Tag Archive for: leadership

Leading with Empathy isn’t Soft. It’s Strategic, Necessary, and Often Exhausting

/in /by

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

I thought I had to be perfect to lead

/in /by

For most of my career, I carried an unspoken rule:
Leaders have to have it all together.

No cracks.
No doubts.
No messy human moments.

Just competence, confidence, and a perfectly polished exterior.

There are quite a number of leaders I know who project exactly that, the kind of poised, untouchable professionalism that looks effortless. One day, when I grow up, maybe I’ll be just like them.

But today?
I’m choosing to embrace the version of myself I’ve always been:
a little quirky, a little sideways, a little messy, and completely real.

Like many founders (and as I’ve spoken about openly before), I am no stranger to imposter syndrome. I can walk into a room full of brilliant minds, CEOs, therapists, compliance directors, creators, and still feel like the teenager who never quite fit in. Add to that the reality of being a high-masking autistic woman running a mental-health charity in an industry the world doesn’t always treat kindly… and, well, you can imagine the pressure I put on myself.

To those who lead from the front and make it look easy:
I salute you. Truly.

But perfection isn’t the sign of great leadership.
Humanity is.

Everyone is learning.
Everyone is trying.
Everyone is human.

This is something I spoke about recently during a Wellbeing by PS training:
If you want a healthy team, you can’t just tell them it’s okay to ask for help.
you have to show them.

People don’t learn from policies.
They learn from permission.
And they learn permission by witnessing vulnerability.

When I stopped trying to tuck away the “odd” parts of myself, the quirks, the humour, the autistic wiring that makes my brain work at slightly unexpected angles, something surprising happened:

I started forming stronger connections.

At shows, in boardrooms, at conferences (9am with terrible coffee or 9pm with terrible wine), the more I allowed the real me to show up, the more others showed up as themselves too.

Conversations became more honest.
Collaborations became smoother.
Relationships became deeper.

And, to my knowledge, no one has run away yet.

Of course, professionalism still matters.
Boundaries matter.
Consistency matters.

But I’ve learned that professionalism doesn’t require dimming your light, even when that light is quirky, chaotic, or unmistakably “Leya.”

When you let people see who you really are, they respond with who they are.
And strangely enough, that makes everything, leadership, teamwork, community, so much stronger.

Because most people aren’t looking for a flawless leader.

They’re looking for a human one.

with love,

Leya

Leadership, Shame, and the Sacred Hidden in the Chaos

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Lately, I’ve been tired. Not burnt out, though if we’re being honest, maybe just a little, but purposefully tired. Soul-tired in the way you get when you’re pouring yourself into work that matters. Between maintaining our existing resources and preparing to launch multiple new projects over the next six months, our team is building something big. Something that saves lives, shifts perspectives, and nudges an entire industry toward compassion.

And yet, even in the midst of that purpose, I find myself sitting with shame.

Shame that whispers I should be doing more, being more, holding everything together with more grace and less chaos. Shame for being human in a leadership role that can feel like it demands something superhuman. When I miscommunicate or make assumptions, I find myself wishing I could shield my team from the fallout. They’re brilliant, passionate, and dedicated, and the truth is, I set the pace. I create the workload. I drive the vision that asks so much of all of us.

But I’m learning, slowly, imperfectly, to meet that shame with empathy.

Instead of asking, Why aren’t you doing more?
I’m asking, What do you need right now?

Instead of slipping into criticism, I’m practicing compassion.

It’s messy. It’s uncomfortable. But it’s necessary. Because when you’re leading something that means the world to you, self-compassion becomes a leadership skill. A survival skill, even.

I want to say it gets easier, but it doesn’t. The goals grow. The pressure builds. The stakes rise.
But so does the impact.

And these next goals? They’re huge.
And I’ve got this.
We’ve got this.

I am endlessly grateful to every person walking this path with me, the team that believes, the partners who trust us, the community that keeps reminding us why the work matters.

The truth is, I haven’t been practicing everything we preach lately. I still make it to the gym, routine is my anchor, but after work, I crash. My social battery is empty. I haven’t checked in on the people I love, and yes, I feel guilty about that too.

But here’s what I do know:

The way we speak to ourselves matters.
Self-leadership matters.

If I can’t offer myself grace, how can I extend it to my team?
How can I offer it to the community we serve?

This work is messy.
But it’s sacred too.

Sometimes the sacred hides in spreadsheets and schedules.
In Slack messages and strategy decks.
In showing up even when you’re tired —
especially when you’re tired.

So here’s to the leaders who show up with empathy.
Here’s to the teams who hold big visions with open hearts.
Here’s to remembering that softness is strength
and rest is part of the mission.

with love,

Leya