When it comes to management successes Sam Schillace has a few under his belt. Often referred to as 'the father Google Docs,' Schillace led the team that created Writely, which would be acquired by Google and become Docs. At Google he continued to lead the team that developed the product. Now he's an SVP at Box.
Assumedly he's learned a couple of things from his years as a leader at these tremendously successful startups. In a recent interview with VC Hunter Walk he shared a few. In between talking about his past experiences, hiring philosophy, and advice for new managers, he shares a simple idea that other business leaders might want to try - Sunday letters.
What's in a 'Sunday letter'?
Just like the name suggests, at the end of every week, Schillace writes a letter to his team. "It actually started out as a personal accountability exercise--I think it's very easy to fool yourself as a senior leader about your effectiveness, so I was trying (in Google snippet style) to just document my goals and accomplishments each week," he tells Walk. But because of confidentiality concerns around hiring, M&A, and new products, he found it impossible to get into the nitty gritty of what he worked on each week. So he changed gears.
"I shifted over into some more personal and cultural thoughts, and it just sort of took off from there. I've been doing it since the very first week I joined, and I've only missed a few--and even then I always have one of my folks write it instead," he says.
What specifically do these letters contain? "I'll typically talk about something I've noticed during the week that I can apply generally. Lots of them are about growth--I explained some things like Dunning-Kruger and how it relates to impostor syndrome, sometimes I'll talk about design philosophy and how to think about what needs to be done first... I've written a lot about the value of humility in leadership and how that manifests, and sometimes I've used them to take ownership of mistakes I've made or challenges I see in the organization," he explains.
Occasionally, the letters even strike a more personal tone. "I think approachability is very important as you get more senior in an organization," Schillace says, "so I walked through my recent winemaking season, for example, and I often talk about my kids or my cooking in a small section at the end."
Why this might be a good idea
Besides the recommendation of a veteran leader like Schillace, there are other reasons to believe a Sunday letter might be a good practice for leaders to try. Productivity experts suggest that Sunday reflection is a great way to set yourself up for a highly productive week, and expressing your thoughts in writing is generally agreed to be a great way to work through issues, celebrate wins, and exercise mental muscles that can start to atrophy if the longest thing you tend to compose all week is a text message.
Would you consider giving Sunday letters a try?