a whole rather than just solving it for today.

A lack of pigeonholing, coupled with the kind of information management that comes out of being an entirely-distributed company, means that the specialisation of individuals becomes a Search-Don’t-Sort problem. You don’t necessarily find an internal specialist by their job title: you’re more-likely to find them by looking for previous work on particular topics. That feels pretty dynamic and exciting… although it does necessarily lead to occasional moments of temporary panic when you discover that something important (but short of mission-critical) doesn’t actually have anybody directly responsible for it.

Crisis response

No examination of somebody’s first 6+ months at a new company, covering Spring 2020, would be complete without mention of that company’s response to the coronavirus crisis. Because, let’s face it, that’s what everybody’s talking about everywhere right now.

Dan in a video meeting, in a hammock.
All workplace meetings should be done this way.

In many ways, Automattic is better-placed than most companies to weather the situation. What, we have to work from home now? Hold my beer. Got to shift your hours around childcare and other obligations? Sit down, let us show you how it’s done. Need time off for COVID-related reasons? We already have an open leave policy in place and it’s great, thanks.

As the UK’s lockdown (eventually) took hold I found myself treated within my social circle like some kind of expert on remote working. My inboxes filled up with queries from friends… How do I measure  output? How do I run a productive meeting? How do I maintain morale? I tried to help, but unfortunately some of my answers relied slightly on already having a distributed culture: having the information and resource management and teleworking infrastructure in-place before the crisis. Still, I’m optimistic that companies will come out of the other side of this situation with a better idea about how to plan for and execute remote working strategies.

Laptop screen showing five people videoconferencing.
Social distancing is much easier when you’re almost never in the same room as your colleagues anyway.

I’ve been quite impressed that even though Automattic’s all sorted for how work carries on through this crisis, we’ve gone a step further and tried to organise (remote) events for people who might be feeling more-isolated as a result of the various lockdowns around the world. I’ve seen mention of wine tasting events, toddler groups, guided meditation sessions, yoga clubs, and even a virtual dog park (?), all of which try to leverage the company’s existing distributed infrastructure to support employees who’re affected by the pandemic. That’s pretty cute.

(It might also have provided some inspiration for the murder mystery party I plan to run a week on Saturday…)

Distributed Work's Five Levels of Autonomy, by Matt Mullenweg.
Matt shared this diagram last month, and its strata seem increasingly visible as many companies adapt (with varying levels of success) to remote work.

In summary: Automattic’s still proving to be an adventure, I’m still loving their quirky and chaotic culture and the opportunity to learn something new every week, and while their response to the coronavirus crisis has been as solid as you’d expect from a fully-distributed company I’ve also been impressed by the company’s efforts to support staff (in a huge diversity of situations across many different countries) through it.

Graph showing Automattic deployments for a typical week. Two of the 144 deployments on Monday were by Dan.× Dan in front of three monitors and a laptop.× An Oxford coworking space.× Batman, with his costume's logo adapted to be "VAT man".× Dan in a video meeting, in a hammock.× Laptop screen showing five people videoconferencing.× Distributed Work's Five Levels of Autonomy, by Matt Mullenweg.×

Getting Hired at Automattic

This article is a repost promoting content originally published elsewhere. See more things Dan's reposted.

I started at Automattic on November 20, 2019, and it’s an incredible place to work. I’m constantly impressed by my coworkers kindness, intelligence, and compassion. If you’re looking for a rewarding remote job that you can work from anywhere in the world, definitely apply.

I’m still overjoyed and amazed I was hired. While going through the hiring process, I devoured the blog posts from people describing their journeys. Here’s my contribution to the catalog. I hope it helps someone.

I’ve written about my own experience of Automattic’s hiring process and how awesome it is, but if you’re looking for a more-concise summary of what to expect from applying to and interviewing for a position, this is pretty great.

How to not make a résumé in React

This article is a repost promoting content originally published elsewhere. See more things Dan's reposted.

I’ve seen a fair share of tutorial links floating around in newsletters and Twitter and the like recently. They all promise the same thing, namely how to use React to create a résumé.

I mean, I get it. It’s important to have something to build towards when learning a new skill, especially with development.

At first blush a résumé seems like a good thing to build towards: They are relatively small in terms of complexity and can probably use content that already exists on your LinkedIn profile. If you’re looking for a job, it’s also a handy way to double-dip on a skill that is in high demand.

I checked out a few of these tutorials, and after noticing some patterns, I’d like to mention a few things you could do to your résumé instead. I’m not going to link to the ones I tested because I don’t want to give bad advice more exposure than it is already getting.

I can’t even begin to conceive of the kind of mind that, when faced with the question of how to put their résumé/CV online, start by installing a Javascript framework. My CV‘s online (and hey, it got me my current job so that’s awesome) and I think it’s perfectly fabulous. Simple, human-readable, semantic HTML with microformats support. Perfectly readable on anything from lynx upwards and you’d probably get by in telnet. Total size including all images, fonts, style and script is under 140kb, and can all be inlined with a quick command so I can have a single-file version that looks just as great (I use this version to email to people, but I’m thinking I ought to just inline everything, all the time). Under 1kb of my payload is JavaScript, and it’s all progressive enhancement: using an IntersectionObserver (which I’ve written about before) to highlight the current “section” of the document in the menu. Print CSS so it looks right when you put it onto dead trees. Etc. etc.

My entire CV requires a quarter of the bandwidth of just the JavaScript of any of the handful of React-based ones I looked up. The mind boggles. I tried disabling JavaScript on a few of them (even if you believe “nobody uses the Web without JavaScript” – and you’re wrong – then you have to admit that sometimes JavaScript fails) and they did horrific things like not loading images or links not working, as if <img> and <a> tags were something that requires you to npm install html@0.9 before they work..

A simpler, faster, more-accessible, more-secure Web is possible. It’s not even particularly hard. It just requires a little thought. Don’t take a sledgehammer to a walnut: the best developers are the ones who choose the right tool for the job. Your résumé/CV is not a real-time backendless application on a post-relational-backed microservices architecture, or whatever’s “hip” this week. It’s a page that you want to be as easy as possible to read by the widest number of people. Why make life harder for you, and for them?

Automattic Transition (days -50 to 78)

Since I reported last summer that I’d accepted a job offer with Automattic I’ve been writing about my experience of joining and working with Automattic on a nice, round 128-day schedule.

My first post covered the first 128 days: starting from the day I decided (after 15 years of watching-from-afar) that I should apply to work there through to 51 days before my start date. It described my recruitment process, which is famously comprehensive and intensive. For me this alone was hugely broadening! My first post spanned the period up until I started getting access to Automattic’s internal systems, a month and a half before my start date. If you’re interested in my experience of recruitment at Automattic, you should go and read that post. This post, though, focusses on my induction, onboarding, and work during my first two months.

(You might also be interested in other things I’ve written about Automattic.)

Kitting Up (day -37 onwards)

Dan in front of a crowded desk: two large monitors, a regular-sized monitor, and a laptop are visible, among clutter.
I could possibly do with a little more desk space, or at least a little better desk arrangement, after the house move.

With a month to go before I started, I thought it time to start setting up my new “office” for my teleworking. Automattic offered to buy me a new desk and chair, but I’m not ready to take them up on that yet: but I’m waiting until after my (hopefully-)upcoming house move so I know how much space I’ve got to work with/what I need! There’s still plenty for a new developer to do, though: plugging in and testing my new laptop, monitor, and accessories, and doing all of the opinionated tweaks that make one’s digital environment one’s own – preferred text editor, browser, plugins, shell, tab width, mouse sensitivity, cursor blink rate… important stuff like that.

For me, this was the cause of the first of many learning experiences, because nowadays I’m working on a MacBook! Automattic doesn’t require you to use a Mac, but a large proportion of the company does and I figured that learning to use a Mac effectively would be easier than learning my new codebase on a different architecture than most of my colleagues.

Dan working on a MacBook covered with Automattic stickers, wearing a WordPress Diversity t-shirt.
Working on location, showing some Automattic pride. You can’t really make out my WordPress “Christmas jumper”, hanging on the back of the sofa, but I promise that’s what it is.

I’ve owned a couple of Intel Macs (and a couple of Hackintoshes) but I’ve never gotten on with them well enough to warrant becoming an advanced user, until now. I’ll probably write in the future about my experience of making serious use of a Mac after a history of mostly *nix and Windows machines.

Automattic also encouraged me to kit myself up with a stack of freebies to show off my affiliation, so I’ve got a wardrobe-load of new t-shirts and stickers too. It’s hard to argue that we’re a company and not a cult when we’re all dressed alike, and that’s not even mentioning a colleague of mine with two WordPress-related tattoos, but there we have it.

Dan wearing a WordPress hoodie and drinking from an Automattic bottle.
Totally not a cult. Now let me have another swig of Kool-Aid…

Role and Company

I should take a moment to say what I do. The very simple version, which I came up with to very briefly describe my new job to JTA‘s mother, is: I write software that powers an online shop that sells software that powers online shops.

Xzibit says:
It’s eCommerce all the way down. Thanks, Xzibit.

You want the long version? I’m a Code Magician (you may say it’s a silly job title, I say it’s beautiful… but I don’t necessarily disagree that it’s silly too) with Team Alpha at Automattic. We’re the engineering team behind WooCommerce.com, which provides downloads of the Web’s most-popular eCommerce platform… plus hundreds of free and premium extensions.

There’s a lot of stuff I’d love to tell you about my role and my new employer, but there’s enough to say here about my induction so I’ll be saving following topics for a future post:

  • Chaos: how Automattic produces order out of entropy, seemingly against all odds,
  • Transparency and communication: what it’s like to work in an environment of radical communication and a focus on transparency,
  • People and culture: my co-workers, our distributed team, and what is lost by not being able to “meet around the coffee machine” (and how we work to artificially recreate that kind of experience),
  • Distributed working: this is my second foray into a nearly-100% remote-working environment; how’s it different to before?

To be continued, then.

John wearing a WordPress t-shirt.
I’m not the only member of my family to benefit from a free t-shirt.

Onboarding (days 1 through 12)

I wasn’t sure how my onboarding at Automattic could compare to that which I got when I started at the Bodleian. There, my then-line manager Alison‘s obsession with preparation had me arrive to a thoroughly-planned breakdown of everything I needed to know and everybody I needed to meet over the course of my first few weeks. That’s not necessarily a bad thing, but it leaves little breathing room in an already intense period!

Leslie Knope (Parks & Rec) presents a pile of binders, saying
What it felt like to receive an induction from the first boss I had at the Bod.

By comparison, my induction at Automattic was far more self-guided: each day in my first fortnight saw me tackling an agenda of things to work on and – in a pleasing touch I’ve seen nowhere else – a list of expectations resulting from that day. Defined expectations day-by-day are an especially good as a tool for gauging one’s progress and it’s a nice touch that I’ll be adapting should I ever have to write another induction plan for a somebody else.

Agenda and Expectations Checklist for Dan's first day at Automattic
Both an agenda and a list of expectations for the day? That’s awesome and intimidating in equal measure.

Skipping the usual induction topics of where the fire escapes and toilets are (it’s your house; you tell us!), how to dial an outside line (yeah, we don’t really do that here), what to do to get a key to the bike shed and so on saves time, of course! But it also removes an avenue for more-casual interpersonal contact (“So how long’ve you been working here?”) and ad-hoc learning (“So I use that login on this system, right?”). Automattic’s aware of this and has an entire culture about making information accessible, but it takes additional work on the part of a new hire to proactively seek out the answers they need, when they need them: searching the relevant resources, or else finding out who to ask… and being sure to check their timezone before expecting an immediate response.

Onboarding at Automattic is necessarily at least somewhat self-driven, and it’s clear in hindsight that the recruitment process is geared towards selection of individuals who can work in this way because it’s an essential part of how we work in general. I appreciated the freedom to carve my own path as I learned the ropes, but it took me a little while to get over my initial intimidation about pinging a stranger to ask for a video/voice chat to talk through something!

Meetup (days 14 through 21)

Dan with a 50 South African Rand note.
How cool is South African currency? This note’s got a lion on it!

I’d tried to arrange my migration to Automattic to occur just before their 2019 Grand Meetup, when virtually the entire company gets together in one place for an infrequent but important gathering, but I couldn’t make it work and just barely missed it. Luckily, though, my team had planned a smaller get-together in South Africa which coincided with my second/third week, so I jetted off to get some facetime with my colleagues.

Dan sitting on a rock on Table Mountain, Cape Town, with a sunset in the background
When they say that Automatticians can work from anywhere, there might nonetheless be practical limits.

My colleague and fellow newbie Berislav‘s contract started a few hours after he landed in Cape Town, and it was helpful to my journey to see how far I’d come over the last fortnight through his eyes! He was, after all, on the same adventure as me, only a couple of weeks behind, and it was reassuring to see that I’d already learned so much as well as to be able to join in with helping him get up-to-speed, too.

Dan with a pair of African penguins
The meetup wasn’t all work. I also got to meet penguins and get attacked by one of the little buggers.

By the time I left the meetup I’d learned as much again as I had in the two weeks prior about my new role and my place in the team. I’d also learned that I’m pretty terrible at surfing, but luckily that’s not among the skills I have to master in order to become a valuable developer to Automattic.

Happiness Rotation (days 23 through 35)

A quirk of Automattic – and indeed something that attracted me to them, philosophically – is that everybody spends two weeks early in their first year and a week in every subsequent year working on the Happiness Team. Happiness at Automattic is what almost any other company would call “tech support”, because Automattic’s full of job titles and team names that are, frankly, a bit silly flipping awesome. I like this “Happiness Rotation” as a concept because it keeps the entire company focussed on customer issues and the things that really matter at the coal face. It also fosters a broader understanding of our products and how they’re used in the real world, which is particularly valuable to us developers who can otherwise sometimes forget that the things we produce have to be usable by real people with real needs!

Happiness Live Chat screenshot, customer's view.
Once I’d gotten the hang of answering tickets I got to try my hand at Live Chat, which was a whole new level of terrifying.

One of the things that made my Happiness Rotation the hardest was also one of the things that made it the most-rewarding: that I didn’t really know most of the products I was supporting! This was a valuable experience because I was able to learn as-I-went-along, working alongside my (amazingly supportive and understanding) Happiness Team co-workers: the people who do this stuff all the time. But simultaneously, it was immensely challenging! My background in WordPress in general, plenty of tech support practice at Three Rings, and even my experience of email support at Samaritans put me in a strong position in-general… but I found that I could very-quickly find myself out of my depth when helping somebody with the nitty-gritty of a problem with a specific WooCommerce extension.

Portering and getting DRI (days 60 through 67)

I’ve also had the opportunity during my brief time so far with Automattic to take on a few extra responsibilities within my team. My team rotates weekly responsibility for what they call the Porter role. The Porter is responsible for triaging pull requests and monitoring blocking issues and acting as a first point-of-call to stakeholders: you know, the stuff that’s important for developer velocity but that few developers want to do all the time. Starting to find my feet in my team by now, I made it my mission during my first shift as Porter to get my team to experiment with an approach for keeping momentum on long-running issues, with moderate success (as a proper continuous-integration shop, velocity is important and measurable). It’s pleased me so far to feel like I’m part of a team where my opinion matters, even though I’m “the new guy”.

A woman carries a large cardboard box.
“Here, I found these things we need to be working on.” Pretty much how I see the Porter role.

I also took on my first project as a Directly Responsible Individual, which is our fancy term for the person who makes sure the project runs to schedule, reports on progress etc. Because Automattic more strongly than any other place I’ve ever worked subscribes to a dogfooding strategy, the woocommerce.com online store for which I share responsibility runs on – you guessed it – WooCommerce! And so the first project for which I’m directly responsible is the upgrade of woocommerce.com to the latest version of WooCommerce, which went into beta last month. Fingers crossed for a smooth deployment.

There’s so much I’d love to say about Automattic’s culture, approach to development, people, products, philosophy, and creed, but that’ll have to wait for another time. For now, suffice to say that I’m enjoying this exciting and challenging new environment and I’m looking forward to reporting on them in another 128 days or so.

Dan in front of a crowded desk: two large monitors, a regular-sized monitor, and a laptop are visible, among clutter.× Dan working on a MacBook covered with Automattic stickers, wearing a WordPress Diversity t-shirt.× Dan wearing a WordPress hoodie and drinking from an Automattic bottle.× Xzibit says: × John wearing a WordPress t-shirt.× Leslie Knope (Parks & Rec) presents a pile of binders, saying × Agenda and Expectations Checklist for Dan's first day at Automattic× Dan with a 50 South African Rand note.× Dan sitting on a rock on Table Mountain, Cape Town, with a sunset in the background× Dan with a pair of African penguins× Happiness Live Chat screenshot, customer's view.× A woman carries a large cardboard box.×

Howdymattic

New employees at Automatticlike me! – are encouraged to make a “howdymattic” video, introducing themselves to their co-workers. Some are short and simple, others more-ornate, but all are a great way to provide the kind of interpersonal connection that’s more-challenging in an entirely-distributed company with no fixed locations and staff spread throughout the globe.

In anticipation of starting, tomorrow, I made such a video. And I thought I’d share it with you, too.

Also available on: VideoPress, QTube, YouTube.

Without The Bod

Eight years, six months, and one week after I started at the Bodleian, we’ve gone our separate ways. It’s genuinely been the nicest place I’ve ever worked; the Communications team are a tightly-knit, supportive, caring bunch of diverse misfits and I love them all dearly, but the time had come for me to seek my next challenge.

(For anybody out-of-the-loop, I’m moving to Automattic after surviving their amazing, mind-expanding recruitment process).

Bodleian staff badge and keyring
My imminent departure began to feel real when I turned over my badge and gun card and keys.

Being awesome as they are, my team threw a going-away party for me, complete with food from Najar’s Place, about which I’d previously raved as having Oxford’s best falafels. I wasn’t even aware that Najar’s place did corporate catering… actually, it’s possible that they don’t and this was just a (very) special one-off.

Partry platters courtesy of Najar's Place along with drinks and cake.
Start from the left, work towards the right.

Following in the footsteps of recent team parties, they’d even gotten a suitably-printed cake with a picture of my face on it. Which meant that I could leave my former team with one final magic trick, the never-before-seen feat of eating my own head (albeit in icing form).

Dan on a cake
Of course, the first thing I was asked to do was to put a knife through my own neck.

As the alcohol started to work, I announced an activity I’d planned: over the weeks prior I’d worked to complete but not cash-in reward cards at many of my favourite Oxford eateries and cafes, and so I was now carrying a number of tokens for free burritos, coffees, ice creams, smoothies, pasta and more. Given that I now expect to spend much less of my time in the city centre I’d decided to give these away to people who were able to answer challenge questions presented – where else? – on our digital signage simulator.

"Play Your Shards Right" on the big screen.
Among the games was Play Your Shards Right, a game of “higher/lower” played across London’s skyscrapers.

I also received some wonderful going-away gifts, along with cards in which a few colleagues had replicated my long tradition of drawing cartoon animals in other people’s cards, by providing me with a few in return.

Coworkers competing agressively for tiny prizes.
“Wait… all of these Javascript frameworks look like they’re named after Pokémon!”

Later, across the road at the Kings’ Arms and with even more drinks inside of me, I broke out the lyrics I’d half-written to a rap song about my time at the Bodleian. Because, as I said at the time, there’s nothing more-Oxford than a privileged white boy rapping about how much he’d loved his job at a library (video also available on QTube [with lyrics] and on Videopress).

It’s been an incredible 8½ years that I’ll always look back on with fondness. Don’t be strangers, guys!

Dan says goodbye to Bodleian colleagues
My department’s made far too much use out of that “Sorry you’re leaving” banner, this year. Here’s hoping they get a stabler, simpler time next year.
Bodleian staff badge and keyring× Partry platters courtesy of Najar's Place along with drinks and cake.× Dan on a cake× "Play Your Shards Right" on the big screen.× Coworkers competing agressively for tiny prizes.× Dan says goodbye to Bodleian colleagues×

Shredding eight years of old payslips

I’ve just cleared out my desk at the Bodleian in anticipation of my imminent departure and discovered that I’ve managed to successfully keep not only my P60s but also every payslip I’ve ever received in the 8½ years I’ve worked there. At a stretch, I might just end up requiring those for the current tax year but I can’t conceive of any reason I’ll ever need the preceding hundred or so of them, so the five year-old and I shredded them all.

If you’ve ever wanted to watch five solid minutes of cross-cut shredding shot from an awkwardly placed mobile phone camera, this is the video for you. Everybody else can move along.

Also available on QTube and on VideoPress.

Automattic Recruitment (days -179 to -51)

I recently announced that I’d accepted a job offer from Automattic and I’ll be starting work there in October. As I first decided to apply for the job 128 days ago – a nice round number – I thought I’d share with you my journey over the last 128 days.

Other people have written at length about their experience of being accepted (sometimes on the second or third attempt) or rejected by Automattic as well as about their interview process and the kind of person who works for them. Or if you prefer, there are more-objective articles about how Automattic’s hiring procedures are unique. My story, though is a work-in-progress: written contemporaneously and still unfolding (see if I’ve written more yet!).

The opening lines of Dan's initial interview with Automattic.
Automattic conduct their entire interview process via Slack online chat. I’ve still never spoken to any of my new co-workers by phone, let alone seen them in person. This is both amazing and terrifying.

Here’s my timeline so far:

Application (days -179 to -178)

Like many geeks, I keep a list of companies that I’ve fantasised about working for some day: mine includes the Mozilla Foundation and DuckDuckGo, for example, as well as Automattic Inc. In case it’s not obvious, I like companies that I feel make the Web a better place! Just out of interest, I was taking a look at what was going on at each of them. My role at the Bodleian, I realised a while ago, is likely to evolve into something different probably in the second-half of 2020 and I’d decided that when it does, that would probably be the point at which I should start looking for a new challenge. What I’d intended to do on this day 128 days ago, which we’ll call “day -179”, was to flick through the careers pages of these and a few other companies, just to get a better understanding of what kinds of skills they were looking for. I didn’t plan on applying for new jobs yet: that was a task for next-year-Dan.

Broad Street, Oxford
I love working here, but over the last 8 years I feel like I’ve “solved” all of the most-interesting problems.

But then, during a deep-dive into the things that make Automattic unique (now best-explained perhaps by this episode of the Distributed podcast), something clicked for me. I’d loved the creed for as long as I’d known about it, but today was the day that I finally got it, I think. That was it: I’d drunk the Kool-Aid, and it was time to send off an application.

I sat up past midnight on day -179, sending my application by email in the small hours of day -178. In addition to attaching a copy of my CV I wrote a little under 2,000 words about why I think I’m near-uniquely qualified to work for them: my experience of distributed/remote working with SmartData and (especially) Three Rings, my determination to remain a multidisciplinary full-stack developer despite increasing pressure to “pick a side”, my contributions towards (and use, since almost its beginning of) WordPress, and of course the diverse portfolio of projects large and small I’ve worked on over my last couple of decades as a software engineer.

VR Day at the Bodleian.
VR experiments are among the more-unusual things I’ve worked on at the Bodleian (let’s not forget that, strictly, I’m a web developer).

At the time of my application (though no longer, as a result of changes aimed at improving gender equality) the process also insisted that I include a “secret” in my application, which could be obtained by following some instructions and with only a modest understanding of HTTP. It could probably be worked out even by a developer who didn’t, with a little of the kind of research that’s pretty common when you’re working as a coder. This was a nice and simple filtering feature which I imagine helps to reduce the number of spurious applications that must be read: cute, I thought.

Automattic puzzle being solved
Fun and simple, and yet an effective way to filter out the worst of the spurious applications.

I received an automated reply less that a minute later, and an invitation to a Slack-based initial interview about a day and a half after that. That felt like an incredibly-fast turnaround, and I was quite impressed with the responsiveness of what must necessarily be a reasonably-complex filtering and process-management process… or perhaps my idea of what counts as “fast” in HR has been warped by years in a relatively slow-moving and bureaucratic academic environment!

Initial Interview (day -158)

I’ve got experience on both sides of the interview table, and I maintain that there’s no single “right” way to recruit – all approaches suck in different ways – but the approaches used by companies like Automattic (and for example Bytemark, who I’ve shared details of before) at least show a willingness to explore, understand, and adopt a diversity of modern practices. Automattic’s recruitment process for developers is a five-step (or something like that) process, with the first two stages being the application and the initial interview.

My initial interview took place 20 days after my application: entirely over text-based chat on Slack, of course.

Two men using laptops opposite one another.
For all you know, your interviewer might be hanging out in the same cafe or co-working space as you. But they probably aren’t. Right?

The initial interview covered things like:

  • Basic/conversational questions: Why I’d applied to Automattic, what interested me about working for them, and my awareness of things that were going on at the company at the moment.
  • Working style/soft skills: Questions about handling competing priorities in projects, supporting co-workers, preferred working and development styles, and the like.
  • Technical/implementation: How to realise particular ideas, how to go about debugging a specific problem and what the most-likely causes are, understanding clients/audiences, comprehension of different kinds of stacks.
  • My questions/lightweight chat: I had the opportunity to ask questions of my own, and a number of mine probed my interviewer as an individual: I felt we’d “clicked” over parts of our experience as developers, and I was keen to chat about some up-and-coming web technologies and compare our experiences of them! The whole interview felt about as casual and friendly as an interview ever does, and my interviewer worked hard to put me at ease.

Skills Test (day -154)

At the end of the interview, I was immediately invited to the next stage: a “skills test”: I’d be given access to a private GitHub repository and a briefing. In my case, I was given a partially-implemented WordPress plugin to work on: I was asked to –

  • add a little functionality and unit tests to demonstrate it,
  • improve performance of an existing feature,
  • perform a security audit on the entire thing,
  • answer a technical question about it (this question was the single closest thing to a “classic programmer test question” that I experienced), and
  • suggest improvements for the plugin’s underlying architecture.

I was asked to spend no more than six hours on the task, and I opted to schedule this as a block of time on a day -154: a day that I’d have otherwise been doing freelance work. An alternative might have been to eat up a couple of my evenings, and I’m pretty sure my interviewer would have been fine with whatever way I chose to manage my time – after all, a distributed workforce must by necessity be managed firstly by results, not by approach.

Dan using his computer with John and Annabel on his lap.
Scheduling my code test for a period when the kids were out of the house allowed me to avoid this kind of juggling act.

My amazingly-friendly “human wrangler” (HR rep), ever-present in my Slack channel and consistently full of encouragement and joy, brought in an additional technical person who reviewed my code and provided feedback. He quite-rightly pulled me up on my coding standards (I hadn’t brushed-up on the code style guide), somewhat-monolithic commits, and a few theoretical error conditions that I hadn’t accounted for, but praised the other parts of my work.

Most-importantly, he stated that he was happy to recommend that I be moved forward to the next stage: phew!

Trial (days -147 through -98)

Of all the things that make Automattic’s hiring process especially unusual and interesting, even among hip Silicon Valley(-ish, can a 100% “distributed” company really be described in terms of its location?) startups, probably the most (in)famous is the trial contract. Starting from day -147, near the end of May, I was hired by Automattic as a contractor, given a project and a 40-hour deadline, at $25 USD per hour within which to (effectively) prove myself.

As awesome as it is to be paid to interview with a company, what’s far more-important is the experience of working this way. Automattic’s an unusual company, using an unusual workforce, in an unusual way: I’ve no doubt that many people simply aren’t a good fit for distributed working; at least not yet. (I’ve all kinds of thoughts about the future of remote and distributed working based on my varied experience with which I’ll bore you another time.) Using an extended trial as an recruitment filter provides a level of transparency that’s seen almost nowhere else. Let’s not forget that an interview is not just about a company finding the right employee for them but about a candidate finding the right company for them, and a large part of that comes down to a workplace culture that’s hard to define; instead, it needs to be experienced.

For all that a traditional bricks-and-mortar employer might balk at the notion of having to pay a prospective candidate up to $1,000 only to then reject them, in addition to normal recruitment costs, that’s a pittance compared to the costs of hiring the wrong candidate! And for a company with an unusual culture, the risks are multiplied: what if you hire somebody who simply can’t hack the distributed lifestyle?

Automattic "Trial Code Wrangler" Contract
Page 1 of 6, all written in the USA dialect of legalese, but the important part is right there at the top: the job title is “Trial Code Wrangler”. Yeah.

It was close to this point, though, that I realised that I’d made a terrible mistake. With an especially busy period at both the Bodleian and at Three Rings and deadlines looming in my masters degree, as well as an imminent planned anniversary break with Ruth, this was not the time to be taking on an additional piece of contract work! I spoke to my human wrangler and my technical supervisor in the Slack channel dedicated to that purpose and explained that I’d be spreading my up-to-40-hours over a long period, and they were very understanding. In my case, I spent a total of 31½ hours over six-and-a-bit weeks working on a project clearly selected to feel representative of the kinds of technical problems their developers face.

That’s reassuring to me: one of the single biggest arguments against using “trials” as a recruitment strategy is that they discriminate against candidates who, for whatever reason, might be unable to spare the time for such an endeavour, which in turn disproportionately discriminates against candidates with roles caring for other (e.g. with children) or who already work long hours. This is still a problem here, of course, but it is significantly mitigated by Automattic’s willingness to show significant flexibility with their candidates.

I was given wider Slack access, being “let loose” from the confines of my personal/interview channel and exposed to a handful of other communities. I was allowed to mingle amongst not only the other developers on trial (they have their own channel!) but also other full-time staff. This proved useful – early on I had a technical question and (bravely) shouted out on the relevant channel to get some tips! After every meaningful block of work I wrote up my progress via a P2 created for that purpose, and I shared my checkins with my supervisors, cumulating at about the 20-hour mark in a pull request that I felt was not-perfect-but-okay…

My project in GitHub Desktop
I’m normally more of a command-line git users, but I actually really came to appreciate the GitHub Desktop diff interface while describing my commits during this project.

…and then watched it get torn to pieces in a code review.

Everything my supervisor said was fair, but firm. The technologies I was working with during my trial were ones on which I was rusty and, moreover, on which I hadn’t enjoyed the benefit of a code review in many, many years. I’ve done a lot of work solo or as the only person in my team with experience of the languages I was working in, and I’d developed a lot of bad habits. I made a second run at the pull request but still got shot down, having failed to cover all the requirements of the project (I’d misunderstood a big one, early on, and hadn’t done a very good job of clarifying) and having used a particularly dirty hack to work-around a unit testing issue (in my defence I knew what I’d done there was bad, and my aim was to seek support about the best place to find documentation that might help me solve it).

I felt deflated, but pressed on. My third attempt at a pull request was “accepted”, but my tech supervisor expressed concerns about the to-and-fro it had taken me to get there.

Finally, in early July (day -101), my interview team went away to deliberate about me. I genuinely couldn’t tell which way it would go, and I’ve never in my life been so nervous to hear back about a job.

A large part of this is, of course, the high esteem in which I hold Automattic and the associated imposter syndrome I talked about previously, which had only been reinforced by the talented and knowledgable folks there I’d gotten to speak to during my trial. Another part was seeing their recruitment standards in action: having a shared space with other candidate developers meant that I could see other programmers who seemed, superficially, to be doing okay get eliminated from their trials – reality TV style! – as we went along. And finally, there was the fact that this remained one of my list of “dream companies”: if I didn’t cut it by this point in my career, would I ever?

Dan, via Slack, says "I'm on the edge of my seat here! Shall look forward to hearing from you all when the time comes." and shared a picture of a nervous Fluttershy.
Two days later, on day -99, I shared what felt like an appropriate My Little Pony: Friendship is Magic GIF with the interview team via Slack.

It took 72 hours after the completion of my trial before I heard back.

I was to be recommended for hire.

Slack message recommending me for hire.
On day -98 I literally jumped for joy. This was a hugely exciting moment.

It was late in the day, but not too late to pour myself a congratulatory Caol Ila.

Dan with a whisky.
OMGOMGOMGOMG.

Final Interview (day -94)

A lot of blog posts about getting recruited by Automattic talk about the final interview being with CEO Matt Mullenweg himself, which I’d always thought must be an unsustainable use of his time once you get into the multiple-hundreds of employees. It looks like I’m not the only one who thought this, because somewhere along the line the policy seems to have changed and my final interview was instead with a human wrangler (another super-friendly one!).

That was a slightly-disappointing twist, because I’ve been a stalker fanboy of Matt’s for almost 15 years… but I’ll probably get to meet him at some point or other now anyway. Plus, this way seems way-more logical: despite Matt’s claims to the contrary, it’s hard to see Automattic as a “startup” any longer (by age alone: they’re two years older than Twitter and a similar age to Facebook).

The final interview felt mostly procedural: How did I find the process? Am I willing to travel for work?  What could have been done differently/better?

Conveniently, I’d been so enthralled by the exotic hiring process that I’d kept copious notes throughout the process, and – appreciating the potential value of honest, contemporaneous feedback – made a point of sharing them with the Human League (that’s genuinely what Automattic’s HR department are called, I kid you not) before the decision was announced as to whether or not I was to be hired… but as close as possible to it, so that it could not influence it. My thinking was this: this way, my report couldn’t help but be honest and unbiased by the result of the process. Running an unusual recruitment strategy like theirs, I figured, makes it harder to get honest and immediate feedback: you don’t get any body language cues from your candidates, for a start. I knew that if it were my company, I’d want to know how it was working not only from those I hired (who’d be biased in favour it it) and from those who were rejected (who’d be biased against it and less-likely to be willing to provide in-depth feedback in general).

I guess I wanted to “give back” to Automattic regardless of the result: I learned a lot about myself during the process and especially during the trial, and I was grateful for it!

Dollars! Photo courtesy Alexander Mils, via Pexels.
Show me the money!

One part of the final interview, though, was particularly challenging for me, even though my research had lead me to anticipate it. I’m talking about the big question that basically every US tech firm asks but only a minority of British ones do: what are your salary expectations?

As a Brit, that’s a fundamentally awkward question… I guess that we somehow integrated a feudalistic class system into a genetic code: we don’t expect our lords to pay us peasants, just to leave us with enough grain for the winter after the tithes are in and to protect us from the bandits from the next county over, right? Also: I’ve known for a long while that I’m chronically underpaid in my current role. The University of Oxford is a great employer in many ways but if you stay with them for any length of time then it has to be for love of their culture and their people, not for the money (indeed: it’s love of my work and colleagues that kept me there for the 8+ years I was!).

Monty Python and the Quest for the Holy Grail.
I’m pretty sure that most Brits are at least a little uncomfortable, even, when Dennis gives lip to King Arthur in Monty Python and the Holy Grail.

Were this an in-person interview, I’d have mumbled and shuffled my feet: you know, the British way. But luckily, Slack made it easy at least for me to instead awkwardly copy-paste some research I’d done on StackOverflow, without which, I wouldn’t have had a clue what I’m allegedly-worth! My human wrangler took my garbled nonsense away to do some internal research of her own and came back three hours later with an offer. Automattic’s offer was very fair to the extent that I was glad to have somewhere to sit down and process it before responding (shh… nobody tell them that I am more motivated by impact than money!): I hadn’t been emotionally prepared for the possibility that they might haggle upwards.

Three months on from writing my application, via the longest, most self-reflective, most intense, most interesting recruitment process I’ve ever experienced… I had a contract awaiting my signature. And I was sitting on the edge of the bath, trying to explain to my five year-old why I’d suddenly gone weak at the knees.

John in the Clarendon Quad.
I wanted to insert another picture of the outside of my office at the Bodleian here, but a search of my photo library gave me this one and it was too adorable to not-share.

Getting Access (day -63)

A month later – a couple of weeks ago, and a month into my three-month notice period at the Bodleian – I started getting access to Auttomatic’s computer systems. The ramp-up to getting started seems to come in waves as each internal process kicks off, and this was the moment that I got the chance to introduce myself to my team-to-be.

"Automattic Bot" brings me into my team-to-be's Slack channel.
I can see my team… and they can see me? /nervous wave/

I’d been spending occasional evenings reading bits of the Automattic Field Guide – sort-of a living staff handbook for Automatticians – and this was the moment when I discovered that a lot of the links I’d previously been unable to follow had suddenly started working. You remember that bit in $yourFavouriteHackerMovie where suddenly the screen flashes up “access granted”, probably in a green terminal font or else in the centre of a geometric shape and invariably accompanied by a computerised voice? It felt like that. I still couldn’t see everything – crucially, I still couldn’t see the plans my new colleagues were making for a team meetup in South Africa and had to rely on Slack chats with my new line manager to work out where in the world I’d be come November! – but I was getting there.

Getting Ready (day -51)

The Human League gave me a checklist of things to start doing before I started, like getting bank account details to the finance department. (Nobody’s been able to confirm nor denied this for me yet, but I’m willing to bet that, if programmers are Code Wranglers, devops are Systems Wranglers, and HR are Human Wranglers, then the finance team must refer to themselves as Money Wranglers, right?)

They also encouraged me to get set up on their email, expenses, and travel booking systems, and they gave me the password to put an order proposal in on their computer hardware ordering system. They also made sure I’d run through their Conflict of Interest checks, which I’d done early on because for various reasons I was in a more-complicated-than-most position. (Incidentally, I’ve checked and the legal team definitely don’t call themselves Law Wranglers, but that’s probably because lawyers understand that Words Have Power and must be used correctly, in their field!)

Mac development environment.
Wait wait wait… let me get this straight… you’ve never met me nor spoken to me on the phone and you’re willing to post a high-end dev box to me? A month and a half before I start working for you?

So that’s what I did this week, on day -51 of my employment with Automattic. I threw a couple of hours at setting up all the things I’d need set-up before day 0, nice and early.

I’m not saying that I’m counting down the days until I get to start working with this amazing, wildly-eccentric, offbeat, world-changing bunch… but I’m not not saying that, either.

The opening lines of Dan's initial interview with Automattic.× Broad Street, Oxford× VR Day at the Bodleian.× Automattic puzzle being solved× Two men using laptops opposite one another.× Dan using his computer with John and Annabel on his lap.× Automattic "Trial Code Wrangler" Contract× My project in GitHub Desktop× Dan, via Slack, says "I'm on the edge of my seat here! Shall look forward to hearing from you all when the time comes." and shared a picture of a nervous Fluttershy.× Slack message recommending me for hire.× Dan with a whisky.× Dollars! Photo courtesy Alexander Mils, via Pexels.× Monty Python and the Quest for the Holy Grail.× John in the Clarendon Quad.× "Automattic Bot" brings me into my team-to-be's Slack channel.× Mac development environment.×

Shifting into Automattic

In October of this year – after eight years, six months, and five days with the Bodleian Libraries – I’ll be leaving for pastures new. Owing to a combination of my current work schedule, holidays, childcare commitments and conferences, I’ve got fewer than 29 days left in the office.

Dan's whiteboard: "You have [29] work days left to ask Dan that awkward question".
I’ve been keeping a countdown on my whiteboard to remind my colleagues to hurry up and ask me anything they need in order to survive in my absence.
Instead, I’ll be starting work with Automattic Inc.. You might not have heard of them, but you’ve definitely used some of their products, either directly or indirectly. Ever hear of WordPress.com, WooCommerce, Gravatar or Longreads? Yeah; that’s the guys.
Automatic gear stick.
It’s a gear stick. For an automatic car. ‘Cos I’m “shifting into Automattic”. D’you get it? Do you? Do you?

I’m filled with a mixture of joyous excitement and mild trepidation. It’s mostly the former, thankfully, but there’s still a little nervousness there too. Mostly it’s a kind of imposter syndrome, I guess: Automattic have for many, many years been on my “list of companies I’d love to work for, someday”, and the nature of their organisation means that they have their pick of many of the smartest and most-talented geeks in the world. How do I measure up?

Dan in the Rewley Library at the University of Oxford.
During my final months I’m taking the opportunity to explore bits of the libraries I’ve not been to before. Y’know, before they revoke my keycard.

It’s funny: early in my career, I never had any issue of imposter syndrome. I guess that when I was young and still thought I knew everything – fuelled by a little talent and a lot of good fortune in getting a head-start on my peers – I couldn’t yet conceive of how much further I had to go. It took until I was well-established in my industry before I could begin to know quite how much I didn’t know. I’d like to think that the second decade of my work as a developer has been dominated by unlearning all of the things that I did wrong, while flying by the seat of my pants, in the first decade.

Roof of the Clarenon Building, Broad Street, University of Oxford, showing the Muses.
I’ll be mostly remote-working for Automattic, so I can guarantee that my office won’t be as pretty as my one at the Bod was. Far fewer Muses on the roof, too.

I’m sure I’ll have lots more to share about my post-Bodleian life in due course, but for now I’ve got lots of projects to wrap up and a job description to rewrite (I’m recommending that I’m not replaced “like-for-like”, and in any case: my job description at the Bodleian does not lately describe even-remotely what I actually do), and a lot of documentation to bring up-to-date. Perhaps then this upcoming change will feel “real”.

Dan's whiteboard: "You have [29] work days left to ask Dan that awkward question".× Automatic gear stick.× Dan in the Rewley Library at the University of Oxford.× Roof of the Clarenon Building, Broad Street, University of Oxford, showing the Muses.×