What if… the one thing standing between you and your biggest goal isn’t skill, resources, or intelligence, but a conversation you’re avoiding?
A conversation with yourself.
A conversation with others.
I think that most breakthroughs—whether in business, leadership, or life—don’t happen because someone works harder or smarter. I think they happen because someone grasps the nettle and has a conversation that truly matters.
Conversations We Avoid
We tell ourselves stories:
• “Now’s not the right time.”
• “I don’t want to rock the boat.”
• “What if it goes badly?”
We hesitate. We skim the surface. We choose comfort over clarity. When we do this, we keep our teams, our businesses, and our ambitions stuck.
Leadership isn’t about waiting for the perfect moment. It’s about leading bold conversations—starting with yourself.
A Bolder Conversation With Yourself might be
• What am I not facing?
• What am I not hearing?
• What am I not understanding?
• What am I not seeing?
Too often, we set ambitious goals but lose the conversation before we even start. We let fear, doubt, or past failures dictate our future.
The boldest leaders don’t just think bigger—they challenge their own thinking.
A Bolder Conversation With Others
• What conversation am I avoiding?
• What conversation am I not really having?
• What conversation could change everything?
It could be in the boardroom, where tough decisions shape the future.
It could be with a team member, where trust and accountability are on the line.
It could be at the kitchen table, where the conversations we avoid are often the ones that matter most.
Wherever it happens, bold conversations drive change.
Richard Dawkins on Getting Depth
Dawkins wrote in The Blind Watchmaker that there are two levels of understanding.
The level where you can hear the words, and get the sense of what they mean.
And then there’s the level where you can feel them in the marrow of your bones.
I think the same is true for conversations.
Surface-level discussions keep things moving, but deep, bold conversations create breakthroughs.
Here’s the Good News
• You don’t need to have it all figured out before you start.
• You don’t need the perfect words or timing.
• You don’t need to force a breakthrough in one conversation.
• And you definitely don’t have to do it alone.
So, Is It Time for a Bolder Conversation?
Bold conversations unlock Big Bold Goals. They create clarity, alignment, and momentum.
Ask yourself: what’s the one conversation you need to have today? And what happens if you don’t?
Because when you have that conversation—the real one, the bold one—everything shifts.