Category: Creative Leadership

You got this.

Through the rosy lens of memory, learning HTML and Photoshop back in the day was a breeze. Now I’m learning new tech, and it’s hard. Maybe you’re in the same boat.

Money and tech

From optimistically conceived origins and message statements about making the world a better place, too many websites and startups have become the leading edge of bias and trauma, especially for marginalized and at-risk groups.

How have so many of our digital services and social networks become a garbage fire of lies, distortions, hate speech, tribalism, snake oil, and privacy violations?

Tips for Hiring Designers for Remote Teams

Creating a great design team and designing great products means hiring great designers. Automattic has been hiring people around the world to work remotely for over 10 years. More recently, we’ve been scaling up and […]

Hangout Life

One huge advantage of remote environments: Face time is a scarce resource. This is a good thing. It makes you treat it as a valuable resource — something you have to be careful not to […]

Designing Your Remote “Office”

Photo credit: Matteo Vistocco “So, where do your designers sit?” I was at a lunch table during a design leadership conference late last year, chatting with other leaders in the industry. This question left me…confused. I […]

The Perception of Presence in Remote Teams

I often get many kinds of questions regarding remote work, often from an organizational and structural perspective. Recently however I’ve been asked a different one: “I’m a freelance about to start working remotely for a […]

Squad Goals

A few keys to distributed success Since becoming the lead of my team I’ve spent a fair bit of time helping my team members  define career growth goals and track their progress. Everyone is different […]

Organization Experiments in Progress

When I started my career in technology I thought the best thing ever was the ability to make things work, so I started learning multiple programming language and building things. I then realized people using […]

Designing a successful IRL meetup for a remote team

Automattic is a distributed company so we don’t get all that much time together.  This means that whenever we do I am always really mindful of how to make the most of it. Team meetups […]