By Benny K P Tan

When “Always Be Closing” Closed the Door

“Always Be Closing.”

This mantra, immortalized in sales culture, has probably done more damage to client relationships than any other phrase in business.

I witnessed this firsthand with Rajiv, a talented account executive at a technology company in Singapore. Despite an impressive resumé and deep product knowledge, he was struggling to break through with enterprise accounts.

During a crucial meeting with a potential client, I observed as Rajiv relentlessly pushed toward the close. Each client comment became an opportunity to steer the conversation back to his solution. Every question was treated as an objection to overcome. He was following the classic ABC playbook perfectly.

The meeting ended politely, but the energy in the room told the real story. We weren’t getting that deal.

Walking out, Rajiv was confused. “I don’t get it. I addressed all their requirements and handled every objection.”

“Yes,” I replied, “but you never actually learned anything about their business.”

“What do you mean? I know everything about their technical environment.”

“But do you know why their CFO mentioned budget pressure three times? Or why the Operations Director kept referencing their Malaysia expansion? Those weren’t objections to overcome—they were invitations to explore.”

Rajiv had been so focused on closing that he’d forgotten something fundamental: genuine curiosity.

This got me thinking about a different ABC that I’ve seen drive exceptional results for sales professionals across Asia Pacific for over three decades:

Always Be Curious.

Why Curiosity Trumps Technique in Modern B2B Sales

The selling environment has fundamentally changed:

• Buyers have access to more information than ever before
• Purchase decisions involve larger, more diverse stakeholder groups
• Solutions are increasingly complex and customized
• Value must be demonstrated before a purchase, not just promised

In this environment, traditional selling techniques that focus on persuasion and closing are increasingly ineffective and can even damage trust.

Research backs this up. A study by Gartner found that B2B buyers spend only 17% of their buying journey meeting with potential suppliers, and when they do engage with sales reps, they’re looking for insights and perspective, not product information.

Meanwhile, a LinkedIn study of over 500 B2B decision-makers found that the top trait they value in salespeople isn’t assertiveness or product knowledge—it’s active listening.

Yet most sales training still focuses on talking points, objection handling, and closing techniques rather than developing the genuine curiosity that unlocks meaningful conversations.

The Three Dimensions of Sales Curiosity

Curiosity in sales isn’t simply asking questions—it’s about developing a mindset of genuine interest that manifests in specific behaviors. Let’s explore the three dimensions of sales curiosity that transform ordinary interactions into extraordinary relationships:

1. Intellectual Curiosity: Understanding the Business

Intellectual curiosity drives you to understand the business context beyond surface-level requirements.

Low curiosity sounds like: “What’s your budget for this project?”

High curiosity sounds like: “Help me understand how this initiative fits into your broader business strategy. What outcomes would make this investment a clear success?”

True intellectual curiosity means going deeper than typical discovery questions to understand:

• Market forces affecting the client’s industry
• Competitive pressures creating urgency
• Organizational priorities that drive decisions
• Success metrics beyond the immediate project

I remember coaching Sarah, a sales leader at a professional services firm who was struggling with a major opportunity. She had a perfect technical fit but couldn’t gain traction with the decision-makers.

We shifted her approach from selling her solution to getting genuinely curious about why this initiative had suddenly become a priority after years of discussion.

This curiosity led her to discover that the client had recently lost market share to a more digitally agile competitor—a fact not mentioned in any meeting but fundamental to understanding their urgency. With this insight, she repositioned her solution as an accelerator for their digital transformation rather than a standalone service.

The deal closed within weeks, at twice the originally anticipated size.

How to develop intellectual curiosity:

1. Read industry publications and analyst reports relevant to your clients
2. Study your clients’ public financial information with genuine interest
3. Research their competitive landscape before meetings
4. Ask “why” questions that explore business drivers behind technical requirements
5. Invest time understanding adjacent business processes that might be affected by your solution

2. Interpersonal Curiosity: Understanding the People

Interpersonal curiosity focuses on the human dimension of business—understanding the people behind the roles.

Low curiosity sounds like: “Who makes the final decision on this purchase?”

High curiosity sounds like: “I’m interested in understanding how decisions like this typically get made in your organization. Who needs to be involved, and what matters most to each stakeholder?”

This dimension of curiosity explores:

• Individual priorities and perspectives
• Career backgrounds that shape viewpoints
• Organizational relationships and influence patterns
• Personal definitions of success

Ming, an enterprise sales executive I worked with in Hong Kong, was struggling with a complex deal involving multiple divisions. Rather than pushing forward with his standard approach, he took a step back and got curious about the stakeholders themselves.

He discovered that the IT Director had previously championed a similar project that had failed to deliver value—creating unstated resistance to our solution. The Operations leader was new to her role and concerned about taking risks. The Finance team was under pressure to reduce capital expenditures but had flexibility on operational spending.

None of these insights came from standard discovery questions. They emerged from genuine curiosity about the people behind the titles.

With this understanding, Ming developed a tailored approach for each stakeholder, addressing their specific concerns and priorities. The result was a unified buying committee that moved forward with confidence.

How to develop interpersonal curiosity:

1. Research stakeholders’ professional backgrounds before meetings
2. Look for clues about their priorities in meeting behavior
3. Ask questions about their personal definitions of success
4. Explore their experiences with similar initiatives
5. Show genuine interest in their professional challenges

3. Situational Curiosity: Understanding the Context

Situational curiosity explores the unique circumstances of each opportunity beyond standard qualification frameworks.

Low curiosity sounds like: “When do you need to implement this solution?”

High curiosity sounds like: “I’m interested in understanding what’s driving your timeline. What opportunities or risks will be affected by when this gets implemented?”

This curiosity investigates:

• Hidden constraints affecting decisions
• Unstated organizational priorities
• Competitive dynamics at play
• Historical context of similar initiatives

I recall working with a team pursuing a major telecommunications deal in Indonesia. The RFP requirements seemed straightforward, but instead of accepting them at face value, the team got curious about the context.

Through thoughtful exploration, they discovered that while the stated requirements focused on cost reduction, the unstated priority was preparing for an aggressive expansion into rural markets. This insight came not from direct questions but from curious conversation about the client’s growth strategy.

The team pivoted their approach to emphasize scalability and rural deployment capabilities. They won the deal despite a higher price point because they addressed the real priorities that competitors missed.

How to develop situational curiosity:

1. Research the client’s recent history with similar initiatives
2. Explore broader market conditions affecting decision timelines
3. Ask about consequences of delays or implementation challenges
4. Investigate how this project relates to other ongoing initiatives
5. Be attentive to environmental cues during site visits or virtual meetings

Why We Aren’t Naturally Curious in Sales Situations

If curiosity is so powerful, why isn’t it more common in sales interactions? Several factors work against our natural curiosity:

1. Performance Pressure When we’re focused on hitting targets and closing deals, our attention narrows to immediate outcomes rather than exploration and discovery.

2. Confirmation Bias We unconsciously seek information that confirms our existing beliefs about a solution fit rather than openly exploring alternative perspectives.

3. The Expertise Trap As we develop product expertise, we become eager to demonstrate our knowledge rather than exploring what we don’t yet understand.

4. Time Constraints Packed calendars and pressure to progress opportunities quickly can discourage the deeper exploration that curiosity requires.

5. Cultural Factors In some Asian business contexts, there can be an expectation that the seller will present themselves as the expert rather than the explorer.

Overcoming these barriers requires conscious effort and a fundamental mindset shift.

Cultivating Curiosity: Practical Techniques

Genuine curiosity can’t be faked, but it can be developed. Here are practical ways to cultivate your sales curiosity:

1. The 2:1 Ratio Rule

For every statement you make, aim to ask at least two questions that explore rather than lead. This simple discipline can transform your conversation patterns.

2. The Five Whys

When you identify an important need or challenge, practice asking “why?” up to five times to get to the root cause. (Just make sure to phrase each “why” thoughtfully to avoid sounding like a persistent toddler!)

3. The Perspective Shift

Before important meetings, ask yourself: “What would I want to know if I were investing my own money in this client’s business?” This mental reframe activates natural curiosity.

4. The Learning Review

After each significant client interaction, ask: “What did I learn that I didn’t know before?” If the answer is “nothing new,” that’s a red flag that curiosity was missing.

5. The Preparation Pivot

Instead of preparing presentations, prepare questions. Develop thoughtful, insightful questions that demonstrate you’ve done your homework and are genuinely interested in exploring further.

Measuring the Impact of Curiosity

How do you know if your curiosity is making a difference? Look for these indicators:

1. Information Reciprocity Clients freely share information not included in formal requirements or RFPs.

2. Access Expansion You gain access to stakeholders beyond your initial contacts.

3. Competitive Insight Clients openly discuss their perspectives on competitive alternatives.

4. Timeline Transparency You receive clear visibility into decision processes and potential delays.

5. Business Context Conversations naturally expand beyond immediate needs to broader business challenges.

When these indicators appear, you’re building the foundation for trusted advisor relationships rather than transactional interactions.

From ABC to ABV: Always Be Valuable

The ultimate outcome of genuine curiosity isn’t just better information—it’s the ability to deliver unique value in every interaction.

When you’re truly curious, you discover opportunities to create value that competitors miss. You identify unstated needs that clients themselves might not have recognized. You connect dots between different challenges and opportunities.

This transforms your role from vendor to valuable partner.

I witnessed this transformation with Rajiv, the account executive I mentioned earlier. After embracing the “Always Be Curious” mindset, he approached his next major opportunity differently.

Instead of pitching his solution, he invested time understanding the client’s business challenges, the personal priorities of key stakeholders, and the context behind their initiative. He asked thoughtful questions that demonstrated genuine interest rather than just advancing his agenda.

The result? A level of client engagement he’d never experienced before. The conversation flowed naturally from exploration to collaborative problem-solving. His solution recommendations emerged organically from the dialogue rather than being forced into it.

Six months later, Rajiv had closed the largest deal of his career—with a client relationship built to last.

Your Curiosity Challenge

Let me leave you with a practical challenge for the coming week:

Select your three most important upcoming client interactions. For each one:

1. Prepare ten genuinely curious questions that explore business context, personal priorities, and situational factors
2. During the meeting, focus on asking rather than telling
3. After the meeting, document what you learned that surprised you
4. Note how the conversation dynamic differed from your typical interactions

Then connect with me on LinkedIn to share what you discovered. I’m genuinely curious to hear how this approach impacts your client relationships and sales outcomes.

After all, in a world where information is abundant but insight is rare, curiosity isn’t just a nice-to-have skill—it’s the competitive advantage that transforms ordinary sellers into extraordinary advisors.

And if you’re wondering what powers truly effective curiosity, don’t miss next week’s newsletter where we’ll explore emotional intelligence—the foundational capacity that enables us to read situations accurately, connect with others authentically, and respond with both empathy and impact.

Always Be Curious.

Until next week,

Benny K P Tan

Did this edition provide value? Share it with a colleague who might benefit, and let me know what topics you’d like to see covered in future newsletters.

Connect with me on LinkedIn

Subscribe to Sharpen Your Sales Acumen

Don’t miss our weekly insights on mastering B2B sales. Subscribe now to receive:

• Weekly articles delivered directly to your inbox
• Practical frameworks and tools you can apply immediately
• Access to our community of sales professionals
• Special invitations to webinars and live coaching sessions