The Dao of Delivery
A FIELD MANUAL for CTOs (and the CEOs who rely on them)
Introduction
For thirty years, I’ve been learning how to see engineering organizations clearly—mostly by seeing them wrong first. Each role taught me something new about what I’d been missing: the dynamics I’d ignored, the signals I’d misread, the leverage I’d wasted on the wrong problems. What I have learned is that there are no easy fixes. There are no nice, tidy frameworks you can apply universally that will solve your problems. That knowledge is hard won. I could have easily called this book “Eric’s Litany of Failures,” because that’s what it really is: thirty years of painful lessons learned the hard way, distilled into the lenses I wish someone had handed me earlier.
The lenses here don’t spring from natural talent or brilliant insight. They come from the political, emotional, and cultural dynamics that repeatedly humbled me until I finally learned to pay attention to what actually matters in leadership.
This pattern isn’t unique to me. Engineering leaders fail a lot. Sixty percent of new managers fail within 24 months, and in engineering specifically, about half eventually return to individual contributor roles (First Round Review, 2021; Arruda, 2023). Those failure statistics only capture the obvious collapses. They miss the soft failures that are more insidious and painful: managers who are just effective enough to keep their jobs but not effective enough to deliver reliably. The causes aren’t technical. They are failures in planning, people management, and adapting to the reality of a messy system composed of people (Pinto and Mantel, 1990; Herz and Krezdorn, 2022).
Most of us who struggle with delivery aren’t incompetent. We optimize for the wrong things. Process gets most of our attention while we ignore the real drivers of delivery: stakeholder relationships, team dynamics, organizational momentum. Their importance shifts constantly, and learning to read those shifts is brutally hard.
It’s natural to reach for methodology fixes. They feel concrete, safe, and measurable. A new framework gives us steps to follow and creates the impression of progress. I’ve reached for them myself more times than I can count. But delivery challenges almost never live there. They are system problems, which means the real work is learning how to read the shifting variables and recalibrate.
That’s where many of us fall into a trap. We copy a method that made another company famous, hoping it will rescue us. Or we borrow something that worked for a colleague without asking whether our own team has the capacity to sustain it or the resilience to face the pushback. Almost inevitably, it doesn’t work, or worse, just sort of works. The approach doesn’t fail because it’s bad. It fails because methodology alone is never enough.
This is why I focus on developing judgment rather than providing another methodology.
This book is called The Dao of Delivery, not The Laws of Delivery, because leadership is never fixed. It’s a living system, always shifting. There are no universal laws. At best, there are lenses that help you decide what matters most right now.
Nothing here works 100% of the time, in every context, for every organization. Many books promise a magic bullet. They describe a process or framework that once fueled a company’s success, then hold it up as cure-all. But those were snapshots of a moment at that company, with that leadership, and that culture, at that time. Some of those ideas may serve you well, and if they do, use them. But you shouldn’t expect them to, because leadership is fundamentally dynamic.
It never becomes easy. Every decision touches people’s lives, organizational momentum, and the credibility of the leader making it. But over time, you grow steadier. You learn how to carry the weight without being crushed by it—and how to protect others from being crushed as well.
The reward isn’t perfect freedom. Constraints, politics, and trade-offs are constants. What changes is your posture. You learn to read the system, and that knowledge brings calm. You stop chasing the next process fix hoping it will save you.
If you’re a CTO or VP of Engineering wondering why your teams miss deadlines, why stakeholder relationships keep souring, why process improvements never stick—this book is for you. You’ll find lenses for understanding political capital, team dynamics, and organizational momentum. Tools for discernment, not recipes.
Throughout the book, you’ll also find callouts addressed to CEOs and other senior executives. These sections help non-technical leaders understand what’s really happening when engineering delivery struggles, when to intervene, and how to support their technical leaders in addressing root causes or symptoms.
When your technical leaders focus on process improvements, technical fixes, and methodology changes while delivery still struggles, they are avoiding harder leadership work. This signals gaps in political capital, emotional control, or organizational awareness that no technical solution can fix.
Consider whether they’re proposing new frameworks and tools while stakeholder complaints persist. Are they blaming methodology instead of team dynamics or communication failures?
Your response depends on context and urgency. If delivery isn’t business-critical, you can afford patience. If you see genuine potential and have capacity to invest, coaching might work. If the business needs reliable delivery now, replacement is your only option. What you must not do is wait for methodology alone to solve what is, at its heart, a leadership problem.