Category: Remote Leadership

Experimenting with One on Ones: A Tale of a Team Lead

One of the best things to come to the forefront of the business world through the Startup superhighway is the commitment to an experimental approach to business. This goes by many different names, “iterative mindset,” Lean Startup, and even Agile in some ways is a particular application of the experimental approach.

Businesses and organizations taking an experimental approach to their work and products is not without its drawbacks, but there is a really neat philosophical argument for the larger picture, which is, if the experimental framework fails to produce the results you’d like, that is itself an acceptable outcome of that framework, as itself can be used as an experiment.

Look, trying new things, tracking their outcomes, and relentlessly pursuing small improvements over time is a great way to build or run a business. One of the very coolest features of working remotely for a results-oriented company is that you’re able to apply this same mindset to yourself, and to your own work and work processes, and even your life in general.

It’s pretty rad.

When I first started working remotely, I stuck to a pretty consistent schedule, around 8A – 5P from Monday through Friday. Over time, I’ve made small changes here and there, found ways to make my schedule more conducive to my work and my life.

 

When Mango (the toddler that is currently terrorizing my house) was first born, I worked four longer days per week, taking a day off to spend with her (and save some cash on daycare).

Since then I’m back to five days per week, but they’re unusual days; I really pack Mondays and Wednesdays, with five or six one on one sessions on each day plus other meetings, etc. Batching that kind of really conversational and personal work helps me to stay focused, to stay in the right mindset.

How do I know that batching that work helps me stay focused? Because I experimented with it, of course!

At first, I tried doing all on my one-on-ones on one single day – that was suboptimal because by the end, I was pretty fried and wasn’t giving my very best to the folks on my team. As a team lead, nothing takes precedence over serving the folks on my team, and accepting that meant that I had to keep experimenting. That took about two weeks.

I tried to spread it out, to have 1-2 one on one sessions per day; this was suboptimal because, as I learned about myself, I have to be pretty intentional about these kinds of personal and professional relationships.

My natural state is to assume that everyone and everything is OK, and that an alarm will go off somewhere, somehow, if things are not in top shape. This is the wrong approach for one on ones, and at least for me, being a leader in general. Bad things often have a long runway, but you have to know where to look, and you have to take the time to look.

So, for me, it takes some effort to get into the right personally curious and empathetic mindset that one on one preparation and execution require. Recognizing that this effort exists and was a cost meant that for me to get into that mindset every day was costing me efficiency elsewhere.

This took probably another four or five weeks. I had identified two points on a larger line that were both suboptimal for different ways: doing all of my one on ones on a single day wasn’t going to work (and was not really scalable), and spreading my one on ones across the week had its drawbacks as well.

What I needed was what Aristotle called the Golden Mean!

(As a sidebar, I think comparing Aristotle’s idea here to Goldilocks is inherently flawed: Goldilocks identified her preference as a nearly-perfect halfway between two points, whereas Aristotle allows for the much more interesting idea that the ideal decision may be closer to one incorrect outcome than another. The ideal point between being a headstrong fool and a coward may be closer to headstrong fool.)

I didn’t come up with anything revolutionary. I followed the Operations Management 101 playbook and tried batching the work to minimize setup costs. It worked, and I’m more productive and (I hope!) better at these small but incredibly important conversations.

This also lets me keep my calendar on Tuesdays and Thursdays relatively open, so I can schedule big blocks of time on projects that require more sustained focus to really find success.

Of course, in time, this might change, or opportunities to improve it may appear, which will require ongoing experimentation.

What I’m saying is, keep experimenting, you crazy kids. Keep on hypothesizing, you wild star people. It’s the way we get better.

Leadership, Feedback, and Ego

Retro Office Space With Books, Furniture And Sun Flare

Working at Automattic has a lot of advantages: working remotely, amazing coworkers, and the chance to make a real difference in the future of the internet (I really believe that!)

Being a Team Lead in this environment, leading one of our many Happiness Teams focused on the WordPress.com customer base, is unlike any job I’ve ever had, and for me, one piece that I really value above all else, is the opportunity to experiment – not just on the work itself, but also on the meta-work, on the work of the work. The larger structure, the larger idea. Being able to question and adjust and iterate is both amazing and a little scary.

Continue reading “Leadership, Feedback, and Ego” →

From the Introduction of The Counterinsurgency Field Manual

This publication can help compress the learning curve. It is a tool for planners, trainers and field commanders. Using it can help leaders begin the learning process sooner and built it on a larger knowledge base…

…Current tactics, techniques and procedures sometimes do not achieve the desired results. When that happens, successful leaders engage in a directed search for better ways to defeat the enemy. To win, the Army and Marine Corps must rapidly develop an institutional consensus on new doctrine, publish it, and carefully observe its impact on mission accomplishment.

This learning cycle should repeat continuously as US counterinsurgents seek to learn faster than the insurgent enemy.

The side that learns faster and adapts more rapidly wins.

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?

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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.