When Jim McCann says, "Tell me something I don't know," he's not being sarcastic. McCann is CEO and founder of 1-800-FLOWERS.com, the $735.5 million florist and gift company, based in Westbury, New York. His recent book, Talk Is (Not!) Cheap: The Art of Conversation Leadership limns a management style based on curiosity, relationships, a sincere interest in other people, and a smidgen of goofiness. In a recent conversation, McCann explained to Inc. editor-at-large Leigh Buchanan how he chats, jokes, and queries his way to insights and information.

You are the boss. How do you put people at sufficient ease to have a conversation with you?

There are two things. This goes back 100 years to when I worked in a group home for young men. The mistake I made at first was to try to have a relationship with the group. You don't have relationships with groups. You have relationships with individuals. I had to find different ways to make contact. There was this one kid, Joe, who was very tough to connect with. He had a touching issue. If you touched him, he would go off. Lose control. It was very tough for me to reach Joe. But, slowly, we built a relationship. It got so that on my shift, when I first saw him, I would purposely bump into him. Two months earlier, that would have caused a riot. But now he realized that was our special way to say hello. It would go to the extreme where I would sneak up behind him--he always knew I was coming--and I would mess up his hair. He had long black hair that was always combed just so with a clean part off to the side. He'd say, "Oh, he did it again." And he would have to go to the bathroom and comb it, just so. That's my thing to this day. I don't always mess up people's hair. But if you are walking down the hall, I will make believe I am bumping into you. Or I'll make believe I am going to trip you while I am standing there in conversation with someone else. You can't help but laugh. And you get the sense that I am approachable and that I want this to be a place where we don't take ourselves too seriously. So I use humor and I use the bump.

How do you turn a meeting into a group conversation?

People value the conversation proportional to the time they participated. So if we are doing a dinner, if we are doing a meeting, I want everyone to speak. We're not leaving the room until everyone contributes. I did a dinner at Cheryl's [a cookie company owned by 1-800-FLOWERS.com] a couple of weeks ago. Everyone expected they would have to sing for their supper. They knew that I would want to know what's new and what's interesting. What ideas do they have for the business? But first I want to know about them. Something I didn't know already. If they are new, I am going to ask a lot more stuff. This time, instead of calling on everyone, which I would have done in the past, I called on the first person and said, "After you talk, your job is to call on the next person. And it can't be the person on either side of you." So now they are looking across the table at each other: "Oh, I knew you were going to pick me!" It was real good relationship building. We had a debate at our end of the table about how big the company could get if it just focused on cookies. It was a great conversation. Three hours in, nobody was looking to get up and leave.

You describe yourself as a "walkabout" CEO. Do you do that in a systematic way or just kind of wander?

It's not systematic. It's a chance for me to stretch my back as well as get a feel for what's going on and create a level of casualness. So I might just pop into a meeting. I might start a conversation with someone in the hall. Then two other people come off the elevator and I will call them over and say, "Hey, we were just talking about this." The conversation starts to take shape. Eventually, I suggest "Why don't you guys meet with Mark about that? Because I think it suggests a whole different direction for us in point of sale." And then I am able to leave the conversation and they follow up on it. So I am the instigator. I cross-pollinate.

If a conversation isn't going well or you're not getting much out of it, how do you get it on track or politely bail?

Say I'm interviewing someone, and after 10 minutes I know they are not right for the job. How long do I need to talk to them from a courtesy point of view? Selfishly, I am going to steer the conversation around to something that is helpful to me. I'm going to turn them into a focus group on B-to-B business. I am going to turn them into a focus group on the brand or consumer behavioral patterns. I'm going to find out if they have children and, if so, how old they are and what kinds of technology they are using. Are they still on Facebook or is everything now Instagram or texting? What price point would they pay for this product? What companies have they had contact with recently that impressed or disappointed them? Why? I am going to turn the dialogue into something I can learn from. I am going to make the remaining 20 minutes interesting to them and to me.

When and why do you sometimes practice conversations in advance?

I did that today. My brother [company president Chris McCann] and I were talking about someone in a performance situation. I told him exactly how I felt about it. He said, "There are five things I heard in what you just said." And then I took those five things that he told me, and I said, "These are the messages. Take the emotion out of it. How do I want to start? How do I want to leave it?" That's what I mean by practicing. It's especially helpful if the conversation is around a negative situation, where you really have to take a person to task. You lay it out unfiltered at first with someone listening to you, or you tape it. But it's better if you can do it with someone who knows you and whom you trust. They can help to make sure you are getting across the important things, putting the right emphasis on them, and getting the outcome that you want.

I like this idea of leaders being intrigued by a word or phrase used by someone else and then using it themselves in conversation to see how others react. David Kelley of IDEO described something similar. He said he keeps trying different things on different people until he sees "a sparkle in their eyes." What's your version of a sparkle--where you know some word or idea you're putting out there is catching on with people?

Vocabulary matters a lot. Not long ago I was having a conversation with my brother Chris about how we need to fine-tune things. You get expense creep everywhere. I said, "We need to come up with a new program." So starting this spring we will look in the organization to say where is there some waste? Where is there inefficiency? Chris and I batted around three or four names for the program. Now we will be socializing those names in our conversations with people, trying them out until we see a look of real understanding in their eyes. "Ah! Got it!" We call that "wallowing." We will be wallowing around on those names until we find the one that best describes this program.

How do you turn a short-term conversation--two people chatting in the moment--into a conversation that ranges over time and multiple media to develop important relationships?

It's about making an investment. I met a fellow a few months ago, whom I thought was a really neat and interesting guy. I wanted to keep the dialogue going. So I read a couple of articles on things I thought would be appropriate for him. I sent him a copy of an article, and I wrote in the margin, "When I was reading this, I thought about the problem you were talking about. I was wondering if this was relevant to you?" So he knows I am still thinking about the things we talked about. That I am investing in the conversation, the relationship. He gets two or three of those. And then, just the other night, he says, "We're getting a group together to go to Madison Square Gardens to see the Nets versus the Knicks. I thought you might like to join us." So now we're both investing in this relationship. It's about caring. You take a lot of notes during conversations.

Any best practices there?

I'm always writing when I am talking. I make different symbols or circles or squares around things that are important. If I talk to somebody new, I will dictate for the Rolodex their personal information so if I chat with them again I can refresh my memory. It's the kind of thing [businesspeople and motivational speakers] Harvey McKay and Zig Ziglar used to teach. I'm always taking notes, at our dinners, during conversations. I don't do it when I'm standing by someone's desk and get two or three people talking about something. But if a couple of points come out of that, then when I get back to my office, I'll whip out my iPhone and do voice notes so I can follow up later. I often ask them for a scrap of paper out of their garbage pail to make sure I don't forget.

Do you try to turn your presentations into conversations?

It depends on the audience: the size and the circumstance. I did a presentation last week with 35 or 40 people in the room, and the fellow who runs it wanted to do a Q&A with me. But there were all these interesting entrepreneurs there. And I said, "I want to enjoy this too. So if you want to have a conversation, let's have a conversation. But I want to have a conversation with this audience." There were two chairs at the front, but I said, "If you don't mind, I'd rather not sit. I'd rather move around." After he went through his first couple of questions I said, "I'd like to know who some of these folks are." So we went around the room, and it really got good. It became fun because they were participating. It was supposed to be 50 minutes, and I think it went two and a half hours. It's different in a big room where you have to wait for people to get to the microphone. People at conferences always say, "Our people want Q&A." But if it's a big room, I try to talk them out of it. If you've got a good momentum, it interrupts the flow. I'm happy to talk to people afterwards.

Zappos gets a lot of attention for hiring nice people who are willing to chat helpfully with customers for as long as those customers want. You folks were doing that 20 years earlier. How did you figure out that a practice so seemingly inefficient actually made good business sense?

We had a call center in Worcester, Massachusetts in the late '80s, 'early 90s. This guy, Vinnie, a former New York City policeman, was managing it. There were all these people sitting in rows, working on screens with their headsets on. One day Vinnie was walking around, and he had a roll in his hand of smiley face stickers. Every so often he would walk over and put a sticker on the frame of someone's computer. He didn't say why. People were wondering, what's he doing? Now some people have 10 stickers around their screen. Now some people have their computers completely covered. Vinnie's starting to put stickers on people's foreheads. And the place is a laugh fest. Because people realized: whenever Vinnie saw somebody smiling when they were on the phone, he gave them a smiley sticker. He did this for hours. Yes, it was corny. But he had created a currency, and he was rewarding the behavior he was looking for. When we looked at the stats at the end of the day, we had the highest close percentage, the best customer satisfaction scores, and the highest average tickets. Because people were enjoying what they were doing. That lesson became an important ingredient in what we do to encourage our service folks to laugh with the customers, to compliment the customers, to smile on the telephone. Because you can't help but hear it in their voice. Zappos invented the branding around it, which is clever. When I was reading about Tony Hsieh, it reminded me that everything old is now again.

What things can leaders can do today to become better conversationalists?

One is be genuinely interested in what other people have to say. Listen more than you talk. And be self-deprecating. Let people know that you don't mind putting yourself at the risk of embarrassment to make them feel relaxed.