It’s Complicated: Our Love/Hate Relationship with Collaboration

Collaboration is a skill that many agree is crucial to deal with big, complex challenges where causes are unclear, and the knowledge and abilities required are diverse. We need to be able to harness the energy of lots of different kinds of people productively, without getting mired in conflict or hiding out on our own where we feel safe and in control. Collaborating well doesn’t happen naturally; it requires an understanding of what helps teams come together, and how to avoid or push back on forces that get in the way.

Working closely with different types of people to solve difficult challenges is something we say we value. Many blog posts and advice columns praise the virtues of collaboration as critical to how we work now, and schools have begun teaching it as a critical skill for the 21st century. We know that we can’t solve the complicated problems before us—from climate change to artificial intelligence to health care for our exploding population—with just a few people who think and act the same. When it goes well, collaboration brings out new ideas and joins varied skills to create something truly inspiring. But when it goes wrong, it drives us back into safe groups with defined rules where we can focus on something that’s easier to control.

And it does go wrong, because the reality is that most people aren’t taught how to work in a collaborative environment, with all of its messy interpersonal dynamics. What I’ve learned from studying and practicing collaboration in many different settings is that getting it right doesn’t happen on its own. Often, “successful” outcomes are not very collaborative at all, but rather the result of someone spending hard-won political capital to drive a vision they care deeply about, whether others are on board initially or not. And at the end, it doesn’t even feel much like a victory. There’s no time to celebrate when they must now spend months rebuilding the relationships they called upon and shoring up their political capital for the next new idea campaign. It’s exhausting!

When collaboration fails, it’s almost a nonevent. Few teams actually come together and launch something absolutely, catastrophically bad. For the most part, collaborations simply dissolve and everyone goes back to the status quo, back to their silos, back to creating the safe, achievable Band-Aid solutions that are easiest to implement. Except most of those involved now have a bad taste in their mouths—for other teams, for leaders, and for collaboration itself.

The collaborations that go off the rails share some common elements, just as the successful ones do. In developing this book, I’ve spoken with people in many different fields to understand how they team up, what works, and what doesn’t to help us get our arms around it. The insights I’ve gleaned from speaking with different types of collaborators—educators, product developers, aeronautics experts, ER doctors, and civil servants—can be applied widely to make collaboration less painful and more productive.

We need to get better at managing diverse groups of people working together, because working in silos that we can control won’t get us where we need to go. Eventually, those Band-Aid solutions become unworkable; breakthroughs are needed. Sooner or later, the breakthrough will come, maybe from a team who just got lucky. But being able to come together to solve problems is too important to leave to luck. Getting different people to work together to solve complex problems that affect us all is a critical 21st-century skill that’s worth mastering.

Why I Wrote This Book

My inspiration for writing this book was watching well-intentioned, capable leaders say all the right things about collaboration and teamwork, only to fumble when trying to pull it off. They express the need to get wider perspectives on initiatives, to improve cross-functional teamwork, to change their order-taking cultures, but in the end they reveal a predefined solution and ask, “Any questions?” Some leaders simply shove a team together into a conference room with a problem to solve and hope for the best. Or, they bring in outside consultants to make the magic happen, and it does, right up until it comes time to take the ideas back inside and it all falls apart. Leaders may think that they love collaboration, but many just don’t know how to embrace it.

Because it’s so important, getting “good” at collaboration can’t require an overnight shift in the way an organization operates. I’ve witnessed, and interviewed others about, huge “transformation” efforts within large, established organizations where the natural environment isn’t conducive (or is downright hostile) to working across silos that can be controlled independently. Attempting to change that environment wholesale is likely to fail since there are too many antibodies you have to contend with. Startups have an advantage in that they have less inertia in the culture and its approach to working together. But even these organizations can resort to just executing on known problems, deferring more complex questions until tomorrow when the company will be (hopefully) more stable, only to find themselves just as stuck when that day comes. Startups carry a level of pressure that favors independent action just as much as large companies.

Instead of trying to change an organization’s whole culture, then, this book aims to arm you with knowledge and tools to succeed in a grassroots scenario where you can build acceptance of working differently by demonstrating results, not by selling a process, methodology, or value system. For those who lead or support efforts to bring people together to solve a problem, you should look to create a space within the organization where a team or teams can bring their diverse talents together, with the right support.

Who This Book Is For

This book is for anyone who needs to bring people together to diagnose problems and explore solutions—from product managers looking to get buy-in for product roadmaps, to engineering leaders looking to support development teams, to students learning to work in groups. Whether you’re looking to support a large-scale initiative or just want some tips to reduce team friction, this book offers practical advice, guiding principles, and simple tactics that you can use to master collaboration.

How This Book Is Organized

This book breaks down four major aspects of how collaboration works and how you can support it. Each part contains advice, troubleshooting, and specific tools that you can use to support healthier working relationships that deliver great outcomes.

Introduction: What’s Collaboration and What Gets In the Way?

In this chapter, we’ll look at what situations call for collaboration, and what makes it a challenge. In each of the four parts of the book you’ll find guidance about how to overcome those challenges.

Part I: Creating the Right Environment

Business settings can challenge collaboration because of the inherent power dynamics and typical workspaces. This part helps you adapt that environment to support healthy teamwork.

Part II: Setting Clear Direction

Many collaborations fail because they lack the structure and focus they need for diverse teams to feel safe and be productive. This part looks at how you can provide the right structure for teams to manage their time, set expectations, and understand what success will look like.

Part III: Exploring Solutions

Teams need support to be open to new ideas and create solutions that blend different perspectives and skills. This part gives you tools to lead teams through creating and testing out ideas early and often.

Part IV: Communicating Clearly

One challenge that plagues many collaborations is communicating with those who aren’t intimately involved day-to-day so that they’re well informed and able to provide useful guidance and feedback. This part will help you communicate clearly within the team and with others to keep the collaboration flowing and reduce friction.

Throughout the book, you’ll also find sidebars that contain tactical exercises, tips, and techniques you can use with your team to improve various aspects of working together. If you and your teams can master these fundamentals and use some of the techniques provided, you’ll be better equipped to tackle messy collaborations with grace and get the benefits your challenges require.


This book may only have one author’s name on the cover, but it contains the insights and stories from many lovely people who were generous with their time and energy. I want to thank those who shared their experiences with me: Jimmy Chin, Jon Rosenberg, Christina Wodtke, John Simpkins, Jim Kalbach, Chad Jennings, Catherine Courage, Mikael Jorgenson, Michael Grasely, Kai Hayley, Vanessa Cho, Sara Ortloff, Alberto Villarreal, Paul Ford, Michael Sippey, Farai Madzima, Matt Bellis, Josh Seiden, Andrea Mangini, Brandon Harris, Adam Richardson, Kate Rutter, and Cyd Harrell.

To my reviewers, Greg Beato, Jorge Arango, Pilar Strutin-Belinoff, Jason Mesut, Matt LeMay, Blair Reeves, David Farkas, and Lane Goldstone, who helped me get from a mess of ideas in my head to something coherent and much improved, I hope that I may repay the favor someday. At the very least, you have paid it forward, friends.

To Susan Killebrew and Pam Lucker, who inspired me by showing me that collaboration wasn’t just something you are born with but something you can teach, you are creating the collaborators of the future, who will likely face even more complex and important challenges. Thank god they have you. And thanks to both for turning me on to Elizabeth Cohen’s Designing Groupwork (Teachers College Press), a book that several educators say they use for teaching collaboration in the classroom.

A special shout-out to some of my past collaborators: I know working with me was not always easy, but hopefully it was worth it. I learned so much from each of you: Eric Bailey, Ben Foss, Ariel Waldman, Kim Goodwin, Mark Seveska, Nikki Lasley, Karissa Sparks, Jen Theaker, and Sharilyn Neidhardt. And to David Cronin, my ultimate collaborator.

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