Buying Another House

Seven years ago, I wrote a six-part blog series (1, 2, 3, 4, 5, 6) about our Ruth, JTA and I’s experience of buying our first house. Now, though, we’re moving again, and it’s brought up all the same kinds of challenges and stresses as last time, plus a whole lot of bonus ones to boot.

Our house in Kidlington
Our old house – seen here in 2013 – has served its purpose. It’s time for us to move on.

In particular, new challenges this time around have included:

  • As owners, rather than renters, we’ve had both directions on the ladder to deal with. Not only did we have to find somewhere to move to that we can afford but we needed to find somebody who’d buy our current house (for enough money that we can afford the new place).
  • The first letting agents we appointed were pretty useless, somehow managing to get us no viewings whatsoever. Incidentally their local branch got closed soon after we ditched them and the last time I checked, the building was still up for sale: it doesn’t bode well for them that they can’t even sell their own building, does it?
  • The replacement letting agents (who sold us this house in the first place) were much better, but it still took a long time before we started getting offers we could act on.
  • We finally selected some buyers, accepting a lower offer because they were cash buyers and it would allow us to act quickly on the property we wanted to buy, only for the coronavirus lockdown to completely scupper our plans of a speedy move. And make any move a logistical nightmare.
  • Plus: we’re now doing this with lots more stuff (this won’t be a “rally some friends and rent a van” job like last time!), with two kids (who’re under our feet a lot on account of the lockdown), and so on.
Dan with his solar panels.
We added significant value to our old house during the time we owned it, for example by installing solar panels which continue to generate income as well as “free” energy. As well as being now conveniently close to a train line to London which I suppose would be good for commuters even though we’ve mostly used it for fun.

But it’s finally all coming together. We’ve got a house full of boxes, mind, and we can’t find anything, and somehow it still doesn’t feel like we’re prepared for when the removals lorry comes later this week. But we’re getting there. After a half-hour period between handing over the keys to the old place and picking up the keys to the new place (during which I guess we’ll technically be very-briefly homeless) we’ll this weekend be resident in our new home.

The Green, our new home
Our new home’s pretty delightful. I’ll vlog you a tour or something once we’re moved in, under the assumption that a housewarming party is still likely to be rendered impossible by coronavirus.

Our new house will:

  • Be out in the fabulous West Oxfordshire countryside.
  • Have sufficient rooms to retain an office and a “spare” bedroom while still giving the kids each their own bedroom.
  • Boast a fabulously-sized garden (we might have already promised the kids a climbing frame).
  • Have an incredible amount of storage space plus the potential for further expansion/conversion should the need ever arise. (On our second-to-last visit to the place with discovered an entire room, albeit an unfinished one, that we hadn’t known about before!)
  • Get ludicrously fast Internet access.

We lose some convenient public transport links, but you can’t have everything. And with me working from home all the time, Ruth – like many software geeks – likely working from home for the foreseeable future (except when she cycles into work), and JTA working from home for now but probably returning to what was always a driving commute “down the line”, those links aren’t as essential to us as they once were.

Sure: we’re going to be paying for it for the rest of our lives. But right now, at least, it feels like what we’re buying is a house we could well live in for the rest of our lives, too.

I certainly hope so. Moving house is hard.

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?

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.

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.

My TED Video on the Future of Work

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

I was thrilled to participate in TED’s new video series, The Way We Work, and not surprisingly I made the case that distributed work is where everything is headed.

Like Automattic (Matt’s company), Three Rings has also long been ahead of the curve from a “recruit talent from wherever it is, let people work from wherever they are” perspective. Until I was recently reading (more than I had previously) about the way that Automattic “works” I was uncertain about the scalability of Three Rings’ model. Does it work for a commercial company (rather than a volunteer-run non-profit like Three Rings)? Does it work when you make the jump from dozens of staff to hundreds? It’s reassuring to see that yes, this kind of approach certainly can work, and to get some context on how it does (in Automattic’s case, at least). Nice video, Matt!

Working From Home

The phone rings. It’s clear to me by the sound it makes and by the image on it’s display that this is a business call.

“Good morning, SmartData; Dan speaking,” I say.

The caller identifies themselves, and asks to speak to Alex, another SmartData employee. I look to my right to see if Alex available (presumably if he was, he’d have answered the call before it had been forwarded to me). This is possible because of the two-way webcam feed on the monitor beside me.

“I’m afraid Alex isn’t in yet,” I begin, bringing up my co-worker’s schedule on the screen in front of me, to determine what he’s up to, “He’ll be in at about 10:30 this morning. Can I get him to call you back?”

Not for a second did it occur to the caller that I wasn’t sat right there in the office, looking over at Alex’s chair and a physical calendar. Of course, I’m actually hundreds of miles away, in my study in Oxford. Most of our clients – even those whom I deal with directly – don’t know that I’m no longer based out of SmartData’s marina-side offices. Why would they need to? Just about everything I can do from the office I can do from my own home. Aside from sorting the mail on a morning and taking part in the occasional fire drill, everything I’d regularly do from Aberystwyth I can do from here.


Back when I was young, I remember reading a book once which talked about advances in technology and had wonderful pictures of what life would be like in the future. This wasn’t a dreamland of silver jumpsuits and jetpacks; everything they talked about in this book was rooted in the trends that we were already beginning to see. Published in the early 80s, it predicted a microcomputer in every home and portable communicators that everybody would have that could be used to send messages or talk to anybody else, all before the 21st century. Give or take, that’s all come to pass. I forget what the title of the book was, but I remember enjoying it as a child because it seemed so believable, so real. I guess it inspired a hopeful futurism in me.

But it also made another prediction: that with this rise in telecommunications technologies and modern microcomputers (remember when we still routinely called them that?), we’d see a greap leap in the scope for teleworking: office workers no longer going to a place of work, but remotely “dialling in” to a server farm in a distant telecentre. Later, it predicted, with advances in robotics, specialist workers like surgeons would be able to operate remotely too: eventually, through mechanisation of factories, even manual labourers would begun to be replaced by work-at-home operators sat behind dumb terminals.

To play on a cliché: where’s my damn flying car?

By now, I thought that about a quarter of us would be working from home full-time or most of the time, with many more – especially in my field, where technology comes naturally – working from home occasionally. Instead, what have we got? Somewhere in the region of one in fifty, and that includes the idiots who’ve fallen for the “Make £££ working from home” scams that do the rounds every once in a while and haven’t yet realised that they’re not going to make any £, let alone £££.

At first, I thought that this was due to all of the traditionally-cited reasons: companies that don’t trust their employees, managers who can’t think about results-based assessment rather than presence-based assessment, old-school thinking, and not wanting to be accused of favouritism by allowing some parts of their work force to telework while others can’t. In some parts of the world, and some fields, we’ve actually seen a decrease in teleworking over recent years: what’s all that about?

I’m sure that the concerns listed above are still critical factors for many companies, but I’ve realised that there could be another, more-recent fear that’s now preventing the uptake of teleworking in many companies. That fear is one that affects everybody – both the teleworkers and their comrades in the offices, and it’s something that more and more managers are becoming aware of: the fear of outsourcing.

After all, if a company’s employees can do their work from home, then they can do it from anywhere. With a little extra work on technical infrastructure and a liberal attitude to meetings, the managers can work from anywhere, too. So why stop at working from home? Once you’ve demonstrated that your area of work can be done without coming in to the office, then you’re half-way to demonstrating that it can be done from Mumbai or Chennai, for a fraction of the price… and that’s something that’s a growing fear for many kinds of technical workers in the Western world.

Our offices are a security blanket: we’re clinging on to them because we like to pretend that they’ll protect us; that they’re something special and magical that we can offer our clients that the “New World” call centres and software houses in India and China can’t offer them. I’m not sure that a security blanket that allows us to say “we have a local presence” will mean as much in ten years time as it does today.

In the meantime, I’m still enjoying working from home. It’s a little lonely, sometimes – on days when JTA isn’t around, which are going to become more common when he starts his new job –  but the instant messenger and Internet telephony tools we use make it feel a little like I’m actually in the office, and that’s a pretty good trade-off in exchange for being able to turn up at work in my underwear, if I like.