Leadership expert shares tips to understand and normalise crying at work

Cathleen O’Sullivan supports leaders to build a human-first approach into their work culture after she suffered from burn out in 2016.

She says experiencing burnout "cracked her open" and forced her to completely overhaul her attitude towards corporate professionalism.

The married mum-of-one from London, said: "In 2016 I felt miserable and robotic. At work I was getting great results but I was broken from trying to perform the role of the perfect boss.

"Now, like Rachel Reeves, I want to bring my whole messy human self to work.

"I’ve cried at work. For grief. For burnout. For anger. For connection. "It didn’t make me any less of a leader. If anything, it reminded me what kind of leader I want to be."

Cathleen who also hosts the Legendary Leaders Podcast wants corporate culture to stop treating emotion like it’s unprofessional.

She added: "We’re human. And sometimes, humans cry. And that’s okay."

When emotions boil over at work Cathleen has shared some insights to help a team recover and connect:

Grief at work can be a shared experience

"A colleague of mine passed away. She was open, kind and light-hearted. Whenever we visited her location, she would show us around the city, give local recommendations, and make sure we felt welcome.

"So when we found out she had been diagnosed with cancer, it was a shock. Sadly her health deteriorated quickly.

"When the news of her passing reached us, I cried. At work.

"Not in a hidden corner, not in the bathroom—but with others. And I wasn’t alone.

"The whole team felt it. There was a collective grief.

"And strangely, it didn’t feel isolating. It felt grounding. There was something beautiful in the way we all came together—not just to mourn, but to honour her life and her energy.

"That moment reminded me that emotions don’t have to be compartmentalised. And that sometimes, tears can bring a team closer than any strategy session ever could."

Injustice and anger can bring people to tears (and action)

"Anger is my biggest crying trigger. I’ve worked in some environments where chauvinistic behaviour wasn’t just tolerated, it was normalised. Brushed off. Even joked about.

"When I raised an incident in a one-to-one with my boss, he responded with a shrug and a tired laugh: “Well, you know what they’re like.” "That hit a nerve. That moment made me cry. Out of sheer frustration. I remember thinking: 'How can this still be happening? Why do I have to sit here and accept that this is just how things are?' It wasnt about being too sensitive. It was about integrity. And those tears were my body’s way of saying: This is not okay."

It takes courage to ask hard questions that might make colleagues cry

"A few years ago, I walked into a regular one-to-one with my manager. Everything was organised and under control, at least on paper. I sat down and began the usual run-through, and then she asked me: “How are you really doing?”

"Something in me just cracked. Tears started flowing, instantly. Not a few polite ones. Waterfalls. Big, messy, uncontrollable sobs. I couldn’t stop.

"I felt mortified and embarrassed and exhausted. But her response changed everything. She didn’t rush me. She didn’t try to fix it. She simply said: “Go home. Rest. Sleep.” That was the beginning of something much deeper. Those tears were the first signal that something was deeply wrong.

"If she hadn’t asked that question, or if I hadn’t felt safe enough to fall apart, I might’ve kept pushing until I broke in a much bigger way."

Cathleen believes crying at work is human. It happens. And we need to stop acting like it’s some sort of disaster when it does.

She added: "We don’t need the camera to zoom in, or the hushed whispers and gossip around the office.

"What we do need is a bit more genuine empathy.

"Because the truth is: We never really know what’s going on for someone.

"Real leadership isn’t about always having the answers or being bulletproof — it’s about being human, honest, and showing up as yourself. Now instead of snapping on a hard day I'll try to connect and share that I am feeling irritable or tired and that I need a moment.

"You might see someone cry in a meeting and assume they’re too emotional, but maybe it’s the first time anyone’s asked how they really are. Or maybe they’ve been holding it all together for far too long.

"Bottling things up doesn’t make us stronger. It just delays the fallout. And often, when it comes, it’s bigger, messier, and harder to come back from."

Find out more about Cathleen at: cathleenosullivan.com