Sunday Letters - what, who, and why
What’s going on here?
About 8 years ago, when I was SVP of engineering at Box, I started to write a short Sunday letter to my team to let them know what I was up to. But I quickly realized that too much of what I was doing was either boringly specific or too confidential to discuss with everyone. I still wanted to write my letter though!
So, over time, the letter started to evolve in the direction of short discussions of things I had observed in the teams during the week. For these to be interesting, they can’t be too specific, so they wound up becoming examinations of broad patterns, system incentives, common pitfalls, and sometimes career advice. The letters have covered ideas like how humility is needed in leadership, how it’s hard for organizations to make tradeoffs between long and short term, how to think about consumer software, how to navigate an engineering career, what disruptive innovation looks like from the inside (I was fortunate enough to be a founder of a company called Writely that became the word processor in Google Docs) and much more.
To some degree, they became almost “letters to my younger self” - things I wish I had known 32 years and six startups ago when I started all this. These letters also help me be a better leader every day - the pressure of having a weekly deadline means that I have to be present and look for those patterns, rather than just reacting to the specifics of each situation.
When I left Google (I’m now deputy CTO at Microsoft. Ok, that’s enough of my bio!) many folks asked me to keep writing these in a public form, and the folks at Microsoft thought it would be cool as well.
I hope these letters are short, easy to understand, and valuable. The topics may wander. There may be strong opinions but they are weakly held, and good faith debate is welcome (trolls will be exposed to sunlight mercilessly and turned to stone). And I promise, this is the only one where I will show up so much as a character.