Courage to Ask, Confidence to Listen
Before Walter Isaacson was a world renowned biographer, he was a lowly high school student working a summer job at a New Orleans newspaper.
On his first assignment, he was covering a child’s murder. Isaacson called the story in to his supervisor who peppered him with questions. “What did the parents say the kid was like? Did I ask for baby pictures of him?”
Isaacson pushed back. He said the family was grieving and he didn’t want to bother them. Isaacson’s argument didn’t sit well. His boss ordered him to knock on the door and talk to the family.
So young Walter trudged up the sidewalk and tapped timidly on the door. To his surprise, the family invited him in, pulled out photo albums, shared stories, and cried. The mother even apologized, saying, “I hope you don’t mind me telling you all this.”
The experience taught Isaacson an important lesson: people like to talk. To get a good story, all you have to do is ask and listen.
This lesson applies beyond journalism. To get most of the things you want, all you need is the courage to ask and the confidence to listen. Ask genuinely, listen intently, and you shall receive.
Courage to ask
Joe Ferraro, a recent guest on my podcast, shared the story of how asking a question led to a drastic improvement to his podcast.
Joe was listening to music on his phone when he was interrupted by an advertisement. The ad was for a meditation app, and the voice pumping through his headphones was mesmerizing. Joe was captivated by the soothing sounds entering his ears. If only I knew the name behind the voice, he thought.
That’s where most people would stop, but being a man of action, Joe acted. He found the creators of the app and sent them a DM complimenting the ad and asking about the voice behind it. They responded almost instantly.
“That’s Ken Scott,” they said. “He’s the best in the business.”
Joe didn’t stop there. Again he reached out, this time to Ken, asking if he would be willing to do the voiceover intro for Joe’s podcast.
“I probably can’t afford you, but would you be interested in helping me out?” asked Joe.
To his surprise, Ken was willing. He gave Joe a special discount, they recorded the intro, and now Joe has one of the best introductions in all of podcasting. All he had to do was ask.
Confidence to listen
The second part of Isaacson’s equation is listening. Asking a question doesn’t do much good if you don’t bother listening to the answer. Too many of us are rushing to fill the silence and giving away value in the process.
The ability to listen is an interesting skill because it has two opposite but equally useful benefits. In the first context, good listening skills induce a feeling of comfort and happiness in your counterpart. Your ability to remain silent—or to offer slight prompts and non verbal engagement—will yield exciting stories and interesting conversations. Knowing when to keep your mouth shut and let the other person talk will ensure everyone enjoys chatting with you.
The trick is confidence. Have enough confidence that you don’t feel the need to talk about yourself. Have the confidence not to worry if your turn to talk is preceded by a few moments of silence. Engagement as a listener draws people to you, and it helps you learn things you wouldn’t learn if you were doing the talking.
The more you allow your counterpart to talk in a casual conversation, the more that person will enjoy talking with you. As he speaks, you collect information. When he ceases, you offer another prompt from the information you collected.
In the second context, listening can be a deadly skill. Sam “The Banana Man” Zemurray had a saying, “Sit and stare and let your opponent fill the silence with his own demons.” This was his version of listening.
It’s similar to the listening that Chris Voss teaches in his negotiation tactics. In a negotiation, you can use strategies called tactical empathy and labeling. Tactical empathy is understanding what your counterpart is feeling. Labeling is giving those feelings a name.
The scenario might sound something like this: “It seems like you’re worried about the interest rate on the loan.”
The next part of the strategy is listening. Use complete silence. If you can master the discomfort of silence longer than your opponent, he will fill the silence with information you can use to your advantage.
The more information you have, the better equipped you are to make a decision, leverage your position, offer advice, or capture a great story. The goal of most conversations and interactions should be information gathering.
Patience, listening, and embracing the discomfort of silence can pay off. He who remains quiet the longest will win. The person who caves to the discomfort of the deafening silence fills the air waves with concessions.
In the first context listening causes comfort. In the second it causes discomfort. Both outcomes can be beneficial depending on the situation.
A power combo
Like Isaacson found, asking and listening were the prerequisites for a good story. If you combine the courage to ask questions with the confidence to listen effectively, you create a skillset that repeatedly and consistently delivers the outcomes you want.
Never hesitate to ask a question, ask for a discount, ask for help, or ask for advice. It may feel uncomfortable in the moment, but the upsides far outweigh the downsides.
Always strive to listen intently. Whether having a casual conversation or navigating a negotiation, the better you are at listening, the better experience you will have.
Take an interest and a chance. You’ll hardly believe the good that comes from it.
Photo by Sam Forrest on Unsplash
