Podcast: Celeste Headlee on How to Have Conversations That Matter

Communication is the lifeblood of leadership—if you can’t communicate, you simply can’t lead. Good communication starts with good conversations: Conversations that are real; conversations that matter.

In this episode of the Leadercast Podcast, we're joined by Celeste Headlee, an award-winning journalist, professional speaker and author of We Need to Talk: How to Have Conversations That Matter. Celeste tells us about how a failed conversation spurred her to learn about how leaders should communicate.

“I was a professional interviewer,” says Celeste. “What I did for a living was talk to other people.”

She thought her conversation skills were well above the average person’s. “It took a disastrous failure in expressing myself in a very important conversation that made me realize I have some major improvements to do,” she explains.

Celeste did all the right things: She prepared for the conversation, did her research, and practiced and rehearsed. “Still, I was sitting there in the middle of that conversation with my boss and realizing he's not hearing me and I'm not expressing what I need to express,” she says. “It was a real eye-opener.”

Celeste used that experience to become a better communicator, and in this episode, she tells us what’s wrong with communication, how to set it right and how leaders can start having better conversations.

The Decline of Communication

Communication isn’t what it used to be, and you can’t completely blame technology, says Celeste. “We have been avoiding conversations for way longer than cell phones and smartphones have been available,” she explains.

She blames fear: the fear of conversations going wrong; the fear of not sounding funny or smart; and the fear of conflict. Technology helps us avoid that fear so that we never have to have conversations with faces and voices. “This means we never get over that fear. In many cases, it just gets worse.”

When to Communicate via Email

Celeste shares a short list with just four items for how you should converse using email: when you have an attachment, when the letter is really long, when you have a list of any kind and when you want to give someone praise (people like to read their praise over and over and forward to their loved ones).

The truth is you can’t lead through email. “In order to lead, you need to hear people's voices and see their faces,” says Celeste.

The Most Important Part of Communication Is...

Listening. It’s been demonstrated clinically that your enjoyment of a conversation goes up as you talk less, she shares. “So if you are learning to listen more, it will be self-rewarding.”

Listening is important because, pragmatically, you already know everything you’re going to say, she says. “If you're going to learn, it's going to have to be from other people.” TWEET

Second, listening increases empathy, which is a crucial survival skill. If you’re at work and someone comes to you saying, “Hey, I know this isn't part of your job description, but could you do blah, blah, blah?” Then you’d say, “Of course!” Because the two of you have a shared goal, which is the success of the business itself. “Hearing someone else's perspectives and experiences gives you a huge boost to your empathy,” says Celeste.

Finally, listening takes practice. “You have to acknowledge that it's hard,” she says. You have to work at it the same way that you go to the gym. “Human beings are not good listeners evolutionarily and biologically,” she adds. “Every single day, sometimes multiple times a day, you’ll have to remind yourself, ‘Oh, my mind is wandering. I need to bring it back and listen to what this person is saying to me.’”

3 Best Practices for Listening in Leadership

A conversation at its heart is a mutual exchange of ideas, explains Celeste. If you lead a conversation in which you've learned nothing, you haven't had a real conversation. She shares three qualities of effective listening in leadership:

1. Brevity

Keep conversations (and meetings) short. As humans, we can only hold about three things in our minds at any given time, she shares. “Don’t have a laundry list of things that you’re telling people on and on.” If it’s a list, send an email.

2. Engagement

By focusing on interacting with the other person, you will keep them engaged and allow yourself to listen better. Ask questions and think about the answers. “If you want to listen better, become better at constructing a conversation that is easy to remain engaged in,” says Celeste. TWEET

3. Honesty

Listening is a skill you have to build. Sometimes, that means you have to stop and ask questions when you don’t understand something. “It's important to say, ‘I don't know,’ or admit, ‘I got completely distracted. My mind went wandering. I'm really sorry. Could you repeat that?’” she says.

If you can’t come clean about that, you’ve missed out on the conversation. “A real conversation—a good conversation—is one in which you've really heard and understood what the other person is trying to tell you and you've expressed yourself in a way that they understand what you're trying to say,” says Celeste. TWEET

How many real conversations are you having with your team?

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This post is based on an episode of the Leadercast Podcast with Celeste Headlee, author of We Need to Talk: How to Have Conversations That Matter and past Leadercast Women speaker. She has a new show, Retro Report, debuting this fall on PBS. Learn more about Celeste here. To hear this episode, and many more like it, subscribe on iTunes, Spotify, Google Play or Stitcher.

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