Introduction to The Seven Challenges Workbook

INTRODUCTION Awakening to and Embracing Conscious Conversations
Moving our conversations from invisible cultural habits (clunky autopilot)
to conscious personal choices (skillful flying)

Overview: Why Our Conversations Keep Failing Us and How We Can Learn to Do Better

Life is challenging in lots of ways, many of them having to do with talking, listening, and negotiating, both at home and at work. I certainly wish that life with others were simpler and easier, but that has not been my experience.

For me, the first giant step toward making my life better was admitting that I had something to learn. I thought I was a pretty clever fellow. I had college degrees from two big universities! So I thought I didn’t need any help from anybody about things as personal as talking and listening.

Wow, was I mixed up about that. I did not take my first communication class until after my second divorce. Ouch! Lots to learn.

If you’re reading this, you probably know what I’m talking about — not my divorces specifically, but the experience of realizing that something in your relationships or conversations isn’t working as well as you want it to. Maybe it’s a marriage where the same argument keeps recycling. Maybe it’s a work situation where people talk past each other. Maybe it’s a family where important things never get said, or get said in ways that make everything worse. Maybe you’ve picked up this book because someone you care about is slipping away, and you sense that the way you’re communicating has something to do with it.

Whatever brought you here, I want you to know two things at the outset. First: you’re not alone. The difficulties you’re experiencing are nearly universal, and they have identifiable causes that we’ll explore in this chapter. Second: the situation is genuinely improvable. Not because I’m going to give you magic words, but because communication is a set of learnable skills, and because we learned the way we talk and listen now, we can learn to talk and listen differently.

And… to learn to do something in a new way, we have to slow down and pay attention to it with a new level of focus. That’s a key ingredient in every chapter of this book — and, as you’ll see, in the entire shift from autopilot to conscious choice.

When I got started investigating communication skills, I was in a hurry and wanted easy answers. I definitely wanted the single-afternoon quick fix that did not ask to much of me. It took me a while, both as a student of communication skills and then as a teacher of them, to realize that the patterns we have practiced for a lifetime don’t change overnight, especially patterns we identify as essential parts of our personalities. And we don’t learn complex new skills overnight, either. We already know this perfectly well in relation to some areas of life. Nobody expects to become a concert violinist by next Thursday, or a top basketball player, either. It is only in relation to areas of living that we have not looked into very deeply, that we can get tripped up by the dream of magic-wand style changes.

In this new edition of the Workbook, I am devoting this entire Introduction to the topic of conscious attention as a way of inviting you to make a deeper friendship with paying attention. My experience has been that paying attention is not a tool like a fire extinguisher, that you use in emergencies once in a great while, and then put back on a hook in a closet somewhere. It is more like a light switch, next to every doorway you will ever enter, that you will use over and over again. And why use it? To reiterate, in order to guide our actions toward new successes, a key ingredient is to observe ourselves in action.

What follows is a developing inquiry — six perspectives that build on one another, each one taking you a layer deeper into understanding why your communication life has been as challenging as it has been, and why there is real cause for hope. An open horizon of development calls to each of us, no matter how many struggles we may have had in the past. Each perspective that follows explores another aspect of that horizon.

 

Perspective 1: Ready or Not, You’re Already Doing the Most Consequential Thing in the World

Every day you’re in dozens of conversations — with your partner, your kids, your coworkers, your friends, your neighbors, sometimes with strangers whose cooperation you need. You’re already communicating constantly. That’s not the question.

The question is whether it’s producing what matters to you — connection, respect, understanding, cooperation. Or whether it keeps producing the same frustrations: the argument that loops forever, the important thing you needed to say but didn’t, the conversation that left someone feeling unheard, the conflict that hardened into a wall of silence.

Most of us communicate on what you might call cultural autopilot. We react instead of responding. We imitate whatever patterns surrounded us growing up. We handle conflict the way our parents handled conflict — or, if their way was painful enough, we swing to the opposite extreme, which brings its own problems. And we rarely stop to ask: is this autopilot actually getting me where I want to go?

This workbook is an invitation to ask that question — and to discover that you have far more choices than you may have realized.

But if most of us are talking and listening on autopilot, and we intend to break free, we will need to know more about how and why autopilot works.

 

 

Perspective 2: Our Autopilot Isn’t Our Fault — But It Is Our Opportunity

Here’s the biology. You were born with a brain magnificently wired for language and connection. But you were born knowing exactly zero communication skills. You could cry. You could nurse. That was it.

Just as you were born with the capacity for language but no particular vocabulary, you were also born with the capacity for communication but no particular communication skills. Everything you know about talking and listening, you learned — by absorbing the patterns of your family, your community, your culture, and increasingly, your screens.

If what you absorbed was skillful, you got lucky. If what you absorbed was sarcasm, avoidance, yelling, guilt-tripping, or silence, you learned that instead. Your communication habits work the way language acquisition works: a baby born in a house full of Portuguese speakers learns Portuguese, not because Portuguese is better or worse than any other language, but because that’s what was there. Your conversational patterns are inherited in the same way — not through your genes, but through your environment, copied from the people around you when you were too little to know what was going on.

I think of this as the “born to learn” predicament. We humans are astonishingly adaptable — we can thrive in Arctic tundra and tropical rainforests, in fishing villages and megacities — but that very adaptability means none of us arrives pre-equipped for the particular communication challenges we’ll face. In contrast with newborn horses, who can gallop within 24 hours of birth, we arrive in life as beginners with an enormous amount of essential stuff to learn. There is no shame in not knowing this stuff.

We were not born knowing it — we were born to learn it.

What we might have missed in our early communication skills learning is not a personal failing — cultures often teach their children how to (A) assert themselves and (B) how to fight, but not necessarily (C) how to nurture and (D) how to negotiate win-win solutions. Now, as adults capable of choosing our own learning paths, I am convinced that we need to develop the last two in order to keep from being unhappily stuck forever in the first two.

There’s no shame in having absorbed imperfect patterns, either. You didn’t pick your first communication habits any more than you picked your first language. But here’s the thing, and this was one of the key teachings of the great twentieth century psychologist, Carl Rogers, you’re old enough now to recognize new opportunities and to choose different patterns. With the cognitive abilities of an adult, rather than the limitations of a child, you can examine what you inherited, keep what works, and learn new skills to replace what doesn’t.

That’s what every chapter of this workbook is about.

So we’ve inherited our autopilot, and it’s not our fault. It is also not our fate. Knowing where the autopilot came from only takes us part way down the road. To understand why it fails us so regularly — even with the people we love most — we need to look at what communication actually requires of us. And what it requires turns out to be many-leveled, more many-leveled than most of us imagined.

 

Perspective 3: The Three Things Every Relationship Needs (and What Happens When Any One of Them Is Missing)

Decades of research on human groups — families, work teams, organizations, neighborhoods — have found the same pattern everywhere. Every human group, from a couple to an entire company, needs to do three things at once:

• accomplish tasks together,
• support one another emotionally, and
• accommodate different temperament types.

Let one fall apart, and the others follow.

This insight lies at the heart of everything in this workbook.

Think about your own life. The partner who handles the household logistics brilliantly and efficiently but never receives any expressions of recognition or gratitude will eventually burn out. The work team that’s all warmth and camaraderie but can’t meet a deadline will fall apart under pressure. The family that’s great at organizing holidays but terrible at talking about feelings will gradually stop gathering at all, or sit frozen at the dinner table. These are not separate problems. They are strands of the same rope.

Into this balancing act of task accomplishment and emotional support comes the third element: all sorts of people who have different talents, temperaments, lifetime experiences, and styles of expression. This variety is a tremendous asset — diverse groups come up with better solutions, avoid more blind spots, adapt more effectively. But that variety doesn’t manage itself. It requires communication across difference, and communication across difference is genuinely challenging. It takes skill, patience, and practice.

It would be nice if communicating well with people who are very different from us were like sneezing, which we can all do without any practice at all. But from my experience, it’s much more like learning to play the piano. It takes conscious attention and sustained effort.

The skills in this workbook address all three sides of this triangle — the task side, the emotional support side, and the navigating variety side — because in real life, they’re inseparable.

Now we can see more clearly why autopilot fails us. It’s not just that we inherited imperfect patterns — it’s that even perfect patterns, repeated without conscious attention, couldn’t balance the multiple levels involved. Weaving together tasks, emotions, and human differences in every interaction requires something that no autopilot can provide. Which brings us to a question that might be forming in your mind: if communication is this demanding, is there any real hope of getting better at it?

 

Perspective 4: It’s Harder Than It Looks — But That’s Not the End of the Story

Communication seems like it should be as easy as breathing, because we do it constantly. After all, you can just yell at someone and get their attention. But it’s not like breathing. And just yelling at someone will not get much done. Weaving together the three elements described above is both a complex skill — and one that gets better with conscious practice.

Life is full of very challenging tasks. That’s the bad news. Life is also full of examples of people who get better and better at those tasks. That’s the good news hidden inside the bad news. You yourself are one of those success examples. You have mastered many skills in the course of your life journey up to now. Standing up, walking, running, learning a vocabulary of thousands of words. It just happened so long ago that you have forgotten both how difficult it was and how successful you were. I am here to remind you of both.

If communication were a fixed personality trait — something you’re born with or without — you’d be stuck. But because it’s a skill, you can develop it, at any age. The awkwardness you feel when you try something new — really listening instead of planning your reply, asking for what you need instead of hinting or withdrawing — is the same awkwardness a beginning guitarist feels. It’s not a sign that you’re doing it wrong. It’s a sign that you’re learning.

The psychologist Carol Dweck has documented something that matters enormously here. People who believe their abilities are fixed (“I’m just not good at talking about feelings”) tend to avoid challenges, because every difficulty feels like proof of a permanent limitation. People who believe their abilities can grow (“I haven’t learned how to talk about feelings yet”) tend to welcome challenges, because every difficulty is simply the next step in learning.

If you’ve spent years — maybe decades — believing that your communication difficulties are just “who you are,” this reframe may be the most important thing in the entire workbook. You are not a bad communicator. You are an untrained one. And untrained is a condition that responds to practice.

In the Challenge Seven chapter, we’ll return to Dweck’s work in much greater depth. By that point, you’ll have had the experience of actually practicing new skills — and discovering for yourself what the growth mindset feels like from the inside, not just as a concept but as a lived experience. For now, just hold this thought: everything in this workbook is learnable. The only question is whether you’ll practice, and that includes finding practice partners.

So communication is learnable, and the growth mindset frees us to begin. But what, exactly, is the engine that makes learning possible? What shifts us from running the old autopilot program to actually doing something different in the middle of a live conversation? The answer is simpler — and way beyond issues of one technique versus another.

 

Perspective 5: You Can’t Get There Alone — and You Don’t Have To

Here is perhaps the most important thing I’ve learned in thirty years of working in this field: reading a book about communication skills, by itself, won’t change much. Not because the information is bad. Because it’s not the largest factor in how human beings actually change.

Journalist Alan Deutschman spent years studying what it actually takes for people to make lasting changes in their lives — not what we wish it took, but what the evidence shows.

His inquiry was galvanized by a heartbreaking puzzle. Doctors know that a lot of illness are the results of the patients’ own behavior. But in spite of the most medically accurate advice given to them, many patients don’t change. They die instead. That motivated Deutschman to title his book, Change or Die. Trying to find out why, he went on a quest. Were there any personal behavior change programs anywhere that actually worked? And if they did work, Why? His findings will provide us with some significant pointers as we embark on our own quest to become much kinder, wiser and more effective listeners and talkers.

His conclusion, drawn from fields ranging from cardiac rehabilitation to criminal justice, is captured in three words: relate, repeat, reframe, each one weaving us into a new web of relationships. Change doesn’t get very far with only new information or new willpower. It really begins to take hold with a web of new relationships — often including an engaging teacher who believes in your capacity to grow and who walks beside you (relates) while you’re learning . Then, within a circle of supportive co-learners, you repeat new behaviors until they begin to feel natural. And in dialogue and practice sessions with those supportive co-learners, you gradually reframe your understanding of yourself and what’s possible.

This sequence — relate, repeat, reframe — is the hidden architecture of every successful behavior change, from quitting smoking to learning a new language to transforming how you handle conflict. And it explains why so many earnest people read books like this one, feel inspired, try some new approaches for a few weeks, encounter resistance or awkwardness, and gradually drift back to their old patterns. It’s not a character flaw. It’s the predictable result of (A) trying to change without the relational support that makes change sustainable, and (B) trying to change without enough repetitive practice to move the new information, skills and attitudes from short-term memory to long-term memory. (Our brain is trying to be helpful and not waste effort. It won’t move anything into long-term memory unless it receives a signal, such as intense sensation, strong emotion, or repetition. One signal we can send at will is repetitive practice.)

If you’ve tried to improve your communication before and felt like you failed, Deutschman’s research offers a different interpretation: you didn’t lack willpower or intelligence. You lacked the support structure that makes deep change possible. The missing ingredient wasn’t inside you — it was around you.

This is why Chapter Eight in this workbook, Developing Your Learning Support Network through Teams of Two and Circles of Six, is entirely devoted to helping you find empowering exemplars, nurture co-learning partners and develop a circle of people to practice with. I encourage you to read that chapter soon — perhaps even before you dive into the skills themselves. You don’t need to master anything first. The whole point is that we develop these capacities together.

For now, just hold this thought: as you read through this workbook, keep one eye open for someone you could invite to explore it with you. A spouse, a friend, a coworker, a neighbor. Even one person makes an enormous difference. Two people committed to practicing together can sustain each other through the awkward early stages in ways that no book, however good, can do alone.

We’ve now seen why our conversations struggle, where our autopilot came from, why the challenge is greater than it appears, and how attention, growth mindset, and companions for the journey can transform our capacity to connect. But there’s one more realization — one that took me decades to fully grasp — and it changes how we think about this entire endeavor.

 

Perspective 6: A Deeper Realization — You Are Already a Communication Skills Trainer

Usually we think of the teacher at the front of the room, and the students sitting quietly in rows of chairs. That may be true for a lot of topics, but that picture can be really misleading when applied to communication skills. You are not only a communication skills learner. You are also, right this minute, already a communication skills trainer. And you have been one every day of your life.

This isn’t motivational rhetoric. It’s a simple observation about how human beings work. We are learning from each other all the time.  From the moment you wake up until you fall asleep, you are demonstrating to everyone around you one particular way that conversations can unfold. When you interrupt someone, you’re teaching the people present that interrupting is normal. When you listen carefully and reflect back what you’ve heard, you’re teaching that careful listening is possible. When you express frustration as an attack, you’re modeling one path. When you translate that frustration into a clear request, you’re modeling another.

Every interaction you have is, at some level, an instruction to the people witnessing it — your children, your coworkers, your friends, your partner. Human beings are deeply social, and learn by observation and imitation. So with every interaction, we are teaching other people how to treat us. Why not teach calmness and kindness, instead of anger and revenge?

The question is not whether you will influence how others communicate. You will, inevitably, whether you intend to or not. The question is whether you will do so consciously — in ways that bring out the best in the people around you. And this is where the “from-to” at the heart of this workbook comes alive: the shift from communicating on invisible autopilot to communicating as a conscious, creative choice.

This understanding also reframes what it means to seek out companions for the journey. When you practice new communication skills with a partner or a small group, you’re not just supporting your own learning. You’re participating in something larger: the gradual spread of more conscious, more compassionate communication through your family, your workplace, your community. Each person who communicates a little more skillfully creates a slightly different environment for everyone around them. This is how culture changes — not through pronouncements from above, but through the accumulation of countless small interactions where someone chose to listen instead of react, to ask instead of accuse, to stay present instead of shutting down.

 

What’s Ahead on This Journey

The remaining eight steps of this workbook each address a specific communication challenge. Some teach practical skills — like listening, self-expression, and translating complaints into requests. Some address the perspectives, attitudes and orientations that make those skills sustainable — like the growth mindset, the practice of self-forgiveness, and the courage to keep learning even when it’s uncomfortable.

In Challenge Seven, we’ll return to many of the ideas introduced here — the growth mindset, the “born to learn” predicament, the relationship between practice and development — but you’ll encounter them differently after having worked on Challenges One through Six. What feels conceptual now will feel experiential then. That’s the spiral this workbook is built on: each pass through the core ideas deepens your understanding because you bring more lived experience to the encounter.

Together, the Seven Challenges form a powerful journey — not a rigid sequence, but an interconnected set of practices and attitudes you can return to again and again as your life presents new situations and new relationships to navigate. You can work through them in the order presented. (We have tried to present them in an order where each prepares you for the next.) But you can also start with whichever step speaks most directly to your life right now, and weave the others in as you go along. We each learn differently, and we each have had a different set of needs, frustrations and successes. That makes following your spontaneous interest an important part of your learning process. You are making your own connections to the material presented.

But before you continue your exploration of this new territory, I’d like to invite you to pause and do two things.  First, start a learning journal for your communication skills explorations.  It can be any kind that meets your needs:  bound book, digital, online, 3-ring binder, even sending youself an email message every day with that day’s new experiences and understandings.  Then as your first entry in your journal, complete the brief reflection exercise below. It takes about ten minutes, and it will help you connect what you’ve just read to your own actual life — which is where all the real learning happens.

 

Introduction – Exercise Intro – 1
Taking Stock of My Communication Journey

Before you continue reading, please take some time to reflect on and write down your responses to any of these questions.

1.–What brings you to this workbook? What situation or relationship do you most want to improve?

2.–Think of a communication moment that went well recently — a time when you felt genuinely connected with someone, or when a difficult conversation resolved better than expected. What made it work?

3.–Think of a communication moment that went poorly — a conversation that left you frustrated, hurt, or disconnected. Without blaming anyone (including yourself), what do you wish had gone differently?

4.–Alan Deutschman’s research suggests that change begins with new relationships, not just new information. Who in your life might you invite to explore this workbook with you? Even one practice partner can make an enormous difference.

…

 

References for this Chapter

Bales, Robert F. Interaction Process Analysis: A Method for the Study of Small Groups. Addison-Wesley, 1950.

Deutschman, Alan. Change or Die: The Three Keys to Change at Work and in Life. Harper Business, 2007.

Dweck, Carol. Mindset: The New Psychology of Success. Random House, 2006.

Edmondson, Amy C. The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. Wiley, 2019.

Kegan, Robert. The Evolving Self: Problem and Process in Human Development. Harvard University Press, 1982.

Pearce, W. Barnett. Communication and the Human Condition. Southern Illinois University Press, 1989.

Putnam, Robert D. Bowling Alone: The Collapse and Revival of American Community. Simon & Schuster, 2000.

Richerson, Peter J., and Robert Boyd. Not by Genes Alone: How Culture Transformed Human Evolution. University of Chicago Press, 2005.

Rogers, Carl R. On Becoming a Person: A Therapist’s View of Psychotherapy. Houghton Mifflin, 1961.

Rosenberg, Marshall B. Nonviolent Communication: A Language of Life. 3rd ed., PuddleDancer Press, 2015.