5 Pain Point Discovery Questions for Remote Sales Reps in Outbound Sales

Transform your remote sales approach with these game-changing discovery questions.

By Diane Almanzor

Without the nuances of face-to-face interactions, the challenge of establishing rapport and uncovering deep-seated customer pain points has intensified. A recent study by Salesforce indicates that 8 in 10 sales reps have shifted to a remote or virtual selling environment, highlighting the urgency for refined tactics that transcend traditional methods.

The transition to remote selling is not without its obstacles. A report by McKinsey reveals that 38% of sales professionals believe understanding customer needs has become more challenging in a virtual context. This shift underscores the importance of deploying sophisticated questioning techniques tailored for the remote sales environment, where every interaction must count, and deeper insights are gleaned from every exchange.

Amidst these challenges, remote sales professionals must elevate their approach to pain point discovery. The goal is not just to identify challenges but to foster a connection that bridges the digital divide, offering solutions that resonate on a more personal and impactful level. Below are questions crafted to deepen understanding and facilitate meaningful dialogue, all within the unique dynamics of remote sales jobs.

1. "How Has Your Strategy Adapted to the Changing Dynamics of [Industry] Over the Last Quarter?"

This question is fundamentally about understanding the agility and responsiveness of a business within its industry.

A study by McKinsey & Company highlighted that about 90% of executives expect the fallout from COVID-19 to fundamentally change the way they do business over the next 5 years, yet only about 21% feel confident in their company's ability to adapt to these changes. This gap signifies a widespread concern over adaptability that your solution could address.

The question invites prospects to share both the logistical and emotional impacts of changes on their team and serves as a gateway to understanding not just operational pain points but also the human element, offering insights into areas where your solution might offer support.

2. "In Your Pursuit of [Specific Goal], What Unexpected Obstacles Have Emerged?"

Given the rapid evolution of market conditions, particularly in response to global shifts, this question surfaces obstacles that might not have been anticipated. It reflects an understanding of the volatility and uncertainty businesses face, inviting a discussion that can reveal deeper, perhaps unacknowledged, needs.

Tailoring the conversation to a prospect's specific goal creates a personalized dialogue that increases engagement. Personalization can drive an increase of up to 19% in sales. This question uncovers not just the apparent hurdles but the unforeseen challenges that might not have been initially considered.

3. "Which Aspects Of Your Business Are You Most Concerned About Sustaining Long-Term?"

Sustainability is a common concern among many businesses. This question touches on strategic priorities and potential vulnerabilities, offering a nuanced view of where your solutions could play a role in their long-term vision.

Asking about sustainability efforts can uncover areas where businesses feel vulnerable or uncertain about the future. It prompts prospects to consider not just the immediate benefits of digitalization but also how they can maintain and build upon these changes.

For instance, issues like data security, technology scalability, or even workforce adaptability to new tools might emerge as critical points of discussion.

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4. "Where Do You See the Greatest Gaps in Collaboration and Communication Within Your Team?"

Different work models can introduce gaps in collaboration and communication. By directly addressing these common pain points, you invite your prospect to discuss specific areas where efficiencies could be improved, setting the stage for your solution to be presented as a vital tool in bridging these gaps.

This could range from issues with existing communication tools, challenges in maintaining company culture, to difficulties in project management and team alignment. Understanding these pain points not only demonstrates empathy but also positions your solution as potentially indispensable for enhancing work efficiencies.

5. "Looking Forward, What Are the Key Barriers You Anticipate Could Impede Achieving Your Upcoming Goals?"

This forward-looking question encourages prospects to consider future challenges in their infrastructure or strategy. It's a strategic way to position your solution as not just a fix for current issues but as a proactive measure against potential future obstacles.

Asking about future barriers not only demonstrates your commitment to understanding and addressing the prospect's needs but also sets the stage for positioning their solution as essential for future-proofing the prospect's operations.

This question also aligns with findings from the McKinsey Global Institute, which indicates that companies who actively engage in scenario planning and anticipate future challenges are more resilient and better positioned for growth.

The insights gained from the responses to this question enable remote sales professionals to tailor their solutions more effectively. According to a survey by Forrester, organizations that engage in future-oriented planning are 33% more likely to lead in their market.

In practice, this not only reinforces the value of the solution but also builds trust and credibility, as it shows that you are genuinely interested in the prospect's long-term success.

How Glencoco Supports Insightful Pain Point Discovery Questioning

Integrating Glencoco into the workflow of remote sales reps in outbound sales enhances the application of the five advanced pain point discovery questions, making their approach more nuanced and aligned with the realities of remote sales environments. Here's a look at how Glencoco supports these questions:

Interactive Training Modules

When fractional SDRs explore how a prospect's strategy has evolved with industry shifts, they need a solid understanding of those dynamics. Glencoco's industry-specific training modules ensure SDRs are well-prepared, enabling more insightful discussions about strategic adaptations and potential solutions.

Inquiries about long-term sustainability tap into strategic foresight. Glencoco aids remote sales reps in framing these conversations thoughtfully, leveraging training that incorporates industry trends to discuss how solutions might address future challenges without overpromising capabilities.

Optimized Communication Tools

Asking about unexpected obstacles in achieving specific goals requires insight into the prospect's industry challenges. Glencoco facilitates this through efficient communication tools that help SDRs engage in deeper conversations, providing a clearer picture of the prospect's unique challenges.

By optimizing the process of reaching out and engaging prospects, Glencoco allows SDRs to delve into these gaps more effectively, facilitating a dialogue on how these issues might be mitigated through improved processes or tools.

Real-Time Performance Analytics

Encouraging prospects to consider future barriers requires a blend of insight and tact. Glencoco's real-time performance analytics help SDRs tailor their conversations based on prior interactions, enabling a focused discussion on overcoming potential hurdles without assuming immediate solutions.

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By leveraging Glencoco, fractional SDRs in outbound sales can significantly enhance their ability to engage prospects with these five pain point discovery questions. Glencoco's platform offers the tools, training, and insights necessary for remote sales reps to conduct deeper, more meaningful conversations that go beyond surface-level challenges.

This strategic alignment ensures that SDRs are not just asking questions but are also engaging in insightful dialogues that uncover critical pain points, thereby positioning their solutions as not just beneficial but essential for the prospect's success.

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