How to talk to a chief executive

By Dale Dauten  |  October 28, 2007

"A conversation is a dialogue, not a monologue. That's why there are so few good conversations: Due to scarcity, two intelligent talkers seldom meet." - Truman Capote

Years ago, I saw a television interview with Norman Mailer. The interviewer was working from a legal pad with a list of questions, and Mailer seemed to find all the early ones beneath him. Finally, sighing, he leaned toward her, pointed at the legal pad and said, "What's on the next page?"

Did that help the conversation? No. But it could have, if the interviewer had responded with something like, "Well then, tell me about the best question you've ever been asked?" or maybe, "I could learn something here - what makes for a great conversation."

What got me thinking about great conversations was listening to a series of them, ones good enough to teach us about being a corporate conversationalist. They're from the series "Conversations From the Corner Office" by Kai Ryssdal of the radio program "Marketplace," which airs on public radio stations. (The interviews are available as podcasts, free via marketplace.publicradio.org/RSS.)

Having gotten to observe many executives, I know that being part of genuine conversations can be difficult for them. The people they meet are often busy trying to be impressive, and people trying to be impressive tend to be sycophants. (Ironically, while the word "sycophant" has come to mean "servile flatterer," its origin is Greek, "show," and Latin, "informer," two words that suggest the revealing of truth to authorities.) Thus they are insulated from unwelcome truths. It's a hard art, learning to get people to tell you what you don't want to hear.

But back to Ryssdal and his conversations with chief executives. Sometimes he merely asks about the tough times, and an expressive executive - like Howard Schultz of Starbucks - comes through with a great story: "In 1986, with my wife pregnant with our first child, her father asked to come over and see me. This is the early stages of the kernel of the idea (of Starbucks), and I was not drawing a salary. We go for a walk and he says, 'With my daughter 7-8 months pregnant and her working and you not bringing in a salary, I want to ask you to do something: Give up this dream/hobby and get a job."

Schultz then describes how he started crying, too embarrassed for words. Who, who has ever dreamed, cannot relate? However, Ryssdal is at his best when his executive is at his worst as a conversationalist. For instance, he takes Joe Gallo, the chief executive of the wineries, and offers him up a chance to reflect: "Did you ever want to do something else with your life?" He gets, in return, this reply: "No." Thud.

But Ryssdal knows how to keep the conversation going, later asking, "What do you want out of the third and fourth generations of Gallos - smart businesspeople or great winemakers?" No "yes" or "no" possible there. Instead, Gallo laughs, then opens up. He is engaged. And so are we.

I spoke with Ryssdal and asked what he'd learned about how to talk to executives. He said, "They are just regular people," and then reminisced about the best answer he ever got. He'd asked Scott McNealy of Sun Microsystems about his legacy, thinking that McNealy would talk about his company and/or his innovations. Instead, his response was a simple, "My boys, my four boys." Ryssdal added, "Numbers aren't what make these guys tick."

That takes us to a movie from 1974 called "The Conversation," where Gene Hackman plays a surveillance expert whose job it is to listen in on conversations. At one point Harrison Ford's character tells him: "I'm not following you, I'm looking for you. There's a big difference." That remark summarizes just what it takes to have a great conversation. You don't "follow" a list of topics or questions, you don't even "follow" what the executive is saying; rather, you "look for" the executive, seeking the person within, the one who was there long before the title.

Dale Dauten is a syndicated columnist. He can be reached at dale@dauten.com.