Engineering Leadership: The Hard Parts

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 ...