The Leadership Moments You Don’t Know You’re Having
You're teaching something every day. Most leaders have never checked what.
It was past midnight. Again.
We were somewhere in a weeks-long stretch of 2:30 a.m. finishes, the kind of hours that blur together until you stop counting them.
And every night, without fail, my boss would look over as we were wrapping up and say the same thing.
“Come on. I’ll share a cab.”
He didn’t have to. He was tired too. He probably would have rather had a quiet ride alone.
But he never left without me. Not once.
It said: I see you. We are in this together.
And I never forgot it.
Around the same time, two jobs earlier, I had the opposite experience.
I was in investment banking, heading to a client meeting with one of the largest technology companies in the world. I’d been up all night preparing. Really, all week.
I stumbled under a duffel bag stuffed with somewhere between forty and sixty presentation books, so bleary-eyed I could barely walk in my suit and heels.
Not one person offered to help.
These weren’t unkind people. They weren’t trying to make a statement.
The absence made one anyway.
It said: rank has its privileges. And you don’t have them yet.
I don’t carry resentments, but I felt that one deeply. Maybe it was the fatigue, or just feeling alone.
The impression never left me. I promised myself I would lead differently.
The imprints we make unintentionally sometimes last longer than the ones we make intentionally.
We spend a lot of energy on the formal moments of leadership. The produced all-hands. The values statement. The message from the top that took three rounds of revisions to get right.
Those moments matter, but they don’t build culture.
Culture is built in the cab ride home. In who picks up the duffel bag. In what you do with your calendar, your attention, and your energy when you think no one is paying particular attention.
Your team is always paying attention.
Not in a surveillance way. Not consciously, necessarily. But the daily choices you make about pace, presence, boundaries, and care are teaching your people something. Every day. Whether you intend them to or not.
The question is whether you know what you’re teaching.
I taught something I would never have said out loud.
I was a COO at a company in startup mode. One of the things on my plate was a conference we were hosting, and I owned it.
It wasn’t landing. Our CEO kept telling me the pieces weren’t coming together, and privately I agreed with him, though for a different reason. I didn’t think the direction was focused enough on the business or on the outcomes we needed.
I had a team. Any one of them could have helped me build a better structure.
I didn’t ask.
Instead I held it. More hours. More iterations. More rounds of asking for feedback on work that had already been reworked twice.
I told myself I was protecting them. They were stretched. They weren’t ready for something this visible.
And there was enough truth in that to let me believe it.
Underneath it was something I couldn’t see at the time. I was afraid to ask them to stretch. And I was more afraid of what would happen if they could.
Because if my team could carry more than I believed, and carry it better than I could, then my role would have to change.
That’s the fear that kept me holding the bag. It was safer to believe I was the one who had to do it all than to find out I wasn’t.
It took me years to hear the reframe. I didn’t have to shift. I got the chance to.
But that shift asks for something harder than more hours. It asks for strategic thinking, honest reflection, and a look at reality that’s easier to avoid.
The overwork was how I avoided it. It just looked like commitment.
And what I modeled to my team, without meaning to, was overthinking. Rumination. A leader who wouldn’t set down a load that was crushing her.
Your habits may be doing more harm than you realize.
Recently, I was on a video call with a senior executive, a potential client. Thoughtful, experienced, someone who cared about his work and his people.
His eyes kept drifting. Typing. Reading something.
He could follow the thread well enough. Our conversation was loose, the topic manageable.
What I felt was unmistakable. Something else mattered more than our conversation, than me.
I’m not telling this as a criticism. I’m telling it because I understand exactly how it happens.
Leaders today are inundated. Dashboard updates, Slack pings, email stacking up, texts arriving underneath all of it. The demands are real and relentless. Over time, without intention, presence becomes a casualty of keeping up.
Team conversations are among the most expensive things we do. They cost you time. They cost the other person time. And they’re one of the richest chances we get to exchange something harder to measure than information: trust, connection, the sense that this person sees me.
When you’re half there, you think you’re juggling, maybe even helping. You’re actually sending a message: what you’re saying doesn’t warrant my full attention.
It’s not what you mean. But your team receives it either way.
The antidote is intention.
A few months ago, I was facilitating a strategic planning session. The leadership team had fractured since the process started. This was high stakes. A lot was riding on the next few hours.
I wasn’t anxious, exactly. But I knew my energy would set the tone in that room before I said a word.
So on the drive over, I put on a specific song, one I knew would make me feel connected to the people I was about to work with and to the meaning of the work itself.
I did this because I know what happens when I don’t. I walk in running on competence, and people can feel the difference.
By the time I parked, my eyes had welled up. It wasn’t manufactured. It was real.
And it changed what I could do in that room. I could be open and pointed at the same time. I could redirect people when the conversation drifted, and it didn’t land as correction, because they could feel I was with them. I could keep drawing each person back in.
That mattered, because the goal of that session was never a set of answers everyone agreed on. It was to rebuild trust in the process, and every person in the room believing their input counted.
I could do that because I was already connected when I walked in. My job was to make those threads visible as the conversation went.
That’s what intention looks like. Quiet. Often invisible. The choices you make before you walk through the door.
The harder question too many leaders leave unanswered.
Most leaders I work with aren’t sleepwalking on purpose. They’re moving fast. And when you’re moving fast, the small gestures go first. The eye contact. The follow-through. The moment of connection before the meeting starts.
The harder question is whether you know how you’re landing. Most of us have never checked.
A 360 can surface some of it. An open conversation with your team can surface more. Both require trust, and if that trust isn’t fully there yet, start by paying attention on your own.
Notice what your daily choices are teaching. Ask yourself whether the culture you think you’re building matches the one you’re modeling.
When there’s a gap, it almost always lives in the small moments.
Your Turn
This week, pick one conversation. One meeting. One moment where you’d normally be half-present.
Show up fully instead. See what it opens.
And if you’re ready for the harder version: ask someone you trust on your team what they notice. What habits land. Where they feel the gap.
That conversation, uncomfortable as it is, is itself a message. It says: I’m paying attention to how I’m showing up for you.
The leaders who shaped you weren’t performing when they shaped you. They were doing the ordinary thing in the ordinary moment, and you never forgot it.
You’re doing the same for someone right now.
May you lead without limits,
If this was useful, tap the ❤️ so more leaders can find it.
And if someone came to mind while you were reading, send it to them.
I write this to reach leaders who need the reminder to check how they’re showing up, and you sharing it is how that reach happens.