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.

Your job is to notice what others miss. To hear between the lines. To catch the real issue, not just the stated one. That means you need access to everything that’s being said AND everything that isn’t.

But if your brain is busy scripting your response, managing your nerves or replaying a separate conversation from earlier in the day, you’re not actually in the room. You’re operating from inside your head, not inside the moment.

That disconnect is subtle but costly.

Here’s what it might look like IRL:

None of those moments seem huge in the moment. But they add up. And over time, they erode your ability to create momentum, clarity and importantly trust.

Level 1 listening, inward listening, is what gives you that presence. It’s what clears the channel so you can absorb, assess and act with intention.

Without it, you're just performing the job. With it, you're doing the job.

I don’t think you become a good listener by trying harder. It happens when you gain awareness and when you set yourself up to succeed.

That success starts before the conversation even begins.

For Chiefs of Staff, meetings stack fast. One decision leads into the next. You shift from high-stakes strategy to emotional support to fixing logistics all in an hour. If you don’t intentionally reset between conversations, you end up dragging the last room’s energy into the next one.

Lately, I’ve been paying close attention to how I walk into every conversation whether it’s a high-stakes meeting or dinner with friends. Over the past few months, I’ve been quietly testing a set of five questions behind the scenes. I wanted to be sure they actually work before offering them to you.

They’ve helped me reset, re-center and show up more present especially when it matters most.

I think they’re pretty close. So here they are.

5 Questions to ask before any important conversation

Once you’ve learned to notice your own noise, you’re finally ready to shift your attention outward—to what’s being said and what shapes how it’s said.

That’s what we’ll cover next week in Part 2: Outward.

We’ll go deeper into:

You’ve made space.
Next, we’ll learn how to fill it with signal not noise.

This is the first edition of Right Hand Brief on Beehiiv and I want to share why I made the switch.

I’ve been thinking a lot about how to make this newsletter more useful, more actionable and easier to consume. That’s what led to two changes:

First, the name.
This newsletter started as Right Hand Chief, but I realized it’s not about the title (or me). It’s about the thinking. The frameworks, questions and mindsets that help you operate more effectively. You know, like the force multiplying animal you are 🦁. Right Hand Brief reflects what I’m really offering: a sharp, strategic hit of clarity you can use in your work, right now. It also opens the door for the occasional well placed pun (briefcase, anyone?).

Second, the move to Beehiiv.
I wanted more flexibility to organize and grow this newsletter into something bigger with a space for tools, resources and thinking that supports Chiefs of Staff (and operators like them) in real time. This platform gives me room to do that.

Thanks for being here and for letting me experiment in public.

Jill