Take Your Discovery Questions to the Next Level

In Brief – Thoughtful, intelligent discovery call questions have the potential to transform your sales meetings. Written for both sales leaders and salespeople, we break down what it takes to elevate your selling by asking next-level questions. Next-level questions are crafted from a blend of what you already know about your prospect—their situation, their challenges—mixed with your own experiences. Structurally, these discovery call questions combine assertive statements with open-ended questions, creating a dynamic that encourages deeper conversation. The magic lies in their outcome: by asking these types of discovery call questions, you pave the way for more insightful discoveries with your prospects, leading to stronger connections and, ultimately, more successful sales outcomes. I hope you find this helpful!

If one thing lights up my day, it’s learning something new through an engaging conversation. One key to helping your sales team gain momentum in discovery calls is well-crafted, insightful questions that cut through the noise and get to the heart of your client’s needs, challenges, and implications for their business.

Here’s a sneak peek at the types of discovery call questions we’re about to explore:

  • Open-Ended Questions: Dive deep beyond the yes or no.
  • Next-Level Questions: Build credibility, rapport, and a deeper understanding of the situation and problems.
  • Follow-up Questions: Keep the conversational momentum building and the insights flowing.

Let’s get started!

Open-Ended Discovery Call Questions

The Shift to 'How'

My journey has taught me that the heart of a successful discovery call lies in the ‘how.’ It’s easy to fall into the trap of asking, “Do you have a budget?” or “Are you looking to make a decision soon?” Yet, these discovery call questions barely skim the surface. They don’t invite the story, the struggles, or the aspirations. 

The Power of Open-Ended Engagement

Start discovery call conversations with open-ended questions or statements that invite conversation. These are your golden tickets to valuable insights. “How are you feeling about the team’s results?” or “Tell me about the challenges you are currently facing.” encourage detailed responses and open the conversation for deeper exploration. Open up closed questions such as “Tell me more about ….” to encourage more than yes/no answers. Let me lay out the potential of open versus closed-ended discovery call questions for you, side by side, to appreciate the difference:

Closed-Ended Discovery Call Question

Q – “Do you have a budget in mind?”

A – No

Provides a specific figure or a yes/no answer. Fails to invite much new information, risks nasty surprises in the sales process.
Open-Ended Discovery Call Question

Q – “How did you determine your budget for this project?”

A – “Mainly we …..”

Encourages discussion on the thought process behind budgeting, revealing priorities and potential flexibility. Might expand a small opportunity.
Closed-Ended Discovery Call Question

Q – “Is timeline a critical factor for you?”

A – Absolutely.

Yields a simple yes or no, without understanding the reasons behind the timeline’s importance. Again, this risks lost deals and unanticipated delays.
OPen-Ended Discovery Call Question

Q – “Tell me more about what’s influencing your timeline for this project?”

A – “This project is linked to our strategic goal to …”

Opens up a conversation about the factors affecting the timeline, offering insights into client constraints and goals. Can help sales shorten deal cycles.

Next-Level Questions - Leverage Knowledge, Insight, and Experience

Incorporating knowledge, insight, and experience into your discovery call dialogue does more than enrich the conversation; it transforms it. By doing so, you prompt reflection and self-revelation, which sets up the potential to provide solutions to urgent and important problems. This approach to discovery call questions allows you to position your service as the answer to their deeper problems based on a profound understanding of their business landscape and past experiences.

But how do you elevate a good conversation to a great one? Enter the trifecta of knowledge (k), insight (i), and experience (e):

Knowledge: What’s their situation?

  • Forget your sales quota for a moment. This is about exercising your curiosity and empathy to understand the client’s business and personal situation. Knowledge of the client’s situation provides a well-rounded context that sets the stage to make your conversation and questions relevant and timely. Look at our discovery call planning template blog to learn more about pre-call research that expands your knowledge.

Insight: What are their problems, and what implications do they face?

  • Reflect on what challenges the client is likely facing. Take a leap. Your insights build on the knowledge of their situation, focused on their problems and the likely implications of their business and performance. Compile what you have learned and use these to challenge your client to go deeper. Don’t worry about being wrong – just worry about being thoughtful and intelligent.

Experience: How do my own experiences provide added perspective?

  • Your stories and struggles are your compasses. Sharing these brings authenticity to your discovery call, builds credibility, and shows that you’ve walked similar paths. It’s about connecting on a human level, showing empathy and your expertise.

Download our free Next Level Question Worksheet

Note – this combination of knowledge, insight, and experience is the raw material that powers next-level questions. Don’t sweat it if you only have two of the three … you can still formulate super powerful discovery call questions. See three examples on the last page!

Crafting your Next-Level Questions

Now, let’s put this together, shall we? Use the Next-Level Question Worksheet I developed to help you rapidly formulate Next-Level questions for discovery calls.

Once you’ve identified some points related to customer knowledge (k), insight (i), and experience (e), play with a combination of statements and an open-ended question to take them deeper into their problem, implications, or potential solutions. 

Next-level questions for discovery calls mix statements with questions to challenge the client’s thinking. If you encounter resistance, take note so you adjust your tone and approach in the future. Try these two tricks to avoid resistance:

  1. Soften your statements or questions to avoid confrontation. For example, change “Why did that project fail?” to “That project sounds challenging. What did your team take away?”
  2. Neutralize statements or questions to remove bias and avoid leading the respondent to a particular answer​​. For example, change “What makes this project a high priority for your team?” to “Sounds like you have several priorities on your plate. Where does this project fit relative to these competing projects?”

And remember your mindset; genuine engagement and openness start when you ask authentic discovery call questions from a place of curiosity.

Follow-up Questions

After you’ve kicked off your discovery calls with next-level questions, don’t just leave it at that. Dig a little deeper and add a “tell me more about that” to discover the underlying motivation behind their answer.

Why Follow-Up Questions Matter

• Understanding Challenges

Consider it an invitation when a client shares a glimpse of a challenge. Follow up with, “You mentioned a few challenges; what are their impacts on the business?” This isn’t nosiness; it’s your way of showing that you care about their challenges and are here to help navigate them.

• Building Relationships

It’s not always about the problems. Follow-up questions also play a huge role in building rapport. Questions like, “How has this been affecting your team?” or “What’s been working well for you so far?” serve dual purposes. They provide insights into their situation and strengthen your bond, building a foundation of trust and mutual respect.

• Staying Present

And sometimes, these follow-up questions are a gentle reminder that you’re here, ready to help whenever they’re ready to take the next step. Asking, “Have you thought about ways to tackle this?” is a subtle way of saying, “I’m here to support you.”

The point of diving back into your discovery with these follow-up questions isn’t just to fill the silence or gather more info. They’re a way of checking in, showing you’re genuinely interested in not just their business but how they’re doing as people. This approach changes the game.

The Juggling Act

Now, how do you balance all these discovery call questions? It’s as much art as it is science. There’s no set formula or sequence to follow. Be present in the conversation, feel out the pace, and adapt as you go. Some calls might need more open-enders before diving deep, while others might jump straight into the meaty stuff with a nudge.

I coach sales teams and leaders to build up a bank of go-to questions they can adapt across most discovery conversations. Try this one:

  • Next-Level Question – “You mentioned X, Y, and Z – if you could fix one of these, which would have the most impact?”
  • Follow-up – Dig a little deeper versus assuming you know which is most impactful or asking about the one you feel most comfortable talking about

It’s a dance. And like any dance, it gets smoother with practice. The more you do it, the better you get at reading the signals, knowing when to push a little and when to pull back, and ensuring the conversation flows naturally.

This balance, this dance of discovery call questions, ensures your clients feel heard, valued, and understood. And that’s the founda


Every call is an opportunity to have a meaningful conversation, where the discovery call questions you ask, and every piece of insight you gain helps to piece the puzzle together. So, next time you’re on a call, remember: it’s not what you ask, but how you ask.

Dive deeper into the art of asking insightful discovery call questions with our downloadable guide, ‘Next-Level Question Worksheet’ and unlock the potential of every sales conversation. Worried about other aspects of your discovery call? We’ve got that covered: plan each call with our Discovery Call Plan Template and conduct regular call retrospectives with our Discovery Call Review Checklist. With these tools at your disposal, mastering the art of discovery calls is just a matter of time.

Catch you on the next call!

Picture of  PETER MEYERS


Peter is an executive advisor, consultant, and facilitator who happily lives and breathes sales strategy and customer experience. With a razor-sharp focus on making sales teams more effective, he combines his creativity, collaborative style, and relentless drive for results. Before Portage, he held VP roles in sales, marketing, and product innovation at LoyaltyOne, Epsilon, The Toronto Region Board of Trade, and Engage People. When he’s not exploring new sales strategies, he’s taking in the great outdoors.

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