What I'm Sitting With

Displaying humanity in leadership can feel risky. Feelings and discomfort invite an element of "too-big-ness" that is hard to hold.

We say people are our priority. But when their humanity shows up in ways that disrupt control, timelines, or our sense of competence, it can feel much harder to stay aligned with that claim.

Years ago, I sat in a 1:1 with an employee whose mother was dying from late-stage dementia. I had been in the role for just a few months and was still getting my managerial legs under me. My return to full-time work when my middle child was 15 months old came with a transition enveloped in armor. I believed I was stepping into leadership by strengthening my executive presence—steady, composed, in control—even as I told myself that my people were my priority.

What I hadn’t yet reconciled was how those two things fit together.

Empathy and emotional intelligence hadn’t been modeled in the management roles I’d held before, so I relied on what I knew: structure, performance conversations, forward motion. Things I could manage.

We probably started that meeting the same way: focused on work, feedback, what was expected. But at some point, the conversation turned. She began to describe what she was carrying as the sole caregiver for a dying parent.

The grief I felt in response to hers was immediate and disorienting. I cried with her. But internally, I was reaching for distance, for anything that would help me regain footing. I didn’t know how to hold what was happening, and I didn’t trust that simply staying with it was enough. The loss of control didn’t feel like leadership. It felt like failure.

So I did what I thought leaders were supposed to do when they didn’t know what to do: I called my manager.

She didn't try to fix it. She just stayed. She reflected that it was probably meaningful for my employee to see that I was human—that I cared enough to sit with her in something hard, even without answers. She modeled a kind of steadiness that wasn’t about control, but about presence. A tolerance for discomfort. A permission that I didn’t need to solve the moment in order to lead through it.

That word has stayed with me: permission. Not because it was explicitly given, but because it was demonstrated. My manager didn't say in that conversation “you're allowed to feel things at work.” (Though, as I type that, I’m pretty sure she said something like that at some point!) She just modeled what it looked like to stay in the room, and that was enough.

Now, years later, I feel far more capable of holding space for complexity, emotion, and the unpredictable ways life shows up at work. But I’ve started to notice something familiar—something that feels a lot like that early instinct to create distance—emerging again. This time, under the umbrella of AI.

On the surface, these statements seem harmless—even helpful. They lower the stakes. They invite candor. But they also create distance. The feedback that follows doesn’t land in quite the same way, because it’s not fully attached to a person.

That instinct I had in that 1:1—to create space between myself and something uncomfortable—AI has now made it easier, faster, and more socially acceptable at scale.

In some ways, maybe we needed a little more of that distance. AI scaffolding can raise the floor of quality. It can help people generate ideas, structure thinking, and move forward when they’re stuck. And when people aren’t worried about protecting someone’s feelings, candor follows.

But this is also where it becomes dangerous if guardrails aren’t in place. That candor isn’t built on trust—it’s offered in the absence of relationship. And there’s a difference between distance that supports thinking and distance that erodes ownership.

Accountability isn’t inherent in an AI scaffold. Someone has to stand behind the idea.

When ideas are attributed to AI instead of claimed by a person, that ownership softens. Feedback becomes less meaningful because it’s not clear who is responsible for integrating it. Candor may increase, but trust doesn’t necessarily follow—because trust is built on knowing someone is willing to stand behind their thinking.

AI hasn’t just enabled distance from feelings—it has made it easier to create distance from ownership. And leadership still requires someone willing to stay in the room and stand behind their work.

My manager didn’t give me permission to be human. She stayed long enough for me to find it myself. That part can’t be outsourced to a manager or tool.

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