Teamwork, but make it COMPLEX: Insights from Team of Teams

As mentioned previously, I found it difficult to restart my reading pace recently. Over the holidays, I reflected on my bookshelf and rediscovered a book I thoroughly enjoyed years ago: Team of Teams by General Stanley McChrystal. Re-reading it felt like catching up with an old friend—familiar, yet still offering fresh insights. Although I have to admit that reading about wars is not something that I enjoy.

This book holds a special place in my professional journey, as it is connected to a pivotal team assignment back when I was working for Tradeshift. Together with two incredible managers, Lindsay and Dan, who were both mentors to me and continue to reside dearly in my "professional soul," I was part of the team tasked with building a Global Support organization. It was an ambitious undertaking, and we approached it with open minds, guided by Dan's enormous expertise. My role involved supporting the team with organizational design, training, and coaching—a transformative experience that profoundly shaped my understanding of teamwork and adaptability, in a global environment.

Drawing from McChrystal’s insights and my own reflections, I’ve identified 10 rules of engagement that anyone can use to navigate the complex, fast-changing working environments we face today. These principles underline the main idea of the book: that grit and adaptability are key to thriving teams, and the best managers listen and implement ideas from their teams, blending these contributions with their own seniority and expertise.

5 rules of engagement for thriving teams in complex environments:

1.Shared purpose above all: McChrystal emphasizes how the U.S. military shifted from a top-down hierarchy to a shared purpose framework. By creating a "shared consciousness," even the most distant teams were aligned to achieve a unified mission.

Foster a collective understanding of your team’s "why," ensuring every member knows how their efforts contribute to the larger mission.

2. Decentralized decision-making: McChrystal’s Task Force realized that centralizing decisions slowed them down. Empowering frontline leaders with decision-making authority enabled faster, more effective responses.

Today's leaders should be able to equip their teams with the tools and trust to make decisions where they matter most.

3.Transparency is non-negotiable, while prioritize relationships over processes McChrystal’s team-building efforts focused on trust and interpersonal relationships, which ultimately drove operational success. Daily operations and intelligence were shared widely within the Task Force, creating a "team of teams" where everyone had visibility into challenges and opportunities.

My takeaway, noted on page 96 is to "promote radical transparency within your team to ensure information flows freely and empowers all members".

4. Adaptability beats rigidity (this is my personal favorite) and cultivate grit and resilience: in fighting an unconventional enemy, McChrystal’s team realized that rigid command structures couldn’t keep up. They adopted agile practices to iterate and evolve rapidly. He describes working with interagency partners, leveraging their expertise to complement his Task Force’s capabilities.

In order to be successful, you have to be willing to pivot strategies and structures to meet changing circumstances head-on. Don’t hesitate to incorporate external expertise to fill gaps or enhance your team’s performance. Encourage a mindset where challenges are met with determination and persistence

5. What got you here, won't get you there. This is a principle from Dale Carnegie, that summarizes the idea of continuous Learning and feedback need. Task Force leaders held regular reviews to learn from successes and failures, embedding continuous improvement into their operations. McChrystal introduced cross-functional teams where junior members could challenge senior leaders, promoting diverse perspectives.

The book also presents some examples from other industries, such as aviation, or healthcare. All teams that were able to foster a culture of feedback and reflection were able to drive sustained growth and innovation.

Team of Teams remains a timeless guide for navigating the complexities of modern work environments. It's not your regular go to personal development book, though. It reminds us that adaptability and grit are crucial for success, and the best leaders are those who listen, learn, and act decisively. Revisiting this book not only reinforced these truths but also transported me back to those early days at Tradeshift, working with Lindsay Lebensohn and Dan Russi to build something truly impactful. Their mentorship continues to shape the way I approach teamwork and leadership.