Episode #344: Questioning Skills In Sales

Even seasoned sales professionals sometimes walk out of a meeting confident… only to discover later that the buyer was imagining something completely different. That gap can cost deals, time, and credibility. This page breaks down what causes that disconnect, why the questioning phase matters more than the pitch, and how to surface resistance in the room — especially in Japan’s B2B context, where internal alignment and silent hesitation are common.

It’s frustrating — even humiliating — when a follow-up email reveals the buyer was only considering a minimal role for you, while you believed you were discussing a full partnership. The shock is sharper when you’re experienced: you may have a strong track record, teach selling, and still miss the signals.

Mini-summary: Misalignment hurts most when you thought the meeting was going well — and experience alone doesn’t prevent it.

Because without clear understanding of what the buyer wants, you can’t truly help them. Many salespeople rush into explaining solutions before validating the buyer’s needs. It’s like learning the buyer’s favorite color is blue, then talking endlessly about your pink products — impressive, but irrelevant.

In Japan, this is even riskier. Buyers in Japanese companies (日本企業 / Japanese companies) or multinational firms (外資系企業 / multinational companies) may avoid direct disagreement, so if you don’t ask carefully, you’ll assume alignment where none exists.

Mini-summary: Questions prevent you from solving the wrong problem — and Japan’s indirect communication makes them essential.

What if the buyer isn’t articulate about their needs?

That happens all the time. Not every buyer has:

• a clear picture of what they need

• a sophisticated understanding of their root issues

• the ability to express internal constraints

Some operate from flawed assumptions. Others haven’t fully diagnosed the problem yet. This means your job isn’t just to hear needs, but to help clarify them through smart questioning.

Mini-summary: If the buyer is unclear, your questions must create clarity — not replace it with your assumptions.

How can your questions accidentally make the problem worse?

Good sales questions challenge buyers to think differently — which builds trust. But they can also awaken concerns the buyer hadn’t consciously considered.

For example, while reframing the situation, you may trigger internal doubts like:

• “Maybe we should do this ourselves.”

• “Is this really worth budget approval?”

• “Will my team resist this change?”

This is normal — but only dangerous if those doubts stay hidden.

Mini-summary: Great questions can raise resistance; the key is surfacing it early, not avoiding it.

Sometimes you fall in love with your own solution because it genuinely fits. That emotional certainty can silently reduce your curiosity. You stop digging.

The result:

1. You keep explaining.

2. The buyer keeps thinking — privately.

3. Hidden barriers stay hidden.

4. Rejection arrives later by email.

In Japan especially, internal barriers (社内の障壁 / internal company barriers) — approval chains, politics, risk avoidance — can block deals even when the solution is strong.

Mini-summary: The better your solution seems, the more disciplined you must be about questioning.

What should you do in the moment when the buyer is thinking?

When you notice the buyer processing deeply, don’t just observe — enter their thought process.

A simple, disarming question like:
“What’s going through your mind right now?”
can reveal:

• doubts

• missing stakeholders

• budget fears

• “we can do this ourselves” thinking

That gives you a chance to address resistance face-to-face, not after the deal is already drifting away.

Mini-summary: If you see the buyer thinking, ask what they’re thinking — silence is not agreement.

You can invite the buyer to justify the investment instead of defending it for them. The approach used by Grant Cardone is a strong example:

• He challenges buyers to explain why they should spend money.

• They become advocates for the purchase.

• Resistance surfaces naturally and early.

Would this work with every Japanese buyer? Not always. But with globally minded or Western-educated decision-makers, it can be effective.

Mini-summary: Push buyers to justify the deal — it exposes objections while you can still solve them.

What’s the practical takeaway for future sales calls?

The real lesson isn’t “ask more questions.” It’s:

• question your assumptions in real time

• stay emotionally detached from your solution

• watch for internal hesitation

• surface resistance before leaving the room

This reduces the risk of receiving the painful “we can do it ourselves” email (痛い返事 / painful reply) after the fact.

Mini-summary: The win is not a perfect pitch — it’s a perfectly accurate read of the buyer.

• A strong solution doesn’t matter if the buyer’s mental picture is different.

• The questioning phase prevents you from selling “pink” to a buyer who wants “blue.”

• Buyers, especially in Japan, may hide resistance unless invited to share it.

• Ask what the buyer is thinking when they’re thinking — not after the meeting.

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.