Stuff I Learned at Carta

Summary

Today’s my last day at Carta, where I got the chance to serve as their CTO for the past two years. I’ve learned so much working there, and I wanted to end my chapter there by collecting my thoughts on what I learned. (I am heading somewhere, and will share news in a week or two after firming up the communication plan with my new team there.)Working in the details – if you took a critical lens towards my historical leadership style, I think the biggest issue you’d point at is my being too comfortable operating at a high level of abstraction. Utilizing the expertise of others to fill in your gaps is a valuable skill, but–like any single approach–it’s limiting when utilized too frequently.One of the strengths of Carta’s “house leadership style” is expecting leaders to go deep into the details to get informed and push pace. What I practiced there turned into the pieces on strategy testing and developing domain expertise.Refining my approach to engineering strategy – over the past 18 months, I’ve written a book on engineering strategy (posts are all in #eng-strategy-book), with initial chapters coming available for early release with O’Reilly next month. Fingers crossed, the book will be released in approximately October.Coming into Carta, I already had much of my core thesis about how to do engineering strategy, but Carta gave me a number of complex projects to practice on, and excellent people to practice with: thank you to Dan, Shawna and Vogl in particular! More on this project in the next few weeks.Extract the kernel – everywhere I’ve ever worked, teams have struggled understanding executives. In every case, the executives could be clearer, but it’s not particularly interesting to frame these problems as something the executives need to fix. Sure, that’s true they could communicate better, but that framing makes you powerless, when you have a great deal of power to understand confusing communication. After all, even good communicators communicate poorly sometimes.Me...