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Irrational Exuberance

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Is engineering strategy useful? While I frequently hear engineers bemoan a missing strategy, they rarely complete the thought by...
3 days ago
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3 days ago
While I frequently hear engineers bemoan a missing strategy, they rarely complete the thought by articulating why the missing strategy matters. Instead, it serves as more of a truism: the economy used to be better, children used to respect their parents, and engineering...
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"We're a product engineering company!" -- Engineering strategy at Calm. In my career, the majority of the strategy work I’ve done has been in non-executive roles, things...
a week ago
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a week ago
In my career, the majority of the strategy work I’ve done has been in non-executive roles, things like Uber’s service migration. Joining Calm was my first executive role, where I was able to not just propose, but also mandate, strategy. Like almost all startups, the engineering...
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Bridging theory and practice in engineering strategy. Some people I’ve worked with have lost hope that engineering strategy actually exists within any...
2 weeks ago
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2 weeks ago
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....
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Uber's service migration strategy circa 2014. In early 2014, I joined as an engineering manager for Uber’s Infrastructure team. We were...
3 weeks ago
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3 weeks ago
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...
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Service onboarding model for Uber (2014). At the core of Uber’s service migration strategy (2014) is understanding the service onboarding...
3 weeks ago
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3 weeks ago
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...
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Refining strategy with Wardley Mapping. The first time I heard about Wardley Mapping was from Charity Majors discussing it on Twitter. Of...
a month ago
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a month ago
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...
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How to effectively refine engineering strategy. In Jim Collins’ Great by Choice, he develops the concept of Fire Bullets, Then Cannonballs. His...
a month ago
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a month ago
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...
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Wardley mapping the LLM ecosystem. In How should you adopt LLMs?, we explore how a theoretical ride sharing company, Theoretical Ride...
a month ago
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a month ago
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...
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Wardley mapping of Gitlab Strategy. Gitlab is an integrated developer productivity, infrastructure operations, and security...
a month ago
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a month ago
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...
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2024 in review. A lot happened for me this year. I continued learning the details of fund accounting at Carta, which...
a month ago
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a month ago
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...
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Measuring developer experience, benchmarks, and providing a theory of improvement. Back in 2020, I wrote a piece called My skepticism towards current developer meta-productivity...
a month ago
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a month ago
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...
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Rough notes on learning Wardley Mapping. In my ongoing efforts to draft a book on engineering strategy, I’ve finally reached the point where...
2 months ago
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2 months ago
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...
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Video of practice run of QCon SF 2024 talk on Principal Engineers. Yesterday at QCon, I got to give a talk with my colleague Dan Fike about the Principal Engineer...
2 months ago
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2 months ago
Yesterday at QCon, I got to give a talk with my colleague Dan Fike about the Principal Engineer role](https://qconsf.com/presentation/nov2024/ambiguous-roles-and-ambiguous-problems-navigating-life-principal-engineer). You can also watch the video on YouTube. The content itself...
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How to get more headcount. One of the recurring challenges that teams face is getting headcount to support their initiatives. A...
2 months ago
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2 months ago
One of the recurring challenges that teams face is getting headcount to support their initiatives. A similar problem is the idea that a team can’t get a favored project into their roadmap. In both cases, teams often create a story about how clueless executives don’t understand...
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Navigating Private Equity ownership. In 2020, you could credibly argue that ZIRP explains the world, but that’s an impossible argument to...
2 months ago
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2 months ago
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. Instead, we’re seeing a number of companies designed for rapid expansion learning to adapt to a world that...
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Using systems modeling to refine strategy. While I was probably late to learn the concept of strategy testing, I might have learned about...
2 months ago
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2 months ago
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...
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Eng org seniority-mix model. One of the trademarks of private equity ownership is the expectation that either the company...
3 months ago
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3 months ago
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. In many organizations, engineering costs have a...
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Modeling driving onboarding. The How should you adopt LLMs? strategy explores how Theoretical Ride Sharing might adopt LLMs. It...
3 months ago
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3 months ago
The How should you adopt LLMs? strategy explores how Theoretical Ride Sharing might adopt LLMs. It builds on several models, the first is about LLMs impact on Developer Experience. The second model, documented here, looks at whether LLMs might improve a core product and business...
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Modeling impact of LLMs on Developer Experience. In How should you adopt Large Language Models? (LLMs), we considered how LLMs might impact a...
3 months ago
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3 months ago
In How should you adopt Large Language Models? (LLMs), we considered how LLMs might impact a company’s developer experience. To support that exploration, I’ve developed a system model of the developing software at the company. In this chapter, we’ll work through: Summary results...
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Testing strategy: avoid the waterfall strategy trap with iterative refinement. If I could only popularize one idea about technical strategy, it would be that prematurely applying...
4 months ago
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4 months ago
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. Pressure changes behavior in profound ways, and many of those changes are intended to make...
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Should we decompose our monolith? From their first introduction in 2005, the debate between adopting a microservices architecture, a...
4 months ago
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4 months ago
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 migrating to a...
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Executive translation. One of my most unexpectedly controversial posts is Extract the Kernel, which argues that executives...
4 months ago
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4 months ago
One of my most unexpectedly controversial posts is Extract the Kernel, which argues that executives are generally directionally correct but specifically wrong, and it’s your job to understand the overarching direction without getting distracted by the narrow errors in their...
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Video of Developing Eng Leadership Styles. The last chapter I wrote for Eng Executive’s Primer was this one about developing engineering...
4 months ago
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4 months ago
The last chapter I wrote for Eng Executive’s Primer was this one about developing engineering leadership styles. It’s an interesting chapter to me peronally, precisely because it’s not something I would have agreed with or written five years ago. This past Friday I gave a...
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Numbers go up. There’s a genre of computer games called incremental games, whose entire design philosophy can be...
5 months ago
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5 months ago
There’s a genre of computer games called incremental games, whose entire design philosophy can be summarized as, “numbers go up.” These games focus on the fundamental gaming loop rather than plot, characterization or anything beyond the foundational satisfaction of numbers...
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When to write strategy, and how much? Even if you believe that strategy is generally useful, it is difficult to decide that today’s the...
5 months ago
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5 months ago
Even if you believe that strategy is generally useful, it is difficult to decide that today’s the day to start writing engineering strategy. When you do start writing strategy, it’s easy write so much strategy that your organization is overwhelmed and ignores your strategy rather...
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Developing domain expertise: get your hands dirty. Recently, I’ve been thinking about developing domain expertise, and wanted to collect my thoughts...
6 months ago
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6 months ago
Recently, I’ve been thinking about developing domain expertise, and wanted to collect my thoughts here. Although I covered some parts of this in Your first 90 days as CTO (understanding product analytics, shadowing customer support, talking to customers, and talking with your...
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Physics and perception. At one point in 2019, several parts of Stripe’s engineering organization were going through a polite...
7 months ago
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7 months ago
At one point in 2019, several parts of Stripe’s engineering organization were going through a polite civil war. The conflict was driven by one group’s belief that Java should replace Ruby. Java would, they posited, address the ongoing challenge of delivering a quality platform in...
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Tags
7 months ago
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Posts
7 months ago
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Management
7 months ago
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Executive
7 months ago
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How to create software quality. I’ve been reading Steven Sinofsky’s Hardcore Software, and particularly enjoyed this quote from a...
7 months ago
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7 months ago
I’ve been reading Steven Sinofsky’s Hardcore Software, and particularly enjoyed this quote from a memo discussed in the Zero Defects chapter: You can improve the quality of your code, and if you do, the rewards for yourself and for Microsoft will be immense. The hardest part is...
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Staff-Plus
7 months ago
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Architecture
7 months ago
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Video of Using LLMs in your product. A month ago, I wrote up some notes on using LLMs in your product, and yesterday I got to present an...
7 months ago
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7 months ago
A month ago, I wrote up some notes on using LLMs in your product, and yesterday I got to present an iteration on those notes to the folks at the Sapphire Venture’s 2024 Hypergrowth Engineering Summit. If you’re interested, you can watch a recording of my talk on Youtube. There’s...
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Talks
7 months ago
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Speaking
7 months ago
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Llm
7 months ago
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No Wrong Doors. Some governmental agencies have started to adopt No Wrong Door policies, which aim to provide...
8 months ago
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8 months ago
Some governmental agencies have started to adopt No Wrong Door policies, which aim to provide help–often health or mental health services–to individuals even if they show up to the wrong agency to request help. The core insight is that the employees at those agencies are far...
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Making engineering strategies more readable As discussed in Components of engineering strategy, a complete engineering strategy has five...
8 months ago
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8 months ago
As discussed in Components of engineering strategy, a complete engineering strategy has five components: explore, diagnose, refine (map & model), policy, and operation. However, it’s actually quite challenging to read a strategy document written that way. That’s an effective...
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Strategy
8 months ago
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Eng-Strategy-Book
8 months ago
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How should you adopt LLMs? Whether you’re a product engineer, a product manager, or an engineering executive, you’ve probably...
8 months ago
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8 months ago
Whether you’re a product engineer, a product manager, or an engineering executive, you’ve probably been pushed to consider using Large Language Models (LLM) to extend your product or enhance your processes. 2023-2024 is an interesting era for LLM adoption, where these...
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Wardley-Map
8 months ago
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Systems-Thinking
8 months ago
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Load-bearing / Career-minded / Act Two rationales One of the common conceits in leadership is that nobody is truly essential for a company’s...
9 months ago
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9 months ago
One of the common conceits in leadership is that nobody is truly essential for a company’s continuity. I call it a conceit, but I do mostly agree with it: I’ve felt literally sick after hearing about some peer’s unexpected departure, but I’m continually amazed at how resilient...
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Constraints on giving feedback. Back when I was managing at Digg and Uber, I spent a lot of time delivering feedback to my...
9 months ago
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9 months ago
Back when I was managing at Digg and Uber, I spent a lot of time delivering feedback to my management chain about issues in our organization. My intentions were good, but I alienated my management chain without accomplishing much. I also shared my concerns with my team, which I...
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My advice for how to use LLMs in your product. Pretty much every company I know is looking for a way to benefit from Large Language Models. Even if...
9 months ago
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9 months ago
Pretty much every company I know is looking for a way to benefit from Large Language Models. Even if their executives don’t see much applicability, their investors likely do, so they’re staring at the blank page nervously trying to come up with an idea. It’s straightforward to...
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Ex-technology companies. One of the most interesting questions I got after joining Calm in 2020 was whether Calm was a...
10 months ago
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10 months ago
One of the most interesting questions I got after joining Calm in 2020 was whether Calm was a technology company. Most interestingly, this question wasn’t coming from friends or random strangers on the internet, it was coming from the engineers working there! In an attempt to...
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Leadership requires taking some risk. At a recent offsite with Carta’s Navigators, we landed on an interesting topic: leadership roles...
10 months ago
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10 months ago
At a recent offsite with Carta’s Navigators, we landed on an interesting topic: leadership roles sometimes mean that making progress on a professional initiative requires taking some personal risk. This lesson was hammered into me a decade ago during my time at Uber, where I...
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Friction isn't velocity. When you’re driving a car down a road, you might get a bit stuffy and decide to roll your windows...
10 months ago
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10 months ago
When you’re driving a car down a road, you might get a bit stuffy and decide to roll your windows down. The air will flow in, the wind will get louder, and the sensation of moving will intensify. Your engine will start working a bit harder–and louder–to maintain the same...
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More (self-)publishing thoughts. I recently got an email asking about self-publishing books, and wanted to summarize my thinking...
11 months ago
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11 months ago
I recently got an email asking about self-publishing books, and wanted to summarize my thinking there. Recapping my relevant experience, I’ve written three books: An Elegant Puzzle was published in 2019 as a manuscript by Stripe Press (e.g. I wrote it and then it was released as...
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Digital release of Engineering Executive's Primer. Quick update on The Engineering Executive’s Primer. The book went to print yesterday, and physical...
12 months ago
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12 months ago
Quick update on The Engineering Executive’s Primer. The book went to print yesterday, and physical copies will be available in March. Also, as of this moment, you can purchase the digital edition on Amazon, and read the full digital release on O’Reilly. (You can preorder physical...
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Thesis on value accumulation in AI. Recently, I’ve thinking about where I want to focus my angel investing in 2024, and decided to...
a year ago
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a year ago
Recently, I’ve thinking about where I want to focus my angel investing in 2024, and decided to document my thinking about value accumulation in artificial intelligence because it explains the shape of my interest–or lack thereof–in investing in artificial intelligence tooling....
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High-Context Triad. The past couple weeks I’ve been working on three semi-related articles that I think of as the “High...
a year ago
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a year ago
The past couple weeks I’ve been working on three semi-related articles that I think of as the “High Context Triad.” Those are Layers of context, Navigating ambiguity, and Tradeoffs are multi-dimensional. One of my background projects, probably happening in 2025 or 2026 after I’ve...
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Useful tradeoffs are multi-dimensional. In some pockets of the industry, an axiom of software development is that deploying software quickly...
a year ago
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a year ago
In some pockets of the industry, an axiom of software development is that deploying software quickly is at odds with thoroughly testing that software. One reason that teams believe this is because a fully automated deployment process implies that there’s no opportunity for manual...
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Navigating ambiguity. Perceiving the layers of context in problems will unlock another stage of career progression as a...
a year ago
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a year ago
Perceiving the layers of context in problems will unlock another stage of career progression as a Staff-plus engineer, but there’s at least one essential skill to develop afterwards: navigating ambiguity. In my experience, navigating deeply ambiguous problems is the rarest skill...
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Layers of context. Recently I was chatting with a Staff-plus engineer who was struggling to influence his peers. Each...
a year ago
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a year ago
Recently I was chatting with a Staff-plus engineer who was struggling to influence his peers. Each time he suggested an approach, his team agreed with him, but his peers in the organization disagreed and pushed back. He wanted advice on why his peers kept undermining his...
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Those five spare hours each week. One of the recurring debates about senior engineering leadership roles is whether Chief Technology...
a year ago
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a year ago
One of the recurring debates about senior engineering leadership roles is whether Chief Technology Officers should actively write code. There are a lot of strongly held positions, from “Real CTOs code.” at one end of the spectrum, to “Low ego managers know they contribute more by...
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Predictability. Right now I’m reading Michael S. Malone’s The Big Score, and one thing that I love about it is how...
a year ago
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a year ago
Right now I’m reading Michael S. Malone’s The Big Score, and one thing that I love about it is how much it believes that key individuals drive and create industries. It’s an infectious belief, and a necessary one to write a concise, coherent narrative story about the origins of...
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2023 in review. Previously: 2022, 2021, 2020, 2019, 2018, 2017 This was an eventful year. My son went to...
a year ago
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a year ago
Previously: 2022, 2021, 2020, 2019, 2018, 2017 This was an eventful year. My son went to preschool, I joined Carta, left Calm, and wrote my third book. It was also a logistically intensive year, with our toddler heading to preschool, more work travel, and a bunch of other little...
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Notes on How Big Things Get Done How Big Things Get Done by Bent Flyvbjerg and Dan Gardner is a fascinating look at why some...
a year ago
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a year ago
How Big Things Get Done by Bent Flyvbjerg and Dan Gardner is a fascinating look at why some megaprojects fail so resoundingly and why others succeed under budget and under schedule. It’s an exploration of planning methods, the role of expertise, the value of benchmarking similar...
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Writers who operate. Occasionally folks tell me that I should “write full time.” I’ve thought about this a lot, and have...
a year ago
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a year ago
Occasionally folks tell me that I should “write full time.” I’ve thought about this a lot, and have rejected that option because I believe that writers who operate (e.g. write concurrently with holding a non-writing industry role) are best positioned to keep writing valuable work...
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Advancing the industry. Early in my career, I navigated most decisions by simple hill climbing: if it was a more prestigious...
a year ago
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a year ago
Early in my career, I navigated most decisions by simple hill climbing: if it was a more prestigious opportunity and paid more, I took it. As I got further, and my personal obligations grew, I started to think about navigating a 40-year career, where a given job might value pace...
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Notes on Enterprise Architecture as Strategy Enterprise Architecture as Strategy by Jeanne W. Ross, Peter Weill, and David C Robertson is an...
a year ago
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a year ago
Enterprise Architecture as Strategy by Jeanne W. Ross, Peter Weill, and David C Robertson is an interesting read on how integrating technology across business units shifts the company’sstrategy landscape. Written in 2006, case studies are not particularly current but the ideas...
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Create technical leverage: workflow improvements & product capabilities More than a decade ago, I typed up a few paragraphs of notes, titled it “Building Technical...
a year ago
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a year ago
More than a decade ago, I typed up a few paragraphs of notes, titled it “Building Technical Leverage,” and proceeded to forget about it. Those notes were from a meeting with Kevin Scott, then SVP Engineering at LinkedIn, while we wandered the Valley trying to convince potential...
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Navigators In Staff Engineer’s chapter on Managing Technical Quality, one of the very last suggestions is...
a year ago
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a year ago
In Staff Engineer’s chapter on Managing Technical Quality, one of the very last suggestions is creating a centralized process to curate technical changes: Curate technology change using architecture reviews, investment strategies, and a structured process for adopting new tools....
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Notes on The Crux The Crux by Richard Rumelt is a fantastic follow on to his Good Strategy, Bad Strategy, providing...
a year ago
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a year ago
The Crux by Richard Rumelt is a fantastic follow on to his Good Strategy, Bad Strategy, providing many of the same core ideas but in a more readable format, and a clearer target to take down: the incoherent outputs of process and goal-driven strategy. Recently, I’ve been looking...
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Engineering strategy notes. Recently, I am thinking quite a bit about engineering strategy, and as part of that have started...
a year ago
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a year ago
Recently, I am thinking quite a bit about engineering strategy, and as part of that have started re-reading previous resources on the topic, and looking for new things to read while I refine my point of view on what makes for good engineering strategy. The best introduction to my...
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Notes on Technology Strategy Patterns Technology Strategy Patterns by Eben Hewitt is a methods-based approach to engineering strategy,...
a year ago
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a year ago
Technology Strategy Patterns by Eben Hewitt is a methods-based approach to engineering strategy, with a particular focus on the methods wielded by McKinsey consultants, software engineering mainstays like Thoughtworks, and philosophy. A valuable read for anyone looking to build...
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Notes on The Software Engineer's Guidebook The Software Engineer’s Guidebook by Gergely Orosz is a broad reference book for software engineers...
a year ago
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a year ago
The Software Engineer’s Guidebook by Gergely Orosz is a broad reference book for software engineers that will be particularly valuable for new software engineers and those who’ve worked most of their career in a small number of companies. It doesn’t go deep everywhere, but leaves...
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Notes on Tidy First? Tidy First? by Kent Beck captures the spirit of Ousterhout’s A Philosophy of Software Design while...
a year ago
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a year ago
Tidy First? by Kent Beck captures the spirit of Ousterhout’s A Philosophy of Software Design while also recognizing the inherent tensions of developing software within a team and business. You can also read it in about two hours. Recommended! A Philosophy of Software Design by...
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Notes on The Value Flywheel Effect The Value Flywheel Effect is a worthwhile read. It’s imperfect, but a fascinating look into...
a year ago
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a year ago
The Value Flywheel Effect is a worthwhile read. It’s imperfect, but a fascinating look into real-world application of Wardley mapping, and a rare view of a company’s engineering strategy. I’m currently diving into the topic of engineering strategy, and a sub-topic that I’ve not...
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Team Charters are a trap. I’m cleaning out old lingering drafts. This one’s on why I dislike Team Charters. Recently an email...
a year ago
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a year ago
I’m cleaning out old lingering drafts. This one’s on why I dislike Team Charters. Recently an email came in asking about writing team charters. I’ve worked at a number of companies that asked teams to write charters, and I think it’s an interesting project. That said, it’s not a...
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A bit late, but I did leave Calm. I meant to post this when I left Calm earlier this year, as a ending note to my post on joining...
a year ago
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a year ago
I meant to post this when I left Calm earlier this year, as a ending note to my post on joining Calm, but instead I got focused on joining Carta and writing An Engineering Executive’s Primer. I’m cleaning out some of my old drafts, and posting this as an artifact of that moment....
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Benchmarking. Many of the most important questions for running an organization don’t have clear answers. In most...
a year ago
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a year ago
Many of the most important questions for running an organization don’t have clear answers. In most engineering organizations, both the teams working on infrastructure and the teams working on product feel they are undersized. It’s also true that most individuals feel they are...
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Getting lucky isn't a plan. One piece of flippant commentary that you’ll hear occasionally is that it’s “Better to be lucky than...
a year ago
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a year ago
One piece of flippant commentary that you’ll hear occasionally is that it’s “Better to be lucky than to be good.” On an individual level, it’s almost certainly true that being very lucky outperforms being quite good: I certainly know a number of folks who are financially...
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Thoughts on writing and publishing Primer. I’m materially finished writing my 3rd book, The Engineering Executive’s Primer. There’s one last...
a year ago
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a year ago
I’m materially finished writing my 3rd book, The Engineering Executive’s Primer. There’s one last chapter to go through tech review, and a fine line editing pass, but the hard stuff is largely done. Of course, that’s an author’s perspective, there is other hard stuff still to be...
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Developing leadership styles For a long time, I found the micromanager CEO archetype very frustrating to work with. They would...
a year ago
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a year ago
For a long time, I found the micromanager CEO archetype very frustrating to work with. They would often pop out of nowhere, jab holes in the work I had done without understanding the tradeoffs, and then disappear when I wanted to explain my decisions. In those moments, I wished...
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Video of Solving the Eng Strategy crisis. A few weeks ago, I shared my script for my latest talk, Solving the Engineering Strategy...
a year ago
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a year ago
A few weeks ago, I shared my script for my latest talk, Solving the Engineering Strategy crisis, which I gave at QCon last week. They’ll have the conference video up in a few weeks, but I also decided to do a recording of the final version (albeit a few weeks after the talk, so...
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Solving the Engineering Strategy crisis. These are speaking notes for my October 4th, QCon talk in San Francisco. Slides for this talk. Over...
a year ago
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a year ago
These are speaking notes for my October 4th, QCon talk in San Francisco. Slides for this talk. Over the course of my career, I’ve frequently heard from colleagues, team members and random internet strangers with the same frustration: the company doesn’t have an Engineering...
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Drafted Eng Executive's Primer! Back in late April, I mentioned that I was working on a new book, The Engineering Executive’s...
a year ago
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a year ago
Back in late April, I mentioned that I was working on a new book, The Engineering Executive’s Primer, with O’Reilly. I wanted to share a few notes on progress! First, there’s a cover, shown above in this post’s image, and also in the right rail (or bottom footer if you’re reading...
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Performance & Compensation (for Eng Execs). Uber’s original performance process was called “T3B3” and was remarkably simple: write the...
a year ago
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a year ago
Uber’s original performance process was called “T3B3” and was remarkably simple: write the individuals top 3 strengths, and top 3 weaknesses, and share the feedback with them directly in person. There was a prolonged fight against even documenting the feedback, which was viewed...
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The Engineering executive’s role in hiring. Everyone in an engineering organization contributes to the hiring process. As an engineer, you may...
a year ago
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a year ago
Everyone in an engineering organization contributes to the hiring process. As an engineer, you may have taken pride in being an effective interviewer. As an engineering manager, you may have prioritized becoming a strong closer, convincing candidates to join your team. As a more...
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Manage your priorities and energy. Back when I was managing at Uber, I latched onto a thinking tool that I drilled into the teams I...
a year ago
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a year ago
Back when I was managing at Uber, I latched onto a thinking tool that I drilled into the teams I worked with: reach the right outcomes by prioritizing the company first, your team second, and yourself third. This “company, team, self” framework proved a helpful decision-making...
Irrational...
Gelling your Engineering leadership team. One of the first leadership books I read was Patrick Lencioni’s The Five Dysfunctions of a Team,...
a year ago
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a year ago
One of the first leadership books I read was Patrick Lencioni’s The Five Dysfunctions of a Team, which introduces the concept of your peers being your “first team” rather than your direct reports. This was a powerful idea for me, because it’s much harder to be a good teammate to...
Irrational...
Building personal and organizational prestige Most months I get at least one email from an engineering leader who believes they’d be a candidate...
a year ago
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a year ago
Most months I get at least one email from an engineering leader who believes they’d be a candidate for significantly more desirable roles if their personal brand were just better known. Similarly, when funding is readily available during periods of tech industry expansion, many...
Irrational...
Playing with Streamlit and LLMs. Recently I’ve been chatting with a number of companies who are building out internal LLM labs/tools...
a year ago
50
a year ago
Recently I’ve been chatting with a number of companies who are building out internal LLM labs/tools for their teams to make it easy to test LLMs against their internal usecases. I wanted to take a couple hours to see how far I could get using Streamlit to build out a personal LLM...
Irrational...
Extract the kernel. As I’ve served longer in an executive role, I’ve started to notice recurring communication...
a year ago
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a year ago
As I’ve served longer in an executive role, I’ve started to notice recurring communication challenges between executives and the folks they work with. The most frequent issue I see is when a literal communicator insists on engaging in the details with a less literal executive. I...
Irrational...
Slides for Measuring an engineering organization. Last week, I gave a 30 minute talk to a group of CTOs and VP Engineerings in San Francisco about...
a year ago
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a year ago
Last week, I gave a 30 minute talk to a group of CTOs and VP Engineerings in San Francisco about measuring engineering organizations. This talk was essentially this blog post, and here are the slides. A few topics worth highlighting: Measurement educates you, and your audience,...
Irrational...
Good hypergrowth/curator manager. In 2016, I wrote Productivity in the age of hypergrowth to discuss the challenges of engineering...
a year ago
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a year ago
In 2016, I wrote Productivity in the age of hypergrowth to discuss the challenges of engineering management during periods of hypergrowth. Managers in such periods spend much of their time on hiring and onboarding, with the remainder devoted to organizational structure and...
Irrational...
The Engineering Executive's Primer. See on O’Reilly’s website for The Engineering Executive’s Primer. In 2019, I worked with Stripe...
a year ago
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a year ago
See on O’Reilly’s website for The Engineering Executive’s Primer. In 2019, I worked with Stripe Press to publish my first book, An Elegant Puzzle, which captured many of the lessons I’d learned as an engineering manager in fast growing Silicon Valley companies. In 2021, I decided...
Irrational...
Balancing your CEO, peers, and Engineering. There are so many stories of hiring a new executive who comes in and wreaks havoc. I’ve seen...
a year ago
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a year ago
There are so many stories of hiring a new executive who comes in and wreaks havoc. I’ve seen engineering leaders start with a giant, doomed migration, marketing leaders who accelerate expenses until they necessitate a round of layoffs, and a number of executives fired in their...
Irrational...
Grab bag of random thoughts. A bit over a week from now, I’ll be joining a company to start a new role, and I wanted to ramble a...
a year ago
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a year ago
A bit over a week from now, I’ll be joining a company to start a new role, and I wanted to ramble a bit to braindump the numerous loose threads in my head as I transitioned from Calm to the past month of full-time writing, and then into this new role. This isn’t really a job...
Irrational...
Interviewing engineering executives. Earlier I wrote about getting hired as an Engineering executive, and it’s perhaps even more...
a year ago
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a year ago
Earlier I wrote about getting hired as an Engineering executive, and it’s perhaps even more important to discuss the opposite question: how should you interview and evaluate Engineering executives? As an Engineering executive, you may not directly run one of these searches, but...
Irrational...
Poking around OpenAI. I haven’t spent much time playing around with the latest LLMs, and decided to spend some time doing...
a year ago
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a year ago
I haven’t spent much time playing around with the latest LLMs, and decided to spend some time doing so. I was particularly curious about the usecase of using embeddings to supplement user prompts with additional, relevant data (e.g. supply the current status of their recent...
Irrational...
How to plan as an engineering executive. Some years back, I interviewed a senior leader for an engineering role, and asked them a question...
a year ago
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a year ago
Some years back, I interviewed a senior leader for an engineering role, and asked them a question about planning. I enjoyed their response, “Ah yes, the ‘P’ word, planning.” That answer captured an oft heard perspective that planning is some sort of business curse word. Even when...
Irrational...
Who runs Engineering processes? Uber ran a tech spec review process called the DUCK Review. “DUCK” didn’t stand for anything–it was...
a year ago
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a year ago
Uber ran a tech spec review process called the DUCK Review. “DUCK” didn’t stand for anything–it was created as a deliberate non-acronym–but was otherwise a fairly typical review process. When I first joined, we’d review one or two specs each week. The volume of requested reviews...
Irrational...
Onboarding peer executives. While many companies build out an elaborate Engineering onboarding program, the process for...
a year ago
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a year ago
While many companies build out an elaborate Engineering onboarding program, the process for onboarding new executives tends to be an ad-hoc, chaotic affair. There usually is an executive onboarding process, but it’s used too infrequently to ever get excellent. Part of the problem...
Irrational...
Deciding to leave your (executive) job. If two friendly executives meet for dinner, it’s likely they start by exchanging just how messed up...
a year ago
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a year ago
If two friendly executives meet for dinner, it’s likely they start by exchanging just how messed up things are at work. Initiatives are behind, layoffs are happening everywhere, the team is in disarray. Then they’ll laugh, and switch topics. Sometimes one of the executives can’t...
Irrational...
Using cultural survey data. When I was at Stripe, I reworked the hiring process for Director-plus engineering managers. My goal...
a year ago
29
a year ago
When I was at Stripe, I reworked the hiring process for Director-plus engineering managers. My goal was to better evaluate polished senior leaders who always said the right thing. I wanted to find the real beliefs and behaviors underneath all the polish. One interview focused on...
Irrational...
Running your engineering onboarding program. Most companies say that it takes three to six months for newly hired engineers to fully ramp...
a year ago
30
a year ago
Most companies say that it takes three to six months for newly hired engineers to fully ramp up. Engineering leaders know it’s impolitic to admit that it takes their team longer than three to six months to onboard new engineers, so that’s what they say out loud, but they...
Irrational...
Engineering’s role in Mergers & Acquisitions. I managed the engineering team at Digg as we ran out of money, and were eventually acquired. It was...
a year ago
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a year ago
I managed the engineering team at Digg as we ran out of money, and were eventually acquired. It was an eye opening experience, and I learned a great deal about the reality and the optics of selling a company, particularly one with no money and a shrinking user base. Humbling was...
Irrational...
Building your executive network. In most of my roles, I’ve learned more from my peers than from my manager. Even when you get along...
a year ago
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a year ago
In most of my roles, I’ve learned more from my peers than from my manager. Even when you get along well with your manager, your peers’ perspective will usually be closer to yours than your manager’s. Once you transition into an engineering executive role, you’ll still have peers,...
Irrational...
ReadME contribution on reliability programs. I was excited to contribute an article, Move past incident response to reliability to Github’s The...
a year ago
27
a year ago
I was excited to contribute an article, Move past incident response to reliability to Github’s The ReadME project. This topic was particularly on my mind when I wrote it towards the end of last year, when I was focused on my Infrastructure Engineering project. That project is a...
Irrational...
Writing an engineering strategy. Once you become an engineering executive, an invisible timer starts ticking in the background. Tick...
a year ago
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a year ago
Once you become an engineering executive, an invisible timer starts ticking in the background. Tick tick tick. At some point that timer will go off, at which point someone will rush up to you demanding an engineering strategy. It won’t be clear what they mean, but they will want...
Irrational...
Better to micromanage than be disengaged. For a long time, I found the micromanager CEO archetype very frustrating to work with. They would...
a year ago
28
a year ago
For a long time, I found the micromanager CEO archetype very frustrating to work with. They would often pop out of nowhere, jab holes in the work I had done without understanding the tradeoffs, and then disappear when I wanted to explain my decisions. In those moments, I wished...
Irrational...
Culture vs systems. Recently, I had a chat with a friend who was frustrated by their company culture. They’d been...
a year ago
26
a year ago
Recently, I had a chat with a friend who was frustrated by their company culture. They’d been pushing the company to operate with more urgency, but didn’t feel like it was landing. “How do we,” they wondered, “get the team to recognize that urgency is essential to our success?”...
Irrational...
Setting engineering org values. Uber’s best known corporate value is probably Super Pumped, which, in addition to being a one-time...
over a year ago
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over a year ago
Uber’s best known corporate value is probably Super Pumped, which, in addition to being a one-time company value, is also the title of Mike Isaac’s account of Uber and the subsequent television show. However, for me personally, the value I remember most is Let Builders...
Irrational...
Safe defaults. Back in 2018, when I first wrote about sizing engineering teams, I was surprised how much my advice...
over a year ago
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over a year ago
Back in 2018, when I first wrote about sizing engineering teams, I was surprised how much my advice rankled a colleague. He wanted to spin up a new engineering team of two people, which I thought was a bad idea. It would be a fragile team that would fall apart quickly if it...
Irrational...
Internal comms for executives. Whenever an executive joins a new company, there is an awkward merger between the executive’s...
over a year ago
40
over a year ago
Whenever an executive joins a new company, there is an awkward merger between the executive’s preferred communication style and the norms that organization has already established. I remember a recently joined executive complaining that engineers weren’t reading his emails. He...
Irrational...
What does it mean to be a cost center? When I shared my piece on Measuring an engineering organization, one point I made was that focusing...
over a year ago
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over a year ago
When I shared my piece on Measuring an engineering organization, one point I made was that focusing too heavily on optimization metrics (e.g. things like CI/CD time) can turn engineering into a cost center. That’s not because optimization metrics aren’t important, they’re...
Irrational...
Meetings for an effective eng organization. Some engineers develop a strong point of view that meetings are a waste of their time. There’s good...
over a year ago
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over a year ago
Some engineers develop a strong point of view that meetings are a waste of their time. There’s good reason for that perspective, as many meetings are quite bad, but it’s also a bit myopic: meetings can also be an exceptionally valuable part of a well-run organization. If you’re...
Irrational...
Mailbag: What should you do if you report to an underperforming executive? Recently, an email came in asking what to do when you report into a mediocre or underperforming...
over a year ago
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over a year ago
Recently, an email came in asking what to do when you report into a mediocre or underperforming executive. I’ve gotten variants of this question a number of times over the years, and it’s worth digging into a bit: Have you written anything about working in middle management where...
Irrational...
Trying Plausible. I’ve been wanting to spend some time trying out recent developer and infrastructure tooling,...
over a year ago
28
over a year ago
I’ve been wanting to spend some time trying out recent developer and infrastructure tooling, starting with taking Tailscale for a spin (it’s quite nice). Next, I’ve been thinking about replacing Google Analytics on this blog for some time, and decided to try out Plausible.io as a...
Irrational...
Getting a job as an engineering executive. I started my first executive job search when I was 25. Eventually, I got an offer to lead...
over a year ago
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over a year ago
I started my first executive job search when I was 25. Eventually, I got an offer to lead engineering at a startup with four engineers, which I turned down to join Uber. It wasn’t until a decade later that I joined Calm and started my first executive role. If you start...
Irrational...
Make an effective executive LinkedIn profile. tl;dr - it’s valuable to update your LinkedIn profile to be a concise, accurate, and current summary...
over a year ago
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over a year ago
tl;dr - it’s valuable to update your LinkedIn profile to be a concise, accurate, and current summary of your accomplishment. Spend at most two hours updating it, then ask a friend (ideally a recruiter) for feedback. Incorporate that feedback and don’t think about your profile...
Irrational...
How to capitalize engineering costs. There are many important meetings in your first ninety days as a new engineering leader, but one...
over a year ago
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over a year ago
There are many important meetings in your first ninety days as a new engineering leader, but one that’s both easy to forget and surprisingly important is your first meeting with the finance team. There’s a lot to learn from the finance team, particularly drilling into your profit...
Irrational...
Trying Tailscale. Like most folks working in infrastructure engineering in 2014, I really enjoyed Google’s BeyondCorp...
over a year ago
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over a year ago
Like most folks working in infrastructure engineering in 2014, I really enjoyed Google’s BeyondCorp whitepaper. My foremost personal interest was grounded in the fact that Uber’s contemporaneous security implementation didn’t include a VPN, so it was interesting to see a...
Irrational...
Measuring an engineering organization. For the past several years, I’ve run a learning circle with engineering executives. The most...
over a year ago
26
over a year ago
For the past several years, I’ve run a learning circle with engineering executives. The most frequent topic that comes up is career management–what should I do next? The second most frequent topic is measuring engineering teams and organizations–my CEO has asked me to report...
Irrational...
A brief rant on converging compliance regimes. Although I’ve never worked exclusively on compliance, much of my work over the past decade has...
over a year ago
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over a year ago
Although I’ve never worked exclusively on compliance, much of my work over the past decade has touched on reconciling between product and compliance goals, and over that time I’ve developed something of a pet theory on the evolution of compliance over the next five to ten years:...
Irrational...
Lessons not worth learning. A few weeks ago I had a call with a startup founder who was frustrated with their team. The team...
over a year ago
25
over a year ago
A few weeks ago I had a call with a startup founder who was frustrated with their team. The team kept getting distracted by interesting work, and was avoiding the most important work to move the business forward. Was it possible to build a team that simply does the important work...
Irrational...
2022 in review. Previously: 2021, 2020, 2019, 2018, 2017 After the past two years, it’s odd to write an annual...
over a year ago
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over a year ago
Previously: 2021, 2020, 2019, 2018, 2017 After the past two years, it’s odd to write an annual reflection where my first thoughts are happy rather than bleak. The truth is that there is a lot of bleak out there right now–just look at the layoffs and the funding environment–but...