A Word from the Authors

As a leader at your company, you’ve given the transformation your full support, and the organization has bought in. You’ve had the consultants in, they’ve trained the teams, and the process is in place. All that’s missing are the promised results. Why aren’t things better?

As a contributor—an engineer, product owner, Scrum Master, system admin, tech lead, tester, or any other “doer”—you’ve had the training, written the tickets, and gone to the meetings. You’ve bought in and are ready to see improvements. All that’s missing are the promised results. Why aren’t things better?

After years of study and many missteps, we have come to understand that the key to success is not only adopting practices but having the difficult conversations that foster the right environment for those practices to work. You, your managers, and your teams are missing the right relationships, built only by having the right conversations. The good news is that you can begin a conversational transformation that builds the foundation for any other improvements you want to make, changing your conversations, improving your relationships, and finally getting results.

We’ve seen it happen. Between us, we’ve consulted with over one hundred organizations across a range of subjects and at all levels. It has been our surprising experience that no matter whether we are talking with a CEO or the most junior developer, a managing director at a multinational bank or an operations engineer at an online retailer, a product owner or a project manager, a designer or a developer, in every case we hear, “Why won’t he do it better? Why won’t she change? I can’t make them. I’m powerless.”

Employees’ frustration and despair at their inability to change things exist at all levels and in almost all organizations we’ve worked with—and we feel empathy, because we get stuck in this pattern ourselves.

So it has been our great joy to offer an alternative: the tremendous power of conversations based on transparency and curiosity.

We have regularly and reliably seen individuals, teams, and whole organizations get unstuck and start seeing improvements faster than they thought possible when they unlocked their conversational superpowers: a children’s book publisher that got artists and marketers talking and harnessed creative inspiration for successful sales; an AI startup that involved everyone in setting strategy, seeing big improvements in user satisfaction; a financial-services firm that stabilized its systems through tough discussions of its failings.

Great results follow when you learn that a conversation is about more than just talking; it is a skilled activity. There is more to a conversation than what you can see and hear. In addition to what is said out loud, there is what has been left unsaid—the thoughts and feelings behind our spoken and unspoken words.

As we become more skillful at conversations, we become more aware of what we think and feel, and why we think and feel the way we do. Therefore, we become better at sharing that information with others. We also become more aware that we don’t have telepathy—that we don’t actually know what information our conversational partners have—so we get better at asking questions and listening to the answers. These skills are so fundamental, and so neglected, that when we get better at them, our conversations become radically more productive and our culture becomes much more collaborative.

There is no shortage of books that tell you how to diagnose cultural problems, offering detailed case studies and stories, diagnostic tests, lots of practices to follow, exhortations to collaborate, and tools to use. But few say anything meaningful about how you actually cure those problems—how to make changes and what to do when you’re stuck.

For example, Patrick Lencioni’s The Five Dysfunctions of a Team: A Leadership Fable details the fall and rise of the fictional company DecisionTech. Through this corporate fable, Lencioni develops a theory of dysfunctional hierarchy: Inattention to Results arises from Avoidance of Accountability, which, in turn, is rooted in a Lack of Commitment, and so on through Fear of Conflict and Absence of Trust.1 Lencioni’s model of dysfunction is helpful, and it inspired four of our Five Conversations (which you’ll learn about later in this book). But crucially, Lencioni offers little practical advice for removing dysfunction once you find it.

To build trust, he says, you can do one of five things: share your personal history, discuss your team members’ most important strengths and weaknesses, provide feedback, run personality type analyses, or go on a ropes course.2 While these are likely to make your team more friendly or intimate, Lencioni offers no evidence or argument that they will actually create trust, nor does he provide any alternatives for building trust if they fail.

Lencioni is not alone in hanging the reader out to dry in this way. Business fables, digital transformation guides, Agile manuals—all of them tell you what’s wrong with your culture but not how to fix it. As a result, we have seen company after company implement all the right practices but fail to see results because they haven’t fixed their cultural glue, the very thing necessary to make those other practices work.

This book and the use of our conversational methods will teach you and your team to not only diagnose your cultural problems but actually cure them. We have seen over and over that holding difficult conversations with an attitude of transparency and curiosity does help teams build lasting trust, reduce fear, and make other key improvements; and that it’s easy to explain how and why this method works, which is what we will do in this book.

If you have the appetite, you can develop the skills that allow you to embrace the painful, candid communication that creates an environment in which teams flourish. At no point will developing these skills be easy. In the words of our friend Mark Coleman, it will demand “difficult, emotional work”3 from you at every stage. You will have to confront your own dread of painful topics—and more than once, instead of taking on yet another challenging discussion, you will wish you could just bring in a consultant, or polish your burndown chart, or add some monitoring. But we can assure you that there is nothing as rewarding as working in an organization whose members have mastered all of the Five Conversations, and for whom the never-ending quest for excellence is a habit and a joy.

We look forward to you joining us in learning, developing, and implementing the conversational skills that get you there.

Keep talking,
Jeffrey and Squirrel

How This Book Is Organized

We’ve divided the book into two parts: Part I describes the ideas and theories that underpin the conversational tools that we will introduce in Part II.

Chapter 1 is a bit of software history. If you want to get directly to techniques, you can skip this chapter; but if you are curious about the origins of Agile, Lean, and DevOps, this chapter is for you. We will examine the dramatic changes that have transformed the software industry over the last twenty-five years, recapping what we lived through, including both the progress and stumbles along the way.

In the 1990s the mass manufacturing paradigm provided the intellectual model for the “software factory.” Just as factory workers were expected to be interchangeable units, bound to the assembly line, so, too, were software professionals expected to be interchangeable units, following the dictates of the document-driven approach to software development. When that model proved disastrously flawed in practice, it created space for the rise of a host of people-centric methodologies and the waves of transformations that have swept across software organizations, such as Agile, Lean, and DevOps.

Ironically, as commonly implemented as these transformations are, they often miss the people-centric core, and a bureaucratic focus on processes and practices leaves organizations stuck with cultureless rituals. To advance, organizations will need to tap into the unique human power of conversations, overcoming their cognitive biases by learning to have difficult but productive conversations.

Chapter 2 provides the core techniques of our method: the Four Rs provide steps to help us learn from our conversations, and the Two-Column Conversational Analysis gives us both a format we use throughout the book for recording conversations and a method for learning from them. We recommend reading at least the two sections on these techniques and the section “Analyzing a Conversation” before proceeding.

We start the chapter by showing that you already know where you need to go. Following illustrious social scientist Chris Argyris, we’ll show you that your “espoused theory” already says that the best decisions require collaboration, transparency, and curiosity from all involved. Unfortunately, your “theory in use,” how you actually behave in conversations, is something quite different. We will show you a method called “the Four Rs,” a set of techniques that allow anyone and any team to improve their skills in approaching difficult topics in their conversations, which will help you learn from your conversations and prepare for what comes next.

In Part II, Chapters 3 through 7, we’ve distilled our experience, learnings, and mistakes into an “instruction manual” for the Five Conversations: crucial discussions of the five key characteristics that all high-performing teams share—not just software teams but all human teams.

The Five Conversations are:

1.The Trust Conversation: We hold a belief that those we work with, inside and outside the team, share our goals and values.

2.The Fear Conversation: We openly discuss problems in our team and its environment and courageously attack those obstacles.

3.The Why Conversation: We share a common, explicit purpose that inspires us.

4.The Commitment Conversation: We regularly and reliably announce what we will do and when.

5.The Accountability Conversation: We radiate our intent to all interested parties and explain publicly how our results stack up against commitments.*

These five conversations address attributes that give teams everything they need to exploit modern, people-centric practices to the hilt. With them it is possible to achieve elite-level delivery speeds, fearlessly adjusting on the fly and committing to show real customers working software that solves their problems. And these are exactly the characteristics missing from the teams we see too often today, where standups are places to hide progress rather than share it, where estimation is a forlorn exercise in futility, where the team’s purpose is lost in a sea of tickets, and where frustration is the shared emotion from one end of the organization to the other.

Starting with the Trust Conversation, and continuing with conversations addressing Fear, Why, Commitment, and Accountability, we will show you in detail and step by step how to improve each of these five key attributes in your team. You’ll be able to use these methods whether you are a junior developer or a senior executive, and we’ll explain how these improvements will translate directly into improved results from your Agile, Lean, and DevOps practices. We’ll illustrate how these methods work in real life, with practical examples of conversations on each topic.

Chapters 3 through 7 are each divided into similar sections:

•A motivational section explaining why the chapter’s featured conversation is important.

•A story section introducing a protagonist experiencing a problematic conversation of this type.

•One or more preparation sections that teach you methods introduced in the chapter’s conversation.

•An explanatory section (“The Conversation”) that describes one way to hold the chapter’s conversation.

•A section that continues the story, where our protagonist learns from the problematic conversation and produces a better result.

•Several example conversations that illustrate variations on the chapter’s conversation.

•A case study, which tells a longer story about how the chapter’s conversation helped an organization improve.

But reading to the end of the book is only the beginning. Having learned how to approach each of the key conversations, it will be up to you to practice what you’ve learned. If you do, we are confident you’ll find the effort rewarded many times over. When you transform your conversations, you transform your culture.

The Many Ways to Read This Book

Perl developers have a catchy acronym: “TIMTOWTDI,” or “there is more than one way to do it.” That’s our philosophy, as you’ll see throughout this book; so long as you address the Five Conversations in one way or another, we aren’t prescriptive about which practices you use. We think answers to questions like how long your iterations should be, whether you need standups, or what color of planning poker cards to use are less important than how you get to those answers. Similarly, we’ve tried to write this book so you can use it in multiple ways, depending on your learning style, needs, or mood.

So here are some suggestions for ways to read the book, but TIMTOWTDI, so we don’t mind if you come up with your own!

Linear. If you like to understand every idea the first time you encounter it, this is the method for you: start at page one and keep reading until you run out of pages. We’ve tried to define and illustrate each new idea or technique before using it, avoiding forward references wherever possible. So if you master Test-Driven Development for People in the Trust Conversation, you won’t have trouble when it crops up two chapters later in the Why Conversation. And within each chapter, you’ll find the kind of logical progression you like: first the reason for having that chapter’s conversation, then techniques to use it, followed by the conversation itself, and finally practical examples. Reinforce your learning by using the Four Rs to work through the sample conversations at the end of each chapter and your own examples. Involve one or more friends in your step-by-step learning if you can.

Technical. “Don’t confuse me with stories; get to the methods I can use.” If this is you, then start in the preparation section of each chapter, where we explain techniques you can begin practicing immediately to improve your conversations and, therefore, your team’s performance. Keep reading through the explanation of the main conversation, which brings the techniques together into a whole, until you get to the example conversations, which illustrate the conversation in action, and from which you can lift phrases and approaches. Having chosen this path, we recommend you proceed at the rate of no more than one method per week, and spend each week deliberately practicing the methods in your everyday conversations. At the end of each day, make a count of how often you were able to apply each method, and choose one conversation to analyze using the Four Rs. Outwardly slow and steady, this reflective practice will quickly build skills if you stick with it.

Social. As we describe in the Conclusion, other people who are also interested in learning these skills can be a tremendous aid in learning the material. The cognitive biases that make these conversations difficult also make it more difficult to spot our own mistakes. Other people will have no such difficulty! If you are fortunate enough to have such a learning group, we would recommend that, as a group, you follow a similar path as the Technical approach on the previous page. Cover no more than one chapter per week, keep and share your count of how often you could apply the methods of that chapter, and then discuss and analyze one of your conversations in a group session. Role playing and reversing roles with others will help you gain confidence in your performance; the practice of giving feedback to others will help you spot opportunities for improvement in your own conversations.

Whatever approach you take to reading the book, it is worth emphasizing that understanding is simply not enough; you build the skills by practicing. There is no other way.

* Four of the Five Conversations were inspired by the Five Dysfunctions identified by Patrick Lencioni.4 The fifth, the Why Conversation, was inspired by Simon Sinek’s Start with Why: How Great Leaders Inspire Everyone to Take Action.5 To each we have added our own experiences and approaches, and we are grateful to both authors for their inspiration.