WordPress was my first introduction to the idea of distributed work — we didn’t need to live in the same place or work in the same office to build something that changes the world. So when I started building Automattic in 2005, we took the exact same approach. All you needed was good WiFi and a dream.
Fast forward to 2019, and Automattic remains a fully distributed company, with 900 employees working from 68 countries and no central office. Now that we’ve been working this way for over a decade, I wanted to create a podcast to tell the story of distributed work — not just sharing everything we’ve learned at Automattic, but speaking with other companies, executives, and creators who are pioneering the future of work. We’re going to learn about the practical application of distributed work in our daily lives, but also answer the bigger questions about why it’s important.
Forward-looking new series about distributed work from the founder of WordPress and Automattic (my employer).
Confidence isn’t optimism or pessimism, and it’s not a character attribute. It’s the expectation of a positive outcome.
I’m inspired by Rosabeth Moss Kanter’s work and philosophy on change management. The consistent message in her writing—many of her essays are in Harvard Business Review—is that a leader’s job is to “provide the tools and conditions that liberate people to use their brainpower to make a difference in a world of constant challenge and change.”
People are almost always confronting what computer science regards as the hard cases. Up against such hard cases, algorithms make assumptions, show bias toward simpler solutions, trade off the costs of error against the costs of delay, and take chances.
These aren’t the concessions we make when we can’t be rational. They’re what being rational means.
This book by Daniel Siegel guided me beyond the popular meditation apps like Calm and Headspace into something different, the “Whole of Awareness.” The idea is to integrate all types of meditation and awareness training practices from focus attention, to open awareness, to connectedness—non-duality.
The core practice involves visualizing a center hub of awareness, a spoke of attention, and a rim which holds all possible focuses. From the 5 senses, body awareness, thoughts/emotions, and feeling connected to other humans, beings, and things.
Dan repeats a phrase over and over to underline why a practice like this leads to improved well-bing: “Where attention goes, neural firing flows, and neural connection grows.”
Increase neural integration in the brain, enabling more coordination and balance in both the functional and structural connectivity within the nervous system that facilitates optimal functioning, including self-regulation, problem solving, and adaptive behavior that is at the heart of well-being.
In The big secret of small improvements Tal Bereznitskey explains how to improve “quick fix days,” where software teams take time to make small improvements. Those small changes can together mean a big win for customers and the business.
At Automattic we’ve experimented with both 1-day bug scrubs in one team all the way up to a full “hack week” — so Tal’s principles strike a chord with me.
Framing the problem is halfway to solving it — I love how he suggests rewording the subject line of a software change to fix a bug as something actionable, not just a description of the problem.
6. Well defined. Only work on tasks that are defined properly. Prefer “Make content scrollable” over “Bug: can’t see content when scrolling”.
Create positive feedback loops — I remember during my days answering WordPress.com Themes bug reports and how rewarding it was to hear directly from the people I helped with a bug fix.
7. Thanks you. There’s nothing like hearing a customer say “Thank you!”. When a quick-fix was suggested by a customer, let the developer email him and tell him the good news.
This is the work: customer kindness — Our latest iteration at Automattic speaks to this customer focus as the goal of the maintenance work — it isn’t just polish or cleanup, this is the product work. We even have a fun acronym for it now! H.A.C.K. — Helping Acts of Customer Kindness.
Tips from my coworker and prodigious mobile app maker Aaron Douglas on being mindful during video calls. Great tips, not just for remote workers, either. “I’ve come up with a bunch of little tweaks to help with attentiveness and mindfulness during the call. It is important to show you’re listening.”
Working remote means I’m on a lot of video calls. I’ve come up with a bunch of little tweaks to help with attentiveness and mindfulness during the call. It is important to show you’re listening.
Look at the camera often
When you’re in person you look at people’s eyes to show them you’re listening. Doing that on a video call requires a bit of counter-intuitive body language by looking at the camera. You won’t be looking at the person but they’ll see you looking directly at them. It’s a subtle difference but I’ve found it highly effective.
Also try to place the video call window up the screen towards the camera. Also decrease the size of the window so the person’s eyes are naturally closer to the top of the window (closer to the camera). When you’re not looking at the camera while the person is speaking it’ll still look…
I’m a fan of Oblique Strategies for triggering a new perspective when I get stuck. To me this method brings active questions to trigger better thinking.
This practice comes up for me frequently in product management when working on both short and long views of a roadmap. As part of any decision making process, whether by myself for reflection, or in a team working on a product change, I might ask something like:
What is the end result for our customers? Where are we going in the long term?
The purpose of active questions, like Oblique Strategies, is to trigger more questions until you get a better answer. A truer answer. An honest answer. To find the why is to find the signal that drives everything else forward.
Who is it for? How will they understand it’s for them? How will we know if it’s a success? What do we expect to see change? How are we measuring it? What would be a surprise here; something that we don’t expect? Have we considered doing the opposite? Who has the most to gain? What’s the context?