Tag: work from home

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?

 

 

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.

Working Remotely, Thinking Globally, and FOMO

You’ve heard of FOMO already, right?

This is for all of you folks at home who would never click that link to Wikipedia:

Fear of missing out or FoMO is “a pervasive apprehension that others might be having rewarding experiences from which one is absent”.[2] This social angst [3] is characterized by “a desire to stay continually connected with what others are doing”.[2] FoMO is also defined as a fear of regret,[4] which may lead to a compulsive concern that one might miss an opportunity for social interaction, a novel experience, profitable investment or other satisfying event.[5] In other words, FoMO perpetuates the fear of having made the wrong decision on how to spend time, as “you can imagine how things could be different”.[4]

Working as a team lead at Automattic, on our flagship product, WordPress.com, is a wild experience for a lot of reasons.

Continue reading “Working Remotely, Thinking Globally, and FOMO” →