How to Improve Your Discovery Calls by Asking the Right Questions

Discovery calls are the gateway to building meaningful relationships with potential customers and ultimately converting leads into loyal users of your product. As someone with 16 years of engineering and leadership experience, including roles at Apple and startups, I’ve seen firsthand how asking the right sales discovery questions during discovery calls can transform sales conversations and outcomes. This post will guide you through why discovery calls matter, common pitfalls, and actionable strategies to ask the right questions that uncover true customer needs and accelerate sales.

A sales discovery call is more than just an initial chat-it is the foundation for understanding your prospect’s pain points, goals, and readiness to buy. According to sales experts, a well-executed discovery call helps you:

• Qualify leads effectively, focusing your time on prospects who are a good fit.

• Uncover hidden challenges and motivations that your product can solve.

• Build trust by demonstrating empathy and expertise.

• Set clear next steps to keep the sales process moving forward.

In my experience leading teams at Apple and startups, the best sales discovery calls are those where the salesperson listens more than they talk, using discovery call questions to guide the conversation rather than pitch prematurely. To maximize the impact of these calls, it's important to understand the sales cycle stages and where your prospect currently stands.

Common Reasons Discovery Calls Fail

Despite their importance, many discovery calls fall short due to:

• Lack of preparation: Sales reps who don’t research their prospect beforehand often ask generic or irrelevant discovery call questions, losing credibility.

• Asking closed or yes/no questions that don’t reveal deeper insights.

• Rushing to pitch solutions before fully understanding the prospect’s needs.

• Failing to build rapport or create a natural conversational flow.

• Not defining clear next steps, causing momentum to stall.

I recall a time early in my career when a sales discovery call went sideways because I jumped into product features without understanding the customer’s real pain points. That experience taught me the value of slowing down and listening carefully. For those looking to further streamline their preparation, check out how AI-driven call prep is revolutionizing sales team efficiency.

When to Use Discovery Calls

Discovery calls are most appropriate when you have a qualified lead who has shown interest but whose needs and fit are not fully understood. This call is ideal:

• Early in the sales process, before demos or proposals.

• When you need to assess budget, timeline, and decision-making criteria.

• To uncover challenges that your product can uniquely solve.

• To build rapport and trust with the prospect.

If a lead is unqualified or not ready to engage, a discovery call can help identify that early, saving time and effort. For more on how discovery fits into your overall presales process, explore our in-depth guide.

Benefits of Asking the Right Sales Discovery Questions

Asking the best sales discovery questions during discovery calls leads to:

• Deeper understanding of customer pain points and priorities.

• Ability to tailor your solution’s value proposition precisely.

• Increased trust and rapport from showing genuine interest.

• Higher conversion rates by focusing on qualified prospects.

• Clearer next steps and faster sales cycles.

In my leadership roles, I’ve seen teams that master discovery call questions consistently outperform others in closing deals and building long-term client relationships. Leveraging the right sales enablement tools can further empower your team to deliver value in every conversation.

1. Prepare Thoroughly

Before the call, research your prospect’s company, industry, and any previous interactions. Understand their market challenges and competitors. This preparation helps you ask relevant sales discovery questions and avoid wasting time on information you could easily find online. For a comprehensive list of effective sales discovery questions to elevate your calls, check out this resource from Qwilr’s Sales Discovery Call Questions.

For example, when I was leading a team at Apple, we made it a practice to gather as much intel as possible about prospects’ strategic priorities and pain points before the call. This preparation enabled us to tailor our discovery call questions and build immediate credibility.

2. Build Rapport Quickly

Start your call by establishing a connection. Use small talk or mention relevant industry news to create comfort. This sets a positive tone for open communication.

Rapport-building can be as simple as acknowledging a recent company achievement or commenting on a shared challenge in the industry. This humanizes the interaction and encourages openness.

3. Set a Clear Agenda

Outline the purpose of the call and what you hope to achieve. This manages expectations and keeps the conversation focused.

For instance, you might say: “Today, I’d like to learn more about your current challenges and goals to see how we might be able to help. Does that sound good?”

4. Ask Open-Ended, Thought-Provoking Discovery Call Questions

Use discovery call questions that encourage detailed responses rather than yes/no answers. Examples include:

1. “Can you describe the biggest challenges your team faces with [specific process]?”

2. “What would happen if you didn’t address this issue?”

3. “How are you currently managing [pain point], and what’s working or not working?”

4. “What are your top priorities for the next quarter?”

5. “What concerns do you have about implementing a new solution?”

These best sales discovery questions help prospects open up about their true needs and motivations. For more inspiration, explore our guide to product demos to see how the right questions set the stage for impactful presentations.

6. Practice Active Listening and Emotional Mirroring

Listen more than you talk. Repeat key phrases your prospect uses to demonstrate understanding and encourage elaboration. Chris Voss, author of Never Split the Difference, recommends mirroring the last few words your counterpart says and labeling emotions with phrases like “It sounds like you…” or “I can see why that’s frustrating.”

Active listening builds rapport and uncovers subtle insights that scripted discovery call questions might miss.

7. Probe Deeper

When prospects give vague answers, gently probe to clarify. For example, “You mentioned that efficiency is a challenge-can you tell me more about how that impacts your team’s daily work?”

This helps you uncover root causes and priorities.

8. Tie Pain Points to Your Product Subtly

Instead of pitching features directly, relate how your product can alleviate their specific pain points. Use storytelling and examples from similar clients to illustrate value without overselling.

For example: “From what you’ve shared about the time your team spends on manual reporting, we’ve helped other clients automate that process, freeing up their time for strategic work.” If you’re interested in how AI can further enhance your conversations, read about the AI advantage in sales conversations.

9. Qualify and Disqualify

Use discovery call questions to assess budget, decision-making authority, timeline, and fit. Don’t hesitate to disqualify leads that aren’t a good match to focus your efforts on high-potential prospects.

Questions like “Who else is involved in the decision?” or “What is your timeline for implementing a solution?” help clarify readiness.

10. Summarize and Define Next Steps

End the call by recapping key points and agreeing on the next action, whether it’s a demo, proposal, or follow-up meeting. This keeps momentum and shows professionalism.

For example: “Based on our conversation, it sounds like improving your reporting efficiency is a priority. I’d love to schedule a demo next week to show you how we can help. Does Tuesday at 10 AM work?”

Understanding the psychology of communication can elevate your discovery calls. The 7-38-55 rule by psychologist Albert Mehrabian states that only 7% of communication is conveyed through words, 38% through tone of voice, and 55% through body language.

While discovery calls are often virtual or phone-based, tone and pacing still matter immensely. Pausing after a discovery call question, allowing silence, and speaking with empathy convey attentiveness and respect.

In one of my early startup experiences, I noticed that simply slowing down my speech and allowing pauses encouraged prospects to share more deeply. This subtle change improved the quality of information I gathered dramatically.

It’s important to strike the right balance in how many sales discovery questions you ask. Asking too few risks missing critical information; asking too many can overwhelm or frustrate the prospect.

Data shows that on average, sales reps ask about 20 questions during discovery calls, while prospects ask around 12 questions back. This two-way dialogue ensures the call is a conversation, not an interrogation or monologue.

Encourage prospects to ask questions by pausing regularly and inviting their input. This builds trust and helps you gauge their interest and concerns. For teams looking to optimize their approach, understanding SaaS sales benchmarks can provide valuable context for performance.

Sometimes discovery calls don’t go as planned. Here are ways to handle common challenges:

• The Silent Prospect: If the prospect is reserved, use open-ended discovery call questions and mirroring to encourage sharing. For example, “I noticed you paused when I mentioned X-can you tell me what you’re thinking?”

• The Overly Technical Prospect: If they dive deep into technical details, acknowledge their expertise and steer the conversation back to business outcomes. “That’s a great point about the system architecture. How does that impact your team’s productivity or goals?”

• The Price Objection Early On: If price concerns arise prematurely, acknowledge them but redirect focus to value and fit. “I understand budget is important. Let’s make sure our solution aligns with your needs first, so we can explore options that make sense financially.” For more strategies, see our post on sales objection handling with AI.

• The Time-Constrained Prospect: If they seem rushed, prioritize your most critical discovery call questions and offer to follow up with detailed info later.

For a comprehensive step-by-step guide on structuring discovery calls and handling challenges, consider this ultimate resource by Cognism.

Modern tools can help you run more effective discovery calls:

• Conversational Intelligence Software: Tools like Gong or Chorus record and analyze calls to identify patterns, successful sales discovery questions, and areas for improvement.

• CRM Integration: Logging call notes and insights immediately helps keep your sales pipeline organized and ensures follow-ups are timely and relevant.

• Video Conferencing: Using video calls instead of phone calls can enhance rapport through visual cues and body language.

At Eubrics, we implemented call recording and AI-driven analysis to coach our sales team on question techniques and listening skills. This data-driven approach improved our discovery call effectiveness by 25% in six months.

At Eubrics, while leading a team of 15 engineers, we once engaged a prospect who was hesitant about adopting AI-driven analytics. Instead of jumping into technical specs, we asked open-ended sales discovery questions about their current data challenges and business goals. By listening carefully, we uncovered that their main issue was data overload and lack of actionable insights.

We then shared a story about a similar client who improved decision-making by 30% after using our solution. This approach built trust, and the prospect agreed to a pilot program, which later converted into a full contract.

This experience reinforced the power of asking the right sales discovery questions and tailoring your conversation to the prospect’s unique context.

Improving your discovery calls by asking the best sales discovery questions is a powerful way to unlock customer insights, build trust, and close more deals. Preparation, active listening, and thoughtful questioning transform a routine call into a strategic conversation that benefits both you and your prospect.

By mastering this skill, you position yourself as a trusted advisor, not just a salesperson, paving the way for long-term success.