Do you think you have a listening problem? I didn’t either.

I thought I was attentive. Sharp. Focused. I could recite back every task, every deadline, every ask from a meeting. But I wasn’t really listening, not in the way that builds trust, creates clarity or uncovers the friction that no one is saying out loud.

That shift didn’t hit me until I started working with my coach, Laurie.

In one of our sessions, she introduced the concept of Level 2 listening and what it means to listen fully to another person. Not just the words. Not just the actions. But the emotion, the intention, the everything else behind the message.

I had never formally considered that perspective before. Luckily, Laurie assured me I was already doing it naturally but the idea that there were actual levels of listening, and that most people never get past the first one was brand new to me. And it immediately clicked as one of the greatest unlocks—for relationships, for influence and as a Chief of Staff.

Because the truth is:

That’s why I’m writing this series.

Over the next three weeks, we’re going to explore what I’m calling The Listening Levels, a simple, three-part framework based on the work of Oscar Trimboli, adapted for the realities of being a Chief of Staff.

The three levels are:

Each one builds on the last. Each one has helped me become a more strategic operator. And each one has allowed me to go deeper in my relationships with my principals, with my teams, with friends and with myself.

So let’s start at Level One where all real listening begins, with yourself.

Listening to yourself sounds like it would mean trusting your gut. But in this context it means noticing your internal noise.

Most of us walk into conversations already full of thoughts, reactions, assumptions and pressure. We're thinking about our next move, our last mistake, our response or some stray worry about how we came across in the last meeting. Our heads are quite loud and we bring that volume with us.

To be clear. That inner chatter isn’t bad, it’s normal.

That’s what Level 1 listening is about.

It’s impossible to have perfect focus. Level 1 listening isn’t about clearing your mind entirely. That’s not realistic and it’s not the point.

The point is awareness. Noticing when your attention has drifted and choosing to return without judgment and without skipping a beat.

I liken it to meditation. You don’t fail when your mind wanders. You notice, and you come back. That return is the listening.

In high-stakes meetings or fast-moving 1:1s, that kind of pause (sometimes just a breath) can shift everything. It creates just enough space for clarity to come in.

When you're a Chief of Staff, listening is more than a communication skill. It's a strategic advantage.