How to Navigate Difficult Conversations for Personal Growth

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  • View profile for Michael Ulin

    3× AI Founder | Building agentic AI | xMcKinsey

    5,179 followers

    Don't shy away from tough conversations, they're the only ones that actually matter. I spent three weeks avoiding a conversation with a key customer who'd gone quiet after our last demo. I kept telling myself they were "just busy" or "evaluating internally." Finally, I called them directly: "I get the sense something didn't land right in our last conversation. Can you help me understand what happened?" Their response changed everything. "Honestly, your solution is impressive, but it solves a problem we had six months ago. Our priorities have completely shifted, and we didn't know how to tell you." That five-minute conversation saved us weeks of follow-up emails and gave us crucial market intelligence about how customer needs were evolving. Here's what I've learned about tough conversations: The longer you wait, the tougher they get. That awkward silence after a proposal isn't going to resolve itself. Address it directly. Most "tough" conversations aren't actually tough. They're just uncomfortable because we're afraid of what we might learn. The information you get is always more valuable than the comfort you preserve. Even brutal feedback moves you forward faster than polite silence. Three conversations I stopped avoiding: "It seems like this isn't a priority anymore. Should we pause?" (Usually reveals the real timeline and decision-making process) "What would need to change for this to be a clear yes?" (Gets to actual objections instead of vague concerns) "Who else needs to be convinced, and what are they worried about?" (Exposes the real decision-making structure) The pattern: Every tough conversation I've delayed has gotten easier once I actually had it. The counterintuitive result: Customers respect directness. They'd rather have an honest conversation than continue a polite charade. What conversation are you avoiding right now? What would happen if you had it this week instead of next month?