During a recent keynote, someone asked me, “What’s your #1 tip for engaging in difficult conversations?”
I didn’t even have to think. “Don’t cannonball into the conversation.”
That’s what most people do. They dive straight in with blame or frustration and then act surprised when the other person shuts down. It’s like diving into a pool and yelling “BOOM!” No one enjoys getting splashed that way.
Instead, start with what you agree on. When you start here, you get the person nodding, saying “yes,” and feeling understood.
Check out my TikTok video where I share specific examples of how to start the difficult conversation effectively.
Afterwards: Ask Permission to Have the Conversation
This action gives them choice, lowers defensiveness, and builds buy-in.
It might sound like:
“Hey, I’ve always felt we have a relationship where we could come to each other and talk about anything. Lately, I’ve been feeling something is up between us but I know I might be misreading things, so I wanted to share my perspective and understand yours. Would you be open to talking through it together?”
That’s not manipulation. That’s emotional intelligence. It’s communicating with both honesty and humanity. That builds trust. That is leadership.
TRUST TAKEAWAY
“Start with what you share, not what you fear.
Trust doesn’t grow in confrontation—it grows in connection. When you lead with empathy and invite collaboration, you remind people they’re not the enemy; they’re part of the solution. The rest of the conversation is likely to go better if you open this way.
YOUR TRUST CHALLENGE
This week, begin every hard conversation with a “yes.”
Start by naming what you agree on or appreciate about the person before diving into what’s wrong. That one sentence can turn resistance into receptivity and transform a confrontation into a conversation.
WATCH JUSTIN: KEYNOTE SPEAKER ON TRUST
