Wardley mapping the LLM ecosystem.
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...
3 days ago
Wardley mapping of Gitlab Strategy.
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...
4 days ago
2024 in review.
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...
13 days ago
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 tools, which laid out my three core problems with developer productivity measurement tools of the time:Using productivity measures to evaluate rather than learnInstrumenting metrics required tweaks across too any different toolsGenerally I found tools forced an arbitrary, questionable model onto the problemTwo 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...
19 days ago
Rough notes on learning Wardley Mapping.
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...
27 days ago
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 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 is largely based on the High-Context Triad of blog posts I wrote in late 2023:I hope you enjoy the talk! (Unfortunately I don’t have a recording of Dan Fike’s portion, but QCon will post their official video at some point, which will have both parts.)
about 1 month ago
How to get more headcount.
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 why their work is important.I understand why dumb executives are such an appealing explanation to problems: it fits perfectly into the Karpman drama triangle by making executives the villian and the team the victim,...
about 1 month ago
Navigating Private Equity ownership.
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 expects immediate free cash flow rather than accepting the sweet promise of discounted future cash flow.This chapter wants to tackle that problem head-on, taking the role of an engineering organization attempting to navigate...
about 2 months ago
Using systems modeling to refine strategy.
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:when systems model is a useful technique, and when...
about 2 months ago
Eng org seniority-mix model.
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 major impact on their free cash flow. There are many costs to reduce, cloud hosting and such, but inevitably part of the discussion is addressing engineering headcount costs directly.One of the largest contributors to engineering...
2 months ago
Modeling driving onboarding.
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 problem: maximizing active drivers on their ridesharing platform.In this chapter, we’ll cover:Where the model of ridesharing drivers identifies opportunities for LLMsHow the model was sketched and developed using lethain/systems package on GithubExercise to exercise this...
2 months ago
Modeling impact of LLMs on Developer Experience.
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 from this modelHow the model was developed, both sketching and building the model in a spreadsheet. (As discussed in the overview of systems modeling, I generally would recommend against using spreadsheets to develop most models, but it’s educational to...
3 months ago
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 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 you believe your strategy is working while minimizing change to the status quo (if you’re an executive) or get your strategy repealed (if you’re not an executive). Neither is particular helpful.While some strategies are obviously wrong from...
3 months ago
Should we decompose our monolith?
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 different database technology is generally a less expensive change than moving from monolith to microservices or from microservices to monolith.The industry has in many ways gone full circle on that debate, from most hyperscalers in the 2010s partaking in a multi-year...
3 months ago
Executive translation.
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 idea.Some executives are skeptical of this idea because they don’t like the implication that they’re usually wrong, but they weren’t the audience that was offended. But the folks who got particularly upset were non-executives who felt it was unfair for...
4 months ago
Video of Developing Eng Leadership Styles.
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 conference talk on this topic at LeadingEng New York, 2024. If you’re interested, you can watch a recording of an earlier practice session from a few days before the talk, and can review the slides. I...
4 months ago
Numbers go up.
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 increasing. The initial idea here was social commentary exposing the addictive core of many games, but like all good commentary it’s also inadvertently spawned the genre of gacha games that focus on extracting revenue from addicted gamers.I’m thinking about numbers...
4 months ago
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 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 than investing time into understanding it.Fortunately, these are universal problems, and there are a handful of useful mental models to avoid both extremes. This chapter covers:when to write strategy, in particular the pain points (like...
4 months ago
Executive
Physics and perception. June 29, 2024Load-bearing / Career-minded / Act Two rationales May 2, 2024Friction isn't velocity. March 15, 2024Those five spare hours each week. January 14, 2024Predictability. January 1, 2024Benchmarking. November 11, 2023Developing leadership styles October 22, 2023Solving the Engineering Strategy crisis. September 23, 2023Performance & Compensation (for Eng Execs). September 3, 2023The Engineering executive’s role in hiring. August 27, 2023Manage your priorities and energy. August 3, 2023Gelling your Engineering leadership team. July 11, 2023Building personal and organizational prestige...
5 months ago
Tags
How to navigate and/or survive your acquihire. January 2, 2020⭐ How the Digg team was acquihired. January 1, 2020acreFreebase Hackday and Image Game July 12, 2009actorsRecurring Events and Message Passing November 25, 2009A Couple of Clojure Agent Examples November 22, 2009Actors in Common Lisp January 3, 2008adultTeaching Adult English Classes October 18, 2007agentsRecurring Events and Message Passing November 25, 2009Scalable Scraping in Clojure November 24, 2009A Couple of Clojure Agent Examples November 22, 2009analyticsWriting, Analytics and Analysis April 10, 2011How...
5 months ago
Physics and perception. June 29, 2024How to create software quality. June 16, 2024Video of Using LLMs in your product. June 14, 2024No Wrong Doors. May 22, 2024Making engineering strategies more readable May 18, 2024How should you adopt LLMs? May 14, 2024Load-bearing / Career-minded / Act Two rationales May 2, 2024Constraints on giving feedback. April 29, 2024Notes on how to use LLMs in your product. April 8, 2024Ex-technology companies. March 22, 2024Leadership requires taking some risk. March 17, 2024Friction isn't velocity....
5 months ago
Developing domain expertise: get your hands dirty.
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 internal experts), I missed the most important dimension of effective learning: getting your hands dirty.At Carta, I’m increasingly spending time focused on our fund financials business, which requires a deep understanding of accounting. I did not join Carta...
5 months ago
Posts
Physics and perception. June 29, 2024How to create software quality. June 16, 2024Video of Using LLMs in your product. June 14, 2024No Wrong Doors. May 22, 2024Engineering strategy template May 18, 2024Making engineering strategies more readable May 18, 2024How should you adopt LLMs? May 14, 2024Modeling impact of LLMs on Developer Experience. May 13, 2024Simple model of driver onboarding with LLMs. May 13, 2024Wardley mapping the LLM ecosystem. May 13, 2024Components of engineering strategy May 4, 2024Diagnosis for strategy May...
5 months ago
Management
Physics and perception. June 29, 2024How to create software quality. June 16, 2024No Wrong Doors. May 22, 2024Load-bearing / Career-minded / Act Two rationales May 2, 2024Constraints on giving feedback. April 29, 2024Friction isn't velocity. March 15, 2024⭐ Useful tradeoffs are multi-dimensional. January 24, 2024Navigating ambiguity. January 19, 2024⭐ Layers of context. January 15, 2024Those five spare hours each week. January 14, 2024Predictability. January 1, 2024Navigators November 24, 2023Team Charters are a trap. November 12, 2023Benchmarking. November 11, 2023Getting lucky...
5 months ago
Physics and perception.
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 the face of both a rapidly growing business and a rapidly growing engineering organization. The other group believed Stripe’s problems were driven by a product domain with high essential complexity and numerous, demanding external partners...
6 months ago
Staff-Plus
How to create software quality. June 16, 2024Leadership requires taking some risk. March 17, 2024High-Context Triad. January 24, 2024⭐ Useful tradeoffs are multi-dimensional. January 24, 2024Navigating ambiguity. January 19, 2024⭐ Layers of context. January 15, 2024Navigators November 24, 2023Solving the Engineering Strategy crisis. September 23, 2023The terminal level rulebook. November 17, 2021How to present to executives. January 2, 2021Weak and strong team concepts. December 5, 2020What do Staff engineers actually do? December 3, 2020Managing Staff-plus engineers. November 27, 2020⭐ Write...
6 months ago
How to create software quality.
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 to decide that you want to write perfect code.If I wrote that in an internal memo, I imagine the engineering team would mutiny, but software quality is certainly an interesting topic where I continue...
6 months ago
Architecture
How to create software quality. June 16, 2024Create technical leverage: workflow improvements & product capabilities December 1, 2023Notes on Tidy First? November 19, 2023⭐ Managing technical quality in a codebase. October 17, 2020The Grand Migration. August 13, 2020How to practice backend engineering. June 20, 2020Hotspotting developer productivity. March 17, 2020Notes on Building Evolutionary Architectures. November 15, 2019Healthchecks at scale. October 27, 2019Describing fault domains. August 17, 2019Distributed systems vocabulary. August 11, 2019⭐ Reclaim unreasonable software. July 28, 2019Notes on The...
6 months ago
Speaking
Video of Using LLMs in your product. June 14, 2024Video of Solving the Eng Strategy crisis. October 21, 2023Slides for Measuring an engineering organization. May 20, 2023Speaking and podcasts in 2020. November 13, 2020Example Call For Proposals submissions. January 25, 2020"How to successfully design organizational processes" November 23, 2019"Investing in technical infrastructure" October 31, 2019"Paying Technical Debt at Scale - Migrations" December 13, 2018Speaking at QCon SF 2018 about migrations. November 5, 2018
7 months ago
Llm
Video of Using LLMs in your product. June 14, 2024How should you adopt LLMs? May 14, 2024Notes on how to use LLMs in your product. April 8, 2024Playing with Streamlit and LLMs. June 19, 2023Poking around OpenAI. April 12, 2023
7 months ago
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 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 a lot of overlap with the notes, but I also go into Carta’s approach thus-far to incorporating LLMs into our product. (Note that it’s a recording of a practice run I...
7 months ago
Talks
Video of Using LLMs in your product. June 14, 2024Video of Solving the Eng Strategy crisis. October 21, 2023Slides for Measuring an engineering organization. May 20, 2023Speaking and podcasts in 2020. November 13, 2020"How to successfully design organizational processes" November 23, 2019"Investing in technical infrastructure" October 31, 2019"Paying Technical Debt at Scale - Migrations" December 13, 2018
7 months ago
No Wrong Doors.
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 better equipped to navigate their own bureaucracies than an individual who knows nothing about the bureaucracy’s internal function.For the most part, technology organizations are not complex bureaucracies, but sometimes they do seem to operate...
7 months ago
Strategy
Making engineering strategies more readable May 18, 2024How should you adopt LLMs? May 14, 2024Leadership requires taking some risk. March 17, 2024Notes on How Big Things Get Done December 15, 2023Notes on Enterprise Architecture as Strategy December 7, 2023Notes on The Crux November 24, 2023Engineering strategy notes. November 21, 2023Notes on Technology Strategy Patterns November 20, 2023Notes on The Value Flywheel Effect November 18, 2023Video of Solving the Eng Strategy crisis. October 21, 2023Solving the Engineering Strategy crisis. September 23,...
7 months ago
Eng-Strategy-Book
Making engineering strategies more readable May 18, 2024How should you adopt LLMs? May 14, 2024Engineering strategy notes. November 21, 2023
7 months ago
Making engineering strategies more readable
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 sequence for creating a strategy, but it’s a challenging sequence for those trying to quickly read and apply a strategy without necessarily wanting to understand the complete thinking behind each decision.This post covers:Why the order for writing strategy is hard to...
7 months ago
How should you adopt LLMs?
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 capabilities have transitioned into the mainstream, with many companies worrying that they’re falling behind despite the fact that most integrations appear superficial.That context makes LLM adoption a great topic for a strategy case study. This document is an engineering...
8 months ago
Systems-Thinking
To innovate, first deprecate. April 7, 2019⭐ Why limiting work-in-progress works. February 17, 2019Binder for hosting Jupyter notebooks. February 10, 2019Writing a reliability strategy: reason about complex things with system models. February 9, 2019Modeling a hiring funnel with Systems library. September 18, 2018Introduction to systems thinking. September 4, 2018
8 months ago
Load-bearing / Career-minded / Act Two rationales
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 companies are to departures, even of important people. About two-thirds of Digg’s team left in layoffs in 2010, but we found ways to amble on. Much of Uber’s leadership team turned over in...
8 months ago
Constraints on giving feedback.
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 thought would help them understand the organization, but mostly isolated them in a Values Oasis or demoralized them instead.Those experiences taught me that pushing your organization to improve is essential leadership...
8 months ago
Notes on 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 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 make an argument for LLMs improving internal efficiency somehow, but it’s much harder to describe a believable way that LLMs will make your product more useful to your customers.I’ve been working fairly directly...
9 months ago
Ex-technology companies.
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 answer those questions, I wrote up some notes, which summarize two perspectives on “being a technology company.”The first perspective is Ben Thompson’s “Software has zero marginal costs.” You’re a technology company if adding your...
9 months ago
Leadership requires taking some risk.
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 kicked off the Uber SRE group and architectured Uber’s self-service service provisioning strategy that defined Uber’s approach to software development (which spawned a thousand thought pieces, not all complimentary). I did both without top-down approval, and...
10 months ago
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 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 speed. Every sensation will tell you that you’re moving faster, but lowering the window has increased your car’s air resistance, and you’re actually going slower. Or at minimum you’re using...
10 months ago
More (self-)publishing thoughts.
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:Building on that, the general elements I’d encourage someone to think through if they’re deciding whether to self-publishing:There’s a learning curve to publishing book, and I’ve learned a lot from every book I’ve written. Both working with publishers and self-publishing accelerate your learning curve. To maximize learning, I’d recommend doing a mix of both. If your goal...
10 months ago
Digital release of Engineering Executive's Primer.
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 digital edition on Amazon, and read the full digital release on O’Reilly. (You can preorder physical copies on Amazon as well.)
11 months ago
Thesis on value accumulation in AI.
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. I’ll describe my understanding of the current state, how I think it’ll evolve over the next 1-3 years, and then end with how that shapes what I’m investing in.My view on the the state of play today:There are three...
11 months ago
High-Context Triad.
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 finished my nascent project on engineering strategy, is publishing a second edition of Staff Engineer, and I intended these three articles as supplements.I’ve really enjoyed writing these pieces, because the first on context layers is really...
11 months ago
Useful tradeoffs are multi-dimensional.
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 quality assurance. In other pockets of the industry, the axiom is quite different: you can get both fast deployment and manual quality assurance by using feature flags to decouple deployment (shipping the code) and release (enabling...
11 months ago
Navigating ambiguity.
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 in engineers, and doing it well is a rarity. It’s sufficiently rare that many executives can’t do it well either, although I do believe that all long-term successful executives find at least one toolkit for these kinds of problems.Before...
11 months ago
Layers of context.
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 approach. After our chat, I followed up by talking with his peers about some recent disagreements, and they kept highlighting missing context from the engineer’s proposals. As I spoke with more peers, the engineer’s...
12 months ago
Those five spare hours each week.
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 focusing on leadership work rather than coding.” There are, of course, adherents at every point between those two extremes. It’s hard to take these arguments too seriously, because these values correlate so strongly with...
12 months ago
Predictability.
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 Silicon Valley. It’s something I’ve thought about a lot as well in my career, and also while writing on my upcoming book on operating as an engineering executive–how much do good...
12 months ago
2023 in review.
Previously: 2022, 2021, 2020, 2019, 2018, 2017This 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 bits and pieces. Here is my year in review summary.I love to read other folks year-in writeups – if you write one, please send it my way!GoalsEvaluating my goals for the year:[Completed]...
about 1 year ago
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 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 projects, and much more. Not directly software engineering related, but very relevant to the work. Also, just well written.“Think slow, act fast”It’s fine for planning to be slow (p17), as long as delivery is...
about 1 year ago
Writers who operate.
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 that advances the industry. This is a lightly controversial view, so I wanted to pull together my full set of thoughts on the topic.The themes I want to work through are:Evaluating believability for operators is...
about 1 year ago
Advancing the industry.
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 rather than prestige. Over the last few years, what I’ve come to appreciate is that there’s another phase: purpose.Purpose isn’t intrinsically the third phase of a career, but it certainly...
about 1 year ago
Notes on Enterprise Architecture as Strategy
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 remains relevant.The technology industry is simultaneously grasped by the optimism that things are changing constantly–your skills from last year are already out of date!–and the worry that nothing particularly important has changed since the 1970s when the unix epoch...
about 1 year ago
Create technical leverage: workflow improvements product capabilities
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 acquirers to buy Digg. It was only this morning that I remembered that the post exists when I started trying to title this post on the same topic.A decade later, I have accumulated...
about 1 year ago
Navigators
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. Most misalignment comes from missing context, and these are the organizational leverage points to inject context into decision-making. Many organizations start here, but it’s the last box of tools that I recommend opening. How can you provide consistent architecture reviews without an...
about 1 year ago
Notes on The Crux
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 for more strategy books to read, and folks pointed out that I’d missed a new book from Richard Rumelt, The Crux. No book has influenced my thinking about strategy more than Rumelt’s previous...
about 1 year ago
Engineering strategy notes.
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 current theory of engineering strategy is Solving the Engineering Strategy Crisis, which has both written and video versions. You can also reading my other strategy writing via the strategy tag.Let me know...
about 1 year ago
Notes on Technology Strategy Patterns
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 their own theory of engineering strategy.In June, 2019, I bought a copy of Technology Strategy Patterns by Eben Hewiit. A the time, I was trying to argue against a large, proposed migration to Java at Stripe, collecting thoughts that became Reclaim...
about 1 year ago
Notes on The Software Engineer's Guidebook
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 a breadcrumb on most topics you’ll encounter as a software engineer, along with enough detail to guide deeper exploration in other, narrower books.Gergely Orosz is the author of The Pragmatic Engineer, and almost certainly the...
about 1 year ago
Notes on Tidy First?
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 John Ousterhout is one of my favorite books on software design. When I heard that Kent Beck had a new book out, Tidy First?, that was deliberately engaging with similar content but a markedly different pedagogy,...
about 1 year ago
Notes on The Value Flywheel Effect
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 previously spent much time on is Wardley maps. As I dug into it a bit more, The Value Flywheel Effect by Anderson, McCann, and O’Reilly was recommended as a primer, so I bought a copy and spend...
about 1 year ago
Team Charters are a trap.
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 project I’d generally prioritize. If you pushed me on this topic, I’d probably suggest you write an engineering strategy document from the perspective of your team. A few thoughts on what team...
about 1 year ago
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 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. Although I ended up starting a role sooner than expected–it was the right opportunity to accept–I did get to spend more time with my kid, finish my...
about 1 year ago
Benchmarking.
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 undercompensated. In the boom times, there is often enough investor money laying around to say yes to all these questions, but many leaders are acutely learning the long-term costs of expanding our budget too far.While there is...
about 1 year ago
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 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 successful after working at companies that succeeded, but where their direct impact was relatively small. Companies get lucky, too. This is true both in the sense that the door to acquisitions was much more...
about 1 year ago
Thoughts on writing and publishing Primer.
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 done by other folks in the process, particularly formatting and printing.Each book is an education of sorts, and I decided to work with O’Reilly on this book to push myself on structure and...
about 1 year ago
Developing leadership styles
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 they would trust me based on my track record of doing good work. If they didn’t trust my track record, could they at least take the time to talk through the...
about 1 year ago
Video of Solving the Eng Strategy crisis.
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 definitely a bit less practiced than the live edition).You can watch that video on YouTube.As mentioned, I don’t think I was quite as practiced in this...
about 1 year ago
Solving the Engineering Strategy crisis.
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 strategy. I don’t think this problem is unique to Engineering: it’s also common to hear folks complain that they’re missing a strategy for Product, Design or Business. But, whereas I don’t feel particularly confident speaking to why so...
over 1 year ago
Drafted Eng Executive's Primer!
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 on a smaller device). I’m quite excited about the cover, which is simple and imperfect. There is nothing pure about being an executive, it’s mostly about balancing opposing forces to...
over 1 year ago
Performance Compensation (for Eng Execs).
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 as discouraging honesty. On the other side of things, there are numerous stories of spending months crafting Google promotion packets that still don’t get their authors promoted. Among those who’ve worked within both Uber and Google’s promotion...
over 1 year ago
The Engineering executive’s role in hiring.
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 senior manager, you will have likely shifted focus to training others and spending time with candidates for particularly senior roles.As an engineering executive, your role in the hiring process will shift once again. You’ll continue to...
over 1 year ago
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 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 tool, and at the time I felt it almost always led to the correct decision. It also helped me articulate why I disagreed with some of my peers’ decisions, which violated this hierarchy by...
over 1 year ago
Gelling your Engineering leadership team.
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 your peers than to your direct reports. While your incentives are usually aligned with the team you manage, it’s very common for your incentives to be at odds with your...
over 1 year ago
Building personal and organizational prestige
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 companies believe they are principally constrained by their hiring velocity–if their engineering organization’s brand was just a bit better, they believe they’d be hiring much faster.Writing a great deal online, and working at companies during periods...
over 1 year ago
Playing with Streamlit and LLMs.
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 lab for a few usecases of my own.See code on lethain/llm-explorer.Altogether, I was impressed with how usable Streamlit is, and was able to build two useful tools in...
over 1 year ago
Extract the kernel.
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 call the remedy, “extracting the kernel.”For example, imagine a team is presenting about their upcoming timeline, and the CTO asks, “Can’t you just use ChatGPT to solve that instead of building a custom model?”...
over 1 year ago
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 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, about the area being measured. Even flawed measures can be very effective educators. Don’t get caught up on not measuring things because they have some flaws, let the audience learn about those flawsInstrumentation is costly to...
over 1 year ago
Good hypergrowth/curator manager.
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 high-level strategy. Their technical expertise is important, but it’s demonstrated indirectly in the quality of their strategy, structure, and hiring.In 2023, our universe has shifted. There’s little hiring happening, and most companies are eliminating roles to meet investor...
over 1 year ago
The Engineering Executive's Primer.
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 to learn the entire process of publishing myself, self publishing my second book, Staff Engineer, which synthesized the stories of a number of individuals into a framework to attaining and operating in Staff-plus engineering roles....
over 1 year ago
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 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 first month. When people tell these stories, it’s almost always framed as a failure of the individual executives, but they happen so frequently that I believe there’s an underlying structural challenge in addition to...
over 1 year ago
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 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 announcement post per se, as I won’t share any details about the job itself until I’ve officially started. Instead, this is a snapshot of...
over 1 year ago
Interviewing engineering executives.
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 you’ll likely be asked for advice about how to run them, and may be asked to design the process to hire your successor.The key topics I want to explore are:Avoiding the unicorn searchHow interviewing executives goes wrongStructuring...
over 1 year ago
Poking around OpenAI.
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 tickets into the prompt where they might inquire about progress on said tickets). This usecase is interesting because it’s very attainable for existing companies and products to take advantage of, and I imagine it’s roughly...
over 1 year ago
How to plan as an engineering executive.
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 it goes well, planning is an objectively difficult task. When it goes poorly, the business loses months or years of potential progress. Despite those challenges, guiding your company’s plans towards the right work...
over 1 year ago
Who runs Engineering processes?
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 kept growing, and six months later there was a one to two week delay between requesting a review and receiving feedback. A year after that the process was disbanded due to lack of bandwidth...
over 1 year ago
Onboarding peer executives.
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 is similar to that of an executive job search: every executive and role is unique, and it’s hard to create a repeatable program to handle one-of-a-kind onboardings.The other part of the problem is that the executive’s manager,...
almost 2 years ago
Deciding to leave your (executive) job.
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 navigate the switch, and will keep ranting throughout their meal. Having problems is part of being an executive, but when you’re that second executive who can’t turn off the frustration, it’s time to start thinking...
almost 2 years ago
Using cultural survey data.
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 a direct report sharing a mediocre strategy proposal for review, and getting a signal on whether the candidate could give useful feedback on improving the document. I knew that interview worked when a candidate...
almost 2 years ago
Running your engineering onboarding program.
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 generally believe it takes longer for a new engineer to become fully productive. They also know that their most impactful engineers are still becoming more productive after years with the company.Running...
almost 2 years ago
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 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 just the beginning.Since then, I’ve had the opportunity to evaluate a number of companies from the other side of the Mergers and Acquisitions (M&A) table. Most of those discussions...
almost 2 years ago
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 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, but they’re a different sort of peer, who will look at problems from a very different perspective than yours. If you ask the head of product for feedback, they will give it,...
almost 2 years ago
ReadME contribution on reliability programs.
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 bit paused at the moment, as I’m focused on another project that I’ll get to announce in the next month or two. (No details there yet, but if you look at my recent...
almost 2 years ago
Writing an engineering strategy.
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 it, really, really badly. If we just had an engineering strategy, their eyes will implore you, things would be okay. For a long time, those imploring eyes haunted me, because I...
almost 2 years ago