What empathetic leadership really asks of us

In a companion piece to her TEDx talk and book ‘The Power of a lollipop: A story from the front line‘ which won at this year’s Business Book Awards, Dr Feena May delves into the power of empathy among leaders.

Empathetic leadership, properly understood, is the harder option

There is a continuation of the frontline story I did not have time to tell on the TEDx stage. Ten minutes is a strict discipline, which means most of what happens in my story, after the lollipops get chosen, after the guns go back on their shoulder straps, after those children finally cross to their parents, stays with me. So let me tell you a bit more, because this is where the real work of leadership actually happens: in really connecting to people you would never choose to sit beside.

Several years ago, I found myself at a dinner party for a nun’s seventy-ninth birthday. The conversation turned to the complexity of living in community and the difficulty of getting on with each other day after day, year after year, decade after decade. One nun, as plainly as you can imagine, said this: “Well, you don’t have to like everyone you live in community with, but you do have to love them.”

I have thought about that sentence more than almost anything else that came out of twenty years of research into good leadership. It is the whole of empathetic leadership in a single line from a nun’s birthday dinner in Ireland.

We talk a great deal about empathy in leadership circles now, and I am glad of it. But I worry we have quietly turned it into something closer to fondness. Be kind. Be understanding. Get on well with your people. That is lovely, and none of it is wrong, but it is not quite the thing.

Liking someone is a feeling that arrives or doesn’t, on its own schedule, for its own, often personal, reasons. You cannot build an organisation, a family or a peace process on whether the feeling shows up. Loving someone, in the sense that nun meant it, is a decision. It is choosing to stay in relationship with someone’s full humanity, including the bits that irritate you, disappoint you, or sit on the far side of a front line from you, because you have decided their wellbeing, their contribution, their humanity matters regardless.

That, in hindsight, is what I was doing with a bag of lollipops in 1992, though I did not have the language for it then. I was twenty-four, six months into my first mission, and I did not particularly like the soldiers on either side of that checkpoint. I had no reason to. Offering them a lollipop was not an act of fondness. It was an act of relating, to the humans in front of me, regardless of the uniform.

Relating is where empathy properly lives, not as a personality trait some leaders have and others don’t, but as a discipline of 360-degree listening. This is what I call storylistening, and it is something that reaches towards people whether or not you have warmed to them yet.

This matters more than most leadership development admits, because the moments that test us are rarely the ones with people we like. Anyone can be present and open and generous with a colleague they get on with. The discipline shows up with the difficult client, the underperforming team member, the political opponent, the neighbour across whatever front line you happen to be standing on this week.

Empathetic leadership, properly understood, is not the soft option. It is the harder one. It asks you to keep listening after you have already decided you know what someone is going to say. It asks you to hold space for a person’s context and history even when their behaviour has made that difficult.

Love in the leadership sense

I met Anne Murray, the principal of my old secondary school, many years after I had left it, on a snowy morning in Dublin when the whole city had ground to a halt. She told me a leader’s horizon must always be expanding, spiralling up and outward, never closing in to simply protect the system. “I’m on the side of the journey,” she said.

That expansiveness, I have come to believe, is what love in the leadership sense actually produces. Liking narrows our attention to the people who are easy. Loving, in the quiet and demanding way I mean here, widens it. It keeps the door open for people you have not yet learned to like, and quite often, for people you never will.

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This is not naive, and it is not the same as tolerating harm or excusing poor behaviour. Loving someone you live or work with does not mean agreeing with them, or failing to hold a boundary, or pretending conflict does not exist. It means the relationship survives the disagreement. It means doing the sensemaking work of understanding where someone is coming from before you decide what to do about where they are going. That is a discipline, not a mood, and like any discipline it can be practised and taught.

On that front line, the soldiers on both sides put their guns down for the length of time it took to choose the colour of their lollipop and crack a joke. It did not last. War does not end because of a lollipop. But something had shifted, because for those few minutes, each side had met as people rather than positions. That, I think, is the real offer of empathetic leadership: not the elimination of difference or difficulty, but the refusal to let difference or difficulty become the whole story.

We are living through a period that makes this discipline feel urgent rather than aspirational. Divisions run deep, in our organisations, our communities, our families, and our politics at national and global levels. It is tempting to reserve our empathy for people who already agree with us, and to tell ourselves that is enough. It isn’t.

That birthday dinner taught me that the people who test our capacity to love are precisely the people who need it most, and that leadership, at its best, is the daily, unglamorous decision to keep showing up for them anyway, to keep seeking our single humanity.

So here is the deeper question behind the one I left you with on stage. It is not only “What will you choose?” It is, “Who will you choose to keep loving, even on the days you do not particularly like them?”

Answer that, in your team, your community and your family, and I promise you, the world does become a much better place.