Some people I’ve worked with have lost hope that engineering strategy actually exists within any engineering organizations. I imagine that they, reading through the steps to build engineering strategy, or the strategy for navigating private equity ownership, are not impressed. Instead, these ideas probably come across as theoretical at best. In less polite company, they might describe these ideas as fake constructs. Let’s talk about it! Because they’re right. In fact, they’re right in two different ways. First, this book is focused on explain how to create clean, refine and definitive strategy ..read more

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 entirety, of the migration workload onto that small team rather than spreading it across the 2,000+ engin ..read more

At the core of Uber’s service migration strategy (2014) is understanding the service onboarding process, and identifying the levers to speed up that process. Here we’ll develop a system model representing that onboarding process, and exercise the model to test a number of hypotheses about how to best speed up provisioning. In this chapter, we’ll cover: Where the model of service onboarding suggested we focus on efforts Developing a system model using the lethain/systems package on Github. That model is available in the lethain/eng-strategy-models repository Exercising that model to learn from ..read more

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. Where the other techniques like systems thinking and strategy testing often zoom in, Wardley mapping is remarkably effective at zooming out. In th ..read more

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, so 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 well before reaching the cannonball stage. We’ll work through an overview of strategy refinement, covering: An introduction to the ..read more

In How should you adopt LLMs?, we explore how a theoretical ride sharing company, Theoretical Ride Sharing, should adopt Large Language Models (LLMs). Part of that strategy’s diagnosis depends on understanding the expected evolution of the LLM ecosystem, which we’ve build a Wardley map to better explore. This map of the LLM space is interested in how product companies should address the proliferation of model providers such as Anthropic, Google and OpenAI, as well as the proliferation of LLM product patterns like agentic workflows, Retrieval Augmented Generation (RAG), and running evals to mai ..read more

Gitlab is an integrated developer productivity, infrastructure operations, and security platform. This Wardley map explores the evolution of Gitlab’s users’ needs, as one component in understanding the company’s strategy. In particular, we look at how Gitlab’s strategy of a bundled, all-in-one platform anchors on the belief that build and security tooling is moving from customization to commodity. This is an exploratory, draft chapter for a book on engineering strategy that I’m brainstorming in #eng-strategy-book. As such, some of the links go to other draft chapters, both published drafts and ..read more

A lot happened for me this year. I continued learning the details of fund accounting at Carta, which is likely the most complex product domain I’ve worked in. My third book was published, and I did a small speaking tour to support it. We started the unironically daunting San Francisco kindergarten application process. I was diagnosed with skin cancer and had successful surgery to remove it. All things considered, it was a much messier year than I intended, but with many good pockets mixed in with the mess. (I love to read other folks year-in writeups – if you write one, please send it my way ..read more

Back in 2020, I wrote a piece called My skepticism towards current developer meta-productivity tools, which laid out my three core problems with developer productivity measurement tools of the time: Using productivity measures to evaluate rather than learn Instrumenting metrics required tweaks across too any different tools Generally I found tools forced an arbitrary, questionable model onto the problem Two and a half years later, I made an angel investment in DX, which at the time I largely viewed as taking a survey-driven, research-backed approach to developer productivity. I was recently ..read more

In my ongoing efforts to draft a book on engineering strategy, I’ve finally reached the point where I need to transition “Wardley Mapping” from a topic to consider including into a topic that I either do or do not include. The first step on that line is getting much deeper at understanding how it works. This is rather different than systems modeling, which is a technique I’ve been using off-and-on at work for 15-plus years, but I will make a solid go at it. My starting point is having read The Value Flywheel Effect by David Anderson, and attempted a few times unsuccessfully to read Wardley Map ..read more