Crafting Engineering Strategy

While Stripe is a widely admired company for things like its creation of the Sorbet typer project, I personally think that Stripe’s most interesting strategy work is also among its most subtle: its willingness to significantly prioritize API stability.

In How should Stripe deprecate APIs?

Many hypergrowth companies of the 2010s battled increasing complexity in their codebase by decomposing their monoliths.

One of the most memorable quotes in Arthur Miller’s The Death of a Salesman comes from Uncle Ben, who describes his path to becoming wealthy as, “When I was seventeen, I walked into the jungle, and when I was twenty-one I walked out.

In Uber’s 2014 service migration strategy, we explore how to navigate the move from a Python monolith to a services-oriented architecture while also scaling with user traffic that doubled every six months.

One of the recurring challenges in any organization is how to split your attention across long-term and short-term problems.

We’ve read a lot of strategy at this point in the book.

Often you’ll see a disorganized collection of ideas labeled as a “strategy.”

Even the best policies fail if they aren’t adopted by the teams they’re intended to serve.

In 2015, the Mini Sky City skyscraper, with 57 floors, was built in Changsha, China, in 19 days.

As someone who writes books, I am continually grateful to the fact that there are people who buy a book, and then actually read that book.

There are many things that LLMs are not particularly good at, and generating a great engineering strategy is one of them.

With your environment working, the obvious task to start with is co-writing a strategy document with an LLM.

In the last chapter, we co-wrote a strategy with an LLM.

Crafting Engineering Strategy has a chapter on systems modeling along with a number of examples.

When I was drafting the first chapters of Crafting Engineering Strategy, I thought I might write a chapter on GitLab’s strategy.

In order to reach this final chapter of the AI Companion to Crafting Engineering Strategy, you’ve co-written and revised a strategy with an LLM.

This book’s introduction started by defining strategy as “making decisions.”

If you talk to enough aspiring leaders, you’ll become familiar with the prevalent idea that they need to be promoted before they can work on strategy.

Discussions around acquisitions often focus on technical diligence and deciding whether to make the acquisition.

Once you’ve written your strategy’s exploration, the next step is working on its diagnosis.

A surprising number of strategies are doomed from inception because their authors get attached to one particular approach without considering alternatives that would work better for their current circumstances.

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.

While I frequently hear engineers bemoan a missing strategy, their complaints rarely articulate why the missing strategy matters.

In my career, the majority of the strategy work I’ve done has been in non-executive roles, things like Uber’s service migration.

Some people I’ve worked with have lost hope that engineering strategy actually exists within any engineering organizations.

In early 2014, I joined as an engineering manager for Uber’s Infrastructure team.

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.

The first time I heard about Wardley Mapping was from Charity Majors discussing it on Twitter.

In Jim Collins’ Great by Choice, he develops the concept of Fire Bullets, Then Cannonballs.

In How should you adopt LLMs?

In 2020, you could credibly argue that ZIRP explains the world, but that’s an impossible argument to make in 2024 when zero-interest rate policy is only a fond memory.

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.

One of the trademarks of private equity ownership is the expectation that either the company maintains their current margin and grows revenue at 25-30%, or they instead grow slower and increase their free cash flow year over year.

The How should you adopt LLMs?

In How should you adopt Large Language Models?

If I could only popularize one idea about technical strategy, it would be that prematurely applying pressure to a strategy’s rollout prevents evaluating whether the strategy is effective.

From their first introduction in 2005, the debate between adopting a microservices architecture, a monolithic service architecture, or a hybrid between the two has become one of the least-reversible decisions that most engineering organizations make.

Even if you believe that strategy is generally useful, it is difficult to decide that today is the day to start writing engineering strategy.

As discussed in Components of engineering strategy, a complete engineering strategy has five components: explore, diagnose, refine (map & model), policy, and operation.

Whether you’re a product engineer, a product manager, or an engineering executive, you’ve probably been pushed to consider using Large Language Models (LLMs) to extend your product or enhance your processes. 2023-2024 is an interesting era for LLM adoptio…

I’ve worked alongside many talented people who spent years waiting for a chance to finally “do strategy.”

Perhaps the most important piece of the Steps to build an engineering strategy is strategy refinement.

This book’s Introduction started with a commitment to grounding its approach in concrete case studies.