It’s Usually Not Your Content

Ultimize. Most people think they have a content problem. They think, I need better stories, I need more interesting experiences, I need to be funnier, smarter, quicker. That's almost never the issue. Let me show you how this actually plays out. You ask someone a simple question, so what do you do for work? And they say, well, I'm in finance. I focus mainly on mid-market accounts, but it depends on the quarter because sometimes we're more focused on restructuring. And lately there's been a lot of volatility, so we've had to— and within 10 seconds, you're gone. Not because finance is boring, although it can be, but because they turned a simple answer into a lecture. Now imagine a different version. Same person, same job, same life. They say, I help companies fix financial problems when things start going sideways. It's actually pretty interesting. Have you ever worked somewhere where things got chaotic? Now you're in. Now you're engaged. Now you have something to respond to. Same content, completely different delivery. This happens everywhere. Someone asks, "How was your trip?" And instead of saying, "Oh, it was great. We got completely lost in this little town and ended up finding an amazing restaurant. I'll tell you the story." They say, "Well, we left early in the morning and then the airport was packed." and then the flight got delayed, and then we landed. And now you're trapped in a timeline you didn't ask for. Here's the uncomfortable truth: most people are not boring because their lives are boring. They're boring because they get too much information too early. They confuse completeness with interest. They think, if I explain everything clearly, people will appreciate it. But Conversation doesn't work that way. Conversation works on curiosity. You don't give people everything, certainly not all at once. You give them just enough to want more. Think about how people naturally talk when they're engaging. They don't say, "Let me walk you through every detail in the correct chronological order of this thing I did." No, they say, "You don't believe what happened to me today," and then they stop. They create the space, they let the other person lean in. Now compare that to what most people do. They eliminate all mystery, they front-load every detail, they fill every silence, and they never give the other person a chance to get involved. I see this all the time with very smart people. They're used to being thorough, they're used to being precise, they're used to explaining things correctly. Well, that can be great in a report. It's terrible in conversation because the other person isn't grading your accuracy. They're deciding whether they want to keep listening to you. Here's another real-world example. You're at a dinner. Someone asks a simple question, "How did you get into your field?" One person answers with a 5-minute story that includes where they went to school, what they studied, their first job, their second job, why they switched, what they're doing now, By minute 2, people are looking down at their plates or their watch or their cell phone. Another person says, 'I actually got into it by accident. I took a job I wasn't even that excited about and it ended up changing everything. What about you? Did you always do what you wanted to do?' Now the conversation is alive. The difference is not intelligence, it's not experience, it's not even personality. It's restraint. It's timing. It's knowing when to stop. And this is the key shift I want you to start making. Before you talk, don't ask, "How can I explain this better?" Ask, "How little can I say to make this interesting to the other person?" That question alone will change how you speak because it forces you to cut the unnecessary detail, get to the point faster, leave room for curiosity, and Invite the other person in. And when you do that, people don't feel like they're being talked at. They feel like they're a part of something. That's where conversations become engaging. Not when you say more, when you say just enough.