To be a great leader, you need to become a great listener. Here are 3 skills to master

I used to have a manager who worked for me and would often come to me with a tricky problem to be solved. We would go to a conference room and she would explain the details. I would ask a few questions, but would mostly listen. After about ten minutes, she would jump up, having solved the problem herself and exclaim, “Thanks, you really helped me!” 

I didn’t have any answers, but my listening helped her find them. One thing I’ve noticed teaching undergraduates is that we train people to give answers, but not to ask questions and listen. By the time they reach my classroom, my students have had an impressive history of academic achievement and will likely go on to prestigious careers.

Yet most will struggle with what is perhaps the most important leadership skill for both business and life: listening. The truth is that leaders rarely get to make decisions that have quick, easy answers. Anyone can handle those. To handle genuinely difficult issues, you need to learn to be a great listener. Here are three listening skills that are easy to learn but take a lifetime to master: 

1. Listening for comprehension

Kevin Sharer was a tough, strong-minded leader.  After graduating from the U.S. Naval Academy, he rose through the ranks to become a lieutenant commander before entering corporate America. Following stints at AT&T, McKinsey, MCI, and GE, he joined the biotech firm Amgen, where he eventually became CEO. Looking back, he wrote: “My approach was: ‘I’m the smartest guy in the room. Just let me prove that here, in the first five minutes.’ I would even interrupt people and tell them what they were going to tell me, to save us time so that we could get to the really important stuff, which was me telling them what to do. And I got away with it. 

Then the company faced a major crisis. The FDA identified problems with Epogen, a treatment for anemia that accounted for a third of Amgen’s profits. That led to restrictions on its use and a significant blow to the company. For the first time in its history, the company announced layoffs. 2,600 employees, or 14% of its workforce, would have to go.

Sharer realized that his leadership style was a big part of the problem and vowed to do better. Every semester in my class at Wharton, we play a video of him explaining how he changed. He said that he learned to listen for comprehension—not to critique, object, or convince—but to understand the information being put in front of him.

Listening not only increased his access to information, but it also showed respect for the people around him. They, in turn, felt empowered to go out and find new perspectives and insights, compounding the positive effects of those conversations. It also allowed him to relax. Without having to exert so much energy trying to control and dominate every exchange, he had more energy to devote to leading the company.

2. Asking deep questions

One of the most common mistakes leaders make is assuming that listening begins when someone else starts talking. In reality, it begins much earlier—with the questions you ask. When you’re in a position of authority, people naturally become more guarded about what they share.

In Supercommunicators, author Charles Duhigg makes the case that the best communicators aren’t simply better listeners. They’re better at asking questions that encourage people to reveal what they’re really thinking and feeling. Rather than interrogating people for facts, they use questions to uncover motivations, concerns, and assumptions.

That’s why great leaders ask questions that reveal motivations and feelings, not just facts. Instead of asking, “Why are you resisting this?” they might ask, “What concerns you most?” Rather than responding to an objection with an explanation, they might ask, “Tell me more about that,” or “What am I missing?” Questions like these signal genuine curiosity rather than a desire to persuade. They invite people to share information that might otherwise remain hidden.

The goal isn’t simply to gather more information. It’s to understand the person sitting across from you. When people feel understood, they’re far more likely to speak candidly, surface problems early, and offer perspectives that improve decisions. The best leaders know that the quality of their decisions depends on the quality of the conversations that precede them. Those conversations begin with thoughtful questions.

3. Promoting metacognition

Listening isn’t just about understanding what others are saying. It’s also about helping them understand their own thinking. Psychologists call this metacognition, the ability to reflect on our own thinking. Great listeners encourage it by helping people examine not just what they believe, but why they believe it, which draws out their thought processes and motivations. 

One simple technique is to ask people to rate their confidence. You simply ask your interlocutor to rate their certainty about a specific issue, such as, “You seem to feel pretty strongly about this proposal. If you had to rate your certainty that this is the right way to go on a scale of 1-10, what would you give it?” Then you can ask why they chose that number, why not higher, why not lower, etc. 

Other techniques are mirroring and labeling. Mirroring means simply repeating the last one to three words the other person said. It’s a simple technique that gets them to expand their thoughts in a way that triggers more reflection. Labeling helps validate their feelings by putting them into words with phrases such as: “It sounds like…”, “It seems like…”, or “It feels like…”.

By combining these techniques with an active listening posture, you encourage others to share what they’re thinking and feeling in a thoughtful way. You aren’t challenging them, you are doing something better: you are encouraging them to challenge themselves in a way that is non-confrontational, but leads to more rigorous conversations. 

Creating safety to operate effectively

People tend to become leaders by first becoming great performers. In school, they raise their hands first and give the right answers. As they begin their career, they learn to speak up in meetings, deliver slick presentations and develop smart strategic plans. They work hard, push their teams harder and do what they need to to win. 

Yet leadership isn’t about performing, it’s about raising the level of those around you and for that you need to create an environment where people feel safe enough to do their best work, share ideas even before they’re fully formed and to collaborate with colleagues in a productive way. Part of that is how you hire, manage and discipline. But the most important thing a leader can do is learn to be a great listener. 

Fortunately, these skills can be learned. David McRaney’s How Minds Change offers an excellent introduction to techniques like Deep Canvassing, Street Epistemology and the Change Conversation Pyramid. Chris Voss’s book Never Split The Difference is another valuable resource, and many of his talks are available online for free.

Yet the most important factor is your desire to overcome years of training and education that rewarded you for speaking up first and delivering the “right” answers in the shortest possible time. In the real world, when you deal with tough, complicated issues, you never know what the “right” answer is. You only have the answer based on your best information.

How good that information is depends on how well you listen.