#13 - The Hardest Conversation of My Career
And what it taught me about emotional labour, leadership, and being stuck in the middle
I was in the middle of a one-to-one when the messages started coming in.
The person I was meeting with was having a difficult time. There were tears, a lot of emotion, and I was doing my best to hold space for them. My attention was fully with them in that moment — but once the meeting ended, I saw that something else had unfolded while I’d been unavailable.
A few colleagues had been frantically messaging me to ask if I’d checked in with another team member. They said this person had completely broken down during a meeting and left abruptly. Now no one could get in touch with them, and people were starting to worry.
I was already emotionally drained from the one-to-one, but I knew I had to respond. I was the manager, and one of my team was potentially in crisis.
I tried calling them but got no response, so I sent messages on every platform we shared. Still nothing.
Then my own manager contacted me, as they had heard from this team member directly. The message said they were feeling suicidal and was signing out of work for the day.
Everything changed at that point.
The concern became urgency. I contacted HR immediately, and they pointed me to the emergency contact listed in our system. It was their partner, so I phoned — no answer. I sent a message explaining who I was and why I was getting in touch. A few minutes later, the partner replied to say they would go and check on them.
After that, all I could do was wait. And try to keep myself together.
In the meantime, I was also speaking with the other people who had been in the meeting — trying to piece together what had happened, what might have triggered this response. Did they seem okay at the start? Was something said that set things off? Was this something that had been building up?
I wasn’t in the room, but I was still responsible. I was holding the emotions of everyone involved, while trying to manage my own. I was in shock. My manager was in shock. Everyone was.
When they eventually got in touch, we had a quiet, careful conversation about what had happened and what they needed. It wasn’t easy, but it was necessary. It reminded me how much emotional labour leadership really demands.
I often talk about the pressure of being in the middle: the organisational middle, the emotional middle, the human middle. You get squeezed from all sides, with expectations of managing and mediating tough situations just like this every day. This particular situation was one of the toughest in my career, but it’s important to recognise that holding space and having hard conversations IS your job as a leader.
And it’s possible to get comfortable with the discomfort that this brings.
Difficult conversations are a daily part of product leadership. Whether you’re managing upwards, leading a team, or navigating matrixed chaos, you’re constantly negotiating between clarity, empathy, and outcomes.
Here are three types of conversations I see come up again and again with the product leaders I coach — and why they’re so hard to get right.
1. Giving tough feedback to a high-performer
They’re hitting targets. They’re sharp. They’ve probably saved your team more than once. But their behaviour is rubbing people the wrong way — dominating discussions, dismissing peers, leaving tension in their wake. You know you need to say something, but you also worry about damaging the relationship or losing their trust (or even losing them altogether!). These conversations are difficult because they force you to hold two truths: someone can be brilliant and still need to change.
2. Pushing back on a senior stakeholder’s pet idea
You can see the idea isn’t right: maybe it doesn’t align with the roadmap, maybe the data doesn’t support it — but the person pushing it has influence. They’re invested, and they might not welcome challenge. You want to speak up, but it feels risky. What if it impacts your reputation? What if it affects future opportunities? This isn’t just a conversation about product strategy. It’s about power, perception, and your ability to hold your ground with calm authority.
3. Supporting your team through emotional or destabilising change
Priorities shift. Teams get restructured. People burn out. And in the middle of it, you’re expected to hold the emotional weight for everyone else — to steady the ship when you might be feeling rocked too. These conversations are often unscripted and unpredictable. They require you to be present, human, and responsive, all while keeping the wheels turning. This emotional labour is invisible, but it’s one of the hardest and most important parts of leadership.
Do any of these sound familiar? What comes to mind when you think of difficult conversations you’ve had in your career?
These kinds of conversations aren’t edge cases: they’re the job. And yet, most product leaders have never been taught how to navigate them, let alone how to do so with clarity, confidence, and compassion.
That’s why I created Courageous Conversations for Product Leaders.
✨ Courageous Conversations starts 18 August
It’s a four-week group coaching programme designed for emerging, new and seasoned product leaders, who want to learn how to handle the conversations that most people avoid — the ones that really define your leadership.
It’s the programme I wished I had earlier in my career when I stepped into leadership for the first time, and found myself in a sink-or-swim situation. It’s for younger me who really wanted to speak up and push back, but felt she couldn’t because she either couldn’t find the words or the courage.
I’ve designed this programme to teach you these vital communication skills, and create a safe space to practice them with others before you need to do it for real. It’s not just theory, it’s experiential, with breakouts to give things a go.
It starts 18 August and meets weekly for 4 weeks, and as a beta cohort, it’s just £250.
If you’re interested, then book a discovery call to chat it through more with me. There’s 8 spaces max, and one has already gone.