Why Your Next Client Dinner Should Start With a Question

Most client dinners start with menus, not meaning.

You've booked the table. Maybe it's somewhere impressive—good lighting, wine list your assistant vetted, the kind of place that signals you care. You arrive on time. You make small talk. You ask about the flight, the family, the golf game. You eat. You say it was great to connect. You part ways feeling like you did the thing you were supposed to do.

And nothing really happened.

Here's the problem: most client dinners are performative. Everyone stays in their professional persona. The conversation skims the surface. You check the box, but you don't build anything. No one leaves feeling seen, surprised, or genuinely curious about working together. It's polite. It's pleasant. It's forgettable.

People remember how you made them think and feel, not what you ordered. If you want a client dinner to actually do something—to build trust, deepen alignment, or spark a real partnership—you have to break the pattern. And the easiest way to do that is to start with a question that matters.

Not "How's business?" Not "What brings you to town?" Something that invites reflection. Something that signals you're curious about them as a person, not just a transaction.

Try this: "What brought you into this line of work?" Or: "What's been surprising you lately?" Or even: "What's something you're thinking about that you don't get to talk about much?"

These questions aren't manipulative. They're not tricks. They're invitations. They say: I'm interested in understanding who you are, not just what you need from me. And when someone feels that, they relax. They open up. The conversation gets real.

This is the core insight behind what we do at Palabra. We create containers where people can stop performing and start connecting. It's not about theatre. It's not about polish. It's about depth. And depth starts with a single, well-chosen question that gives people permission to be honest.

Here's what you can do: Before your next client dinner, decide on one opening question. Share it with them ahead of time if you want—it sets the tone even before you sit down. Then, when the dinner starts, skip the weather and the traffic. Lead with the question. Let the conversation unfold from there.

If you want trust, start with a question, not a pitch.