Resources
Good operations work doesn't happen in a vacuum.
It happens when leaders have the right frameworks, the right language, and a clear-eyed sense of what's actually worked — and what hasn't.
This page is built for COOs, operations leaders, and the managers who support them. You'll find Bearing Check, my biweekly newsletter, alongside a curated reading list of books that have genuinely impacted the way I think about the work. If you're new here, this is a good place to start.
Bearing Check Newsletter
If you lead operations, Bearing Check was written for you. Each issue draws on research and real experience to explore the decisions, dynamics, and friction points that determine whether complex organizations move well — and what gets in the way when they don't.
The smartest person in the room isn’t always the most valuable one — and this book explains why.
Leadership
Wiseman draws a clear line between leaders who amplify the intelligence around them and those who, often unintentionally, suppress it. I return to this book whenever I’m working with teams where capability exists but isn’t surfacing. For ops leaders, the Diminisher patterns are especially worth sitting with — many of them show up in high-pressure, results-driven environments without anyone noticing.
Multipliers by Liz Wiseman
Most feedback problems aren’t about being too harsh — they’re about being too careful.
Leadership
Scott’s framework — care personally, challenge directly — sounds simple until you try to live it under pressure. I appreciate that this book is honest about how hard it is to give feedback well, especially in cultures where avoiding conflict gets mistaken for professionalism. For ops and team leaders, the section on ruinous empathy hits closest to home: the cost of softening honest feedback until it disappears entirely.
Radical Candor by Kim Scott
If your organization assumes the people at the top have the best information, this book will challenge that directly.
Organizational Design
McChrystal rebuilt the Joint Special Operations Command not by adding more control, but by distributing trust and shared consciousness across the organization. The operational parallels to complex, fast-moving environments in the private and public sector are hard to ignore. I recommend it to anyone managing teams where decisions need to happen faster than information can travel up the chain.
Team of Teams by Gen. Stanley McChrystal
Most organizations don't fail because of strategy. They fail because of politics, confusion, and unnoticed dysfunction.
Organizational Health
Lencioni makes the case that organizational health — not smarter strategy or better technology — is the ultimate competitive edge. I’ve seen this play out repeatedly: technically sound plans that collapse under the weight of misaligned leadership teams. This is a practical book, not a theoretical one, and it’s worth reading slowly if you’re in a season of building or rebuilding team cohesion.
The Advantage by Patrick Lencioni
Silence in a meeting is not agreement — and the cost of that silence is higher than most leaders realize.
Culture
Edmondson’s research on psychological safety gave language to something I had observed for years: people consistently underperform when they don’t feel safe to speak up, take risks, or admit mistakes. This book is essential for any leader who wants to build teams that can surface problems early and adapt quickly. The chapter on how leaders inadvertently create fear is worth the read alone.
The Fearless Organization by Amy Edmondson
Change is hard not because people are resistant — it’s hard because the environment isn’t set up to support it.
Change Enablement
The Heath brothers break change down into three elements: the rational case, the emotional pull, and the environment that either enables or blocks the behavior you want. I’ve used this framework in real change initiatives, and the ‘shape the path’ concept in particular reframes how you think about removing friction for teams. If you’re leading any kind of transformation, this one belongs on your desk, not your shelf.
Switch by Chip Heath & Dan Heath
Busyness is not a strategy. This book makes the case that the most productive leaders are doing less, deliberately.
Focus, Priorities
Keller’s central argument is deceptively simple: identify the one thing that, if done well, makes everything else easier or unnecessary. I recommend it to ops leaders because it cuts against the instinct to optimize everything at once — a trap that’s especially common in complex organizations. The focusing question alone is worth the read, and it applies as much to team prioritization as it does to personal effectiveness.
On the Bookshelf
Books I've returned to — and why they've stayed on the shelf.
The One thing by Gary Keller & Jay Papasan
Most organizations don't fail because of strategy. They fail because of politics, confusion, and unnoticed dysfunction.
Operations
Repenning and Kieffer built their Dynamic Work Design framework across 25 years of real organizations — not case studies from a distance. The five principles are practical and field-tested, and the firefighting culture diagnosis will hit close to home for anyone who has watched urgent work crowd out important work. It's especially relevant if you're leading teams where the gap between promised results and delivered results keeps showing up.
There’s Got to Be a Better Way by Nelson Repenning & Donald Kieffer
Complex problems don't get solved in committee. They get solved when the right people build a solution together — in the same room, in the same week.
Problem Solving, Innovation
Sprint is a five-day framework for moving a cross-functional team from problem to prototype to tested solution. What I find most useful is that alignment isn't something you engineer after the fact — it's built into the process. The team that builds the solution is the team that owns it. I've used this in both innovation and problem-solving contexts, and the structure holds in both.
Sprint byJake Knapp