Crossing Over: What It Really Means to Be Empathetic Beyond Understanding

The past couple of weeks, I have been living a life that is not quite my own.

With my father away due to a health challenge, I stepped in to cover the daily rhythms of his business — managing clients, handling finances, filing tax reports. Tasks I knew existed but had never truly touched.

Before he was admitted, he asked me to read his diaries. And so I did — line by line. I did not expect what I found there.

I thought I knew my father well. We talked regularly. I knew, in broad strokes, what he was carrying. But there is something that regular conversations cannot reach — the things left unsaid, the weight that a father’s instinct quietly absorbs so that those around him do not have to. That invisible holding. I had no idea how much of it there was.

The more I stepped into his day-to-day — not just reading about it, but doing it, feeling the texture of the decisions he made, the pressure that accumulated quietly over time — something shifted in me. It was no longer I understand what he went through. It became something closer to: I am inside it. As though I had stepped into a simulation of his reality, and it was more real than I had anticipated.

That shift made me think about empathy differently.

Most of us, myself included, practice what researchers call empathic concern — we see someone struggling, we feel for them, we offer our care. And that matters. It is not nothing.

But there is another layer. Adam Grant, in his research on how we relate to one another, draws a distinction between feeling for someone and truly stepping into their shoes — what psychologists call perspective-taking. These two experiences produce very different things in us. Empathic concern keeps us on our side of the window, looking in. Perspective-taking asks us to cross over — to inhabit someone’s reality rather than simply observe it.

Immersing myself in my father’s reality — covering his work, reading his diaries line by line — gave me exactly that opportunity. And it offered me a far richer and deeper understanding of what he actually went through than anything our conversations had given me.

Stanford psychologist Jamil Zaki takes this further. In his TED talk and research on empathy, he argues that this deeper capacity is not a fixed trait we either have or don’t. It is a skill. A choice we make. Which means the question is not am I an empathetic person? The question is: how deeply am I willing to go?

I wonder how often we stop at the first layer in our closest relationships. With our teams, our colleagues, the people we lead. We acknowledge their reality. We nod. We say, I understand, that must be hard. And we mean it. But we stay on our side of the window, looking in.

What would it take to actually cross over?

It does not always require reading someone’s diaries, of course. But it might require more than we typically offer — more curiosity, more imagination, more willingness to be intentional in inhabiting their reality. To ask not just how are you feeling? but to sit quietly and wonder: if I were truly in their position — their history, their pressures, their fears — what would this feel like? And what questions could I ask differently to understand them beyond the surface?

Something opens when we do that. The frustration we carried toward someone softens. The distance closes. We begin to see not just their behavior but the whole human context behind it.

Invitation for Reflection

Think of one relationship — someone on your team, or in your life — where you sense there is more beneath the surface than what has been shared. This week, try something small. Sit with their reality more deliberately. Ask yourself: if I were in their exact position — their background, their pressures, what they carry that they haven’t said — what would this feel like? And what questions could I ask differently to understand them beyond the surface?

Notice what shifts.

Imagine turning one relationship into a deeper connection — one at a time — simply by embracing this posture. As a leader, as a colleague, as a human being. What difference would that make to the people around you and their world?

Change often comes through subtle micro actions. And one posture towards empathy can be more powerful than we think.

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