6Mastering Sales Conversations: Asking the Right Questions, at the Right Time

If there's anyone who knows how to conduct an interview, it's Oprah Winfrey. She makes it look effortless, and hiding behind that easygoing facade is rigorous intentionality.

Oprah has a singular way of shaping interviews that tackle tough topics and leverage provocative questions to create intrigue and uncover surprising information—yet she still manages to do this in a way that feels collaborative and conversational. As sales professionals, this mix of deliberate questioning and collaboration is our ultimate goal: We must uncover the information we need to validate if we're the right fit and collaborate with the potential buyer to select and implement the right solution.

Don't Question the Value of Good Questions

Think back to the last time you went to dinner with a good friend.

You likely recall the restaurant and the food, the little sensory details like the man twirling the neon green sign outside the carwash across the street or the squawking birds in the background. But what about the first meal you shared together—what can you recall? Suddenly, it's much more difficult to remember the details that paint a vivid scene—but I'm willing to bet there's one thing you do remember: the conversation.

I'm also willing to bet it wasn't a monologue. You likely exhibited a genuine curiosity about the other person; the conversation naturally flowed from question to answer and back again; and you probably ...

Get The Power of Value Selling now with the O’Reilly learning platform.

O’Reilly members experience books, live events, courses curated by job role, and more from O’Reilly and nearly 200 top publishers.