Engineering Leadership The Hard Parts (Juan Pablo Buriticá and James Turnbull) (z-library.sk, 1lib.sk, z-lib.sk)

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B uriticá & Turnb ull Juan Pablo Buriticá & James Turnbull Navigating Chaos to Build Teams That Deliver Engineering Leadership The Hard Parts

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9 7 8 1 0 9 8 1 7 5 6 3 4 5 4 5 9 9 ISBN: 978-1-098-17563-4 US $45.99 CAN $57.99 TECHNOLOGY / ENGINEERING Whether they’re building a startup or scaling an established org, engineering leaders know the real job is keeping chaos under control. In a world of shifting priorities, scarce resources, and rapid change, leadership means embracing the unknown, managing moving targets, and creating clarity where there’s none. Sometimes, you’re building the plane as you’re flying it— writing the roadmap as you go, designing processes in real time. Engineering Leadership: The Hard Parts cuts through the noise, offering a guide for tackling these gritty, real-world challenges. Current and future leaders, this is your toolkit. It’s packed with principles, techniques, and mental models for thriving in uncertainty. • Navigate the full scope: Step into engineering leadership’s complex, multifaceted role • Build high-impact teams: Master advanced techniques to grow and lead your technical talent • Align and execute: Connect strategy to business outcomes, scale effectively, and balance innovation with precision • Lead with resilience: Adapt quickly and drive continuous improvement • Accelerate your career: Develop your leadership edge and unlock new growth Juan Pablo Buriticá is CTO at Convergint and has built engineering teams at Stripe and Splice. Known for scaling distributed teams and cultivating technical excellence, he’s also helped grow Latin America’s tech community through events and by founding a major Spanish- speaking JavaScript collective. James Turnbull is a product and engineering leader with experience across startups and enterprise tech. He has held roles at Smartrr, Kickstarter, Venmo, Sotheby’s, and Microsoft. A former chair of the O’Reilly Velocity Conference series, he also advises startups and has authored 11 technical books. Engineering Leadership: The Hard Parts “This book gets something most leadership guides miss: you can’t optimize your way out of chaos with frameworks alone. Juan Pablo and James show how psychological safety, clear direction, and disciplined execution work together, and why getting that wrong costs teams more than they realize.” Dr. Nicole Forsgren Senior director of developer intelligence at Google and coauthor of Accelerate B uriticá & Turnb ull

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Praise for Engineering Leadership: The Hard Parts This book gets something most leadership guides miss: you can’t optimize your way out of chaos with frameworks alone. Juan Pablo and James show how psychological safety, clear direction, and disciplined execution work together, and why getting that wrong costs teams more than they realize. —Dr. Nicole Forsgren, senior director of developer intelligence at Google and coauthor of Accelerate With tools to help you diagnose the roots of your organization’s chaos and concrete paths for working within it, this book provides a practical guide to under-examined leadership challenges and how to navigate them. —Camille Fournier, vice president of engineering at CoreWeave and author of The Manager’s Path

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Juan Pablo Buriticá and James Turnbull Engineering Leadership: The Hard Parts Navigating Chaos to Build Teams That Deliver

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978-1-098-17563-4 [LSI] Engineering Leadership: The Hard Parts by Juan Pablo Buriticá and James Turnbull Copyright © 2026 Worthwhile Technology LLC and James Turnbull. All rights reserved. Published by O’Reilly Media, Inc., 141 Stony Circle, Suite 195, Santa Rosa, CA 95401. 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: Shira Evans Production Editor: Clare Laylock Copyeditor: Piper Content Partners Proofreader: Vanessa Moore Indexer: nSight, Inc. Cover Designer: Susan Brown Cover Illustrator: José Marzan Jr. Interior Designer: David Futato Interior Illustrator: Kate Dullea January 2026: First Edition Revision History for the First Edition 2026-01-20: First Release See http://oreilly.com/catalog/errata.csp?isbn=9781098175634 for release details. The O’Reilly logo is a registered trademark of O’Reilly Media, Inc. Engineering Leadership: The Hard Parts, the cover image, and related trade dress are trademarks of O’Reilly Media, Inc. The views expressed in this work are those of the authors and do not represent the publisher’s views. While the publisher and the authors have used good faith efforts to ensure that the information and instructions contained in this work are accurate, the publisher and the authors 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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Table of Contents Preface. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xiii 1. Embracing the Unknown. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 What Does Chaos Look Like? 1 Lack of Ownership 2 Absence of Structure 2 Outsized Responsibility 3 Undefined Process 3 Poor Communication 4 Blame Culture, Scapegoating, and Recrimination 4 High Turnover 5 Lack of Strategy and Planning 5 Frequent Crisis Mode 5 No Meaningful Measurement 6 Chaos or Opportunity? 6 Well, That Was Fun 7 This Sounds Scary 8 What Are We Going to Do to Help? 9 Conclusion: From Chaos to Clarity 10 2. Understanding Your Role. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 What’s Your Job, Exactly? 13 The Five Pillars of Engineering Leadership 15 Boss, Where’s the Roadmap? 15 Don’t Retreat to the Comfortable 16 Engineering Leadership Is About Being a “Generalist with Range” 16 Action Beats Inaction Every Time 17 Role Description: A Do-It-Yourself Blueprint 17 v

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People: It All Starts with Your Team 18 What’s Your Starting Point? 18 What’s Your Mission? 19 What Tools Do You Need to Get There? 19 Mission: You’ve Got a Crew; Now You Need a Place to Go 22 Where to Start 22 Getting Your Team on Board 23 Turn the Mission into Action 23 Plan: You Know Where to Go; Now Chart the Course 25 Build with Your Partners 25 Know What to Prioritize 25 Turn Strategy into Action 26 Adjust, but Stay Focused 26 Process: The System That Keeps Things Moving 28 Keep It Lean, but Effective 28 Make Process a Team Effort 29 Adjust As You Go 29 Product: What Are We Actually Delivering? 31 Know What Success Looks Like 31 Balance Quality with Speed 32 Outcomes Aren’t Always Features 32 Conclusion: Pulling It All Together 34 3. Navigating Chaos. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 Diagnose Context 37 Why Diagnosis Matters More Than Style 37 Four Lenses for Reading Context 38 The Reality of Power and Identity 40 Rapid Assessment When You’re New 41 When Diagnosis Reveals Hard Truths 42 Connecting Diagnosis to Action 42 Thrive in Chaos 43 The Trap of Bureaucratic Control 44 The Punk Alternative: Motion Creates Clarity 44 From Energy to Discipline 45 Open Source: Punk Principles at Scale 45 What This Means for Seasoned Leaders 46 The Political Reality 46 When Momentum Matters Most 46 Focus on Outcomes 47 The Sophistication Trap 47 vi | Table of Contents

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Why Outcome Frameworks Miss the Point 47 When Outcomes Are Genuinely Unclear 48 The Political Dimension 48 Context Shapes Outcome Focus 49 Failure Modes of Outcome Obsession 49 What This Looks Like in Practice 50 Making It Sustainable 51 Shift Between Roles 51 The Cost of Leadership Rigidity 51 Three Essential Modes 52 The Switching Skill 54 The Reality of Constraints 54 Leading Through Others 55 What This Looks Like in Practice 55 Conclusion: Pulling It All Together 58 4. Building Cohesive Teams. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59 It Starts with Safety 59 Get a Functional Team, Fast 61 Understand the Work 61 Renegotiate Commitments 62 Remove Blockers 63 Get Capacity Under Control 64 Understand Skills, Dynamics, and Performance 65 Capacity Is Not Enough; Build Capabilities 67 Capabilities as a Team-Level Tool 67 What Great Teams Do 68 Growing Without Losing the Plot 71 From Supporter to Supported 72 You Make Yourself Replaceable 72 You Scale the Culture, Too 72 The Bottom Line 73 Conclusion: From Chaos to Cohesion 73 5. Setting Direction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75 What Causes Drift 76 The Drift Diagnostic 77 The Silent Cost of Drift 78 What Good Direction Looks Like 79 Traps That Cause Drift 81 No Clear Inputs 81 Table of Contents | vii

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Too Many Inputs 81 Hesitant Leadership 82 Reactive Roadmaps and Consensus Traps 82 Be the Lighthouse 83 Creating Alignment 84 Why Alignment Breaks 85 Alignment Is Not Agreement 85 How Leaders Create Alignment 86 Adapting Without Losing the Plot 87 If the Plan Changes, the Story Stays Intact 88 Clarity Is the Work 88 Reflection 90 Conclusion: Pulling It All Together 91 6. Shipping Products and Code in Chaotic Environments. . . . . . . . . . . . . . . . . . . . . . . . . . . . 93 Inspire Confidence 94 Be Execution-Focused 95 Be Lightweight and Adaptable 96 Foster Continuous Learning 98 Focus on Communication and Collaboration 98 Celebrate 99 Other Prioritization Concerns 99 Not All Work Is Created Equal 100 Not All Work Can Use the Same Process 100 Not All Work Is Known at the Start of Prioritization 100 Prioritization Techniques 101 Key Inputs for Decision Making 101 Utilize Established Frameworks 102 Managing Backlogs Effectively 111 A Good Cadence 112 Approaching Estimates Wisely 113 Balancing Different Types of Work 114 Addressing Technical Debt 115 Monitoring Progress and Adjusting Priorities 116 Communicating Priorities Transparently 117 Not Everything Is a Product 118 When Linear Makes Sense 119 Creating Just Enough Structure 120 Working the Plan, Not Serving It 120 Connecting Linear and Iterative Work 121 Conclusion: Driving to Execution 121 viii | Table of Contents

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7. Budgeting, Costs, and Vendors. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 123 Why Budgeting Matters 124 Strategic Alignment 124 Cost Management 124 Risk Mitigation 127 Performance Monitoring 127 Resource Optimization 127 Stakeholder Management 128 Innovation and Growth 129 Organizational Learning 129 Competitive Advantage 129 Understanding Cost Management 129 Fixed Costs: The Foundation 130 Variable Costs: The Flex Players 130 Step Costs: The Level-Up Costs 130 Who Pays? 131 The Human Side of Cost Management 131 Creating and Managing a Budget 131 Starting with History 132 Categorizing Expenses 132 Headcount Planning and Costs 133 Setting Goals That Make Sense 136 Creating Your Budget Template 137 Tracking and Managing 138 Learning from Experience 138 Vendor Management 139 The Great Build-Versus-Buy Debate 139 Picking Your Partners 140 Managing the Relationship 140 Outsourced People and Teams 141 Ethics 142 Taking Care of Our People 143 Being a Good Neighbor 143 The Global Perspective 143 Looking to the Future 144 Making It Real 144 Conclusion: Budget as Strategy 144 8. Technical Principles and Strategy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147 Why Does Technical Strategy Matter? 148 Building a Foundation 149 Table of Contents | ix

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You Need More than Technical Widgets 151 Establishing Technical Principles 153 Example Technical Principles 154 Crafting Technical Principles Workshop 156 Living Your Principles 158 Scaling Without Overengineering 158 Choose Boring Technology 160 Developing Your Technical Strategy 162 Choosing Granularity 163 Balancing Flexibility with Direction 164 Collaborative Development 164 Elements of a Technical Strategy Document 164 The Living Document Approach 167 Making Technical Strategies Real 167 Conclusion: Enabling Execution with Technical Strategy 171 9. Collaborative Technical Practices and Decision Making. . . . . . . . . . . . . . . . . . . . . . . . . . 173 Shared Technical Principles 174 Communication, Collaboration, and Execution 177 Communicate, Communicate, Communicate 179 Collaboration 189 Execution 192 Decision Making in Chaotic Conditions 201 Psychological Safety 201 Inclusive and Data-Driven Decision Making 203 Continuous Improvement 204 Conclusion: Collaboration Is the Glue 205 10. Metrics That Matter for Engineering Teams. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207 Why Measure Anything at All? 207 Metrics as a Product 208 Design Intentionally 209 The Trap of Want Versus Need 209 Constructing Questions 211 Choosing the Right Metrics for Your Context 212 Take Stock of What You Already Measure 214 Velocity: The Most Misused Metric in Software 215 Why Velocity Goes Wrong 215 How to Use Velocity Correctly 216 Build Your Metrics with Your Customers in Mind 216 The Human Side of Metrics 217 x | Table of Contents

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Balancing Quantitative and Qualitative Data 218 Humans and Metrics 219 Make Metrics Visible and Accessible 221 Metrics Need Ongoing Maintenance, Just Like Code 221 AI Doesn’t Change Your Approach to Metrics 223 Conclusion: Measurement as Illumination 224 11. Fitting It All Together. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 227 The Symphony of Chaos 228 The Foundation: People and Safety 228 The Lighthouse: Direction, Not Drift 229 The Engine: Process and Execution 230 The Compass: Metrics and Measurement 231 The Ecosystem: Building Beyond Your Team 232 The Evolution: From Chaos to Capability 233 The Reality: It’s Harder Than It Looks 234 The Practice: Making It Real 235 The Future: Beyond Survival 236 The Call: Your Turn to Lead 237 The End, and the Beginning 238 Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241 Table of Contents | xi

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Preface When we—Juan Pablo and James—first met, it was in a breakfast group for startup engineering leaders. We both worked at startups with varying levels of chaos and dysfunction. What was interesting to both of us were the similarities between our experiences. Despite different organizations, people, and products, we saw that when rapid change and chaotic situations occurred (startup life™), people and organizations responded similarly—with the same, less-than-optimal outcomes. Our wider break‐ fast group also shared similar experiences. (The group was part networking and part support system.) Fast-forward 10+ years, and we’ve both been in big and small organizations where we’ve had to deal with the same chaos and dysfunction. In recent years, we’ve worked together on several projects and been able to compare notes in greater depth. What continued to intrigue us was that these recurring patterns persisted. Over those years, we’ve developed approaches, strategies, and techniques to handle chaotic environments and achieve better outcomes for our teams and organizations. We don’t approach these problems identically, and we each have our spheres of strengths and domains that interest us. Hence, a regular part of our interactions involved comparing notes on areas where we were weaker. In addition, several significant chaotic events have stressed leaders and their teams in recent years—for example, dealing with COVID-19 or managing teams of engineers living in war zones and facing political and environmental upheaval. Those experien‐ ces, along with anecdotes we heard from our peers, suggested that dealing with chaos was an industry-wide challenge for engineering leaders. We decided to codify our developed approaches and techniques, first as a training course and now as a book. While the ideas we share in this book may help you survive engineering leadership in chaotic organizations and times, we don’t believe they are a cure-all. Still, we hope they will support you on your leadership journey. This book contains hard-won knowledge gathered through some tough professional challenges that we’d prefer you not to face, or it might at least help lessen the impact of those experiences you cannot avoid. xiii

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Who Should Read This Book As an engineering leader, you’re responsible for your team’s success and the delivery of complex technical projects. This is challenging even under the best circumstances, but it can feel downright impossible within a chaotic environment. You may be a new engineering manager, suddenly responsible for a team and a codebase that you’re still learning to navigate. You’re trying to figure out how to balance your team’s needs with the business’s demands, all while establishing your own leadership style and earning the trust of your reports. Or perhaps you’re a seasoned director or vice president, but you’ve landed in an organization that’s growing faster than its processes and structure can keep up. You’re working long hours to keep things on track, but it feels like you’re always firefighting and never have time for strategic planning or team development. You might be a technical leader—a staff engineer or architect—trying to lead without formal authority. You see the technical challenges and risks that must be addressed, but need help gaining buy-in and alignment from organizational stakeholders. Regardless of your specific role or context, leading in a chaotic environment is draining. You likely juggle multiple roles and navigate endless obstacles and surprises. It can be frustrating, stressful, and demoralizing. But here’s the thing: as hard as it is, your leadership matters now more than ever. In the face of chaos and uncertainty, your team needs someone to provide direction, clarity, and support. They need someone to advocate for them and clear the path for their work. They need someone to create a pocket of sanity and stability where they can focus and do their best work. That someone is you. You have the opportunity and responsibility to be the leader that your team needs. It won’t be easy, but it is possible—and this book is here to help. By sharing our experiences and lessons, we aim to equip you with the mindsets and techniques necessary to navigate and succeed as a leader under challenging circumstances. Why You Should Read This Book When it comes to books on leadership and management, there is no shortage of options. Walk into any bookstore or browse online, and you’ll find shelves upon shelves of titles promising to make you a better leader. Many of these books are excellent—we’ve read lots of them and have learned a great deal from their insights and advice. However, we’ve also found that much of this advice implicitly assumes that you oper‐ ate in a relatively stable and functional environment. The case studies and examples xiv | Preface

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often feature organizations with clear structures, well-defined processes, and ample resources to invest in new initiatives and professional development. But what if that’s not your reality? What if you’re trying to lead in an organization that’s more chaotic than calm—where roles and responsibilities are unclear, priorities change by the day, and you’re lucky to get through a meeting without being pulled into the latest fire drill? In these situations, much of the standard leadership advice falls flat. It’s not that it’s bad advice—it’s just not feasible to implement when you’re barely keeping your head above water. Telling a leader in a chaotic environment to “just” implement a new process or “just” carve out time for strategic planning is like telling a drowning person to “just” swim to shore. It’s not helpful when you’re consumed by treading water. That’s where this book comes in. We’ve both been in the thick of chaotic organiza‐ tions and had to figure out how to lead and ship products despite the disorder. We’ve had to adapt the best practices and principles of engineering leadership to fit the constraints and challenges of our environments. In this book, we want to share what we’ve learned. We offer a framework for making sense of the chaos and finding your footing as a leader. We provide concrete strategies and techniques for common challenges like clarifying priorities, making decisions with limited information, communicating effectively, and caring for your team and yourself. Importantly, our advice is grounded in the realities of leading in less-than-ideal circumstances. We know you need more time, resources, and authority. We know you’re dealing with ambiguity, politics, and competing demands. Our goal is to equip you with tools and mental models that you can adapt and apply in your unique context. If you’re looking for a playbook to transform your organization into a perfectly oiled machine, this isn’t it. But if you’re looking for practical guidance on navigating the messy, human realities of leading in times of uncertainty and change, keep reading. In the book, we’ll also walk you through the skills and techniques you’ll need to be successful in leading through chaos. The book is divided into two halves. The first part focuses on understanding your role, navigating chaos, setting directions and strategy, and building your team’s resilience and skills: • Chapter 1: Understanding what chaos and its symptoms look like • Chapter 2: Understanding your role and creating leadership foundations • Chapter 3: Navigating your role in chaotic environments and learning how to deal with the challenges that chaotic environments throw at you Preface | xv

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• Chapter 4: Building your team into people who thrive in chaos • Chapter 5: Setting direction for your team The second half of the book focuses on techniques that you can use to deliver software and set your team up for technical success: • Chapter 6: Shipping products and code in chaotic environments • Chapter 7: Budgeting, costs, and dealing with vendors • Chapter 8: Developing technical strategy and principles that are resilient to chaos • Chapter 9: Building collaboration and making technical decisions in a chaotic world • Chapter 10: Metrics that help your team navigate the chaos • Chapter 11: Wrapping it all up—bringing together the principles and techniques we’ve shared We believe that chaos doesn’t have to be a barrier to effective leadership—it can be an opportunity. By embracing the uncertainty and learning to lead through it, you can emerge as a more resilient, adaptable, and confident leader. And in turn, you can help your team and your organization find stability and success on the other side. Conventions Used in This Book The following typographical conventions are used in this book: Italic Indicates new terms, URLs, email addresses, filenames, and file extensions. Constant width Used for program listings, as well as within paragraphs to refer to program elements such as variable or function names, databases, data types, environment variables, statements, and keywords. This element signifies a tip or suggestion. This element signifies a general note. xvi | Preface

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O’Reilly Online Learning For more than 40 years, O’Reilly Media has provided technol‐ ogy 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. 141 Stony Circle, Suite 195 Santa Rosa, CA 95401 800-889-8969 (in the United States or Canada) 707-827-7019 (international or local) 707-829-0104 (fax) support@oreilly.com https://oreilly.com/about/contact.html We have a web page for this book, where we list errata and any additional informa‐ tion. You can access this page at https://oreil.ly/engineering-leadership. For news and information about our books and courses, visit https://oreilly.com. Find us on LinkedIn: https://linkedin.com/company/oreilly-media. Watch us on YouTube: https://youtube.com/oreillymedia. Acknowledgments Juan Pablo To all the nerds who have joined my crew over the years, especially those who keep following me around to increasingly chaotic environments—Bob, Brian, Checho, Elizabeth, Ernesto, Gorsuch, Lara, Nico, Pinilla, and Urbano—you make the impossi‐ ble feel merely difficult. Preface | xvii

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Camille, thank you for the walks that helped me think through hard problems; Renee, for the perspective that kept me grounded; Kellan, who coached me out of chaos and showed me that leadership is not about having answers but about asking better questions. The FiasCo and Mimosaconf crews taught me that the best ideas emerge when smart people feel safe enough to disagree. Ann, you somehow keep hiring me. You’re stuck with me. Special thanks to James (friend, coauthor, and colleague), without whom this book literally would not have happened. Somehow, he still talks to me after we survived writing it together. A mi mamá, que si no la nombro no me vuelve a hablar. Finally, Juliana, whose patience with my writing obsessions made everything else possible. James Thank you to the wonderful folks I’ve worked with over the last few years, who helped us all survive the chaos. Thanks to my amazing CTO dinner group: Camille Fournier, Peter Miron, Harry Heymann, Kellan Elliott-McCrea, and Illia Papas, who have always managed to make the chaotic slightly more palatable or provided wine when that didn’t work. Thanks to Renee Orser and Monique Garth for good-naturedly listening to me rant about my work on numerous occasions. Finally, thanks to my best friend and partner in life, Ruth, who has again put up with more nights of me tapping at a keyboard—last book, I promise. xviii | Preface