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Cultivating Curiosity: Coaching Sales Professionals to Ask Innovative Questions

We have come so far in sales coaching. And if one thing is certain, it is the need to connect with customers on a deeper level. Yes, traditional sales techniques can only take you so far. In today’s competitive landscape, the only way to stand out is by forming a deep bond with customers.

It is the art of appealing to their hearts and not their minds. Turns out that most customers make decisions based on their gut feelings and what their hearts say. To play to this strength and make it your advantage, you need to ask probing questions and turn more innovative.

Let us observe the transformative impact of cultivating curiosity in sales professionals to form a deeper rapport with their customers. Whether your approach is as a hunter and farmer salesperson, how can you cultivate a curiosity-driven approach to ask questions and deepen customer connections?

The Curiosity-Driven Sales Approach

Imagine a sales scenario where instead of pitching products or services, your sales team engages customers in meaningful conversations. This is the best way to make them reveal their unique needs and desires.

Curiosity-driven questioning is all about understanding your customers on a profound level. This shows that you are “present” during the conversation and hope to take home more than just a closed deal. This will make customers open up and help you tailor your offerings to precisely what they require.

Hunter vs. Farmer Sales Professionals

Before diving into the HOW, it’s essential to understand the WHO. Here is a distinction between hunter and farmer sales professionals.

Hunters are the front-line sales professionals who actively seek out new clients.

Farmers focus on nurturing and retaining existing accounts.

Cultivating curiosity is valuable for both types of sales roles. However, it is worth noting that the approach may vary.

For Hunters

Strategy 1: Research with a Purpose

Hunters should start by researching their prospective clients extensively. However, the key is to research with a purpose. Instead of merely gathering general information, guide your sales team to look for specific insights that can spark curiosity during the initial conversation.

Example: Let’s say your salesperson is targeting a potential client in the healthcare industry. Instead of just knowing the industry’s basic trends, they should dig deeper and find out if the company has faced recent challenges in patient care or cost management.

This targeted research can help them ask questions like, “I noticed your organization has been implementing cost-saving measures. Can you share your experience with those initiatives?”

Strategy 2: The Three ‘Whys’

Encourage your hunter sales professionals to go beyond surface-level questions by employing the “Three Whys” technique. For every piece of information they gather, they should ask “why” three times to uncover the underlying motivations and pain points.

Example: If the prospect mentions a recent budget cut, your salesperson could ask, “Why was there a budget cut?” The response might be, “To allocate resources to a new project.”

The salesperson can then inquire, “Why was the new project a priority?” This line of questioning not only uncovers the immediate issue but also reveals broader business goals and challenges.

Also Read: The Neuroscience of Sales Coaching: How Brain Science Can Help Improve Sales Performance

For Farmers

Strategy 1: Continuous Relationship Assessment

Farmer sales professionals have one core aim — to maintain and deepen relationships with existing clients. Encourage them to assess these relationships continuously by seeking feedback and understanding changing client needs.

Example: If a farmer sales professional has been serving a client in the software industry for several years, they could periodically ask, “How have your business needs evolved since we started working together?” This question demonstrates a genuine interest in the client’s success and opens the door for new opportunities.

Strategy 2: Stay Inquisitive

Even when working with long-term clients, it’s crucial for farmer sales professionals to remain curious. Urge them to explore potential upselling or cross-selling opportunities by asking questions that uncover unmet needs.

Example: If your client has been using a specific software package, your salesperson could ask, “Are there any new challenges or goals in your business that we might address with our expanded software suite?” This approach shows that you’re proactive in finding solutions to their evolving needs.

The Power of Open-Ended Questions

Open-ended questions are the cornerstone of curiosity-driven questioning. They encourage customers to share more about their thoughts, challenges, and aspirations. Teach your sales professionals to replace closed-ended questions with open-ended ones.

Closed-ended question: “Did you have a good experience with our product?”

Open-ended question: “Can you tell me about your experience with our product?”

The latter question invites the customer to provide detailed feedback and insights.

Example: Imagine you’re selling marketing services to a potential client. Instead of asking, “Did you have success with your previous marketing agency?” which prompts a simple “yes” or “no” response, you could inquire, “What were your most significant successes and challenges when working with your previous marketing agency?”

This question encourages the client to delve into their experiences and provides valuable insights for tailoring your proposal. It also shows that you are listening and aim to implement the suggestions shared.

Curiosity in Action: Storytelling

One of the most effective ways to cultivate curiosity during sales interactions is through storytelling. Sharing real-world examples and success stories can pique the customer’s interest and make your offerings more relatable.

Example: Let’s say you’re selling a data analytics tool to a potential client in the retail industry. Instead of bombarding them with technical details, you can start by sharing a success story.

Tell them how your tool helped another retailer improve inventory management and increase sales. This story not only captures their interest but also demonstrates the practical benefits of your solution.

It also shows the client that someone else (potentially a competitor) is faring better than them with the solution in action. This creates a sense of FOMO (Fear of Missing Out) which will make them more likely to hop on the bandwagon.

Active Listening

Active listening is a critical skill for any sales professional. It involves not only hearing what the customer says but also understanding the underlying emotions and motivations. Train your sales team to practice active listening by:

  • Maintaining eye contact and non-verbal cues that convey interest.
  • Summarizing and paraphrasing the customer’s statements to show understanding.
  • Asking clarifying questions to dig deeper into the customer’s thoughts.

Example: If a customer mentions challenges with their current supplier, an active listener would respond with empathy.

They would say something like, “It sounds like you’re experiencing some frustration with your current supplier. Can you tell me more about the specific issues you’ve been facing?” This approach not only shows empathy but also invites the customer to share more about their pain points.

The Art of Follow-Up

Many sales professionals underestimate the power of follow-up questions. After an initial conversation or meeting, encourage your team to send follow-up emails that not only express gratitude but also include thought-provoking questions.

Example: Suppose your salesperson recently had a discovery meeting with a potential client in the manufacturing industry.

Instead of sending a generic thank-you email, they could write, “I appreciated our conversation and your insights on the challenges in the manufacturing sector. One question that came to mind afterward: How do you see emerging technologies impacting your production processes in the next five years?”

This follow-up question keeps the conversation going. It has a higher chance of receiving a response as it shows a genuine interest in the prospect’s business.


In the world of sales, where customer relationships are at the core of success, cultivating curiosity becomes an invaluable asset. It’s not just about satisfying immediate needs; it’s about diving deeper, asking questions that others might not, and uncovering hidden insights that can transform a transaction into a partnership.

By coaching sales professionals to develop and refine their curiosity skills, organizations empower their teams to forge stronger connections, truly understand customer needs, and explore innovative solutions. It’s a journey of continuous improvement, where each question asked is a step toward a more successful sales outcome. Remember, curiosity isn’t just a trait. It’s a skill that can be honed and refined over time.

Meenakshi Girish is a professional Content Writer who has diverse experience in the world of content. She specializes in digital marketing and her versatile writing style encompasses both social media and blogs. She curates a plethora of content ranging from blogs, articles, product descriptions, case studies, press releases, and more. A voracious reader, Meenakshi can always be found immersed in a book or obsessing over Harry Potter.
Chandrani-datta-Content-Manager-Tripura-Multinational-Singapore-our-team 2
Chandrani Datta works as a Manager-Content Research and Development with almost a decade’s experience in writing and editing of content. A former journalist turned content manager, Chandrani has written and edited for different brands cutting across industries. The hunger for learning, meaningful work and novel experiences keeps her on her toes. An avid traveller, Chandrani’s interests lie in photography, reading and watching movies.

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