April 17, 2023

8 Questions to Ask Early in the Sales Process

In a world where economic pressures constantly shift the buying landscape, the only constant in sales is change. To outpace the competition and keep your sales engine revving, you need to be agile, adaptable, and always ready to ask the right open-ended sales questions. That's where pressure testing comes into play—a high-octane sales technique designed to help you pinpoint decision-makers, expedite the sales cycle, and close more deals with precision.

Pressure Testing: Why Asking New (and Proven) Questions Matters

Before we dive into the sales discovery questions that can help you pressure test your prospects, let's talk about why it matters. Pressure testing is all about understanding their level of interest, commitment, and obstacles or objections that may be preventing them from moving forward. By deploying targeted questions early in the game, you can uncover the driving forces behind their decision making and uncover how you can help them achieve their goals.

When done correctly, pressure testing can help you to zero in on the decision-makers from the get-go, making the space to concentrate on cultivating individual relationships  and addressing their unique needs. With that in mind, let's take a closer look at the open-ended sales questions you should be asking your prospects early on to fuel the sales cycle — even if that means prioritizing a different lead in your pipeline.

8 Sales Questions to Ask ASAP

1. Future-Focused: What are Your Short and Long-Term Goals?

In inbound sales, you're not just selling a product, you're selling a vision. And that starts with understanding your buyer's goals. So ask yourself, are you helping your prospect see a brighter future? Are you inspiring them to achieve their wildest dreams? If not, it's time to ask the tough questions and get that future-focused mindset in gear.

When to ask: Kick it into gear early. Your customer's goals will serve as the roadmap for the rest of the sales journey. Be sure to revisit these objectives throughout the engagement, as the buyer's North Stars may evolve or become clearer over time. It's also wise to check in after significant events, such as major changes in the prospect's industry or company structure.

Decoding Responses

  • Buyer with defined goals/KPIs: If the prospect is aiming to increase revenue by X% in the next year or decrease production costs by X% within the next two quarters, use these specific targets to present a tailored solution. Showcase how your product/service can help achieve these goals and provide data-driven examples from similar clients, illustrating the direct impact on their bottom line.
  • Buyer with unclear goals/vision: Encourage them to discuss current pain points, such as lagging productivity or inefficient processes. With this information, offer guidance on setting realistic, achievable goals, and illustrate how you can address these issues, using case studies that resonate with their situation.

2. Human-Centric: What Inspired You to Get Where You Are?

Sales is all about relationships, and relationships are all about people. So take a moment to connect with your buyer on a personal level. Ask about their journey, their inspirations, their challenges. Let them know that you care, and watch as that connection turns into a lifelong partnership.

When to ask: Personalize the discovery by making a connection. This question can come after a more general "getting to know you" introduction. It's a great way to break the ice and establish rapport.

Decoding Responses

  • Buyer influenced by a mentor/role model: For example, a customer sharing that their success is driven by a mentor who helped them navigate a challenging industry, connect by sharing your own story of mentorship or admiration for someone influential in your field. Use this connection to illustrate how your product/service embodies the same values and guidance their mentor provided, positioning it as a natural extension of their journey.
  • Buyer who overcame obstacles: If they talk about overcoming a major industry shift or recovering from a failed venture, emphasize your solution's resilience and adaptability features. Share success stories of clients in similar circumstances who achieved remarkable results with your offering, reinforcing your commitment to empowering them through future challenges.

3. Outcome-Oriented: How Do You Define Project Success?

The customer's definition of success may not always align with yours. To deliver an effective solution, you need to understand what success looks like for them. By establishing clear goals and milestones, you can measure progress and demonstrate value throughout the process. This alignment can also set realistic expectations and avoid potential miscommunication down the line. So, find out what they're really after, and then go above and beyond to deliver it.

When to Ask: Inquire on this topic after learning about the customer's goals and pain points but before proposing solutions. Call out these KPIs during the solutioning phase to ensure that the proposal aligns with the buyer's definition of success.

Decoding Responses

  • Buyer focused on specific outcomes/results: If the buyer defines success by achieving a X% increase in customer retention or a X% reduction in production downtime, emphasize the measurable benefits your product/service provides. Share case studies or success stories of similar clients who reached comparable results to bolster your business case.
  • Buyer focused on subjective or intangible factors: If the definition of success involves improved team morale or better collaboration, for example, concentrate on building trust and highlighting long-term value. Showcase soft benefits, such as smoother communication or increased employee satisfaction, which might be harder to quantify but equally valuable. Another example could be a prospect aknowledging that their customer support needs improvement but lacks specific targets. 

4. Strategic: Why Is Now the Right Time for This?

Timing is everything on both ends of the deal. By understanding the "trigger for change" that motivates the buyer to engage with you, you can pinpoint the factors driving their interest. Is it a need for change, a desire for growth, or a fear of falling behind? Whatever it is, use it to your advantage by addressing any immediate concerns early in the process, and map the rest of the engagement to the overaching goal or insights gained along the way.

This question also serves as a pulse check on the prospect's motivation to make a purchase now or if they're simply exploring options.

When to Ask: Ask this question once you've got a grasp on their goals, but they may have stopped short of describing the obstacles, alternative solutions, and other pivotal parts of their journey.

Decoding Responses

  • Buyer motivated by growth or change (e.g., product launch/expansion): Emphasize your solution's scalability and adaptability to their evolving needs. A defined deadline allows you to stress the urgency of acting quickly to capitalize on opportunities or mitigate risks. For example, if they're prepping for a new product launch, emphasize how your marketing automation platform can streamline campaign management, enabling them to scale their efforts.
  • Buyer driven by internal factors (e.g., budget constraints/resource limitations): Highlight the ROI and cost-saving benefits of your product/service, addressing their concerns while demonstrating the long-term value of your solution.

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5. Priority-Driven: What Factors Will Drive Your Final Decision?

Closing a deal is like playing a game of chess. You need to think ahead, anticipate your opponent's moves, and plan your strategy accordingly. So ask your buyer what factors are most important to them. Is it price, quality, service, or something else entirely? This question is also an excellent opportunity to uncover any objections or concerns that may be preventing the deal from closing. Figure it out, and then make your move.

When to ask: Ideal timing is when more decision makers or external factors start to join the conversation, so you have more opinions (and context, and objections) in the room. It can also be an alternative to screaming WHY?! as a reaction to responses such as "we're not ready to make a decision yet."

Decoding Responses

  • Buyer focused on specific features/benefits: Tailor your approach to emphasize the feature that matters most to the buyer, illustrating how your product/service delivers the desired benefits and outshines the competition. For example, if they prioritize seamless integration with their existing tech stack, explain how your software's API capabilities allowed a similar client to connect your solution with their current systems, automating data flow and reducing manual entry errors by X%.
  • Buyer focused on price: If they're price-sensitive, communicate the value and ROI of your solution in your sales pitch, illustrating how the investment will pay off in the long run. Offer comparisons with competitors, highlighting cost savings or superior features that justify the price difference. Consider presenting a cost-benefit analysis, focusing on cost of ownership and resource optimization in driving value. 

6. Consultative: How Long Will the Status Quo be an Option?

The status quo is a sales roadblock. Change may be intimidating, but it's crucial for progress. As a critical sales discovery question, ask your buyer how long they can afford to stick with their current processes, legacy tools, or competitor solutions before their competitors overtake them. Use this sense of urgency to demonstrate how your solution can help them surge ahead. Plus, this question is a clever way identify the champions in the buying committee who are advocating for change—and those who are against it.

When to ask: Ideally, pose this open-ended sales question after the prospect has shared their goals and obstacles or in response to objections related to change management.

Decoding Responses

  • Buyer resistant to change: If they say their current process or legacy tools can suffice for another year or two, you may need to spend more time addressing their concerns and building trust. Share examples of businesses that delayed adopting new solutions, only to suffer significant losses or missed opportunities. This resistance might also indicate the need to reassess your sales pipeline and prioritize engaged leads, as it may not be the right time for this prospect.
  • Buyer using a competitor's solution: If they are open to change, provide competitor-specific content that differentiates you. For instance, if the they're using a competitor's CRM, share a case study where a similar company switched and observed a X% improvement in sales team productivity due to more efficient processes and better automation features.

7. Collaborative: Who Needs to be Involved to Ensure Success?

Success is a team sport, and winning takes everyone. So ask your prospect who else is on their team. Who are the decision-makers, the influencers, the champions in the buying committee? Get to know them, build relationships with them, and watch as the whole team comes together to achieve greatness.

When to ask: Ask this question early in the sales process, preferably during the initial discovery call or meeting.

Decoding Responses

  • Multiple stakeholders with differing opinions: If various stakeholders are involved in the buying decision, work to identify common ground and foster consensus among the group. For example, if cost reduction and increased efficiency are shared goals, demonstrate how your solution addresses both concerns effectively.
  • Involvement of external consultants or third-party advisors: Establish a relationship with these individuals and position your offering as the superior choice. For instance, if a third-party consultant is advising on software selection, provide them with comprehensive information about your solution's features, benefits, and customer success stories to support their recommendation.

8. Flexible: How Does This Align with Your Expectations?

Navigating the twists and turns of a buyer's expectations requires agility, attentiveness, and adaptability. So, ask your buyer how your solution fits into their overall vision. Are their expectations, hopes, and fears aligning with your proposal? By listening closely and adapting quickly, you can make your sales process more dynamic and effective than ever. Plus, this grants you the chance to gather real-time feedback and bridge any gaps to ensure a successful, long-term partnership.

When to ask:  You should ask this open-ended question throughout the sales process, starting in the early discovery phase and revisiting it during solutioning, proposal, and contract stages to ensure alignment and avoid miscommunication or scope creep in both the sales and the service delivery process.

Decoding Responses

  • Unrealistic or misaligned expectations: Manage expectations by clearly communicating what's possible and consult on alternatives if needed. For example, suppose a buyer expects your software to integrate seamlessly with all their existing systems within a week. In that case, you can explain that the integration process typically takes three weeks due to the complexity of their systems and provide a detailed timeline. Offer a phased integration plan with prioritized systems to minimize disruption and maximize efficiency. 
  • Exceeded expectations: Continue demonstrating value and building a strong post-sale relationship to support their evolving needs. Suppose your CRM solution not only streamlines their sales process but also uncovers new opportunities for cross-selling and upselling. In that case, you can offer a complimentary workshop on strategies to help their team capitalize on these new opportunities. This display of committment could also lead to referrals and testimonials, further expanding your market reach.

The Takeaway

The sales environment is ever-changing, and your ability to navigate it depends on your capacity to listen, learn, and evolve. By incorporating these sales discovery questions into your process, you'll not only delve deeper into your buyer's needs and motivations but also hone your agility to stay ahead of the curve.

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Elizaveta Shkurina

Sr Creative Strategist specializing in B2B brand creation, sales enablement, and SaaS demand generation. With 8 years of experience, she excels in driving ROI and revenue-driven KPIs through collaborative innovation.


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