Playing Catch? - The Art & Science of Asking Great Questions in Sales

Ever been on the receiving end of a rapid-fire sales pitch and felt like ducking for cover? You’re not alone. Too often, sales conversations feel like a monologue rather than a game of Catch. Optimé International coined the term "Playing Catch?" to describe the ideal sales conversation: a genuine back-and-forth exchange, where each question and response is like tossing a ball to your conversation partner, giving them time to respond before the next pitch.

Asking great questions is an art — it requires empathy, intuition, and timing — but it’s also a science. Studies confirm that people who feel listened to and understood are more likely to trust and, eventually, buy. Yet, many salespeople skip the question-asking phase entirely or ask questions that are so shallow they barely scratch the surface. This isn’t just a missed opportunity; it’s almost like throwing the ball at someone’s head. So, let’s explore how to ask great questions that create meaningful dialogue and help you build relationships and close deals.

Why Questions Matter in Sales

Great sales questions are more than a setup for a product pitch; they’re a means to explore the client’s world. Harvard Business Review explains that effective sales questions can increase trust, clarify needs, and uncover motivations, laying the groundwork for a genuinely collaborative relationship.

According to a report by Salesforce, nearly 60% of buyers feel that their sales rep doesn’t understand their needs. This gap is often due to sales reps making assumptions rather than asking thoughtful questions that lead to valuable insights.

How to Ask Questions that Keep the Game Going

Let’s break down a few principles of question-asking in the context of Playing Catch?:

1. Don’t Start with the Big, Scary Fastball

Imagine starting your sales conversation with, “What keeps you up at night?” or “What’s your biggest weakness?” Sure, it’s direct, but it might feel more like an interrogation than a friendly game. In Playing Catch?, you start with a few soft throws, questions that are easy to answer and set the stage for deeper discussions. Think: “What are some goals your team is excited about this year?” or “How has your approach evolved recently?”

2. Listen for What’s Behind the Response

Playing Catch? isn’t just about lobbing questions and waiting for answers; it’s about actively listening to what’s behind the answers. Are they excited? Hesitant? Don’t jump to your next question without showing them you’re tuned in. A follow-up could be as simple as, “That sounds like an interesting challenge. How did that come about?”

3. Use the ‘Rule of Three’

The best salespeople dig deeper, often following up with three questions on a single topic. So, instead of moving on after one surface-level question, explore different facets to gain depth and clarity. For example, if they mention a new strategic initiative, ask:

?? - “What inspired that direction?”

?? - “How will this impact the team in the short term?”

?? - “Are there any obstacles you foresee?”

These questions signal that you care and are genuinely curious. They also encourage your customer to reveal details they may not have planned to share.

4. Stay Curious, Not Invasive

There’s a fine line between curiosity and intrusion. When asking questions, ensure they don’t feel intrusive or overly personal. A good rule is to ask yourself, “Would I be comfortable answering this if the roles were reversed?” If not, dial it back.

5. Echo & Paraphrase

We all like to be heard and understood, and by repeating a word or phrase your prospect uses, you give them a chance to elaborate naturally. If they say, “We’re dealing with a lot of growth challenges,” you might respond, “Growth challenges? Tell me more.” This gentle nudge can open up new areas for discussion that a scripted question might miss.?

The Science Behind the Art

You might wonder, “Do these question-asking techniques actually work?” Science says yes! Research from Stanford University found that asking follow-up questions signals interest and strengthens interpersonal connections, making people feel heard and respected. Moreover, a study by the University of Pennsylvania revealed that in sales, asking open-ended, non-leading questions improves outcomes by around 25% on average.

Wrapping Up: Playing Catch? for Better Sales Conversations

Asking great questions is both an art and a science, requiring curiosity, intentionality, empathy, and active listening. Think of your conversation as a game of Playing Catch?, where each question is a carefully considered throw, setting your client up for their best response. By focusing on the interaction as a shared exchange, not a presentation, you create conversations that foster trust, reveal needs, and make the sale a natural outcome of a real connection.

Remember, asking great questions isn’t just about closing deals faster. It’s about opening doors wider.

Good Luck, and Good Selling!

At Optimé International we work with some of the greatest sales organizations in the world, big and small, helping them to achieve and exceed their performance goals. If would like to learn more about our passion for the sales profession and making a difference we’d love to chat with you, maybe over a coffee, virtual or IRL! Click here: Connect with Optimé for a coffee!?

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Sources:

1. Harvard Business Review, “The Surprising Power of Questions,” 2018.

2. Salesforce Research, “State of Sales,” 2022.

3. Stanford University, “The Impact of Follow-up Questions on Trust,” 2021.

4. University of Pennsylvania, “Question Quality in Sales Outcomes,” 2020.

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And there you have it – a guide to masterful questions in sales, keeping the game going without dropping the ball.