Skillful Conversations: A Practice Worth Perfecting

One night over dinner with a handful of agency leaders I didn’t know very well, I found myself deeply engaged in the most curious, magnetic and balanced conversation I’d ever had.

I remember wishing my brain had a video recording of it stored somewhere so I could return to it and study the craft I had just experienced and felt so in awe of.

It started with a simple question asked by the least-known guest at our end of the table: “So Jess, what was your first job?”

That question, so simple, yet masterfully posed—with connections created in and between and around each one of our responses—became the golden thread through a meandering three-hour dinner conversation that left five out of six near strangers feeling like lifelong friends.

Why five and not six?

Because the gentleman who initiated that conversation, let’s call him “Six,” nurtured it so selflessly over the course of the evening and with such deep curiosity about each person at the table that no one ever stopped to ask him questions about himself.

His superpower was his deft ability to keep all five of us engaged collectively with new questions that bred new connections.

It reminded me of when Charles Duhigg said that “conversations are the most powerful thing on earth” in his book “Supercommunicators.”

The subtly with which Six spun the most curious conversational web around our group was like watching a magician’s sleight of hand. We all experienced the magic—and most of us, so engrossed in the conversation, had no idea how it was done.

So began my obsession with skillful conversations.

Great marketers know the value of effective communication through skillful conversations. It’s a core ingredient for relationship-building.

It can ...

• Make or break a research team’s in-depth interview or focus group
• Build an engrossing story arc in documentary-style content
• Help strategists and brand leaders get to the root desires and goals of our CMO counterparts

I bet a multitude of examples are filling your mind as you read.

I believe that, as marketers, we can always be looking for ways to improve ourselves and the approach to our craft.

That takes time and self-reflection.

Our industry is constantly evolving, and we must do the work to keep up and stay ahead. With technology, trends, changing consumer behavior, best practices ... the list goes on.

It’s no wonder the last thing on marketers’ minds might be how to communicate better, whether that’s with each other or their customers.

It takes a self-aware marketer—a great marketer—to take that pause and realize that being able to create really strong conversations is a skill. One that every marketer has in their toolbox and should continue to improve.

Recognizing this is the first step. Going about it is the next.

One approach is using what Duhigg describes as the “How Do We Feel” conversation—those that are shaped by emotions and help build connections. To begin, “The best thing you can do is ask questions. Ask about people’s lives, about what they’re feeling, about their hopes and fears, and listen for their struggles, disappointments, joys and ambitions. Hearing people describe their emotional lives is important because when we talk about our feelings, we’re describing not just what happened to us, but why we made certain choices and how we make sense of the world.”

Six was exceptional at asking questions that connected a group of near strangers through storytelling.

The stories told had us enraptured. The connections created glued us together. There were no side conversations. We were in this conversational space with each other, entirely.

Let me start with a question:

How often have you experienced conversations where you’re interrupted? Even when the other person was the one who asked you the question?

Time, attention and connection vanish. Resentment for the emptiness builds.

It’s left me wondering what it really takes to capture someone’s focus in conversation.

Six inherently demonstrated a core principle that Celeste Headlee spoke of in her 2016 Ted Talk “10 Ways to Have a Better Conversation”—that a conversation requires a balance of talking and listening. The only talking Six did that night was when he asked another question or guided the group to a connection between us from something he had heard or picked up on that related to another person’s story.

Six used the 5 W’s, (who, what, where, when, why and how) to probe for understanding, and this caught on as others began asking questions of one another.

When someone shared a story, Six didn’t reply with his own story to match it or level up. Instead, he made space for another person to share theirs or would share a connection he’d identified through listening, then ask another question.

When someone else had been quiet for a bit, he’d reach out with a direct question to bring them back into the conversation or recall a connection from earlier that created a relation to the story being told.

Six was an orchestrator of meaningful conversation.

I remember asking him “How do you do this? Creating conversation comes so easy to you.”

Six replied, “I’m incredibly shy and so to help build my confidence meeting new people and interacting, I decided to practice asking questions. I keep practicing and, in return, I’m rewarded by learning something new about someone every time.”

Therein lies the lesson I took home—not just personally, but professionally, too.

As marketers, our jobs are never done. There’s always more to research, strategize, create and analyze. (Like I said, we’re constantly keeping up with all the things.)

We rarely stop to assess how giving others the space and time to talk, to share, to teach us something we didn’t know we needed to learn can actually be rewarding.

Asking questions and having conversations like this isn’t something you have to perfect before you can reap the rewards. As our friend Six has taught us, it pays off right away.

So I’d like to leave you with this thought ...

How would things change if you worked to improve the ways you create, engage in and fuel conversations with your peers?

With your leadership team? Your clients?

What about your target audience—your customers, even?

With your loved ones, too?

Ask more questions. It’s a practice worth perfecting.