People don’t always say what they mean, and this is even more true for prospects. 

To turn a deal from an initial conversation to a signed agreement, it’s essential to uncover both the spoken and unspoken elements. This process goes beyond just the words exchanged. 

Here are  three questions I find particularly effective during discovery, as they often reveal crucial insights that can make a real difference. 

1. Timeline exploration: Fixed or flexible? 

When discussing a prospect's project or solution timeline, the initial question might be simple:  “When are you hoping to have this implemented?” However, instead of taking their answer at face value, it’s important to dig a little deeper to understand how fixed or flexible that timeline really is. 

A useful follow-up could be, “If we had to push it back by another quarter, would that be  feasible?” 

Their response can reveal a lot.  

If they suggest that a delay wouldn’t be a problem, it may indicate that there isn’t a compelling event or urgent need driving the project. A flexible timeline often implies that the initiative is more of a “nice-to-have” rather than a critical priority. 

At this point, it’s your opportunity as a seller to probe further and identify any underlying pain points—showing both the positive outcomes of addressing these issues and the cost of inaction. 

Additionally, one common reason for closed lost deals is a lack of urgency. 

A flexible timeline frequently reflects this, suggesting that the pain point may not be pressing enough to justify immediate action. Take on the role of a detective: challenge their narrative and look for inconsistencies in their responses. 

Ultimately, your goal is to establish a clear timeline that remains consistent throughout your sales process. 

Sales discovery call checklist | Free download
A structured guide designed to help sales representatives effectively navigate initial conversations with prospective clients.
Sales Enablement CollectiveJames Shaw

2. Organizational goals: Reverse engineering your talk track 

Another effective way to uncover hidden needs is by inquiring about the organization’s broader goals.

Asking, “What are your organization’s primary goals for this fiscal period?” encourages the prospect to share what they’re working toward without having to explicitly outline the  problems. 

Let’s say they mention a goal of having a “single source of truth” for their data. On the surface,  this sounds like a proactive goal, but it hints at a larger challenge: perhaps they’re currently dealing with fragmented datasets or conflicting reports, leading to confusion within their teams.  

At this point, you could follow up with a question like, “Does this mean you’re currently  managing multiple data sources that sometimes conflict?” This approach helps you uncover the underlying problem of data inconsistency, which may not have been directly expressed. 

Reverse-engineering your talk track based on their goals enables you to present your solution as a vital tool for achieving those objectives. Rather than pushing your product, you frame it as an essential step toward their success. 

This client-centered strategy transforms your pitch into an unpresumptuous, consultative dialogue rooted in a genuine understanding of your prospect's needs and positions you as a trusted advisor. 

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3. Scale of 1 to 10: Measuring potential and satisfaction

Prospects aren’t always comfortable discussing the limitations of their current setup. They may hesitate to admit the issues they’re facing. It’s rare someone will voluntarily air their dirty laundry to strangers on the very first call. 

The “1 to 10 scale” approach defuses sensitivities around the negatives as it starts with an easy  “1 to 10” question and slowly transitions into a collaborative conversation about improving the setup. 

Most people wouldn’t rate their current setup a 10/10.

If they do, it’s also a hint that there isn’t a significant pain to solve, or you may need to speak to other stakeholders within that account. 

If the rating is below 10, ask them, “In an ideal world, what would it take to get us to a 10?” This encourages them to confide the frustrations or limitations keeping them awake at night. 

By framing the question this way, you create an environment for them to identify gaps and acknowledge issues without feeling pressured. In my experience, lowering the barrier to response and softening the ask often leads to more insightful and candid answers during discovery conversations. 

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Combining them all 

Using these techniques in tandem allows you to gain a nuanced understanding of your prospect’s situation. 

By exploring the flexibility of their timeline, reverse-engineering your questions based on organizational goals, and using the “scale of 1 to 10” question, you can build a more complete picture of what the prospect truly needs. 

These methods move beyond surface-level responses and help you uncover the underlying drivers that might otherwise go unspoken. 

Reading between the lines in sales conversations isn't about pressuring a prospect to share their pain points. It's more about discovering those hidden gems of information. 

These insights can significantly shift the dynamics of your sales discussions. Remember: The devil’s in the details.

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Sales Enablement CollectiveKatie Van Hoomissen