7 Great Sales Discovery Questions for Your Next Prospecting Meeting

Buyer receptivity is at an all-time low. As ASLAN CEO Tom Stanfill puts it, "The customer's willingness to listen is more important than your ability to position your solution." This fundamental truth makes discovery not just important, but critical to your success.

Most sales professionals walk into discovery meetings with the questions "all up here" (pointing to their head). John Ferguson, former EVP of Sales and partner at ASLAN, bluntly states: "Respectfully, you're not that good. You will forget something."

To help you uncover the truth and increase buyer receptivity, here are seven Other-Centered® discovery questions that will transform your next prospecting meeting.

1. Uncovering Their Point of View

DON'T ASK THIS: "What keeps you up at night?"
(Watch as your prospect gives the same generic answer they've given to the last ten reps who asked)

ASK THIS INSTEAD: "We've found that most [title] are focused on [specific challenge] right now. Based on your experience, how accurately does that reflect what's on your whiteboard?"

Why it works: This approach demonstrates you understand what's likely on their whiteboard (their priorities) while giving them space to clarify what's really important to them. This isn't about getting information to sell—it's about genuinely understanding their perspective.

2. Digging Deeper into Their Plans

DON'T ASK THIS: "What are your goals this year?"
(Your prospect mentally prepares their sanitized, surface-level response)

ASK THIS INSTEAD: "Most organizations in your industry are tackling [specific initiative] to address [specific challenge]. Where does this fit into your current strategy, if at all?"

Why it works: This question positions you as knowledgeable while creating a safe space for them to share their actual plans. Remember: "If you haven't done the time or done discovery well, you can only be selling a generic product or solution," as John Ferguson emphasizes.

3. Identifying Potential Pitfalls

DON'T ASK THIS: "What challenges are you facing with your current approach?"
(Your prospect gives a partial answer, keeping the real issues hidden)

ASK THIS INSTEAD: "In our experience, when companies implement [their current approach], they often struggle with [specific obstacle]. Has your team encountered anything similar?"

Why it works: By sharing a "disruptive truth," you create space for them to acknowledge real challenges without feeling exposed. This helps them see that you understand the nuances of their situation, elevating you from "salesperson" to trusted advisor.

4. Understanding Their Decision-Making Process

DON'T ASK THIS: "How does your company make decisions?"
(Your prospect gives you the formal process, hiding the informal influences)

ASK THIS INSTEAD: "When you implemented [previous similar solution], what did that evaluation process actually look like? Were there any unexpected steps or influencers in the process?"

Why it works: This question acknowledges that formal and informal decision drivers exist in every organization. As Tom Stanfill notes, "Until you know what the heart really wants, the will chooses, and the mind justifies," you don't know how decisions are really made.

5. Determining True Priority

DON'T ASK THIS: "Is this a priority right now?"
(Your prospect hedges with "We're evaluating several options")

ASK THIS INSTEAD: "We've found that companies tackle this issue when [specific trigger event] happens or when [specific pain] reaches a certain threshold. What's prompting your organization to look at this now?"

Why it works: This helps uncover whether there's a compelling event driving action. As ASLAN teaches in their discovery roadmap, understanding priority is crucial—without a compelling reason to change, deals stall indefinitely.

6. Exploring the Leadership and Coaching Dynamic

DON'T ASK THIS: "Who else needs to be involved in this decision?"
(Your prospect becomes guarded, wondering if you're trying to go around them)

ASK THIS INSTEAD: "One challenge we've seen is that even great solutions fail without proper leadership support and coaching. How does your leadership team typically get involved in initiatives like this?"

Why it works: This question addresses what John Ferguson calls "the difference between a good organization and a great organization"—the quality and cadence of coaching from leaders. By bringing this up, you're demonstrating that you care about actual results, not just making a sale.

7. Bridging to Their Future State

DON'T ASK THIS: "What are you hoping to achieve?"
(Your prospect gives vague outcomes that don't connect to real value)

ASK THIS INSTEAD: "If we fast-forward a year after successfully implementing a solution, what specifically would be different in your business? What metrics would have changed, and by how much would they need to change for this to be considered a success?"

Why it works: This question helps them visualize the bridge between their current state and future state—a fundamental concept in ASLAN's methodology. It shifts the conversation from features to outcomes that matter.

Drop the Rope® in Discovery

The key to effective discovery isn't just asking good questions—it's approaching the conversation with the right mindset. ASLAN calls this "Dropping the Rope." Instead of playing tug-of-war with the customer by trying to pull them toward your solution, release the pressure.

Communicate genuinely that you aren't sure what they need or should do. Your goal is simply to serve, not force your way into a meeting or get an order. This eliminates the adversarial relationship and allows both you and the customer to work together to solve real problems.

The Discovery Roadmap

To ensure you don't miss critical information, organize your discovery around ASLAN's "Five P's":

1. Profile – Understanding the company and person
2. Point of View – Their perception of their current situation
3. Plans – Their initiatives to reach their desired future state
4. Pitfalls – Obstacles that might prevent success
5. Preferences – How decisions are made and what they value

As Tom Stanfill explains, "If I can really figure out where they are, where they want to go, what's their plan to get there, and then what's the problem with their plan...that's what discovery is about."

Be a Journalist, Not an Attorney

Approach discovery like a journalist, not an attorney. An attorney has an agenda and tries to back someone into a corner with leading questions. A journalist genuinely seeks to understand the full story.

When you truly listen, validate perspectives, and demonstrate genuine curiosity, you create receptivity. As Tom Stanfill says, "Until you can communicate and validate their point of view, they're never going to listen to your point of view."

The truth is, effective discovery isn't about collecting information—it's about creating the conditions where the customer wants to hear what you have to say. When done well, the customer moves from thinking "this is just another sales rep" to "this person really understands me and might actually be able to help."

Remember: "Great salespeople are great listeners, but they're great listeners because they ask great questions."

Want to learn more about effective discovery? Check out these ASLAN resources:

• The Sales Training Program That Makes It Easy
• Other-Centered® Selling
• Listen to the full discussion on discovery in ASLAN's Sales Podcast Episode 161