Dynamic Reteaming, 2nd Edition

Preface

Expertcity was about to die! Conceived as the eBay for tech support, this startup that my colleagues and I poured our hearts and souls into had failed in the marketplace. By 2001 our leadership team said it was time to stop all development. I cried.

Fortunately, our cofounder Klaus Schauser had a plan. His plan involved a pivot that would ultimately lead us to breathtaking success with two best-selling products. To get there, we needed to begin with what I now call dynamic reteaming.

Klaus asked me to join a small, isolated team to work on a brand-new product. Because we reteamed, we were a new team and were able to work differently. We could innovate. We were given explicit permission and encouragement to abandon the Waterfall way of working that we had grown accustomed to. We had process freedom. It was liberating.

The team was comprised of software engineers. I was along as a writer. We didn’t have any other roles, unlike other teams at our company, who were told to leave us alone. Not having the standard roles meant that we had to do it all. Developers designed the interface and didn’t have to wait for pixel-perfect mock-ups illustrating the frontend design. We named the product Easy Remote Control—or ERC for short. Those initials would live on in the codebase for years. The product was later named GoToMyPC after a company contest was held.

If we had not reteamed at that time and had gone down a different path, I think we would have never created these successful products—GoToMeeting and GoToWebinar—that enable anywhere from two to more than a thousand people to connect online for meetings and webinars. Our success later turned into the acquisition of our startup by Citrix in 2004, and we were renamed Citrix Online.

Nearly 10 years later, when I was working at a startup called AppFolio, Inc., this isolation reteaming pattern happened again. In this case, the company wasn’t about to go under, but rather invent a new product line to diversify its offerings.

The product this team invented was also successful. It wound up becoming an entirely different company called SecureDocs, which offers a secure, online virtual data room for storing your company’s files for sharing with others later, such as during mergers and acquisitions. It exists today and is headquartered in Santa Barbara, California. Reteaming is so powerful that it even starts companies.

I was exposed to this isolation reteaming pattern yet again back at Citrix Online with a product called Convoi. A close friend was part of this team, where she and other innovators got together and were encouraged to disrupt their flagship product, GoToMeeting. The result of that reteaming was another isolated team that validated the acquisition of a company called Grasshopper.

The three isolation examples mentioned here form what I’m calling a pattern. They are examples of the same type of team changes that I came across three or more times in my experience and research for this book.

This is a book about dynamic reteaming, also known as team change. Team change is real, and this book proves it. It feels like I’m stating the obvious; however, there is a bias in the software industry toward having stable teams. That message has been so strong it’s as if you might feel like you’re doing it wrong if you change up your teams deliberately. You might read quotes like, “Teams with stable membership perform better,”¹ or you might try to heed advice like, “Keep your teams the same for predictability.”² For many of us, however, team stability is more like a pipe dream. Our teams are more like moving targets than unchanging entities. It’s time that we acknowledge that team change is real and that we share stories and ideas for how to not only get good at it, but also dominate it—the essence of this book.

After working in three successful, fast-growing companies since 1999, and after interviewing countless people at other software companies, I present to you a variety of team-change stories and patterns that you can leverage when thinking about how to grow your company, or attempt to change it in your pursuit of excellence.

The topics in this book vary depending on geography, company type, and size, and aren’t always pretty. Included are stories of quite emotional mergers, layoffs, and anti-patterns for unskillfully done reteamings. When the team members choose or catalyze the reteaming, it might be positive. When reteaming happens to us, we might not like it—at least not initially, especially when it’s done in a top-down, command-and-control manner.

In Part I you will discover some background information on dynamic reteaming. This includes the evolution of teams, basic definitions to get an understanding of teams, and the power and politics involved in dynamic reteaming. I also detail why you might consider deliberate forms of reteaming in your company to reduce risk and to promote sustainability.

Part II gets into specific reteaming patterns and stories. These “transformations” show up as five base dynamic reteaming patterns: one by one, grow and split, isolation, merging, and switching. I also include a discussion of what I consider to be anti-patterns for reteaming.

Part III includes more practical ideas for how you can make things easier before, during, and after your reteaming. I’ll share how to design and prime your company for reteaming so when it happens later, it’s easier. I’ll also share my favorite tools for planning large-scale reteaming initiatives and explain how to run calibration sessions to get your teams up and running after they change.

No matter what your opinion is on dynamic reteaming, you will face it in the future whether you like it or not. People will come and go from your teams and your company. Your company might reorganize or get taken over by a competitor. Key players will join, and at some point they will leave. You might even decide to completely switch up your teams to accomplish a new company goal. No matter what your opinion is on this topic, reteaming is inevitable, so you might as well get good at it.

Approach

My research approach is qualitative and is inspired by the emergent nature of grounded theory as written about and used by Brené Brown in her book Daring Greatly.³ Much of what I have written about in this book has been discovered in my interviews. To collect qualitative perspectives from others, I spent an hour with each person and asked them to tell me stories about how their teams had formed and changed over the years. I then had the conversations transcribed, and I coded the data for themes that emerged and composed this book. Some of these respondents have permitted me to use their company names in the book examples. Others told me stories with the agreement that I would keep their company names confidential.

From these stories, I’ve derived unique patterns and themes that illustrate the concept of dynamic reteaming. All of these organizations are quite adaptive. That means that what I present here is really a snapshot in time for these companies. Today they might do things differently than described in this book. And that’s a good thing. We need to reflect on our teams and organizational structures in our companies. What worked yesterday might not be appropriate tomorrow. In addition, these companies range in size from 30 people to thousands of people. What is shared here is not necessarily representative of the organizational patterns within all parts of their companies.

Audience

This book is for people who make decisions about how teams are formed and changed in their companies, or for companies with whom they consult. When writing this book, I imagined that I was speaking to people with titles like vice president of engineering, chief executive officer, founder, chief technology officer, director, manager, or consultant. This book is also for the many people who influence reteaming decisions in their companies, such as software engineers, quality assurance engineers, user experience engineers, ScrumMasters, and coaches.

Participants

My sincere thanks goes to all of the participants who have graciously shared their stories with me:

• Richard Sheridan: Founder and Chief Storyteller at Menlo Innovations (Michigan, USA)  

• Jon Walker: CTO and Cofounder of AppFolio, Inc. (California, USA)

• Comron Sattari: Founder and Architect at SecureDocs (California, USA)

• Andrew Mutz: Chief Scientist at AppFolio, Inc. (California, USA)

• Kristian Lindwall: Engineering Site Lead at Spotify (California, USA)

• Chris Lucian: Engineering Lead at Hunter Industries (California, USA)

• William Them: Delivery Manager at Trade Me (Wellington, New Zealand)

• Sandy Mamoli: Agile Coach and Consultant at Nomad8 (Aukland, New Zealand)

• Damon Valenzona: Engineering Director at AppFolio, Inc. (California, USA)

• Mark Kilby: Agile Coach at a DevOps tooling company (Florida, USA)

• Rachel Davies: Agile Coach and Engineering Lead at Unruly (London, UK)

• Evan Willey: Director of Program Management at Pivotal Software Inc., Pivotal Cloud Foundry (California, USA)

• Carey Caulfield: Principal Product Manager at LogMeIn (California, USA)

• Thordur Arnarson: Agile Coach Lead at Tempo Software (Reykjavik, Iceland)

• Cristian Fuentes: Engineering Manager at Jama Software (Oregon, USA)

• Thomas O’Boyle: Software Engineer at Procore Technologies (California, USA)

• Jason Kerney: Full Stack Software Engineer at Hunter Industries (California, USA)

• Elaine Bulloch: Manager, Interactive Program Management at FitBit (California, USA)

• Paige Garnick: Engineering Manager at Procore Technologies (California, USA)

• Andrew Lister: Senior Director of Engineering at Greenhouse Software (New York, USA)

• Mike Boufford: CTO at Greenhouse Software (New York, USA)

• Chris Smith: Head of Product Delivery at Redgate Software (Cambridge, UK)

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How to Use This Book

If you want an introduction to what dynamic reteaming is, read Part I.

If you want to read about the patterns and anti-patterns, read Part II.

If you want to dig into practical ideas for how to make reteaming easier now or in the future, read Part III, as well as the rest of the book where practices are described in context.

Acknowledgments

I want to thank everyone who has supported this learning quest. In particular, I’d like to thank Leanpub, the publishing platform that empowered me to release the first version of this book, which I later shared with O’Reilly, who published this edition. Without both companies, this material would not be in your hands. Special thanks to editor Melissa Duffield, who believed in me and gave me many opportunities to showcase my ideas, and Melissa Potter, my development editor, who helped me refine and craft this edition. Kate Galloway helped me become much more articulate in expressing so many important details in this book, and I thank her immensely for that. I also thank Chris Smith of Redgate Software and Mark Kilby for their detailed feedback on this edition.

I also want to thank all of the contributors listed in the previous section, who shared their reteaming stories with me. Their stories as well as my personal experience are what revealed the five patterns of dynamic reteaming and brought them to life.

Diana Larsen contacted me about writing the original book’s foreword, which has been republished for this version. It still means the world to me that she did that! John Cutler is a friend and former colleague of mine from AppFolio. He is one of the most thoughtful and creative people I know, and I am delighted to have his foreword for this edition.

Back in 2015, Joshua Kerievsky encouraged me to write this book in its entirety so that I would write the book that I wanted to write before approaching publishers. That let me work at my own pace and shape my thoughts and research into something complete. I now give that incredible advice to other aspiring writers.

Klaus Schauser and Jon Walker were two key managers and mentors in my career, and they are also the cofounders of AppFolio. I am so grateful to have learned software development with them. We built two amazing companies together—Expertcity, where we invented GoToMeeting and GoToWebinar, and AppFolio. They gave me a solid foundation to apply at other companies. I share many of our stories and philosophies in this book.

Sam Crigman, now head of R&D at Procore Technologies, told me, “Don’t slow down,” and encouraged me to speak about dynamic reteaming at industry events. His ongoing support has helped me to pursue the concept of dynamic reteaming to a greater level of understanding.

My parents have always been very supportive and encouraging. In particular, I want to thank my father, Alan Shetzer, who always advised me to pursue the work that I would love to do and look forward to doing every day. You can find his influence in this book.

Michael Feathers was the original inspiration for my writing about the topic of dynamic reteaming. He might have even named the topic in our early conversations. I am so grateful for our life together.

Most of all I’d like to thank my children, Samuel and Julia. I hope that through my example I have instilled some sort of work ethic that will inspire them now and in the future.

¹ Hackman, Leading Teams, 55.

² Scrum PLoP, “Stable Teams”

³ Brown, Daring Greatly, 251.