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?



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