Tag: team lead

Iterating on One on Ones

I know, I know – I’ve written about one on ones before.

If you’re not familiar, a one on one is a short sit down between a team lead and a member of the team. Folks much smarter than me have written some really insightful stuff about them, why they’re important, what they’re for. Here’s a great one, from Rands.

I do them once a week, for about thirty minutes, with every member of my team. I’ve been thinking about one on ones quite a lot recently – some feel really productive, some feel like I’m really getting to know the team member, and some feel functional, perfunctory, useful not maybe not productive.

This coming week, we’re starting a new structure of weekly updates. Since Athens’ inception we’ve done roughly weekly updates with our sister team (Sparta, obviously) on Wednesdays.

These updates weren’t really structured at all – folks would write about their home being remodeled, or their recent projects, or their ticket or chat count, or maybe an upcoming vacation. They were nice, but not especially helpful, as someone trying to understand how folks were doing, what they were working on, etc.

We didn’t even have a great reason to be doing them on Wednesdays – at one time, all of the teams at Automattic did updates on Thursdays, so it made sense to schedule internal team updates on Wednesdays.

Our company wide updates are still called Thursday Updates, but they are usually posted on Fridays, sometimes the following Monday, depending on what time zones the team’s members tend to work from.

The time we scheduled the updates didn’t make sense anymore. Our internal stats for chats and tickets run Sunday > Saturday, so to do any kind of regular volume updates meant folks had to do some math by hand, which was a point of friction.

Wednesday was also suboptimal because it was right about the point in the week where folk started to catch their groove – breaking it up with unstructured reflection (or being ignored, or populated with throwaway content), wasn’t the best we could do.

Short story long – starting this coming week we’ll be doing our updates on Monday morning, with a consistent structure for each person on the team, including me. There are expectations for clear and transparent reporting of individual volume, as well as how it compares to our team baseline, which is a sort of cooperative understanding of what a day’s work looks like for us at this time.

This brings us around to the obvious question; what does this have to do with one on ones?

In considering the one on ones that I really enjoy, that I feel are Working, they’re consistent in that they are not simply status updates – they’re not “I did X. This week I’m doing Y.”

Instead, they’re about experiences and approaches, friction and family. They’re about building a relationship rather than communicating things I can easily find elsewhere, especially with our commitment to communication and transparency.

As our weekly personal updates become more focused, I think it’s entirely possible that they could take the place of the more status-update-like one on one conversations. This isn’t to say that I’ll stop doing them (I love one on ones), but rather I’ll have a chance to start doing them correctly – using them to get to know my team, rather than getting to know the stuff around them.

I think it is probably also a good move for me to start being more clear to my team how I think about one on ones – if they are meant for talking about bigger career thinking, about navigating the waters within Automattic, about finding the right way to be impactful, there is likely a better way to structure that.

I’m not sure what that structure will look like – I have been reading about OKRs quite a lot, and it seems like they could fill that not-daily-work-but-still-important-work structure.

I am also trying to be more aware that my natural inclination toward more structure is not always the right move – although, I think I’m probably right about this one!


Efficiency is Behavior

Working remotely and leading a remote team is not always so different from doing that same work locally. Many of the challenges are similar, if not exactly the same.

One thing that’s been on my mind a lot, and if you work in any sort of revenue-driven enterprise, it’s something you think about a lot as well, is the idea of efficiency, and how we can create more efficient situations.

I find a tension exists between traditional operations management ideas and approaches to efficiency gains (calculate throughput, build a sensitivity analysis, reduce waste) and my own approach to leadership, which is a sort of mix of servant leadership and hopeless romantic labor reformer.

That tension is the natural pressure that exists between the idea of employees, Workers, as a numerical input into a larger system (the average Subway sandwich maker can produce one point four sandwiches every five minutes. Reducing that to one point three would represent etc etc, just an example) and the belief that every person has creative value, that the folks working closest to the problem (the sandwich) are those most qualified to solve that problem better, or faster.

I’m not the first person to see this tension – we can read the massive acceptance of and growing excitement about Lean as an antidote to this very tension, if we’re generous, since we can see in the Toyota Production system great empowerment of what you’d call line workers to identify problems, repair, and improve their own Work.

There is a difference between efficiency on a spreadsheet (or, even worse, a Powerpoint presentation) and efficiency in action.

My team is fairly small – it’s me and eleven Happiness Engineers – and for us, efficiency is behavior. It’s actions – it’s not such a fungible idea, it’s not a board room topic. It’s about doing something One Way or This Other Way, and seeing which gets better results in the same amount of time – or the same results in less time, then going with it.

If you’re leading a team, especially a smaller team and double especially if you’re leading a remote team, you must recognize that efficiency comes from behavior, and by testing and changing behavior.

We will never get more efficient with a poster with a quote from Deming under a high res photo of a  fighter jet. The only way we’re going to get more efficient is by trying out new stuff, and chucking it if it doesn’t work.

That means leaving room for failure. That means kicking out the sacred cows and rejecting dogma. There is enormous value in reading and in discussing and in building spreadsheets – don’t get me wrong, I love spreadsheets – but all of those things have to result in action, in trying some shit out.

Otherwise, it’s just air, it’s just value locked up inside your head, and we’ve been over that.

Try something new today. Sleep one less hour. Sleep one more hour. Don’t check your email. Turn off Slack. Listen to one song on repeat.

Leading a Remote Team: Roundup!

I was chatting with a friend from my SUNY Binghamton days about working remotely, and he was asking me a bit about the way that remote leadership works – how to approach it, how to convince folks that you can lead teams remotely effectively and without hassle, etc.

I have a lot to say on this topic (of course), but I figured a good place to start (especially for newer readers) would be to round up my existing work on the topic, so we can all move forward with the same shared understanding.

I think the best thing I’ve written about working remotely in general, which also applies to leading a team remotely, is this longer Post about Working Remotely and an idea I call Aggressive Transparency.

At the end of the day, the lifeblood of a remote organization (or a remote arm of a larger organization) must be communication.

I would argue not just communication, but a particular flavor, that defaults not just to communication, but what many people would call overcommunication – I’d contend that the current state of communication within many companies is deplorable, and that is what leads folks to object to aggressive transparency in many cases.

Another really great starting point for thinking about what it means to lead a remote team is this talk by my friend and colleague Paolo Belcastro – he’s been at Automattic even longer than I have, and shares a great deal of insight in this workshop.

Additionally on the topic of communication, here is a more recent post about using your asynchronous tools most effectively – Communicating in 2016: Leave Good Messages

One thing I’ve been spending a lot of time thinking about and really trying to figure out over the last year is feedback and expectation setting in a remote environment.

One thousand thank-you notes to the folks on my team who have been so gracious and understanding when it comes to the many, many experiments and iterations that we’ve been through.

Posts about feedback start here: Figuring Out Feedback, where I hastily sketch out the plan for how we first tried rotating monthly feedback exercises – this is something I really should revisit in more detail, we’ve learned a ton since then.

After that Post, we did a couple rounds of what we called Leadback Surveys, which are anonymous surveys providing the team an opportunity to let me know how they think I’m doing. You can imagine how potentially fraught with vulnerability and anxiety that might be – so I wrote a Post about the process, Leadership, Feedback and Ego.

One of the things I try to stick to, and would recommend for anyone else looking to lead a remote team, or to get better at leading a remote team, are weekly one on one conversations with everyone on my team. They’re generally around 30 minutes long, and I strongly prefer voice, though I can waver a little on that. Here’s a Post about one on ones in general.

Since, like everything, learning this lead role is a process of experimentation, failing magnificently, and then getting better, I also recently published a post outlining how I’ve experimented with one on ones over the last year.

That brings us to today – this is a topic I think about a lot, and something I could write volumes and volumes about. Is there anything in particular you’re curious about?



Remote Leadership: Figuring Out Feedback

Remote Leadership: Figuring Out Feedback

Working in a fully remote environment creates some unique challenges. One piece, that I’ve written about before, is the need to intentionally make visible one’s work.

This intentionality comes from the nature of the remote environment: we don’t have the natural day-to-day contact, the sort of diffusion of knowledge that one can gain from being in the same physical space.

Similarly, the need for feedback, for eyes on your work and your working style, is a very real need, and one that can be hard to figure out in a fully remote enviroment. I’m outlining here the way my team and I currently approach it – this approach has developed somewhat organically, out of company-wide surveys and smaller team discussions, and it’s working pretty well as far as I can tell. Like anything and everything we do, when it stops working, or when a better way to do it comes around, we’ll change!

Our current feedback structure has three types of feedback, each of which is quarterly, on a rolling basis. This means we end up engaging in one type of feedback every month. The three types:

  • Peer Reviews – where each member of the team reviews one random other member (including me!) on ticket and live chat transcripts.
  • 3-2-1-Oh Roadmapping – where I meet with each member of the team, and we chat about what they’re good at, what they’d like to be good at, and how I can support their journey.
  • Leadback Surveys – where the team anonymously provides me feedback on how I’m doing as their team lead. Yes, there are Likert scales involved!

In this way we’re able to provide feedback to one another, I’m able to understand how folks are feeling and how they see their personal professional journey, and my team is able to help me understand how best to serve them.

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.