Issue 55: What 14 Conversations Taught Me About Leadership

ISSUE 55

3 SEPTEMBER 2025 | READ ONLINE

Hello Reader,

We’ve just wrapped up Season 1 of the Headline Podcast. Fourteen guests. Fourteen conversations that left me scribbling notes long after the recording stopped. Each one felt like a private masterclass in leadership, culture, and human connection.

But here’s what surprised me most: the lessons weren’t just about what our guests said. They were about what the process taught me. About how asking better questions, sitting with silence, and leaning into curiosity are the very same muscles leaders use every day, whether you’re hosting a podcast or leading a team.

What I’ve Been Learning

Curiosity is a leadership strategy.
The best conversations happened when I followed my genuine curiosity, not the script. Research from Harvard Business Review shows that curiosity not only sparks new ideas, but it also deepens trust and engagement inside organizations. Curiosity signals to others that their perspective matters.
The hardest part is asking a simple, human question.
A polished question sounds smart. A vulnerable one creates a connection. Brené Brown’s work reminds us that vulnerability is the birthplace of trust, and I felt that in real time, every time I dared to ask the unpolished question.
Listening takes more energy than speaking.
Silence can feel uncomfortable. But when I resisted the urge to jump in, the richest insights often surfaced. McKinsey research on “listening leaders” found that teams perform better when leaders intentionally create space for voices other than their own.
Amplification is part of leadership.
When someone entrusts you with their ideas, your role is to elevate them. That’s as true in a podcast interview as it is in a boardroom or a team meeting. Words spoken by leaders are magnified, so using that platform to amplify rather than overshadow is powerful.

How This Applies to You

Not everyone hosts a podcast (or wants to). But everyone leads conversations that matter. Maybe it’s a performance review. Perhaps it’s a strategy session. Or a chat with a colleague over coffee. The same principles apply: curiosity, courage, and presence.

Think about it this way: every conversation is a chance to either close someone down or open them up.

This Week, Try This

In your next meeting, swap one “safe” question for one you’re genuinely curious about.
Notice the silence. Let it breathe before you respond.
Amplify someone else’s voice: repeat their point, give it weight, and watch the room shift.

I'll be taking a little break from podcasting now, as our producer/editor gets them ready for release. But this season is one I'll never forget, and hope you also get a chance to reflect on your own conversations, whether they are in front of the mic (or not).

See you next week,

Megan