Reader Note: This article is the final piece in a 3-part series on Listening Levels, a framework for Chiefs of Staff to lead more effectively by listening deeply, adapted from Oscar Trimboli’s work. Check out his book, How to Listen.

This past weekend, I walked to the farmers market like I always do. I stopped by to say hello to Victor, he’s my nut guy. That’s what I call him (to his face). We’ve known each other for over a year now. I see him every Saturday, we chat for a few minutes and I buy my usual. It’s routine.

But this time was different.

As soon as I saw his face, I knew something was different. He had a look that was part distracted and part heavy, like his mind was elsewhere. So I slowed down. Instead of speeding through my usual hello, I asked a few soft questions and let the silence fill the space.

What came next wasn’t planned.

He started talking about an old love, someone he still keeps tabs on through her mother. Someone he’s clearly not over. It spilled out slowly, unevenly. He wasn’t looking for advice. He wasn’t even really talking to me. He was talking through me. Using me as a prompt to hear his own thoughts out loud.

I had to catch myself as he was sharing. My instinct was to jump in, ask a clarifying question and offer a tidy solution. Which I did then immediately backed off. I said less. I nodded gently. I let the pauses breathe.

That moment was unexpected, human and honest. That is what Level 3 listening feels like.

It’s not about hearing what’s said. It’s about being present enough to catch what isn’t.

Level 3 listening is where you stop listening to the words and start listening for the person. The shift is subtle but huge.

At this level, you’re not trying to gather information or formulate a response. You’re helping the speaker explore their own thinking, sometimes even helping them say something they didn’t know they needed to say.

This blew my mind:

That’s it friends. Listening at Level 3 is simply the gap between what we say and what we’re thinking.

It’s where people stumble. Where they try to express something meaningful and fall short. Not because they’re unclear or bad communicators, but because their brain is moving faster than their mouth.

That’s why Level 3 isn’t about understanding the message. It’s about helping the speaker find the message.

Great listeners (and especially great podcasters, I’ve noticed) create the conditions for clarity. They stop solving or suggesting and instead hold space for the real thought to emerge. If you’re only listening to the words, you’re missing the signal. Because it often comes wrapped in hesitation, emotion and contradiction.

That’s why watching for the unsaid and the meaning behind it is essential.

In Level 3 we listen for the unsaid, and the unsaid lives in the pause.

It’s revealed through presence, not by crafting the perfect follow-up. This is why understanding levels 1 & 2 (particularly level 1) matter so much. You can’t access Level 3 unless you’ve already quieted your own internal noise.

When someone pauses mid-thought, most of us rush to fill the silence. We offer reassurance, clarify our understanding or reframe the point. We don’t even realize we’re trying to move things along.

At Level 3, your urge to speak is no longer a prompt. It’s a signal to stay quiet.

Silence isn’t a void or dead air. It’s part of the conversation. Most importantly, silence is where the real insight is about to break through.

Try this: when the speaker stops talking, silently count “1... 2... 3…”

Don’t rescue them from the pause. Let them finish the thought they haven’t fully formed yet. When you do this you let them hear themselves.

Then, it’s easy to pick up a few queues from Level 2 and ask questions that invite more context:

Your job here isn’t to interpret. It’s to invite. Instead of reflecting on what they just said, reflect about it:

That one shift turns the focus back where it belongs—on the speaker.

The goal of level 3 isn’t clarity, it’s comfort. When someone feels safe enough to keep speaking (even when their words are messy) they’ll often get to the thing they really needed to say.

This is what listening to the unsaid is all about.

If listening to the unsaid is about honoring the pause, then listening for meaning is about what’s beneath the words and driving the speaker.

At first, this might sound like Level 2 (listening outward) but here’s the difference:

Level 2 listens around the message: tone, timing, energy, body language.
Level 3 listens beneath it: emotion, motive, memory, identity.

Level 2 helps you understand the moment while Level 3 helps the speaker understand themselves.

At this level, you stop listening to the story. You start listening for what the story means.

Meaning often reveals itself through friction. Like a reaction that’s too strong for the moment or a story that loops or lands with more weight than expected. A clear signal is when emotion surfaces in ways that don’t quite match the words.

These are clues that something else is at play.

For example, think about a couple in their kitchen fighting over dirty dishes. The anger usually isn’t ever about the dishes. It’s about something unspoken like disconnect, a feeling of disrespect or unmet needs.

You see this in the workplace too when a teammate overreacts in a meeting. A leader insists on rehashing a decision that’s already been made. In both cases, the energy just doesn’t match the surface level issue.

That’s your cue: there’s something deeper underneath.

If you’re anything like me you’re probably thinking:

Same.

So I added this part just for us.

Level 3 listening isn’t always appropriate.

Not everyone wants to unpack their feelings in a group setting. Not every moment is a therapy session and not every silence is an invitation.

Sometimes, meaning needs a buffer. It can happen after the meeting in the hallway or the walk to the elevator. Trying to go deep too soon can feel performative or just plain annoying. But if you never come back to it, the tension sticks.

Here’s where it gets uncomfortable for us.

You will sense when something’s off. And as Chief of Staff, you don’t get to ignore it like everyone else. Your role is to do everything but smooth it over, look away or move on. You pull up a seat and dig in.

Level 3 listening doesn’t push.
It notices.
It waits.
And it returns when the moment is right.

Here’s a masterclass of what level 3 looks like in real time:

The Diary of a CEO, Steven Bartlett interviewing Nischa Shah

Start at 1:49:00, when Steven asks: “Who is the person responsible for her sitting with him?” Nischa begins to talk about her dad.

1:49:34 — She pauses, reflecting on her answer. Then she dives deeper into the context. Her voice begins to crack.

1:49:57 — She pauses again. Steven doesn’t jump in. He lets the silence stretch, so long you might think the recording cut out (only 15 seconds).

1:50:12 — He gently reflects on what she just said and probes further: what else is unsaid in her relationship with her father? Nischa keeps going.

What comes next is a real-time example of Level 3: Helping someone explore what they want to say and giving them the space to actually say it.

1:51:30 — Steven makes a clarifying statement and asks a follow-up. For the next 10 minutes, their exchange stays fully in Level 3. He never once says “I.”
Instead, he asks what questions, holds silence and stays focused entirely on her.

And you can watch it happen: Nischa is clarifying her thoughts as she speaks, discovering what she really means in the moment.

We don’t listen well enough anymore not at work, not at home and not even with friends. And by “we,” I mean me too.

That’s selfishly part of the reason I wrote this series. I wanted to clarify what listening actually is and how to get better at it myself. But I also believe it’s one of the most underrated executive skills, especially for Chiefs of Staff.

Level 3 listening isn’t at all casual. It takes awareness and discipline to even attempt it. It requires you to get out of your own head, stay present with someone else, and resist the urge to fix, react or move on.

Over this series we unpacked three levels:

Mastering these levels unlocks trust and trusted relationships unlock everything.
They allow you to do your best work behind the scenes, the kind of work that makes your principal more effective, often without them realizing why.

At the end of the day, your real job is to hear what no one else does and act accordingly.