The Things Leaders Don’t Say Out Loud
This month, we’re asking a question that rarely gets answered honestly in public: “What keeps you up at night?”
Leadership looks polished on the outside. But behind closed doors -and sometimes at 2 am – it’s a different story.
We’re asking it at our CEO Lunch, our Board and Chair Lunch, and our EA Breakfast. Not because we expect neat answers. But because we know the real ones matter.
The Quiet Weight of Leadership
- For CEOs, it’s the pressure to be everything at once: visionary, empathetic, decisive, and calm.
- For Board members, it’s the fear of missing something that could have been prevented.
- For EAs, it’s the emotional labour of holding everything together while supporting those who are quietly falling apart.
These aren’t just professional concerns. They’re deeply personal.
What We Think We’ll Hear
We expect to hear about:
- The fear of reputational risk in a hyper-connected world
- The challenge of leading through burnout—your own and others’
- The complexity of succession planning when the future feels uncertain
- The emotional toll of being the one who’s supposed to have the answers
But we also expect to hear about hope. About resilience. About the quiet strength that keeps leaders going, even when sleep doesn’t come easily.
Why This Conversation Matters
We’re not asking this question to be provocative. We’re asking it because leadership is lonely, and the more we talk about what keeps us up at night, the more we realise we’re not alone.
At Windsor Group, we work with leaders across all levels, not just to fill roles, but to support the humans behind them.
Because sometimes, the most powerful thing we can offer isn’t a solution.
It’s a space to say, “Me too.”
Join us at the table.
Let’s talk about what really matters, before the next sleepless night.
Enjoyed this article? Discover more stories like this on our LinkedIn and website, or give us a call today on (07) 3211 0001 to find out more about our services!