Tag: leadership

Create Leadership Workshops at Your Company!

One ongoing project that I have at Automattic that I am especially proud of are our Developing Leadership Workshops. 

The workshops take place once per month, and last about an hour each. So far it’s been almost entirely Team Leads from within the company, with one guest speaker, Kevin Goldsmith of Spotify.

The workshops are stolen directly from Work Rules and Google’s similar practices – the idea, broadly, is to help individuals unlock the value in their own experience and practices to the rest of the folks at the company.

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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?

 

 

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.

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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.

Communicating with a Remote Team: One on Ones

Communicating with a Remote Team: One on Ones

Leading a team at WordPress.com is a great opportunity – I wrote about my approach this a little bit before – we’re a fully distributed company, and we’re always able to switch things up, iterate on our work as well as our meta-work, the labor that enables us to work at our best.

Continue reading “Communicating with a Remote Team: One on Ones”