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?

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(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?

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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.

Chipotle’s 39 Point Checklist for Managers

Really interesting read – on one level I’m glad that my own performance working at WordPress.com does not involve a 39 point quantification,  but on another level that type of highly specific expectation setting does have its appeal.

If I were a manager at Chipotle, you’d better believe I wouldn’t be doing much that didn’t contribute directly to one of those checklist items – and maybe that’s the point.

Inside Chipotle’s extremely intense, 39-point checklist for outstanding management.

Two Notes from ‘Quiet’

In reading Susan Cain’s ‘Quiet,’ recommended by my colleagues Paul and Gus (and others), there have been two notable takeaways for me. I’m only about eighty pages in, and I’ve learned a lot about introversion and how society works (or fails to work) for folks who think that way.

Like anyone, though, when I have a hammer, all I see are nails. Two neat things I’ve picked up:

The Bus to Abilene:

…a family sitting on a porch in Texas on a hot summer day, and somebody says, ‘I’m bored. Why don’t we go to Abilene?’ When they get to Abilene, somebody says, ‘You know, I didn’t really want to go.’ And the next person says, ‘I didn’t want to go–I thought you wanted to go,’ and so on. Whenever you’re in an army group and somebody says, ‘I think we’re getting on the bus to Abilene here,’ that is a red flag. You can stop a conversation with it. It is a very powerful artifact of our [the army’s] culture.

I’m guilty of this, both as the suggestion-giver and the go-along-with participant. Having a name for it will be helpful in the future.

Solitude and Creativity:

If solitude is an important key to creativity – then we might all want to develop a taste for it. We’d want to teach our kids to work independently. We’d want to give employees plenty of privacy and autonomy. Yet increasingly we do just the opposite.

This resonates with me as coming from the same place that inspired Solitude in Leadership, a piece I’ve written about in the past. Even as someone who waffles between introversion and extroversion, I appreciate and value time spent alone, sometimes in quiet reflection, sometimes daydreaming.