Why top sales reps ask 4× more questions and close more deals

Most sales reps believe that closing a deal depends on a strong presentation. During meetings and calls, they talk a lot about the product, features, and case studies. This is where a common problem arises: the rep starts selling before fully understanding the client’s real need. “90% of sales reps don’t know how to ask questions and uncover needs. They switch into presentation mode before they understand the client’s problem,” says Kostiantyn Chervyakov, Head of Sales at Ringostat. Read on to learn why the right questions outperform presentations, how many you should ask on a discovery call, and which techniques help you truly understand the client.

Harvard Business School research: people ask dramatically too few questions

In 2018, Harvard Business School professors Alison Wood Brooks and Leslie John published the study “The Surprising Power of Questions” in Harvard Business Review. The core idea is simple but uncomfortable for most professionals: we underestimate the power of questions in conversations.

In many professions—such as journalism, medicine, or law—asking questions is a trained skill. But managers, entrepreneurs, and sales reps rarely treat it as something that needs practice. As a result, their conversations often turn into monologues instead of real dialogue.

The researchers found another interesting insight: after job interviews, business meetings, and even first dates, one of the most common thoughts people have is: “I wish they had asked me more questions.”

Why does this happen? According to the authors, people hold back for several reasons:

• they want to appear smart, so they talk more than they listen;
• they assume they already know the answers;
• they’re afraid of asking the “wrong” question and seeming incompetent.

But the study reveals a paradox: questions are what make conversations more productive. They help build trust and improve collaboration between people.

What do speed dating and sales have in common?

To test how questions affect first impressions, the researchers ran several experiments. One of the most well-known took place during speed dating.

Speed dating is a structured networking format that emerged in the late 1990s in the United States. It was created by Rabbi Yaacov Deyo to help people quickly find potential partners for serious relationships. The concept is simple: participants meet multiple people for short 3–10 minute conversations. After each interaction, they indicate whether they’d like to meet that person again. If the interest is mutual, organizers share contact details.

The format quickly gained popularity because it allows people to meet many potential partners in a single evening. That’s why it’s often used in sociological and psychological research on communication and first impressions.

This experiment followed the same logic. Participants were split into two groups:

• the first group had to ask at least nine questions during a 15-minute conversation;
• the second group asked four or fewer.

The results were striking: people who asked more questions were liked significantly more and received more follow-up meeting requests.

It’s simple: when someone asks questions, the other person feels heard and valued. This builds trust and makes the conversation more engaging.

The same principle applies to sales. When a rep dominates the conversation, the client feels like they’re being sold to. But when the rep asks questions and clarifies answers, the conversation starts to feel like a joint problem-solving process rather than a product pitch.

And it’s not just about asking questions—it’s about digging deeper into the answers. That’s how real context emerges: problems, needs, constraints, motivations. Without this, even the strongest presentation risks missing the mark.

The most powerful type of question: follow-ups

The Brooks and John study highlights another key point: it’s not just the number of questions that matters—not all questions are equally valuable. The biggest impact comes from follow-up questions. These are questions you ask after the other person responds, building on their answer and helping explore the topic more deeply. They show that you’re actually listening, not just waiting for your turn to speak.

Let’s look at a simple example. A client says: “It’s hard for us to control our managers’ work over the phone.” A weak response from the sales rep is to jump straight into a pitch: “Then our system is definitely the right fit for you…” A strong response is a follow-up question: “What exactly is difficult to control—missed calls, call quality? Or something else?”

These questions serve multiple purposes:

• they show interest and empathy;
• they help gather more information;
• they make the conversation feel natural.

This is critical in sales. Clients almost always describe their problem in general terms at first. Follow-up questions are what help you move from a surface-level issue to the real root cause. Without that, it’s hard to propose a solution that truly fits the need.

Moreover, the researchers call follow-up questions “the simplest way to demonstrate attention to your counterpart.” When people see that they’re being listened to and that details are being clarified, they start sharing more information. As a result, the conversation becomes deeper, and trust grows.

And the opposite is also true: when no follow-up questions are asked, people often perceive it as a signal that they’re not really being listened to.

Five principles of questions that help you understand the client better

In the same study, Brooks and John outline several principles that make questions far more effective. Most of them apply directly to sales.

1. Ask follow-up questions. Again and again. They are what help you go deeper. If a client mentions a problem, don’t rush to a solution. Clarify the context, causes, and consequences.
2. Prioritize open-ended questions. Questions that can be answered with just “yes” or “no” quickly shut down the conversation. Open-ended questions like “Why?”, “How exactly?”, “What do you mean by that?” encourage the other person to explain the situation in more detail.

For example:
— What is currently slowing down your sales the most?
— What happens if you don’t change anything in the next six months?
— Why did you start looking for a new solution right now?

3. Think about sequencing. The order of questions matters too. In difficult or tense conversations, it can be better to start with a more direct question to quickly remove tension. In conversations where trust needs to be built, it’s better to move from simple topics to more sensitive ones.

For example, if a potential client is already working with another provider, many reps circle around the topic:
— Could you tell me how your process is currently set up? What tools are you using?

Sometimes it’s better to ask a direct question right away:
— Why did you start considering other solutions if you’re already working with your current provider?

This question may sound sharp, but it quickly uncovers the real reason: dissatisfaction with service, pricing, or functionality. And that shifts the conversation from polite information exchange to real discovery.

4. Use a natural tone. People are much more open when the conversation feels informal. If questions sound like a survey or an interrogation, respondents start answering briefly and cautiously.
5. Keep the context of the conversation in mind. In group conversations, people tend to be less open and often follow the reactions of others. That’s why complex or important questions are better discussed one-on-one.

These principles determine whether a conversation becomes a real discovery call or just another product presentation.

Another interesting article about questions: “Turbocharge Your Business with the SPIN Sales Method”.

How many questions should you ask on a discovery call: Gong data

The first phone call with a potential client is often called a discovery call. The goal of this conversation is to understand the full context, as well as the client’s needs and problems, before proposing a solution.

So how many questions should you ask during such a call for it to actually drive results?

Sales platform Gong, which analyzes thousands of sales calls, used AI to compare the behavior of successful and average sales reps across more than 519,000 discovery calls. And it uncovered an interesting pattern.

The optimal number of questions on a discovery call is 11–14

If there are fewer questions, the rep doesn’t uncover enough of the client’s problem. If there are more than 15, the conversation starts to feel like an interrogation, and the win rate drops.

“It’s very important to understand who you’re dealing with, who your client is. How they think, what they need, what problems they have. Essentially, during discovery calls I ask 10–15 open questions to figure this out. Not only the questions matter, but also active listening and analysis, which help get to the core.

The main mistake sales reps make is moving too quickly to an offer instead of deeply exploring the problem. A successful call is defined not by the client saying ‘yes,’ but by the number of relevant insights you gather to shape your proposal”.

Serhii Korolkov Co-founder Needplex, Owner JuristCRM

Another interesting insight: weaker reps ask ten questions at the beginning of the conversation and then switch to a presentation, while stronger ones distribute their questions throughout the entire call.

What should a Head of Sales do about it?

If the right questions have such a strong impact on the outcome of a conversation, a logical question arises: how can a Head of Sales control this skill within the team? Here are a few things worth checking in your reps’ calls.

1. Was there a sufficient number of questions during the discovery call? It’s useful to periodically analyze call recordings and check how many questions a rep asks and how they are distributed throughout the conversation.
2. Does the rep ask follow-up questions? The key difference between average and strong sales reps is follow-up questions. They are what help move from a general problem to a specific context.

For example, if a client says: “It’s hard for us to control managers’ work,” it’s important that the rep clarifies:

• what exactly is difficult to control?
• how does this process currently work?
• what impact does this have on the business?

Without these clarifications, the discovery conversation will remain superficial.

3. Does the conversation end with a clear next step? Another common problem with discovery calls is the lack of a defined next step. Even if the conversation was meaningful, without an agreed action the deal often “gets stuck.” This could be:

• a product demo;
• a follow-up call;
• involving a technical specialist;
• testing the solution.

That’s why it’s important to analyze call recordings and check whether the call ends with a concrete agreement.

In practice, most companies face two problems. First, a manager cannot listen to all calls, especially if the team handles dozens or hundreds of calls daily. Second, even when listening to recordings, it’s difficult to quickly understand how the dialogue is structured, whether the rep asks enough questions, whether they clarify client responses, and whether they lead the conversation toward a next step.

That’s why many companies use business telephony systems with speech analytics.

In Ringostat, all calls are recorded, and AI analytics can automatically transcribe conversations, identify key moments in the dialogue, and evaluate communication quality. With such a tool, a manager can quickly find strong and weak discovery calls, analyze each rep’s performance, and train the team on real examples to improve the sales process.

Conclusion

Sales is rarely won by the one who talks the longest and most convincingly. More often, it’s won by the one who understands the client better. And you can only understand the client through the right questions. They help uncover the problem, see the context, and offer a solution that truly delivers value.

That’s why effective selling doesn’t start with a presentation. It starts with the right question.