The Engineering Executives Primer Impactful Technical Leadership (Will Larson) (z-library.sk, 1lib.sk, z-lib.sk)

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WILL LARSON The Engineering Executive’s Primer IMPACTFUL TECHNICAL LEADERSHIP

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ISBN: 978-1-098-14948-2 US $39.99 CAN $49.99 As an engineering manager, you almost always have someone in your company to turn to for advice: a peer on another team, your manager, or even the head of engineering. But who do you turn to if you’re the head of engineering? Engineering executives have a challenging learning curve, and many folks excitedly start their first executive role only to leave frustrated within the first 18 months. In this book, author Will Larson shows you ways to obtain your first executive job and quickly ramp up to meet the challenges you may not have encountered in nonexecutive roles: measuring engineering for both engineers and the CEO, company-scoped headcount planning, communicating successfully across a growing organization, and figuring out what people actually mean when they keep asking for a “technology strategy.” This book explains how to: • Get an engineering executive job, negotiate the contract, and onboard at your new company • Run an engineering planning process and communicate effectively with the organization • Direct the core meetings necessary to operate an effective engineering organization • Hire, onboard, and run performance management • Manage yourself and remain effective through many challenges • Leave the job when the time is right Will Larson has served as CTO at both Carta and Calm and as a software engineering leader at Stripe, Uber, and Digg. He’s the author of An Elegant Puzzle and Staff Engineer. He’s also a prolific writer on his blog, Irrational Exuberance. Before moving to San Francisco, Will grew up in North Carolina and studied computer science at Centre College in Kentucky. EXECUTIVE LE ADER SHIP “Will Larson’s Engineering Executive’s Primer is a must-have for senior engineering leaders looking for approachable and practical advice they can instantly deploy.” — Michael Lopp, senior engineering leader and author of randsinrepose.com Twitter: @oreillymedia linkedin.com/company/oreilly-media youtube.com/oreillymedia The Engineering Executive’s Primer IMPACTFUL TECHNICAL LEADERSHIP

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Praise for The Engineering Executive’s Primer In this practical and accessible guide, Will Larson unpacks the engineer- ing executive role with his usual clarity and insight. I learned a ton from this book—I recommend it for all engineering leaders, and for any- one who has wondered about the constraints and tradeoffs that go into executive-level decisions. —Tanya Reilly, senior principal engineer and author of The Staff Engineer’s Path Will does an exceptional job of capturing the need to work on ourselves— and how to do it—while we work on people, products and strategy. —Julia Grace, engineering leader Will Larson’s Engineering Executive’s Primer is a must-have for senior engineering leaders looking for approachable and practical advice they can instantly deploy. —Michael Lopp, senior engineering leader and author of randsinrepose.com

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The Engineering Executive’s Primer Impactful Technical Leadership Will Larson

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978-1-098-14948-2 [LSI] The Engineering Executive’s Primer by Will Larson Copyright © 2024 Will Larson. All rights reserved. Printed in the United States of America. Published by O’Reilly Media, Inc., 1005 Gravenstein Highway North, Sebastopol, CA 95472. O’Reilly books may be purchased for educational, business, or sales promotional use. Online editions are also available for most titles (http://oreilly.com). For more information, contact our corporate/institutional sales department: 800-998-9938 or corporate@oreilly.com. Acquisitions Editor: David Michelson Development Editor: Virginia Wilson Production Editors: Jonathon Owen and Kristen Brown Copyeditor: Nicole Taché Proofreader: Piper Editorial Consulting, LLC Indexer: Sue Klefstad Interior Designer: Monica Kamsvaag Cover Designer: Susan Thompson Illustrator: Kate Dullea February 2024: First Edition Revision History for the First Edition 2024-02-06: First Release See http://oreilly.com/catalog/errata.csp?isbn=9781098149482 for release details. The O’Reilly logo is a registered trademark of O’Reilly Media, Inc. The Engineering Executive’s Primer, the cover image, and related trade dress are trademarks of O’Reilly Media, Inc. The views expressed in this work are those of the author and do not represent the publisher’s views. While the publisher and the author have used good faith efforts to ensure that the information and instructions contained in this work are accurate, the publisher and the author disclaim all responsibility for errors or omissions, including without limitation responsibility for damages resulting from the use of or reliance on this work. Use of the information and instructions contained in this work is at your own risk. If any code samples or other technology this work contains or describes is subject to open source licenses or the intellectual property rights of others, it is your responsibility to ensure that your use thereof complies with such licenses and/or rights.

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Contents | Preface vii 1 | Getting the Job 1 2 | Your First 90 Days 15 3 | Writing Your Engineering Strategy 31 4 | How to Plan 53 5 | Creating Useful Organizational Values 77 6 | Measuring Engineering Organizations 89 7 | Participating in Mergers and Acquisitions 99 8 | Developing Leadership Styles 115 9 | Managing Your Priorities and Energy 129 10 | Meetings for an Effective Engineering Organization 137 11 | Internal Communications 149 12 | Building Personal and Organizational Prestige 157 13 | Working with Your CEO, Peers, and Engineering 167 14 | Gelling Your Engineering Leadership Team 175 v

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15 | Building Your Network 183 16 | Onboarding Peer Executives 191 17 | Inspected Trust 203 18 | Calibrating Your Standards 211 19 | How to Run Engineering Processes 217 20 | Hiring 227 21 | Engineering Onboarding 243 22 | Performance and Compensation 255 23 | Using Cultural Survey Data 269 24 | Leaving the Job 277 | Closing 289 A | Additional Resources 291 B | Interviewing Engineering Executives 295 C | Reading a Profit & Loss Statement 301 D | Starting Engineering Hubs 311 E | Magnitudes of Exploration 319 | Index 325 vi | CONTENTS

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Preface This is the book that I wish I’d read before starting my first Engineering exec- utive role, and that I would have reread before starting my second executive role—to reflect on how my beliefs had evolved after doing this expansive, com- plex work. I hope reading this book serves you well and, more importantly, that it helps you form your own opinions rather than convinces you to take on mine. My favorite chapter in this book is the third, which discusses creating an Engineering strategy. I also wrote a chapter about Engineering strategy in my last book, Staff Engineer. It’s interesting how different those two chapters are, despite the fact that I wrote both of them, and only three years apart. At first, I wanted to believe this difference reflected some kind of deep insight I’d acquired between writing the two books, but the real difference is more fundamental: being an Engineering executive is a meaningfully different job, and it’s forced me to adopt a different perspective than my previous roles as an engineer and engineering manager. As an Engineering executive, you will deal with many familiar problems but will have new tools to solve them. For example, the hardest part of developing an Engineering strategy in my previous roles was usually building consensus around the solution. As an executive, the hardest part is building conviction that your strategy is right for your company. There are also new problems that you’ve probably not spent time with before, if you’re new to the executive role. Everyone deals with a planning process, but only executives have to debate the algorithms to attribute platform costs across various business lines. This book surveys the new challenges, and new tools for old problems, that you’ll encounter as an Engineering executive. There are no universal answers to the most interesting questions, but you’ll come away from this book with an understanding of the problems and at least one recommendation for how to approach each one. vii

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What This Book is Not If you’re looking for details on how to run one engineering team, this won’t be the most useful book for you. This book does not explore practices for run- ning your weekly team meetings, conducting one-on-ones, or giving feedback effectively. Instead, it focuses on how multiple teams work together effectively across a company’s Engineering function. For those omitted topics, I heartily recommend Camille Fournier’s The Manager’s Path (O’Reilly) and my own An Elegant Puzzle (Stripe Press). Likewise, this book is focused on the whole Engineering function, which is the intersection of technology-focused and people-focused leadership. There is no meaningful way to talk about leading an Engineering function that doesn’t engage with both those leadership aspects. If you’re looking for a book more focused on technology-focused leadership, consider picking up Tanya Reilly’s The Staff Engineer’s Path (O’Reilly) or my own Staff Engineer. Finally, this book won’t be helpful if you’re looking for advice on how to build a specific piece of technology. There are a thousand effective ways to build any given product, and this book won’t suggest any of them. Instead, it will dis- cuss the value of standardizing, or not standardizing, your company’s approach to building and maintaining a large portfolio of products and systems. There are simply too many books out there about building technology to recommend any given one, so I’ll leave you to decide what might work better for that focus. Navigating This Book This book is designed to be used in two different ways. If you’re a new Engineer- ing executive, or starting a new role, then you should get the most out of reading this book front to back. That will give you a broad perspective on the topics that will come up while operating in an Engineering executive role. The second way to use this book is to come to it when you’re dealing with a particular challenge, jump to the relevant section, give it a read, and put it down until you run into your next challenge. Many topics within the book are connected—what use is an Engineering strategy if you don’t have a clear way to communicate that strategy to your team?—but they’re all designed to stand on their own. viii | PREFACE

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Clarifying Terms To communicate more effectively, there are a handful of terms that I’m defining here to reduce potential confusion caused by inconsistent usage across compa- nies and industry verticals: Executive This is the functional leader of an area for the entire company. Many companies refer to certain titles as executives, for example Vice Presidents, despite them reporting to another member in the same function—a Vice President of Product reporting to a Chief Product Officer. Those Vice Presidents are not included in this book’s definition of Executive. Engineering executive This is the functional leader for Engineering, who is responsible for both technical execution and people management within Engineering. Depending on the company, its Engineering executive might be called a Chief Technology Officer, Vice President of Engineering, or Head of Engineering. Team This describes those directly reporting to a manager. Organization This describes the entire organizational chart, composed of multiple teams and their managers reporting to an executive. For example, all members of Engineering would be referred to as the Engineering organization. Engineering (uppercase) This is shorthand for the Engineering organization. The teams that make up an Engineering organization will vary considerably by company. Some companies would include Product, Data Science, and Security in Engineer- ing, and others would follow a much narrower definition. All those organi- zations qualify as Engineering by this book’s definition. engineering (lowercase) This is the industry or profession. As a final warning, these terms are clarified to facilitate communication, not because I’m a big believer in dogma. If someone tells you that your Engineering organization must, or must not, include any particular sub-team, or insists on a PREFACE | ix

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particular definition of “executive,” then be wary of their advice. There are no truths, only trade-offs, when it comes to defining terms. O’Reilly Online Learning For more than 40 years, O’Reilly Media has provided tech- nology and business training, knowledge, and insight to help companies succeed. Our unique network of experts and innovators share their knowledge and expertise through books, articles, and our online learning platform. O’Reilly’s online learning platform gives you on-demand access to live training courses, in-depth learning paths, interactive coding environments, and a vast collection of text and video from O’Reilly and 200+ other publishers. For more information, visit https://oreilly.com. How to Contact Us Please address comments and questions concerning this book to the publisher: O’Reilly Media, Inc. 1005 Gravenstein Highway North Sebastopol, CA 95472 800-889-8969 (in the United States or Canada) 707-827-7019 (international or local) 707-829-0104 (fax) support@oreilly.com https://www.oreilly.com/about/contact.html We have a web page for this book, where we list errata and any additional information. You can access this page at https://oreil.ly/EngineeringExecPrimer. For news and information about our books and courses, visit https:// oreilly.com. Find us on LinkedIn: https://linkedin.com/company/oreilly-media Follow us on Twitter: https://twitter.com/oreillymedia Watch us on YouTube: https://youtube.com/oreillymedia x | PREFACE

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Acknowledgments There’s a convenient myth that books are written solely by their authors. My experience is quite different. Technically, I wrote this book, but in practice it is the culmination of my career in engineering leadership, a decade of writing online, everything I’ve been taught through writing my two prior books, working closely with hundreds of engineering leaders, the direct input from dozens of industry leaders, the remarkable team at O’Reilly, and technical review by Julia Grace, Kevin Stewart, Tanya Reilly, Jasmine Tsai, and Uma Chingunde. Virginia Wilson deserves particular mention for exceptional editing and collaboration in creating this book. Finally, I simply could not have created this book without the support of my wife, Laurel, and our son, Emerson. PREFACE | xi

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Getting the Job At Digg, I ended up running Engineering, but I certainly wasn’t hired to do so. It wasn’t until a decade later, when I joined Calm, that a company deliberately hired me into my first executive role. If you start researching executive career paths, you’ll find folks who nominally became Engineering executives at 21 when they founded a company, and others who were more than 30 years into their career before taking an Engineering executive role. As these anecdotes suggest, there is no “one way” to get an Engineering executive job. However, the more stories you hear about folks assuming execu- tive roles, the more they start to sound pretty similar. I’ve condensed the many stories I’ve heard, along with my own experiences, into a repeatable process that prospective candidates typically follow. This chapter will cover: • Deciding whether to pursue an executive role • Why each executive job search is unique, and how that will shape your process • Finding executive roles externally and internally • Navigating the often chaotic executive interview process after you’ve gotten comfortable interviewing in well-designed middle management interview processes • Negotiating an executive contract, particularly the terms that rarely come up in the non-executive contracts you may have negotiated prior • Deciding whether to accept an executive offer once you have it If you’re kicking off the search for your first executive role, reading through this chapter will provide a clear roadmap through the process. 1 | 1

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Why Pursue an Executive Role? If you’re spinning up your first executive role search, you should have a clear answer to a question you’ll get a number of times, “Why are you looking for an executive role?” It’s important to answer this for yourself, as it will be a valuable guide throughout your search. If you’re not sure what the answer is, spend time thinking this through until you have a clear answer—maybe in the context of a career checkup. There’s no right answer, but here are some examples from real people: • “I’m heavily motivated by learning. I’ve directly reported into an Engineer- ing executive for my past two roles, and I’m looking to step into the role myself.” • “I’ve enjoyed working in a fast-growing company, but I also miss the direct ownership and pace of working at a small company. I’m excited to combine my previous startup experience with my recent experience at scale as an Engineering executive.” The rationale doesn’t need to be particularly compelling, just something positive that expresses your excitement and qualifications for the role. Don’t get discouraged if your statement isn’t profound—there are very few profound ways to say that it’s the next logical step in your career. Once you’ve written down your rationale, review it with a few peers or mentors who have already been in executive roles. Incorporate their feedback, and you’re done. (If you don’t have peers or mentors in executive roles, do some cold outreach to executives at companies where you’ve worked and see if they’ll weigh in.) The other side of this is that interviewers are also very curious about your reason for pursuing an executive role, but not necessarily for the reason you’d expect. Rather than looking for your unique story (although, yes, they’ll certainly love a memorable, unique story), they’re trying to filter out candidates with red flags: ego, jealousy, excessive status-orientation, and ambivalence. One of One Limited-release luxury items like fancy cars are sometimes labeled with their specific production number, along with the size of the overall run. For example, you might get the fifth car in a run of 20 cars overall. The most exclusive possible production run is “one of one.” That item is truly bespoke, custom, and one of a kind. 2 | THE ENGINEERING EXECUTIVE’S PRIMER

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All executive roles and processes are “one of one.” For non-executive roles, good interviewing processes are systematized, con- sistent, and structured. Sometimes the interview processes for executive roles are well-structured, but more often they aren’t. If you approach these bespoke pro- cesses like your previous experiences interviewing, your instincts may mislead you through the process. The most important thing to remember when searching for an executive role is that while there are guidelines, stories, and even statistics, there are no rules when it comes to finding executive jobs. In executive hiring, there is a selection bias for confidence. This is something that’s relatively easy to find; many an executive will tell you with complete confidence how things work, but be a bit wary. It’s not just the hiring process that is not standardized; the Engineering exec- utive roles themselves vary greatly as well. Sometimes they’ll include managing Product Management, and sometimes they’ll exclude managing some parts of Engineering. Working with technology-oriented founders you may provide more organizational support than technical guidance, whereas working in an older business may mean there are few other executives with a technology background. “One of one” means that anything is possible, in both the best and worst possible sense. Finding Internal Executive Roles Relatively few folks find their first executive job through an internal promotion. These are rare for a couple reasons. The first is that each company only has one Engineering executive, and that role is usually already filled. The second is that companies seeking a new Engineering executive generally need someone with a significantly different set of skills than the team they already have in place. Even in cases where folks do take on an executive role at their current company, they often struggle to succeed. Their challenges mirror those of taking on tech lead manager roles, where they are stuck learning how to do their new job in addition to performing their previous role. They are often also dealing with other internal candidates who were previously their peers and who may feel slighted by not getting the role themselves. This makes their new job even more challenging, and can lead to departures that hollow out the organization’s key leaders at a particularly critical time. That’s not to say that you should avoid or decline an internal promotion into an executive engineering role; just that you should go into it with your eyes open. GETTING THE JOB | 3

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In many ways, it’s harder to transition internally than externally. Because of that, even if an internal transition into an executive role goes poorly for you, don’t assume that means you wouldn’t do well as a newly hired executive at another company. Finding External Executive Roles Most executive roles are never posted on the company’s jobs page. So before discussing how you should approach your executive job search, let’s dig into how companies usually find candidates for their executive roles. Let’s imagine that my defunct company Monocle Studios had been a wild success and we wanted to hire our first CTO. How would we find candidates? Something along the lines of: 1. Consider any internal candidates for the role. 2. Reach out to the best folks in our existing network, seeing if any are interested in interviewing for the role. 3. Ask our internal executive recruiter to source candidates. (I’d skip this step if we didn’t have any internal executive recruiters, as generally there’s a different network and approach to running an executive search than a non-executive search; executive candidates also tend to ask different questions than non-executive candidates, which makes hiring them with non-executive recruiters even messier.) 4. Reach out to our existing investors for their help, relying on both their networks and their firms’ recruiting teams. 5. Hire an executive recruiting firm to take over the search. Certainly, not every company does every job search this way, but it does seem to be the consistent norm. This structure exposes why it’s difficult to answer the question, “How do I find my first executive role?” The quick answer is to connect with an executive recruiter—ideally one that peers have worked with before—but this approach comes with some implications regarding the sorts of roles you’ll get exposed to. Typically, these will be roles that have been challenging to fill for some reason. It’s important to note that the most desirable roles, and roles being hired by a well-networked and well-respected CEO, will never reach an executive recruiting firm. If you try to enter your search without an established network 4 | THE ENGINEERING EXECUTIVE’S PRIMER

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and rely solely on executive recruiters to find roles, you are almost certain to be selecting from second-tier opportunities. This is, by the way, absolutely not a recommendation against using exec- utive recruiters. Executive recruiting firms can be fantastic. A good executive recruiter will coach you through the process much more diligently than the typical company or investor’s in-house recruiter. I found my first executive role through an executive recruiter, as did the majority of my peers. (Note that the executive recruiters of tomorrow are your internal recruiting colleagues of today, so learning to partner effectively with Recruiting will pay dividends in both your current hiring and your long-term career options.) Similarly, it’s not true that all founder-led searches are for desirable jobs—almost all executive roles start as founder-led searches before working their way through the pipeline. Looking at the pipeline, there are many ways to increase your odds of getting executive opportunities at each step. The basics still matter: maintain an updated LinkedIn profile and respond politely to recruiters who do reach out. Both have a surprising way of creating job search serendipity, and ensuring your network is aware that you’re looking. If you don’t personally know many recruiters at investors or executive recruiters, your network can be particularly helpful for making those introductions. There are also a small number of companies that do post executive roles publicly, and there’s certainly no harm in looking through those as well. The one challenge is that you’ll have to figure out whether it’s posted publicly because the company is very principled about searching for talent outside their personal networks (often a good sign), or if the role has already passed unsuccessfully through the entire funnel described above (often not a good sign). Most compa- nies with strong principles like to talk about them a lot, and you should be able to find public evidence to support whether their posting is coming from a principled belief. If you can’t, then it’s likely desperation. Finally, if you’re laying the groundwork for an executive search to take place a few years down the road, there’s quite a bit you can do to prepare. You can join a large or high-growth company to expand your network (more on this in Chapter 12), work in a role where you get exposure to the company’s investors, create more visibility of your work (more on this in Chapters 12 and 15) to make it more likely for founders to reach out to you, or get more relevant experience growing and operating an Engineering organization. GETTING THE JOB | 5

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Interview Process The interview process for executive roles is always a bit chaotic. The most sur- prising thing for most candidates is that the process often feels less focused or effective than their other recent interviews. This is because your hiring manager as a director of Engineering is usually an experienced engineering leader, but your hiring manager as an Engineering executive is usually someone with no engineering experience at all. In the first case, you’re being interviewed by some- one who understands your job quite well, and in the second, the interviewer usually has never worked in the role. There are, inevitably, exceptions! Sometimes your interviewer was an Engi- neering executive at an earlier point in their career, but that usually isn’t the case. A relatively common scenario in startups is when a technical founder interviews you for the role, potentially with them staying as the CTO and you taking on the VPE title. But, even then, it’s worth noting that the title is a bit of a smokescreen and they likely have limited experience as an Engineering executive. Consequently, Engineering executive interviews depend more heavily on perceived fit, prestige, the size of the teams you’ve previously managed, how personable you are, and how well you would navigate the specific, concrete concerns of would-be direct reports and peers. This makes the “little things” par- ticularly important when it comes to executive interviews: send quick and polite follow-ups, use something like the STAR method to keep your answers concise and organized, prepare questions that show you’re strengthening your mental model of how the company works, and generally show energy and excitement. The general interview process that I’ve seen for executive roles is as follows: 1. A call with a recruiter to validate you meet the minimum requirements, are a decent communicator, and won’t embarrass them if you talk to the CEO. Recruiters are heavily scrutinized on the quality of candidates they bring forward and will go out of their way to help you show up well. This is also a good opportunity for you to understand whether there are obvious issues that might make this a bad role for you, such as wrong job location, wrong travel expectations, and so forth. 2. A call with the CEO or another executive to assess interest in the role and very high-level potential fit for the role. You’ll be evaluated primarily on your background, your preparation for the discussion, the quality of your communication, and perceived excitement for the company. 6 | THE ENGINEERING EXECUTIVE’S PRIMER