Leading with Empathy isn’t Soft. It’s Strategic, Necessary, and Often Exhausting
I can tell you right now – I’m f*cked.
Too tired to talk to friends.
Too tired to check in on family.
Too tired to even play with my dogs.
Today has been a blur of spreadsheets, last-minute donation emails, and conversations with team members. A day spent listening, supporting, fixing, holding. All of it done with as much compassion, and as big a smile, as my current capacity allows.
And here’s the truth most leaders don’t say out loud:
Leading with empathy doesn’t mean being endlessly calm, infinitely patient, or having all the answers.
It means caring enough to keep showing up even when your internal battery is flashing red.
At Pineapple, we’ve built everything on the belief that people need to feel seen, heard, and held in order to thrive. And if we’re going to practice what we preach as an organisation (though clearly not as individuals today), that applies just as much to our team as it does to the community we serve.
Every email deserves a little care.
Every meeting deserves presence.
Every person deserves to feel safe being honest, even on the messy days, the tired days, the “barely functioning” days.
Because empathy in leadership isn’t a softness; it’s a strategy.
A sustainable one.
When we lead with empathy, we build resilience, in ourselves, our teams, and our companies. It’s not about wellness perks or feel-good slogans. It’s about creating cultures where compassion drives performance, and care is woven into the foundation of how things get done.
That’s what keeps people connected.
That’s what builds strong teams.
That’s what turns organisations into communities.
And honestly?
That’s what makes Pineapple what it is.
Even on days like today, when my tank is empty and my brain feels like soup, I can feel the strength of the culture we’ve built holding everything steady. Empathy doesn’t just support people, it sustains the mission.
And tomorrow, when I’m a little less tired, I’ll get back to practising it with myself too.
with love,
Leya
