How to Have Hard Conversations Without Breaking Trust
- 2 days ago
- 2 min read
Hard conversations don’t have to be harsh.
In fact, the best hard conversations often strengthen relationships rather than damage them. I’ve watched this happen many times — both as a leader and as a coach.
The difference isn’t whether you have the conversation. It’s how you have it. Here’s what I’ve seen work:
Lead with intent, not content. Before you deliver the message, share why you’re having this conversation. “I care about your success, and there’s something I need to share” lands differently than jumping straight to the feedback. People can receive almost anything when they understand the intent behind it.
Be specific, not general. “You’re not strategic enough” shuts people down. “In last week’s leadership meeting, your presentation focused entirely on operational details and never addressed the three strategic questions the CEO asked for” gives them something to work with. I call this “naming the pattern with evidence.”
Own your perspective. “I noticed…” “My experience was…” “The impact on me was…” You’re not delivering objective truth. You’re sharing how things land. This distinction matters more than most leaders realize.
Make space for their experience. After you’ve shared, stop. Ask what they’re thinking. Listen — really listen. You might be missing context. Even if you’re not, they need to be heard before they can hear you.
Focus forward. The goal isn’t to relitigate the past. It’s to create clarity about what happens next. End with alignment on a specific path forward, not a vague “let’s do better.”
I’ve had to deliver hard messages as a COO — restructurings, performance conversations, strategic pivots that affected people’s careers. The pattern is consistent: hard conversations handled with directness and care don’t break trust. They build it.
Because they demonstrate something rare: you care enough to be honest, and you’re skilled enough to be kind about it.
What hard conversation could you approach differently?
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