Oct 6 • General discussion
Principle of the week: Hard Conversations
I was nervous. I knew I had to have the hard conversation, but I didn’t want to at all. Honestly, I even tried to push it off on someone else—which was wrong—but that’s how badly I wanted to avoid it.
So what issue had me tied in knots for weeks? Good question.
I was a new broker at an office we had just taken over. One agent stood out—she had a ton of potential to rise above her current performance. She was sharp, personable, and well-spoken. But every day she came to work in sweatpants and a sweatshirt.
I knew I needed to encourage her to dress for success—not only because of how others perceived her, but also because of how it could impact her own mindset and confidence. The problem? There’s almost nothing more uncomfortable than a man having to talk to a woman about how she dresses. Be real—when your wife asks how she looks in a new dress, there’s only one right answer: “You look incredible, baby!”
But when you’re the leader, you don’t get to dodge the uncomfortable. You don’t get to ignore it. If you want to set a standard and build a strong culture, you have to run toward the tough conversations.
Finally, I asked her to step into the office. I began with genuine compliments about her talent and potential, then gently leaned into how her attire might be holding her back. When I finished, I braced myself—I was half-expecting a stapler to come flying at my head.
Instead, she smiled and said, “Caleb, you’re right. I never really thought about it that way. I’ll start dressing more professionally.”
What happened next blew me away. Over the next few weeks, not only did she dress sharper—she walked taller. Her confidence grew, and by the end of the year, she had her best production year ever.
It left me wondering: what if I had never had that hard conversation? How much would I have taken away from her by avoiding what could actually help her grow?
As Stephen Covey said, “Holding people to the responsible course is not demeaning; it is affirming.”
It shows someone you care enough about them—and that you see so much potential in them—that you refuse to let them stay where they are.
The key is this: hard conversations must always come from the right place—with kindness, compassion, and respect. But they must also be rooted in truth. When truth is spoken with the right heart, it moves from the head to the heart—where real change happens.
So who do you need to have a hard conversation with today? Stop living in fear. Step into it. It just might set you both free.
Be Principled,
Caleb
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Principle of the week: Hard Conversations
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