3️⃣ things I'm rethinking about leadership this week

September 19, 2025

Hi Reader

This week, I'm rethinking and reframing.

Questioning things I thought I believed.

Tl/dr: You might well be operating off a flawed operating systems of baked in assumptions.

(3-minute read)

You know that feeling when someone says something that makes you realise you've been thinking about something backwards? That's been my past two weeks.

Three separate conversations forced me to confront assumptions I didn't even know I was making. About authenticity. About feedback. About what "busy" actually means.

Most leadership content this week will tell you what to do. This might be the only place that asks whether what you're already doing is based on ideas that sound right but don't actually work.

Upfront warning: if you prefer your leadership wisdom unchallenged and your beliefs unexamined, skip this one. But if you're curious about why some widely accepted leadership principles might be holding you back, read on.

More and more the most valuable thing you can do is question what everyone else takes for granted.

Authenticity misunderstood

Three conversations this past fortnight made me question everything I thought I knew about authentic leadership. At one seminar a CEO told me her "authentic" response to staff mistakes was frustration, but showing that frustration consistently damaged performance. Then a tech startup founder admitted he'd been confusing authenticity with emotional incontinence. To top it off, a conversation with a retired military officer shifted my perspective completely.

He said something that stuck: "Authentic doesn't mean unfiltered. My authentic self includes the discipline to be what my people need in the moment."

Maybe the whole "bring your whole self to work" movement misses the point. Perhaps authentic leadership means being genuinely committed to your people's success, even when that requires restraining your natural impulses. Worth considering whether we've mixed up being real with being helpful.

The obsession with feedback

I had coffee last week with someone who runs a luxury yacht company here. She mentioned something interesting about feedback culture that's been nagging at me since. Her best performers, she said, rarely ask for feedback. They seek specific information instead. "How can I improve?" versus "What does the client expect in the next 30 days?"

It made me think and naturally I started paying attention to this pattern in other conversations. A basketball coach I know mentioned his top players request data, not opinions. They want to know shooting percentages from specific court positions, not general thoughts about their performance.

Makes me wonder if our feedback obsession actually keeps people dependent on others' judgments rather than developing their own performance instincts?

Maybe the question should be: are we teaching people to fish, or teaching them to ask others how the fishing went?

The Busy Badge

Someone challenged me on something recently that resurfaced an old lesson. We were discussing a leader who constantly talks about being busy, wearing exhaustion like a medal. "Busy doesn't mean important," they said. "Sometimes busy means you can't prioritise."

Even though I know this, it hit harder than it should have. I started noticing how often business leaders, sometimes still myself included, equate activity with achievement.

But observing some of the most effective people I work with, they rarely mention being busy.

They seem to have time for conversations that matter, space for unexpected opportunities, capacity for deep thinking. I’m going back to an old learning that sustainable high performance might look more like strategic calm than frantic productivity.

What do you think? Could be that "I'm so busy" is actually code for "I haven't figured out what really matters yet."