Lessons on Leadership
Learn hard-won lessons from leaders who’ve put Team of Teams to the test—real-world stories, concise insights, and strategies you can use now.
The Prologue
By General Stanley McChrystal, US Army, Retired
A decade later, General McChrystal demonstrates how to lead at an enterprise scale by building trust that travels, a purpose that aligns, a shared consciousness, and making decisions at the edge. If you’re ready to move your organization as one without losing control, start here.
From Commander to Gardener
By Danielle Tenconi, David Livingston, and Kevin Claypool
Danielle, David, and Kevin dismantle the “heroic commander” myth and recast leadership as cultivation, not control. The best leaders are not chess masters, but rather gardeners who create conditions for people to excel.
Scale Without Slowing
By Ryan Flynn
Ryan Flynn tackles the growth paradox: as organizations scale, speed and alignment erode. He lays out “Prehab:” three disciplined hours each week for the senior executive to anchor identity, make coordination continuous, and hardwire empowered decisions.
The Case for Middle Managers
By Cricket Oles and Anna Roberts
Middle management isn’t overhead to cut; it’s the strategic layer that turns strategy into results. Cricket and Anna show how to activate “the middle” as translators and integrators to clarify decision space, install proactive systems, and balance change with stability.
Surfer or Life Raft?
By Afiba Edwards
Afiba Edwards shows how senior leaders can turn data overload into a competitive advantage with Organizational Intelligence. From big-wave surfing to crisis response, he demonstrates how to build a system where information travels fast and teams deliver coordinated outcomes at scale.
The Empowerment Paradox
By Chris Jones
When leaders step back, autonomy rises, but execution can still lag. Chris Jones addresses this empowerment paradox and outlines the focused controls that turn empowerment into momentum, keeping alignment tight while decisions happen fast at the edge.
Last to Leading
By Erin Sutton
At the height of COVID-19, Virginia vaulted from 49th to 11th in vaccine distribution by replacing siloed command with structured communication design. Erin Sutton shows how to get the right information to the right people at the right time, so field insights reshape tactics, and speed and coordination become reinforcing strengths.
Leading Across Organizations
By Meghan Bourne
Using the U.S. Overdose Epidemic, Meghan Bourne shows how multi-organization efforts actually win: blend network agility with intentional structure. An engaged executive core, a single definition of joint success with shared metrics, and a disciplined communication/decision rhythm turn loose alliances into coordinated execution.
Change Doesn't Fail, Leaders Do
By Tim Lynch & Donnie Brzuska
Tim and Donnie argues that enterprise transformation hinges on an executive’s mobility—knowing when to architect change and when to stabilize it. He shows how to read the moment and match posture to the level of change—preserve, signal, optimize, transform.
Human Ingenuity in the Age of AI
By Shawn Tyrie
AI is table stakes. Shawn Tyrie argues that the edge belongs to human teams that turn information into outcomes. He surfaces the “AI overconfidence trap” (great models, stalled results) and counters with small, cross-functional teams, tight learning loops, and leaders who treat AI as radar—not the captain.
The Compass I Carry
By Will Smith
Team of Teams was never a product or playbook. It’s a compass grounded in human truths. The work is to wire organizations for adaptation, cohesion, and clarity of purpose. Leaders don’t “achieve” Team of Teams; they commit to it and pick up the compass and navigate the unknown. The ones who do will define the future.
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