Book Review: Questions that Sell

The Powerful Process for Discovering What Your Customer Really Wants

As small business operators we’re often inundated with techniques to close deals; Questions That Sell by Paul Cherry offers a paradigm shift — one that emphasizes the power of questions over pitches. Cherry’s insights show how asking the right questions can uncover deeper customer needs, build meaningful relationships, and ultimately drive your sales success. Let’s distill the key lessons and surprising revelations from the book:

The Power of Good Questions

Cherry argues that effective sales start with understanding — not selling. Customers are not just looking for products or services; they want solutions that bring tangible value to their businesses. To achieve this, you must shift the conversation away from yourself and onto the customer. The key lies in asking thoughtful, engaging questions that reveal your customer’s vision, challenges, and motivations.

• Move Beyond Superficial Connections: Building genuine relationships requires delving into a customer’s desires, fears, and aspirations. Questions like, “What would success look like for you?” or “What challenges are holding you back?” open the door to meaningful dialogue.
• Listen to Understand: Instead of overwhelming your customers with a long list of product details, you should focus on listening actively. By creating an environment where your customer feels heard and understood, they become more likely to share their implicit needs — those unspoken drivers behind their decisions.

Differentiation Through Questioning

Cherry highlights that most salespeople fail to ask impactful questions, with 90% of seasoned professionals sticking to surface-level inquiries. To differentiate yourself, ask questions that challenge the status quo and encourage deeper thinking:

• Help Customers Recognize Problems: Many of your customers are unaware of the full scope of their challenges. Questions like, “What is causing these issues?” or “What would need to change for this to improve?” help them uncover and articulate their needs.
• Uncover Decision-Making Processes: Understanding how decisions are made is extremely important. Ask, “Who is involved in the decision-making process?” or “What criteria are most important to you?” to align your approach with their priorities.
• Quantify the Impact of Problems: Use impact questions to help customers realize the cost of inaction. For example, “How much is this problem affecting your bottom line?” motivates them to act.

The Psychology of Customer Motivation

Cherry’s book emphasizes that customers are more driven by the need to solve problems than by the pursuit of pleasure. Salespeople must act as trusted advisors, guiding clients toward recognizing and addressing their challenges. This requires understanding implicit needs such as:

• Security: The need to feel safe and protected.
• Recognition: The desire to be appreciated and valued.
• Independence: The yearning for control and autonomy.

By addressing these underlying motivations, you can tailor your solutions to resonate more deeply with customers.

From Value to Vision

Customers buy into solutions, not products. Cherry encourages you to paint a compelling picture of what the future could look like:

• Vision Questions: Inspire your customers to imagine success by asking, “What would your ideal outcome look like?” or “How would solving this problem transform your business?” These questions not only evoke emotions but also create urgency.
• Shift the Focus to Value: Price is often a sticking point, but you can redirect the conversation by emphasizing value. Ask, “How do you define success in a vendor relationship?” to highlight your role as a partner, not just a supplier.

Preparation and Execution

Success in sales is rarely accidental. Cherry underscores the importance of preparation:

• Research Thoroughly: Before meeting with a client, study their company and industry to craft tailored questions that demonstrate professionalism and insight.
• Strengthen Existing Relationships: Regularly engage customers to ensure satisfaction and uncover opportunities for improvement. Questions like, “How can we better support your goals?” help solidify long-term partnerships.

Challenging Conventional Wisdom

One of the book’s most surprising revelations is how little interpersonal charm in sales matters. Citing a Gallup study, Cherry highlights that good people skills do not correlate strongly with top sales performance. Instead, the ability to ask thoughtful, engaging questions is the true differentiator.

This finding overturns the traditional belief that rapport and likability are the cornerstones of effective selling. While building trust remains essential, it’s the strategic, problem-solving approach that transforms you into a valued advisor.