Developing Leadership at Automattic


The company I work for, Automattic, is bleeding edge in a lot of ways – I’ve spoken about this before (here, here and here). Recently I moved into a Team Lead role, working with a team of Happiness Engineers. This new team, Athens, is also doing some really cool stuff – but this Post is about the Lead role.

The nature of Automattic leads to a lot of responsibility for everyone: having the level of freedom and autonomy that we do is incredible, but it comes with a certain weight. That weight is the weight of responsibiity: when there isn’t anyone to tell you what to do, what to think, or how to approach problems, you’re faced with a situation that is not so common in professional life – you have to decide for yourself what is important, and how to accomplish things that advance toward your own vision.

Self direction is not easy!

Plus, I do not know how to lead a distributed team. I have some traditional management experience, which is nice to have, but I’m not sure it’s really helping me all that much. I could hear Impostor Syndrome scratching at the door. Luckily, I had been reading Work Rules about the same time that I took on this new challenge.

In Work Rules, Laszlo Bock describes one component of Google’s approach to leadership development – they hold regular internal skillshares and workshops, with more experienced leaders sharing their lessons and systems with folks who are receptive to learning more about leading teams. I remember thinking, “Wow, those sound awesome. I wish we had something like that.”

Here are the first two lines of the Automattic Creed:

I will never stop learning.

I won’t just work on things that are assigned to me.

So, I surveyed our Team Leads, set up a schedule, and thus was born Automattic’s Developing Leadership workshops.

In these workshops, you guessed it, more experienced Team Leads share their processes, thinking, and systems with the rest of the leadership at the company. They take the form of hour-long video sessions, with a talk or workshop or interview, followed by Q&A.

These sessions are all recorded and stored in our internal field guide, making them an evergreen resource for team leads old and new, as well as a great place for folks looking to move into a leadership role to hone their understanding of what it means to be a Team Lead at Automattic.

Over time, I’m looking forward to getting more and more Leads involved, as well as pulling in authority figures from outside of the company, to bring in ideas and challenge us with perspectives from other parts of the Work World. Places like Gore, that operate at a massive scale with the lattice style of management, or Spotify, to explain their Guild/Tribe/etc setup – these are folks who are pushing the envelope of what it means to organize a business, and I’d love to get them into the workshop circuit.

I’ve built a lot of things at Automattic that I’m proud of, but I think these sessions could end up being my largest contribution to the ongoing success of the company.

4 thoughts on “Developing Leadership at Automattic

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