Good Talk: How to Design Conversations that Matter

PART ONE

The limits of my language are the limits of my world.

Ludwig Wittgenstein, Austrian Philosopher, popularized the duck-rabbit.

Conversations Matter

Our lives are built one conversation at a time.

Each day we have dozens of conversations. Some conversations are once-in-a-lifetime interactions that light us up and shift our course. Others seem stuck in an infinite loop, eventually becoming stale and repetitive.

We count on conversations to help us get what we want and need from other people, and we all put significant effort into making our conversations go well.

It can take work to start them off right: We need to talk, rarely starts an exchange anyone is looking forward to. When conversations get off track, it’s hard to walk away without regrets or replaying them in our heads.

Conversations can be hinge points, igniting new growth or ending a phase in our lives. No matter how difficult, any conversation can be an opportunity to connect, learn, and grow.

Each and every conversation is an opportunity to change your life. You can take hold of that opportunity, or let it slip through your fingers.

Conversations matter.

Awkward Laundry Room Conversations

My journey into designing conversations started in a laundry room. I had finished my two-year master’s degree in industrial design, and was working as a researcher and strategist for a small firm in the Flatiron section of New York. Most of my job was journeying out into the suburbs to talk to homemakers about the appliances they used in their daily lives, and how we could make them better.

I had an experience that has stayed with me, nearly a decade later. Standing in a laundry room with my interviewee, a dark-haired Italian-American mother of three teenagers who made sandwiches for her kids every day (when was the last time my mother made me a sandwich, I wondered?), I steadily worked through my list of questions. She was offering me some great information, but time was getting short and I still had a lot to ask. She paused for a moment, done with her response, or so I thought.

I took a breath and started to ask my next question. At the same time she took a breath to continue her thoughts. We both stammered as the opening of our sentences collided.

What were you going to say? I asked. It was my job, after all, to get her to give us as much good information as possible.

Oh, I can’t remember now! she said. I blanched. In one breath, I had erased her entire half of the conversation.

In that moment, I saw the power of conversation: connection and insights would only ever happen if I could be patient and open to silence. What else was I missing in my life, in my rush to move things forward?

From Good to Great

We spend a tremendous amount of time talking to other people. At work alone, some estimates figure that the average worker spends about five hours in meetings each week. For managers, that number rises to 12 hours. In the public sector, it’s 14 hours. Most of these hours are reported to be ineffective at delivering solid outcomes. That’s a huge financial loss in productivity. That loss could be as much as 37 billion (with a B!) according to one study. And that’s just official meetings¹.

Outside of work, think about the challenges of bringing up difficult issues with our family, spouse or friends. It’s impossible to estimate the cost of not having good conversations with the most important people in our lives.

A good conversation might mean that we get out of it what we wanted and planned. When everything goes according to our plan, that’s good. While a good conversation delivers what we expect, a great conversation exceeds our expectations. As powerful as the human imagination is, even if everything went according to our plans, we’d still live smaller lives.

Stepping into a conversation expecting to be surprised means being open to possibility. Even the toughest conversations can be opportunities for transformation, if we look carefully.

It’s hard to dig deep during a conflict to find common ground or to discover where the issue started. I’ve walked into firing squads and walked out with friendships intact because I was willing to listen and be patient with my own panic.

That’s the power of conversation to transform lives.

From Defaults to Design

I didn’t write this book just to help you have good conversations. This book exists to help you break through to a new level of communication and collaboration within your team, in your organization, and in your life. That’s my passion and my purpose—helping teams and organizations work together better, by talking and collaborating more mindfully. The problem is, most of our conversations run on a multitude of default decisions.

When we come together to talk with a person or people, the conversation starts in a familiar way: someone kicks things off and someone responds. Then, a free-for all ensues. The conversation ping-pongs back and forth, with everyone taking a turn whenever the urge strikes. When conversations are left to these default, unconscious patterns, they can wind up going in circles and causing heartache.

What if we (insert idea)?

We tried that last season.

Oh, okay.

Why is it okay for us to generate and critique ideas at the same time? Why are we sitting around a table looking at a screen? Why aren’t we going for a walk and talking about this? Why are we having this conversation over email? Why are these the default choices? Who made them?

Instead of default decisions, we can make mindful, intentional choices and design our conversations, for the better.

Your Work Starts Now

Being intentional and mindful about all the conversations in your life might sound like a big task, and you’re right: it is. And the bad news is, I can’t do any of that work for you, but I can create time and space for you to do it and ask you some helpful questions.

Throughout the book you’ll find boxes like the one below that are there for you to slow down and internalize the material in the book. Each box asks you to find ways to make the principles practical in your work and life. I’m going to throw a lot of concepts at you and I want you to take some time to absorb them. The best way to do that is to create a space for your internal conversation. Grab a pack of three inch sticky notes and get started. Reflect on the questions in the box below. Jot your thoughts on a sticky note, and stick it here.

+What’s one conversation that matters in your life?

+If you woke up tomorrow morning and that conversation was magically transformed for the better, how would it feel?

+How would you know things had changed?

+What are the default choices in the conversation?

+What can you shift that might help make this change possible?

The Conversations We Won’t Have

A friend of mine (let’s call her Eleanor) was annoyed that her brother never called her. She always had to call him.

Have you told him that you wish he’d call you more and how much that would mean to you?

There’s no point, she replied. He wouldn’t get it.

And there the conversation ended, before it even started.

If she won’t bring it up, she is 100 percent correct. He will never get it if she doesn’t find a way to share it. Unless she’s willing to be surprised, she’ll never try.

+What’s one conversation that is hard for you to initiate?

+What’s at stake?

+What’s an ideal resolution look like for you?

+What does an ideal resolution look like for your counterpart?

+Jot down a few words about that on a sticky note and place it here.

Organizations Are Limited by the Conversations They Won’t Have

Organizations, in essence, are simply a conglomeration of conversations and the people who have them. These people are connected, not just through economics but through relationships. Those relationships dictate which conversations they’re supposed to have. Individuals are meant to talk to some people and not to others. We’re supposed to talk to certain people before we talk to other people. And there are definitely things we’re not supposed to talk about.

Just like a person can’t get what they don’t ask for, an organization can’t do what it can’t talk about. The conversations they can’t have limit them entirely. What seems impossible in one organization might be a simple task at another, a non-event. Asking for a meeting on a topic that’s taboo or tender might be blisteringly political and risky…or it may be welcome.

Ed Catmull, president of Pixar says, If there’s more truth in hallways than in meetings, you have a problem. If you can’t even talk about something in the hallways, you have a bigger problem.

Like positive and negative numbers canceling each other out, the conversations your organization isn’t having can negate the impact of the conversations they are having.

Choose Your Own Adventure

A client of mine (let’s call her Samantha) was head of the design organization for a conglomerate of fashion brands. She’d been hearing frustrated reports from her Design team: The Sales team wasn’t listening to their ideas. Meanwhile, the Sales organization complained to Samantha that the Design team would bring half-baked concepts to meetings that their customers would never buy.

Samantha felt stuck. She wanted her Design team to push the boundaries and create new products that their customers would love. But without cooperation and insights from the Sales team, these products wouldn’t sell. How could she help these two feuding teams see eye-to-eye?

Should she:

A.Teach the design group some strategic frameworks to help ground their ideas and communicate them better?

B.Bring Design and Sales together to teach them both a shared set of critique skills?

C.Bring Design and Sales together to discuss the tension, and ask them how to proceed?

D.Break the big, messy design versus sales conversation into smaller discussions, based on the brands they each serve?

E.Something else?

What Conversation Is Possible?

Samantha came to me for help. Given her budget and timeline (small and fast), I suggested a combination of C and D. I sketched a workshop inspired by the open-space conversation model (page 60) where all interested parties in Sales and Design could talk about how they currently pitch and critique, and then develop a new way forward collaboratively. Why this approach? Sales and Design have very different perspectives on what the problem is. New skills (A or B) won’t solve an unwillingness to work together.

Samantha assured me that no one would come to a cross-brand effort, as each brand was only concerned with their own work. We would have to work team by team, via option D. No other conversation seemed possible, unless the CEO got involved to motivate (i.e., force) people to show up.

+What’s one conversation that is hard for your organization to have?

+List all the stakeholders you’d like to include in the conversation. What would it take to get all of them to the table?

+If they came together and had a surprising conversation, what could be possible for your organization?

Leaders Create the Conditions for Transformative Conversations

Eleanor and Samantha both had the opportunity to start fresh conversations that had the potential to transform their relationships with the people involved. Both hesitated to invite a deeper or larger dialogue. Both were limited by what they thought was possible, neither was willing to be surprised. Based on their understanding of the power structures at play, the willingness of people to engage, and who’s turn it was to do something about it, they both decided that no good options were within their power.

Instead, each was hoping for someone else to lead the transformation, to open the door. Neither felt the reins were theirs to take. But leadership isn’t a title; it’s a role that anyone can take on at any time. Anyone can, at any time, guide a conversation through a hard topic by bringing a willingness to engage and the right questions.

Waiting for someone else to act won’t do. If we see the problem, we have to do something about it. If we want others to open up to new possibilities, we might try to open as well. It’s our responsibility to frame the challenge so that others can be open to exploring the issue. This is what an old business partner of mine called making problems huggable. If we can approach the problem together, we can solve it together.

These conversations can inspire new futures. We can create the conditions for these types of conversations intentionally, by design.

Drawing Conversations

+Try drawing your organization, not as an org chart but as a web of conversations.

+Which conversations are easy and fluid?

+Which conversations are isolated?

+Which conversations are difficult and prickly?

+What conversations aren’t happening?

+It might take more than one sticky note to draw - you might need a whole whiteboard.

We Design Important Conversations