Write five, then synthesize: good engineering strategy is boring.

November 26, 2020.Filed understaff-plus26strategy7

Few companies understand their engineering strategy and vision. One consequence of this uncertainty is the industry belief that these documents are difficult to write. In some conversations it can feel like you’re talking about something mystical, but these are just mundane documents. The reality is that good engineering strategy is boring, and that it’s _easier_ to write an effective strategy than a bad one.

Managing technical quality in a codebase.

October 17, 2020.Filed underarchitecture30staff-plus26

If there's one thing that engineers, engineering managers, and technology executives are likely to agree on, it's that there's a crisis of technical quality. One diagnosis and cure is easy to identify: our engineers aren't prioritizing quality, and we need to hire better engineers or retrain the ones we have. Of course, you should feel free to replace "engineers" with "Product Managers" or "executives" if that feels more comfortable. It's a compelling narrative with a clear villain, and it conveniently shifts blame away from engineering leadership. Still, like most narratives that move accountability towards the folks with the least power, it's both unhelpful and wrong.

Work on what matters.

September 10, 2020.Filed understaff-plus26

We all have a finite amount of time to live, and within that mortal countdown we devote some fraction towards our work. Even for the most career-focused, your life will be filled by many things beyond work: supporting your family, children, exercise, being a mentor and a mentee, hobbies, and so the list goes on. This is the sign of a rich life, but one side-effect is that time to do your work will become increasingly scarce as you get deeper into your career.

Your first 90 days as CTO or VP Engineering.

2020年1月13日。Filed undermanagement127cto1

Whenever I transition to a new opportunity, I think about how to “start well.” How can I ramp up as effectively as possible? How do I balance the urge to “show value” immediately with making the right decisions?

How the Digg team was acquihired.

1月1, 2020.Filed understories9digg6acquisition2

About a year after the catastrophic Digg V4 launch, our last-ditch experiment to salvage the site showed a spark of hope. We’d cajoled our way into a Facebook beta that allowed us to publish each Digg users’s read articles into their Facebook newsfeed, sending every clicking friend directly to Digg’s permalink page, where they might click on our ads and maybe even create an account.

A forty year career.

October 8, 2019.Filed under职业生涯20

The Silicon Valley narrative centers on entrepreneurial protagonists who are poised one predestined step away from changing the world. A decade ago they were heroes, and more recently they’ve become villains, but either way they are absolutely the protagonists. Working within the industry, I’ve worked with quite a few non-protagonists who experience their time in technology differently: a period of obligatory toil required to pry open the gate to the American Dream.

Reclaim unreasonable software.

July 28, 2019.Filed underarchitecture30

Big Ball of Mud was published twenty years ago, and rings just as true today: the most prominent architecture in successful, growth-stage companies is non-architecture. Crisp patterns are slowly overgrown by the chaotic tendrils of quick fixes, and productivity creeps towards zero.

How to invest in technical infrastructure.

May 19, 2019.Filed underinfrastructure34

I'm speaking at Velocity on June 12th on 'How Stripe invests in technical infrastructure', and this is the rough outline of the content the talk will cover. I hope to see y'all there.

How to evolve an engineering organization.

March 5, 2019.Filed undermanagement127

I recently had the opportunity to present to a small group of early-stage founders about evolving their engineering organization as their company scaled. While preparing, I realized that the most relevant piece I've written about organization design was about running reorganizations.

Why limiting work-in-progress works.

February 17, 2019.Filed undermanagement127systems-thinking6

Several years ago, my friend Bobby showed me an article about a CEO who used systems thinking to understand their company's bottlenecks, which eventually lead to him buying out his cofounder, who had been leading their sales team. As is the case for most stories about ourselves that we decide to publish widely, this decision turned out to be the right one, and their business flourished.