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Leadership-Level Listening: 3 Skills to Build, 4 Bad Habits to Break

Too often, leaders neglect to build up their listening skills as they advance, which can lead to alienating key talent and missing critical information. Here's how to turn that around.

manager listening to an employee

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A family friend called me the other day for some career advice. He’d hit a ceiling in his and didn’t understand why—and I couldn’t tell him. More accurately, I could have, but it wouldn’t have helped. The listening skills that served him well enough to reach his current role weren’t sufficient to excel in his new position, where listening had become both more critical and more difficult. And so, we had a talk about listening.

It’s something I see frequently. Executives who don’t step up their listening skills as they advance undermine their leadership on two fronts: they miss crucial information, and even when they don’t, if their listening style doesn’t make their people feel heard, it alienates them.

Leadership-level listening requires new mental models and deliberate practice, but it may be the secret superpower behind continued advancement. Great leaders are expert listeners. They avoid the four most common listening mistakes, practice three key listening skills, ask two kinds of listening questions, and summarize their learning with one final technique. It may sound daunting, but I’ve found the simple practice of mentally counting down, “Listening in 4-3-2-1″ helps me remember the basics, stay focused and get more out of conversations.

Four Bad Habits to Drop

1. Multi-Tasking 

Leadership often comes with a seemingly endless to-do list which can make multi-tasking look like a reasonable solution. But multitasking is really the art of doing two things badly instead of one thing well. Model the focus you want to see in your people. They won’t be inspired to come up with innovative ideas or motivated to work their hardest for you if you’re unfocused or distracted. Allowing your attention to drift erodes trust, undermines confidence, and sets a bad example. Avoid letting your mind wander or dividing your attention between tasks when listening.

2. Listening With a Goal in Mind

Leaders are typically goal-oriented problem-solvers, but listening with a goal in mind puts a filter on the conversation that can lead you to miss crucial details. Rather than bringing a preconceived agenda to your listening, try to keep an open mind. Hear all of what the other person is actually saying rather than listening selectively to the portions of their message that are relevant to your goal. It may seem paradoxical, but you’re more likely to achieve your long-term leadership objectives by discarding conversation-specific goals. Make understanding your only conversational goal.

3. Judging  

After listening, decision-making may be the core skill of leadership. In fact, according to research by the consulting group McKinsey, executives spend almost 40% of their time making decisions, but the evaluative skills needed to make good decisions can create interference for a leader’s listening. Mentally critiquing or judging the content or disagreeing with the presentation of the speaker shuts down our ability to understand their perspective. When you listen, try to suspend judgment, and just listen.

4. Preparing Your Response

Leaders often rise to their position because they have an innate bias toward action. It’s a positive attribute that can have negative consequences for listening, as it can be frustrating for this personality type to stay present and listen patiently. If you find yourself starting out well and listening attentively but then starting to prepare your response before the other person is finished speaking, this kind of outcome-driven impatience may be the cause. Remind yourself that there’s always more than one purpose to any conversation. Yes, you want to understand what the other person is saying, but if you move on as soon as you “get it,” you’re not communicating the respect people need to feel confident sharing their ideas with you in the future. Learn to listen until the other person is finished before you formulate your reply.

Three Skills to Build

1. Engagement 

High-level listening begins with engagement, so go all in when you listen. Giving your full, undivided attention to the speaker is so important that it’s worth doing some advance planning. I try to make sure my phone is face-down and beyond arm’s reach before I join a video conference and whenever I’m preparing for an in-person conversation. Being (and staying) fully present is challenging, so set yourself up for success to avoid the bad habit of distraction and master the skill of full engagement.

2. Attunement 

The second skill of great listening is tuning into what the other person is saying with empathy. Try to put yourself in their position and see things from their perspective. If you want to see attunement in action, watch musicians. They’re literally tuning into each other to synchronize rhythms and harmonize pitch. When you’re attuned to the person you’re speaking with, you’re doing the same kind of calibration—not with the sound of their words, but their meaning. Pay attention to nonverbal signals and listen for what they’re not saying. What’s motivating their words? Hear what they’re saying but listen even more closely for what they mean.

3. Respect 

Even if you’re giving the person your complete attention and are attuned with them, if you don’t believe in the intrinsic value of their opinion, they’ll feel your lack of respect. As you move up the professional hierarchy, it can be tempting to feel superior to the people you lead. You may know more than they do and have more experience, but if you can remind yourself to stay curious about people, you won’t have trouble recognizing—and respecting—your shared humanity. Respect is a critical part of good listening, and good listening is a fundamental mark of respect; it’s also the foundation of a healthy company culture. Nothing is more toxic to a workplace (or relationship) than respect’s inverse—contempt.

Two Listening Questions to Ask

If you can master the three skills of listening and avoid the four mistakes, you’ll already be a better listener than most, but to really level up your listening game, you must do more than listen. We tend to think of listening and speaking as separate, even contradictory skills, but asking thoughtful questions is a part of listening.

1. Clarifying Questions 

Ask clarifying questions to help you zero in on facts and confirm details. This shows close and careful listening and avoids the kind of minor confusion that can result from unchecked assumptions. Clarifying questions are also great memory aids for everyone. A simple, “So you said the report will be ready by 3:00, right?” tells the person you heard them and sets the deadline more firmly in both your minds.

2. Diagnostic Questions 

Diagnostic questions are more open-ended and can deepen your understanding. If you’re listening empathetically to what the other person isn’t saying, diagnostic questions are an opportunity to confirm or refocus your insight and to guide the conversation. Diagnostic questions help you go deeper. These are howwhat, and why questions like “What happened next?” or “Why do you think that the sales numbers are down?” and even, “How did you feel when that happened?” These questions guide the conversation by directing the speaker’s attention and asking them to think more deeply about one aspect of the situation. But remember to be subtle. Questions like, “Why didn’t you just do X?” aren’t diagnostic. They aren’t even really questions.

One Reflection Technique

When you’re listening to understand, check your understanding by paraphrasing to reflect back to the person what you’ve heard. Reflection is especially powerful when you’re listening to help someone solve a problem. Done clumsily, this is just a summary or repetition of the person’s main point in their own words. At a higher level, it’s a three-part process of paraphrasing, confirming, and restating. This “paraphrase sandwich” puts the person’s message in your own words to show that you get it and aren’t just parroting what they’ve just said, then demonstrates respect by asking for confirmation and concludes with a final restatement to build understanding.

If you can express their thoughts more succinctly and clearly than they have, you help them make sense of their situation. If you’ve heard what they didn’t verbalize but expressed in their tone of voice or body language and included it in your paraphrase sandwich, they’ll feel deeply understood and often better understand themselves as a result.

As leaders rise through the ranks, they need to evolve their listening skills or risk career stagnation. By avoiding common mistakes like multitasking and judgmental thinking, honing skills like engagement, attunement, and respect, strategically employing clarifying and diagnostic questions, and using reflection techniques, executives can unlock deep understanding. Superior listening builds trust, connects people, uncovers opportunities, and accelerates decision-making. It draws out fresh ideas and unlocks innovation. For leaders facing increasingly complex challenges, listening is quite simply a superpower – and it can be honed through deliberate practice. Make a commitment to level up your listening. Not only will your career benefit, but you’ll build stronger teams, boost organizational culture, and potentially transform your entire leadership impact.


Damon Lembi is is CEO of Learnit, a learning and development company, and the author of The Learn-It-All Leader: Mindset, Traits and Tools (Lioncrest Publishing, Spring 2023). This article is adapted from with permission from Chief Executive. © 2024. All rights reserved.


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