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Reader Note: This article is Part 2 of 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.
In Part 1: Inward, we focused on quieting your internal noise. In this article we turn outward to what’s said, how it’s said and the context that gives it meaning.
The Tell
People know when you’re not listening.
Just like you know when someone’s not listening to you.
It’s instant. Their eyes drift. They stop nodding in rhythm with your words. Worse their Apple Watch buzzes and they glance down mid-sentence. (Honestly, that’s one reason I stopped wearing mine.)
Even on the phone, you can feel it. The cadence flattens. The rhythm slips. The pause after your sentence lingers a little too long.
We’ve all been there. Deep listening isn’t just hearing. It’s seeing, sensing and being fully present.
Outward listening, the second level in the Listening Levels Framework (read part 1 here), is about tuning into what’s beneath and around the words: the delivery, the cues the context.
Interestingly, almost no one has had formal listening training and yet we all instantly know when we’re not being heard.
The Two Dimensions of Outward Listening
In every important conversation comprehension runs on two tracks:
Content – How something is said: tone, pace, emphasis, body language, what’s rushed, what’s loud or quiet and what’s skipped altogether
Context – Why it’s being said that way: the emotion, the timing, the backstory, the assumptions underneath the message
Together, they tell the real story. They deepen understanding and build connection.
Level 2 listening asks you to step outside yourself. To slow the pace, embrace silence (even 5 seconds of it) and drop “I” from your responses. It’s about staying with what’s unfolding without jumping in to solve or steer.
Listening to the Content
Focus on how things are said.
When you only hear the words, you miss what’s actually being communicated.
This is where friction first shows up. It’s a mismatch between message and tone or delivery and emotion. Catching that early lets you redirect confusion, clear up misalignment and help the speaker find better language.
Here’s how I listen for content:
Watch the delivery
Pay attention to tone, pace, repetition, trailing off, quietness or speed. If the words don’t match the energy, your gut will notice first.Slow the pace
In tense conversations, I ground myself by slowing my own tempo. I’ll nod more slowly and intentionally pause before speaking. That resets the rhythm and gives the speaker more space.Use clarifying prompts
My go-to questions:“Can you say that a different way?” (Signals care without judgment)
“Say more.” (Just two words. It’s disarming, direct, surprisingly effective)
Name what you notice
Avoid “why” questions when emotions are high. Instead, reflect what you’re sensing: “It seems like that landed the wrong way” which I like to use to invite confirmation or deeper context.Remove yourself from the frame
That means:Dropping “I” statements and “me too” stories
Resisting the urge to finish someone’s thought
Avoiding questions that sound curious but don’t go anywhere
The less you interfere, the more space the speaker has to think clearly. That’s where real clarity happens for both of you.
Listening for the Context
Focus on why things are said.
Context is mostly invisible but shapes everything.
It’s the backstory, the power dynamics, the history, the timing, even who’s in the room (or not). Context explains urgency, tone and hesitation.
Every conversation has at least three layers of it:
Their context – What just happened to them? Were they out of the loop, blindsided or walking in from a tough meeting? What might they be carrying emotionally or logistically?
The conversation’s context – Where is this coming from? Is this a flashpoint or part of a slow build? Is there a looming decision behind the scenes?
Your context – What pressures, assumptions or urgency are you bringing in? Even your mindset can shape how you hear things.
Misunderstandings often come from missing the context. And naming it briefly can shift everything.
Here’s how I listen for context:
Consider what happened just before
Did someone walk in from a tense meeting? Did they get bad news? Even a 10-minute buffer (or a quiet pre-huddle) can change the dynamic completely.Anticipate the knowledge gaps
Has someone been out on leave, out sick or newly looped in? If they don’t have the full picture, they can’t engage with it.Look backward and forward
What’s the bigger arc here? Is this part of a longer pattern or tied to a high-stakes moment ahead? Context isn’t just the past, it’s also the weight of what’s next.Watch for assumptions (yours and theirs)
You don’t know what you don’t know. Stay aware of the stories you’re telling yourself about someone’s tone or behavior. Just because you wouldn’t respond that way doesn’t mean it’s unreasonable for them.
Listening that Builds Influence
Listening is core to the Chief of Staff role.
Note taking and summaries are surface level. The real work is absorbing how something was said and why. That’s where trust forms and trust is what makes you indispensable.
Level 2 listening connects what happened with what it means. Once Level 1 becomes a habit, this is where you’ll operate most of the time.
But listening at this level isn’t about solving (even if that’s your instinct). It’s about creating space for others to process, find clarity and move forward.
The simplest way to do that? Stay curious.
Ask open, neutral prompts like:
“What else?”
“Say more.”
“How are you thinking about it now?”
These don’t direct or advise. They invite. And when people feel heard, they share more freely and think more clearly.
Up Next Part 3: Below the Surface
Once you’ve trained your attention beyond yourself then outward you’re ready for the level most people never reach.
The unsaid. The emotional undercurrent. The meaning behind the message.
In Part 3: Below the Surface, we’ll explore:
How to listen for what’s not being said
What it means to reflect meaning, not just repeat content
Why space is more powerful than solutions
The prompts that invite truth without pushing for it
How this level of listening builds transformation
See you next week!
