Dig Deeper with Questions: The Secret to Unlocking Sales Success  

Chapter 6

1. Why Questions Are the Key to Successful Sales

In any consultative sales methodology—particularly in Gap Selling—the salesperson’s ability to ask insightful questions often determines the success of the sale. While many sales reps default to pitching products or features, Keenan underscores that the right questions are what:

• Uncover hidden, root-level problems that buyers might not fully understand themselves.
• Demonstrate empathy and expertise, building the trust needed to address those problems.
• Reframe the buyer’s perspective, helping them grasp the cost of inaction and potential benefits of change.

In short, questions turn you into a problem-solver rather than just another vendor making a pitch.

2. Three Levels of Questions: From Surface to Transformative

Keenan categorizes questions into three tiers:

1. Surface-Level Questions
   
   • Purpose: Gather basic information (e.g., “How big is your sales team?”).
   • Benefit: Provides foundational context, but does not reveal deeper challenges.
   • Example: “What CRM are you currently using?”
     
     
2. Probing Questions
   
   • Purpose: Dig deeper to understand why certain symptoms or issues exist.
   • Benefit: Helps isolate the root causes, motivations, and broader business impacts.
   • Example: “Why do you think your team is consistently missing follow-up deadlines?”
     
     
3. Transformative Questions
   
   • Purpose: Challenge the buyer to reassess their status quo and envision the consequences of inaction or benefits of change.
   • Benefit: Encourages prospects to think critically, often exposing hidden costs or missed opportunities.
   • Example: “If you continue at this pace for another year, what will it cost your team or organization—and how will it impact your strategic goals?”

Key Insight: Moving seamlessly from surface-level to probing to transformative questions guides the conversation from simple awareness of a problem to deep recognition of its urgency and impact.

3. The Importance of Digging Deeper

3.1 Uncover Hidden Problems

Buyers often present a symptom—such as “We’re missing sales targets” or “We have poor visibility into our pipeline”—without understanding the underlying root cause. By probing, you might discover issues like:

• Outdated systems
• Misaligned incentives for sales reps
• Inadequate training or onboarding processes

Why It Matters: Solving the wrong problem (e.g., addressing a surface symptom instead of the deeper issue) can leave the buyer unsatisfied and your solution appearing ineffective.

3.2 Create Clarity

When you ask thoughtful, pointed questions, you help the buyer articulate their challenges, goals, and constraints more precisely. Often, this clarity benefits both parties:

• The buyer gains a better grasp of their challenges.
• You can tailor your solution to exactly match their pain points and objectives.

3.3 Build Trust as a Problem Solver

Buyers often encounter salespeople who push a product-first pitch. By contrast, when you consistently ask questions, it shows you genuinely want to understand and help. This positions you as a trusted advisor, not just another salesperson.

4. Detailed Steps to Dig Deeper

Step 1: Start Broad, Then Narrow Down

1. Open-Ended Questions: Begin with broad, open-ended questions that invite the buyer to share their perspective.
   • Example: “Tell me about your current process for tracking sales performance.”
2. Follow-Up for Specifics: Once they mention a challenge or frustration, zoom in with more specific questions.
   • Example: “How often do you need to generate these reports, and who typically requests them?”

Step 2: Explore the “Why” Behind Problems

1. Root Cause Analysis: Ask “Why?” or “What’s causing this?” to delve into underlying reasons.
   • Example: “Why do you think your reporting process is so manual? Is it a lack of tools, lack of integration, or team training?”
2. Look for Secondary Impacts: Ask how these issues affect other departments, teams, or projects.
   • Example: “How does this manual reporting slow down your forecasting or budget allocation?”

Step 3: Quantify the Problem

1. Numeric Benchmarks: Probe for concrete metrics: “How much time do you spend each week on that?” or “What’s the average cost of a missed lead?”
2. Financial/Operational Impact: Encourage the buyer to see the real cost in lost revenue or wasted hours.
   • Example: “If your rep’s time is worth $40/hour, how much is that costing you monthly?”

Step 4: Challenge Assumptions

1. Encourage a Fresh Perspective: Ask questions that get the buyer to rethink their current approach.
   • Example: “What if the real issue isn’t your reporting tool, but how your team is collecting data?”
2. Address Potential Blind Spots: “Could there be other areas where these inefficiencies are causing hidden costs?”

Step 5: Envision the Future

1. Future-State Questions: Shift the focus to potential solutions and outcomes.
   • Example: “If you solved these reporting inefficiencies, what would your ideal process look like?”
2. Cost of Inaction: “What happens if you don’t address this now? How will it impact you in 6 or 12 months?”

5. Real-World Example: Going from Surface to Depth

Scenario

• Initial Statement from Buyer: “We need a better way to track our sales performance because we’re not hitting our numbers.”

Surface-Level Question:

• Q: “What CRM system are you using?”
• A: “We have an outdated CRM, but it’s what we’ve always used.”

Probing Questions:

• Q: “Why do you think your team isn’t hitting targets? Is it lack of insight into lead quality, delays in follow-up, or something else?”
• A: “We’re finding that leads aren’t getting proper follow-up because our reps spend too much time on manual reporting.”

Transformative Question:

• Q: “If you continue losing leads to manual processes, how will that affect your pipeline and revenue goals over the next 12 months?”
• A: “We could lose $50,000 in revenue each quarter, and that might put us behind competitors and even risk some staff layoffs.”

Outcome

• Buyer realizes the gravity of the situation—$200,000 annual risk.
• Salesperson can now position a solution that automates reporting and frees reps to focus on high-value tasks, quantifying how much revenue could be recaptured.

6. Common Pitfalls and How to Avoid Them

1. Asking Leading Questions
   
   • Pitfall: “Wouldn’t you agree that your outdated CRM is the main issue here?” This shuts down the buyer’s thinking.
   • Solution: Keep it open-ended and neutral: “In your opinion, what’s the biggest obstacle to timely follow-up?”
     
     
2. Rapid-Fire Interrogation
   
   • Pitfall: Bombarding the buyer with question after question without pausing to listen or acknowledge their answers.
   • Solution: Practice active listening—after each response, reflect or paraphrase to show you understand.
     
     
3. Ignoring Emotional Cues
   
   • Pitfall: Focusing solely on business data while overlooking the buyer’s personal concerns (e.g., job security, stress).
   • Solution: Interweave emotional drivers by asking how these challenges affect the buyer’s day-to-day or overall career goals.
     
     
4. Not Following the Thread
   
   • Pitfall: Hearing a mention of a potential deeper problem, but moving on to another question.
   • Solution: If the buyer says something intriguing, dig deeper: “Tell me more about that.”

7. Key Takeaways

1. Listen More Than You Speak
   • Skilled salespeople often talk less than the buyer, using focused questions to guide the conversation.
     
     
2. Ask High-Value Questions
   • Move beyond “What CRM do you use?” to questions that uncover why and how. That’s where insights lie.
     
     
3. Help Prospects Reflect
   • The best questions prompt buyers to self-discover the full scope and urgency of their challenges.
     
     
4. Connect Questions to Solutions
   • Continuously tie newfound insights back to how your product or service addresses those specific pain points.

8. Practical Tips for Immediate Implementation

1. Prepare a Question Bank
   • Before any sales call, list out the potential questions you might ask at each level (surface, probing, transformative).
     
     
2. Use Active Listening Cues
   • Nodding, paraphrasing, or asking clarifying questions ensures the buyer feels heard.
     
     
3. Stay Flexible
   • Have a framework, but don’t force a script. Adjust your questions based on the buyer’s responses.
     
     
4. End with “Anything Else?”
   • Often, the most revealing details come right after the buyer thinks they’ve finished speaking.

Mastering the art of asking thoughtful, probing, and transformative questions is at the heart of Gap Selling. This chapter underscores that the better your questions, the better your understanding—and the better your solutions. By guiding prospects through a journey of discovery, you help them uncover the full scope of their challenges, see the cost of inaction, and realize the urgent need for the right solution.

Remember: Your goal isn’t to interrogate; it’s to enlighten—leading buyers to a place where they see clearly what’s holding them back and how you can help them move forward.