Why Every Client Conversation Should Start with One Simple Question

It took me longer than I’d like to admit to really learn this. But once I got it, everything changed.

Every time you sit down with a client, whether it's over coffee, Zoom, or in a boardroom, they’re not just meeting with you because you booked time.

They’re meeting with you because they’re trying to do one of three things:

• Fix something that’s broken

• Avoid something that’s risky or painful

• Achieve something meaningful or urgent

That’s it.

And once you truly see that, every conversation becomes clearer, more focused, and more useful.

In sales training, this gets thrown around as "find the pain." But I think that misses something vital, not all clients are hurting. Some are building. Some are dodging bullets. Some are climbing mountains.

Your job isn't just to find the pain. It's to find the story.

That means:

• Asking, “What’s happening in your world that brought you to this conversation today?”

• Noticing what’s said, and what isn’t

• Listening not to reply, but to uncover

• Genuinely caring about what they’re up against

The moment you can clearly name what they’re trying to fix, avoid, or achieve, you unlock trust. Because it’s not about pitching. It’s about partnering.

A coaching move for salespeople: Pause before jumping into your solution. Ask yourself, “Have I really understood what this person needs to fix, avoid, or achieve?” If not, pause, rewind, ask better questions.

Why this works (a behavioral science lens): We are all motivated by a blend of approach goals (what we want to gain) and avoidance goals (what we want to prevent). Daniel Kahneman’s loss aversion theory tells us that people are twice as motivated to avoid loss than to secure a gain. But we shouldn’t underestimate the pull of aspiration either. The best sales conversations tap into both.

In short: Don’t just sell what your product does. Help your client do what they came to do.

Try This: Next meeting, ask your client: “What’s the best outcome we could create together today? ”Their answer will tell you everything you need to know. Because when you get clear on what matters to them, you become more than a salesperson. You become someone worth listening to.