Tag: remote work

Communicating in 2016: Leave Good Messages

Communicating in 2016: Leave Good Messages

Subtitled; Never Just Say ‘Ping’

I was chatting with my friend Dan today, who works for one of the biggest publishing houses in the world. I’ve known Dan for a really long time. Here’s a picture of us from almost ten years ago:


Dan was telling me that his subsection of the company was starting to use Slack for communication at work. You know Slack right? We’ve been using Slack for a while at Automattic (for a time, the open source WordPress project was the biggest single group using Slack – or so I heard. Couldn’t tell you if that’s still true!).

Continue reading “Communicating in 2016: Leave Good Messages”

Work from Home but Still Eat with Friends

Working remotely has tons of advantages, and it’s one of the best features of being a Happiness Engineer at Automattic.

(In fairness, all positions at Automattic are fully remote!)

I’ve worked remotely for over two years, and I’ve learned a few tricks, a few tactics to do battle with the parts of working from home that can be challenging.

Continue reading “Work from Home but Still Eat with Friends”

Work Remotely: Shrink Your Office

Work Remotely: Shrink Your Office

I love working remotely. Working for Automattic is especially solid, since our entire company is distributed. There is no office anywhere, although we do have a building in San Francisco for events and visiting Automatticians.

Scott recently tweeted about one of the advantages that working remotely offers:

He’s absolutely right. Over the last two years I’ve shrunk my required inventory to be productive down to a pretty tiny footprint. Check it out:

Continue reading “Work Remotely: Shrink Your Office”

Communicating with a Remote Team: One on Ones

Communicating with a Remote Team: One on Ones

Leading a team at WordPress.com is a great opportunity – I wrote about my approach this a little bit before – we’re a fully distributed company, and we’re always able to switch things up, iterate on our work as well as our meta-work, the labor that enables us to work at our best.

Continue reading “Communicating with a Remote Team: One on Ones”

My Team Lead Page

My Team Lead Page

As a Team Lead at WordPress.com, I’m constantly trying to improve, trying to learn how to be the best lead I can be. It can be hard: leading a team remotely is a new skillset, not just for me but for humans in general.

On one hand, humans have been organizing into groups to accomplish bigger goals for about as long as there have been humans, so the ground I’m walking is pretty well trod at this point. On the other hand, there are aspects of remote leadership that are totally new – we’re pushing the boundaries, and seeing what sticks and what doesn’t.

One thing I’ve done – maybe totally self-indulgent, I acknowledge that – is set up a page specifically about me, and my leadership style, on my team’s internal O2. Here’s an old post from Matt about P2s (the precursor to O2).

The goal of this page is to introduce myself to new team members, to help current team members understand my approach and thinking, and to try to be more transparent about the way I think and the way I work.

The Big Premise is, I guess, that being more transparent and up front about this stuff is better than letting people slowly figure it out on their own. It seemed like an appropriate thing to share here, and seek some feedback. Like anything, this is a work in progress, and will change over time.

The rest of this Post is the copy from that Page – what do you think? Am I ridiculous?

Team Lead

Who is this dude?

(I’m the one on the right)

What does he do?

That’s a great question 🙂 Leads at Automattic approach the job differently.

Athens is an experimental team: we’re not bound to any one support medium, and we’re trusted quite broadly to strike where we see the biggest wins available. In such an experimental environment, I try to keep an open and flexible mindset around the lead role.

My general approach to the lead role is one of servant leader. I’m here to support you, to coach you, to help you become the person you’d like to become.

I like to have one-on-one chats with each of my team members every week, especially during the early days of a Happiness Engineer’s career at Automattic, or after a team switch or other big move. This isn’t a forever thing: I’m comfortable having one-on-ones less frequently, or sometimes not at all. The real question behind these chats is: How can I best support you? Not everyone wants to talk every week, and it isn’t the best tool for everyone. I get that.

I also spend time reviewing chat transcripts and tickets – this is tricky because, like any improvement effort, the focus is almost entirely on the Sad Robots (these are our form of needs-improvement feedback from customers). To improve, one must focus on the pieces that are not yet performant, and the best way for me to identify those pieces is through existing negative feedback. You don’t fix a sink that doesn’t leak 🙂

One thing I really enjoy and find great satisfaction in is career development and goal setting: In our one-on-ones, I want to hear from you about your goals, about your dreams, about the change you’d like to see in the world. From the lead perspective, I’m able to see a broader picture of you, your work, and how it can fit into the jigsaw-puzzle-in-a-hedge-maze that is Automattic. I can use that broader picture to help you navigate to a place where you’re more impactful, more satisfied – in general terms, a superhero.

What is his philosophy?


Substitute “Lead” for “Teacher” and “HE” for “Student.”

“Someone wise or smart” is not me; you need to find an inspiring figure in your own life. Read books and watch movies, you’ll find someone. Maybe lots of someones.

We really are breaking all the rules: leave space for serendipity. 🙂

If you’re the type of person who wants to know more about my thinking on The Work, you can find lots of it here.