What It Means to Listen Generously

Why Active Listening Isn’t Enough (and What to Do Instead)

The book has been out for a week, and one theme keeps coming up in reader responses: generous listening.

A reader who’s been coaching for years wrote:

“The section on how active listening without generous listening leads a coaching conversation in an unresolved circle completely blew my mind. It’s a coaching mistake I’ve made SO. MANY. TIMES.”

I think this idea is confronting for people because it challenges something we were all taught. We learned that good listening looks like nodding, making eye contact, and paraphrasing what we heard.

“So what I’m hearing you say is…”

Sound familiar?

Another reader described active listening as being about “demonstrating attention,” and something clicked for me. Attentive listening. That’s actually a better name for what most of us were taught. You’re not really listening. You’re proving you’re paying attention. Gold star. But proving attention isn’t the same as helping someone think.

The Problem with Attentive Listening

Attentive listening simply repeats content. It tells people what they already know. It stays at the surface.

I see this pattern constantly when I train managers and coaches. Someone brings you a problem. You nod. You paraphrase. They nod back. You ask a follow-up question. They give you more detail. You paraphrase again. Twenty minutes later, you’ve both repeated the same information three different ways, and nothing has shifted.

The person leaves the conversation feeling heard but not helped. And you leave wondering what you missed.

What you missed is everything beneath the words.

What Generous Listening Actually Looks Like

Here’s how I think about it: if you’re having a conversation meant to help someone learn, your job is to listen for what they don’t realize they’re saying. And then reflect it back to them in a way that helps them see something new. Not just repeat what they already know.

That means you’re not only hearing words. You’re observing patterns, noticing contradictions, tracking energy shifts, and listening for the beliefs that underlie behavior.

A senior leader in finance told me that right after finishing the book, he was in a one-on-one with one of his most important leaders. Mid-conversation, he noticed something he would have completely missed before: the person’s words were supportive, but their body language told a different story.

Because of what he’d learned about generous listening, he knew what questions to ask. Turns out, this leader had real concerns about a recent change and hadn’t felt comfortable sharing them.

That’s the difference. Attentive listening would have taken the words at face value. Generous listening caught the disconnect and opened a conversation that actually mattered.

Three Things to Pay Attention To

When you’re listening generously, you’re looking for:

1. Patterns they don’t realize they’re repeating. Words or phrases that come up again and again. I recently had a client describe himself as “lazy” three times in one conversation about building an exercise habit. He didn’t even realize he was doing it. When I named the pattern, he paused and realized he wasn’t lazy at all. He was overtaxed. That shifted the entire conversation.

2. Contradictions between what they say and what they believe. We all hold opposing beliefs simultaneously. Someone might tell you they’re “totally on board” with a new initiative while their shoulders creep toward their ears and their voice goes flat. Both are true: the words and the body. Your job is to name the gap so they can explore it.

3. Energy shifts. When someone’s voice lifts, their posture relaxes, or their face lights up, that’s data. When they physically contract, get quieter, or lose momentum, that’s data too. These shifts tell you when you’ve hit something significant.

The Part That Scares People

Here’s where most people get stuck: they notice something beneath the surface, but they don’t say it out loud. They’re worried about getting it wrong.

I get it. It feels vulnerable to name what you’re observing, especially when you’re not 100% certain.

But here’s what I’ve learned after nearly two decades of coaching: even when your observation is “wrong,” it’s useful. You’ve given the other person something to react to. And their reaction will almost always sharpen the conversation.

You say, “It sounds like you’re hesitant about this new role because you’re worried about failing publicly.”

They say, “Actually, no. I’m not worried about failing. I’m worried it’s going to take over my life and I’ll never see my kids.”

You were off. But now you’re much closer to what’s really going on.

The goal isn’t to be perfectly accurate. It’s to be observant enough to notice something beneath the surface, brave enough to name it, and humble enough to hold your interpretation lightly.

One Question to Try This Week

The next time someone gives you a quick answer to a meaningful question, resist the urge to respond. Instead, ask:

“What else?”

Then wait.

First responses are almost always automatic. They’re what people have already told themselves a thousand times. “What else?” signals: keep going, there’s more here. And there usually is.

That’s where the real conversation begins.