Listening · 4 min read
The art of listening: what leaders rarely do
Most of the executives I work with are excellent talkers. They can walk into a board meeting and land a message in ninety seconds. They can read a room, adjust their pitch, hold a stage. What’s rarer, and what I find myself coming back to again and again in our sessions, is the ability to actually listen, to someone else, and just as importantly, to themselves.
I don’t mean listening as in waiting for your turn to speak, or listening as in nodding while your mind is already three steps ahead planning your response. I mean something slower and less automatic. The kind of listening that asks: what is this person actually saying, underneath the words they chose. What are they not saying. What would I hear if I weren’t so busy formulating what I think next.
This kind of listening is hard to practice at pace, and pace is the water most leaders swim in. Founders and senior executives are trained, often for good reason, to move fast, decide fast, respond fast. Speed becomes a proxy for competence. The person who answers quickly seems sharp. The person who pauses seems uncertain. So a habit forms, quietly, over years: process information quickly enough to respond, rather than slowly enough to actually understand. It works, until it doesn’t. Until a team member stops raising concerns because they’ve learned nobody really hears them. Until a founder misreads a co-founder’s hesitation as disengagement, when it was actually fear. Until a leader, so fluent at reading a room, loses the ability to read their own.
Here’s where this connects to something I believe at the center of my work. People don’t experience reality directly. They experience reality through identity, memory, and perspective. This is true of the person speaking to you, and it’s true of you as the one listening. When someone tells you their team is struggling with a deadline, you’re not just hearing information about a deadline. You’re hearing it filtered through your own history with deadlines, your own relationship to pressure, your own story about what it means when someone says they’re struggling. Real listening means noticing that filter is there, and trying to hear past it, to what the other person’s own identity and memory and perspective are actually shaping in what they say.
I saw the cost of not doing this up close, building the people function at Traveazy through a period of enormous change, a pandemic and two mergers layered on top of ordinary growth. In that kind of environment, everyone is talking, constantly, and very little of it is actually being heard. People say “I’m fine” in a tone that isn’t fine. They say “no concerns” while their body language says otherwise. The leaders who navigated that period well weren’t the ones with the best communication skills in the traditional sense. They were the ones who had trained themselves to hear what wasn’t being said directly, and to ask one more question instead of accepting the first answer.
This is also, not coincidentally, the core discipline of coaching. When I sit with a client, my job in that hour isn’t to have the smartest response ready. It’s to listen generatively, which means listening in a way that creates space for the other person to hear themselves more clearly, often for the first time. I’m not analyzing what they say against a mental checklist. I’m noticing the words they return to, the ones they stumble over, the moment their voice changes when they get close to something true. That kind of attention is a practice, not a personality trait. Nobody is naturally gifted at it forever. It has to be tended.
The same applies to listening inward, which is where I’d ask any leader reading this to start. Most people are far better at listening to their teams, their partners, their clients, than they are at listening to themselves. They override the quiet discomfort that’s trying to tell them something isn’t sustainable. They talk over the part of themselves that already knows the answer to the hard decision, because the answer is inconvenient. Slowing down enough to actually listen to your own thinking, without immediately managing or fixing or arguing with it, is one of the most underused leadership skills I know.
None of this requires more time than most leaders think. It requires a different kind of attention in the time you already have. A pause before you respond. A second question instead of a first assumption. A willingness to sit with what someone said, or what you just noticed in yourself, before rushing to decide what it means. In a world moving as fast as this one, that kind of listening isn’t a soft skill. It’s a strategic one, and in my experience, it’s the one that changes everything else.