Reflecting on a year of COVID, WFH, and the distributed workforce.

When I was deciding to join Square a year ago, I was the first hire in my +200 person organization to be based outside of San Francisco. Despite Jack’s prior announcement to work from Africa, and the fact I was going to be working out of Square’s second largest office (NYC), this was a BIG deal.

I can remember the number of warnings I received from friends and HR that this would be tough. Not many people do this successfully. Fortunately, my manager and I were on the same page. This was the future of work and we were both excited to test and lead this transition. In retrospect, I don’t think I would have boldly made this leap if it weren’t for my manager’s commitment and reassurance.

She and I devised a plan which would have me regularly traveling to SF to build relationships and meet people. I read up on everything I could find about remote work. Then COVID happened.

After working from home for now a year, I think there are three key points managers should remember and lean into in order to successfully lead a distributed team:

• Build an environment of trust and candor right from the beginning. Do this through maintaining transparency with your team and articulating positive intent in your communication.
• Increase access to information through documentation. One of the reasons we need to be in the office is to often bridge information asymmetry, which is quickly rectified by dropping by someone’s desk.When your team works remotely, it’s harder for them to catch someone’s attention via email/Slack or to pick up information in side conversations. Having all information (goals, plan, discussion, feedback) documented offers all team members equal context.
• Your team is still human. Oftentimes when we don’t see others in person, relationships become transactional and shallow. Foster team camaraderie through different but consistent communication channels. It’s ok to let loose and have casual conversations

Our teams at Square have adapted well to remote work, but I still miss catching up with co-workers and friends over coffee and lunchtime walks. Those moments fostered camaraderie, increased the depth and dimension of relationships, and encouraged creative discussion. While I do believe distributed workforces are here to stay and can work, it’ll be interesting to see how organizations find the right balance in order to create workplace serendipity and shared energy.

For those interested, I’d also recommend the Sam Harris podcast episode on The Future of Work. Harris interviews Matt Mullenweg, CEO of Automattic. This company is the parent company of Wordpress, Tumblr, and WooCommerce, and is 100% distributed. While I’m skeptical of Matt’s WFH nirvana state, the conversation has helped me reframe how to embrace the distributed work model.

Let me know if there’s something that has worked for your team or how you think about successfully building and leading a distributed team.