Last week I went to see Michelle Obama in Conversation in Sydney.
I was incredibly excited for the event. I had absolutely loved her memoir, Becoming, and devoured every word.
You know that rare feeling when you read a book and it seems as though every page has been written just for you? Becoming was one of those books for me.
I arrived expecting to be deeply inspired. In fact, my biggest concern heading into the evening was whether my fingers would be able to type quickly enough into the Notes app on my phone to capture all the pearls of wisdom I was certain were about to drop.
As it turned out, that wasn’t a valid concern.
I don’t want to dwell on the negatives, but from a woman with such an extraordinary breadth of life experience, I hadn’t expected the conversation to focus so heavily on early childhood memories.
I certainly wasn’t expecting her to “dish the dirt” - not from someone renowned for the phrase, “When they go low, we go high.” But I had hoped for deeper reflections on how she navigated life as one of the most visible women on the planet.
That insight never really came, and that in itself was an important reminder.
Sometimes the best lessons aren’t the ones you expect, because despite my disappointment, I actually came away from the evening with two really valuable leadership insights.
The first came from one of Michelle’s opening comments. I’m paraphrasing, but the essence was this: when we remove fear by overprotecting people, we also remove the sense of accomplishment that comes from overcoming it.
She shared this in the context of being expected to walk to school alone from a very young age, but the idea resonated strongly with me.
As leaders, we shouldn’t try to eliminate every source of discomfort for ourselves or our teams.
Growth requires challenge.
Confidence is built by doing things that feel daunting.
And the greatest sense of achievement often comes from confronting something that initially felt beyond our capabilities.
The second lesson had nothing to do with what happened on stage.
I attended the event with a wonderful group of women. We had dinner beforehand, shared stories and laughter, and thoroughly enjoyed each other’s company.
What stood out most was that we felt safe enough with one another to admit that we didn’t think the event itself was particularly good.
That might sound like a small thing, but it is actually a powerful indicator of trust.
Too often, we feel pressure to conform to the prevailing opinion - especially when a globally admired figure is involved. We hesitate to express an unpopular view, even when it is our genuine experience.
Groupthink is one of the greatest risks in leadership.
When people don’t feel safe to speak honestly, poor decisions go unchallenged and valuable perspectives are lost.
The most effective leaders create environments where respectful dissent is welcomed, where differing views are explored, and where people feel secure enough to say what they really think.
We shared our honest reactions, laughed about the evening, and continued the conversation long after the event was over - the WhatsApp group chat ran hot!
In the end, the headline act didn’t deliver in the way we had expected, but the experience was still immensely valuable.
It reminded me that our heroes are human, that growth requires us to experience fear rather than avoid it, and that one of the greatest gifts in leadership is creating relationships where people feel safe enough to tell the truth.
When have your significant leadership lessons appeared in an unexpected way?
Responses