Engineering Leadership The Hard Parts (for . .) (Juan Pablo Buriticá James Turnbull)（Z-Library）

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

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

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. 978-1-098-17563-4 [LSI]

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 breakfast 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 experiences, 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. 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 operate in a relatively stable and functional environment. The case studies and examples 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 organizations 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 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.

TIP This element signifies a tip or suggestion. NOTE This element signifies a general note. O’Reilly Online Learning NOTE For more than 40 years, O’Reilly Media has provided technology 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 information. 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 impossible feel merely difficult. 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.

Chapter 1. Embracing the Unknown It’s essential to know what you’re up against when trying to lead in a chaotic environment. Understanding the nature and extent of the chaos is crucial for effective leadership, as it enables you to identify the root causes of dysfunction and address them strategically. This awareness helps you to navigate challenges more effectively, prioritize critical issues, and implement solutions to restore order and drive progress. What Does Chaos Look Like? Sometimes, it can be hard to tell whether your organization is chaotic or if there’s just some fuzziness around the edges. Chaos can become a creeping normality. There’s a fable about boiling frogs: a frog placed in boiling water will immediately jump out, but if placed in tepid water and heated gradually, it won’t perceive the danger and will boil to death. That fable, while factually incorrect, has parallels for how chaos can creep up within an organization. Your ability to assess the level of chaos can also be variable, especially when starting a new role. In these situations, sometimes you know what you’re getting yourself into; your new employer has been transparent about their issues. But sometimes the challenges are presented to you in a rosier light than is really the case. Indeed, you’ve probably interviewed for a new job in a new environment; you put your best foot forward, and the company, in turn, tried to sell you on their mission, product, and culture. But lo and behold, when you start, you discover challenges and chaos existing that you did not expect. Even if you’re already part of an organization, chaos can sometimes be more evident from different perspectives. James once worked in a large

corporate environment where several teams were functional because their leaders shielded them from the broader organization’s dysfunction. The organization’s state was revealed more accurately when James was promoted to leadership level. Understanding the symptoms and behaviors in chaotic environments can also be helpful, even if you know things are chaotic—especially if you’re going to develop strategies to work through, over, around, or under that chaos. Chaos can manifest in many ways within an organization. Some common symptoms include the following: Lack of ownership Absence of structure Outsized responsibility Undefined processes Poor communication Blame culture, scapegoating, and recrimination High turnover Lack of strategy and planning Frequent crisis mode No meaningful measurement Let’s dive deeper into some of these areas. Lack of Ownership In a chaotic environment, it is often unclear who is responsible for what. This ambiguity gives rise to a range of problems. Tasks and decisions can easily fall through the cracks because no one is clearly accountable for them. Confusion and delays are common; either people assume someone

else is handling a task, or multiple individuals might redundantly attempt to tackle the same issue. This lack of ownership makes it difficult to resolve issues or implement improvements. Without clear responsibility, it’s easy for things to devolve into a blame game or a state of learned helplessness where everyone waits for someone else to step up and take action. Absence of Structure Closely related to the lack of ownership is a lack of organizational structure. In a chaotic environment, teams and roles are often poorly defined. Individuals often struggle to understand their place within the broader context and the impact of their work on overall goals. This lack of structure makes collaboration and decision making extremely difficult. Without clear lanes, teams often duplicate effort or work at cross- purposes. The left hand doesn’t know what the right is doing, leading to wasted resources and conflict. Outsized Responsibility When ownership and structure are lacking, it’s common for individuals to assume outsized responsibility relative to their role or level of experience. A junior engineer might find themselves as the sole owner of a critical system. A manager might be responsible for multiple teams and products without sufficient resources or support. This situation is a recipe for burnout. Individuals are stretched too thin and lack the experience or authority to handle their responsibilities effectively. It also creates significant risk for the organization, as a single person becomes a bottleneck or single point of failure. Undefined Process In chaotic organizations, processes are often made up on the fly or exist only as institutional knowledge. Documentation is lacking, and the way

work gets done is inconsistent and unreliable. These gaps make it extremely difficult to onboard new team members. Without transparent processes to follow, new hires struggle to become productive contributors. It also means that the organization often reinvents the wheel, with each team or individual creating their own way of doing things. This lack of process creates resistance to change and stifles innovation. People cling to what they know “works,” even if it’s suboptimal, because change introduces the risk of failure. Turning inward and being insular also breeds a culture of “not invented here,” where the organization aggressively rejects external innovation. We know this sounds contradictory. Indeed, how can a chaotic organization —where nothing is stable and things change minute by minute—also be risk-averse and resistant to innovation? People become accustomed to their situations. The chaos becomes predictable. We’ve both had situations where people have reached a state of fatalistic acceptance of their organizational chaos—or even worse, they believe any change will only deepen the dysfunction. Attempts to address that chaos must defeat both this fatalism and the underlying causes of the chaos.1 Without a clear and safe way to evolve processes, the organization stagnates. Poor Communication Communication breakdowns are common in chaotic organizations. Information often becomes siloed within teams and isn’t effectively shared. Updates and decisions are communicated haphazardly, if at all, and relevant stakeholders are left out of key conversations. Sometimes, there is an active effort in chaotic organizations to restrict communication—either because “no news is good news” or because communicating the current state can make you or your team a target of blame or recrimination.

This effort leads to people feeling out of the loop and disconnected from the bigger picture. It breeds confusion, resentment, anger, and a lack of alignment. Like the lack of structure, this also results in duplicated effort and teams working at cross-purposes. Blame Culture, Scapegoating, and Recrimination In a chaotic organization, a blame culture often prevails. This manifests as individuals or teams looking for someone to blame when things go wrong rather than focusing on solving the problem. This culture discourages risk- taking and innovation, as employees fear the repercussions of failure. Blame culture creates an environment of fear where employees are reluctant to take ownership of their work or make decisions. This hesitancy can lead to stagnation and a lack of progress; individuals become more focused on avoiding blame than contributing positively to the organization’s goals. Over time, this will significantly erode trust and morale within the team. James worked in an environment where, before any attempt to resolve an incident, there was a cycle of “whose fault is it?” One of his colleagues coined the term “blamestorm” to describe the incident-management process. Repeatedly, these efforts to assign blame added significant delays to the recovery time. In turn, this led to conflict and friction among internal teams, external vendors, and leadership. Scapegoating is another symptom in which individuals or teams are unfairly blamed for systemic problems. This can lead to high turnover, low morale, and a toxic work environment in which employees prioritize self- preservation over collaboration and progress. Scapegoating fosters a hostile work environment where collaboration is stifled and fear prevails. It diverts attention from addressing the root causes of issues and instead creates an atmosphere of mistrust and division. Employees may become disengaged and disconnected from the organization’s mission, exacerbating the chaos.

Ultimately, this results in recrimination, characterized by retaliatory accusations and back-and-forth blame exchanges. This hampers effective problem-solving and deteriorates trust among team members and across departments, further entrenching chaos. Recrimination can create a cycle of negativity that is hard to break. It often leads to a toxic work culture where energy is spent defending oneself rather than on productive activities. This environment can cause significant emotional stress for employees, reducing overall job satisfaction and increasing turnover rates. High Turnover High turnover rates are a significant indicator of chaos. Employees leave due to burnout, dissatisfaction, and a lack of career development opportunities. This constant churn disrupts team cohesion and results in the loss of institutional knowledge. Frequent turnover can disrupt work continuity and increase recruitment and training costs. In addition, the loss of experienced employees can weaken the organization’s ability to maintain quality and consistency in its operations. High turnover also sends a negative signal to remaining employees and potential hires, damaging the organization’s reputation. Lack of Strategy and Planning Chaotic organizations often operate purely reactively, lacking clear strategy and planning. Teams and individuals frequently lack a clear sense of purpose or prioritization to guide their efforts. They respond to the latest fire drill rather than proactively working toward defined goals. Without strategic direction, effort is wasted on low-impact or even counterproductive activities. Resources aren’t optimally allocated because there is no clear prioritization of initiatives. The organization ends up frantically treading water rather than deliberately swimming toward a destination.

This disconnect between vision and implementation is also the primary driving force behind fissures between leadership and team members outside the engineering team. These fissures result in distrust and conflict between business units. A classic example is interactions between sales and engineering teams over what to sell and what is feasible to sell, with sales teams overselling and engineering teams overcommitting, undercommitting, or underdelivering. Frequent Crisis Mode Organizations in chaos often operate in a constant state of emergency. Every issue is treated as a crisis, which prevents strategic planning and leads to burnout. This mode of operation can also create a volatile work environment, where employees are constantly under stress. Living in a perpetual state of crisis can create a reactive rather than proactive culture. This environment can prevent the organization from focusing on long-term goals and improvements, as immediate issues consume all attention and resources, leaving little room for strategic planning and development. Chronic stress and burnout can lead to high absenteeism and increased turnover. No Meaningful Measurement Finally, chaotic organizations often lack meaningful measurement. They don’t define or track metrics that provide a clear picture of the health and performance of the product, team, or business. Without data, it’s nearly impossible to spot problems, measure progress, or make informed decisions. Issues fester unnoticed until they blow up into major crises. Improvements or regressions happen without anyone understanding why. The organization is making decisions in the dark. This lack of measurement makes it difficult to celebrate successes or learn from failures. There’s no reliable way to tell whether an initiative achieved its desired impact or to conduct a productive postmortem on an incident.