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.) The most important things I learned at Carta were:| lethain.com
Discussions around acquisitions often focus on technical diligence and deciding whether to make the acquisition. However, the integration that follows afterwards can be even more complex. There are few irreversible trapdoor decisions in engineering, but decisions made early in an integration tend to be surprisingly durable. This engineering strategy explores Stripe’s approach to integrating their 2018 acquisition of Index. While a business book would focus on the rationale for the acquisiti...| lethain.com
Once you’ve written your strategy’s exploration, the next step is working on its diagnosis. Diagnosis is understanding the constraints and challenges your strategy needs to address. In particular, it’s about slowing yourself down from jumping to solutions before fully understanding the nuances and constraints of the problem. If you ever find yourself wanting to skip the diagnosis phase–let’s get to the solution already!–then maybe it’s worth acknowledging that every strategy tha...| lethain.com
At some point in a startup’s lifecycle, they decide that they need to be ready to go public in 18 months, and a flurry of IPO-readiness activity kicks off. This strategy focuses on a company working on IPO readiness, which has identified a gap in internal controls for managing user data access. It’s a company that wants to meaningfully improve their security posture around user data access, but which has had a number of failed security initiatives over the years.| lethain.com
In early 2014, I joined as an engineering manager for Uber’s Infrastructure team. We were responsible for a wide number of things, including provisioning new services. While the overall team I led grew significantly over time, the subset working on service provisioning never grew beyond four engineers. Those four engineers successfully migrated 1,000+ services onto a new, future-proofed service platform. More importantly, they did it while absorbing the majority, although certainly not the ...| lethain.com
In Jim Collins’ Great by Choice, he develops the concept of Fire Bullets, Then Cannonballs. His premise is that you should cheaply test new ideas before fully committing to them. Your organization can only afford firing a small number of cannonballs, but it can bankroll far more bullets. Why not use bullets to derisk your cannonballs’ trajectories? This chapter presents a series of concrete techniques that I have personally used to effectively refine strategies before reaching the cannonb...| lethain.com
The first time I heard about Wardley Mapping was from Charity Majors discussing it on Twitter. Of the three core strategy refinement techniques, this is the technique that I’ve personally used the least. Despite that, I decided to include it in this book because it highlights how many different techniques can be used for refining strategy, and also because it’s particularly effective at looking at the broadest ecosystems your organization exists in.| lethain.com
While I was probably late to learn the concept of strategy testing, I might have learned about systems modeling too early in my career, stumbling on Donella Meadows’ Thinking in Systems: A Primer before I began my career in software. Over the years, I’ve discovered a number of ways to miuse systems modeling, but it remains the most effective, flexible tool I’ve found to debugging complex problems. In this chapter, we’ll work through:| lethain.com