Episode #109: Forensic Sales Questioning Skills

Why do sales calls fail when we skip questions?

Many sales calls fail because the salesperson starts pitching before understanding the buyer’s real needs. You can’t reliably “hit a target you are not aiming for.” If the target is a sale, the buyer must feel a meaningful need. Without questions, the conversation isn’t aimed at that need—and the buyer has no reason to act.

Mini-summary: Pitching first is guessing. Questions first are targeting.

This insight isn’t new. For nearly 80 years, top sales systems have shown that asking buyers questions is the fastest way to gain agreement. Yet many salespeople still rely on canned pitches, assuming persuasion means talking more. In reality, persuasion starts with discovery.

Mini-summary: The method is old, but the habit of pitching first is stubborn.

In Japan, asking direct questions can feel rude because of cultural hierarchy. Many salespeople worry they are challenging the buyer’s authority. The buyer can be treated like “GOD,” and “GOD brooks no questions from mere mortals.”

But here’s the truth: buyers will answer questions willingly if the salesperson asks permission correctly and frames questions respectfully.

Mini-summary: The barrier is cultural style, not buyer resistance.

How can you ask permission to question buyers in Japan?

Use a simple four-step permission approach:

1. Briefly explain what you do in general terms.

2. Share a concrete success case with numbers.

3. Suggest you may be able to do something similar for them.

4. Ask politely if you can confirm by asking a few questions.

Most Japanese buyers will grant permission when you approach them this way. A few may still demand a pitch first—but they’re the exception.

Mini-summary: Respectful permission turns questioning into good manners, not rudeness.

When should you start preparing your questions?

Way before the meeting. Planning the call is not optional if you want consistent wins. If you’re just delivering a canned pitch, planning feels unnecessary. But if you want real outcomes, you must think deeply about the client’s business before you show up.

Mini-summary: Great questions begin in planning, not in the room.

What research helps you plan powerful buyer questions?

Do light but focused research:

• Understand the industry and main competitors.

• Read annual reports for listed companies.

• For unlisted firms, gather public information online.

You’re not doing heavy analysis—you’re identifying what you need to ask in order to discover priorities, risks, and goals.

Mini-summary: Research isn’t about knowing everything—it’s about knowing what to ask.

What questions should you ask during the call?

Aim for four core question types:

1. “As Is” questions — What is happening now?

2. “Should Be” questions — Where do they want to go?

3. “Barrier” questions — What is stopping them?

4. “Payoff” questions — What does success mean personally to them?

A sale is easiest when there’s a big gap between current reality and desired future. Small gaps are bad news because buyers feel they can handle it themselves.

Mini-summary: Your job is to uncover the gap and what blocks it.

How do you go deeper instead of skimming buyer answers?

Many salespeople ask a question, get an answer, and move on. That’s where they lose the deal.

Instead, dig deeper with soft, respectful “why” follow-ups:

• Why is that important?

• Why now?

• Why has it become difficult?

Do this gently. Without preparation, repeated “why” questions can feel harsh. With thoughtful phrasing, they feel like professional curiosity.

Mini-summary: The first answer is the surface. “Why” reveals the real deal.

Why does asking “why” multiple times work so well?

Deep “why” questioning helps in two ways:

1. You understand the buyer’s true situation.

2. The buyer understands it better too.

Busy leaders are constantly “putting out fires and beating off crocodiles with their oars.” They often can’t step back to see hidden gaps, inconsistencies, or looming problems. Your questions make them reflect, refine, and sometimes realize new costs of doing nothing.

Mini-summary: “Why” clarifies reality, surfaces urgency, and strengthens your solution.

Because instead of spraying a pitch like a shotgun, you:

• identify real needs,

• expose opportunity costs,

• personalize value to the buyer, and

• present solutions that match their own logic.

That’s how agreement happens naturally—even in 日本企業 (Japanese companies) and 外資系企業 (multinational companies in Japan), especially in 東京 (Tokyo) where competition and change move fast.

Mini-summary: Discovery beats pitching—especially in Japan’s relationship-driven market.

• Questions are the fastest path to agreement because they reveal buyer needs and gaps.

• In Japan, permission-based questioning avoids cultural friction and earns trust.

• Planning and research shape the quality of your “As Is / Should Be / Barrier / Payoff” discovery.

• Deep, respectful “why” follow-ups uncover real urgency and decision drivers.

Founded in the U.S. in 1912, Dale Carnegie Training has supported individuals and companies worldwide for over a century in leadership, sales, presentation, executive coaching, and DEI. Our Tokyo office, established in 1963, has been empowering both Japanese and multinational corporate clients ever since..