The Sales Questioning Model

Sales meetings go off the rails when the seller has no structure and just “follows their muse,” wings it, or refuses to be “shackled” by a system.

In real markets you don’t have unlimited buyer time, and you’re surrounded by competitors offering similar solutions—so you need a questioning journey that keeps the conversation on the track of your choosing and leads to a purchase result.

Dr. Greg Story, Ph.D. in Japanese Decision-Making, is President of Dale Carnegie Tokyo Training and Adjunct Professor at Griffith University. He is a two-time winner of the Dale Carnegie “One Carnegie Award” (2018, 2021) and recipient of the Griffith University Business School Outstanding Alumnus Award (2012). As a Dale Carnegie Master Trainer, Greg is certified to deliver globally across leadership, communication, sales, and presentation programs, including Leadership Training for Results.

Do you really need a sales questioning model, or can you just “follow the conversation”?

You need a questioning model because buyers will pull the discussion in random directions—and you still have to get to a decision. A lot of salespeople show up with very little structure: they’re untrained, they’re constantly winging it, or they want to be a “free bird” and let the conversation fly wherever it goes.
That sounds relaxed, but it’s risky. The questions you ask need a cadence, a logical order, and a flow—because the fastest way to credibility is clarity.

In complex B2B selling (think multi-stakeholder deals, procurement, long timelines), a model keeps discovery from becoming a wandering chat. In faster B2C or SME selling, it stops you from jumping straight into “solution mode” before you understand what’s actually going on. Your model is your navigation system: you can handle detours, but you don’t lose the destination.

Do now: Write your “buyer journey” as 4–6 steps and decide what you must learn at each step before you advance.

What are “As-Is” questions, and what do they uncover in discovery?

As-Is questions establish the baseline—what the client is doing now, how it’s performing, and what isn’t working well enough.
This is where you stop guessing. You find out what’s happening inside the organisation at the moment, what processes exist, what results they’re getting, and where the friction lives.

Clients will sometimes jump ahead and start talking about where they want to be. Great—but if you don’t anchor the “before” picture, you can’t measure the distance between current reality and the desired future.
That distance is where your value usually sits (time saved, risk reduced, missed revenue recovered).

Do now: Ask three baseline questions before you pitch anything: “What are you doing now?”, “How well is it working?”, “What’s not working well enough?”

What are “Should Be” questions, and how do they reveal the real target?

Should Be questions uncover the goals—strategic or financial—that define success for this buyer and this business.Clients have aims, and they might be published (annual report) or “secret,” but you still need to know them to judge whether you can help.

This is where many sellers stay too surface-level: “So, what are you trying to do?” isn’t enough. You’re trying to discover the actual finish line—what the organisation must achieve, what the buyer is measured on, and what outcomes matter most. If you can’t clearly define “Should Be,” your proposal becomes generic, and generic gets beaten by price.

Do now: Ask: “What are your goals and aims for this?” then follow with: “Are these publicly stated, or internal targets?”

What are implication questions, and why must you include time?

Implication questions create urgency by casting doubt about whether the buyer can reach the goal by themselves—fast enough and cost-effectively enough.
The key is time. Always include time factors, because “they may get to where they want to be, if it takes 100 years”—and they don’t have 100 years.

A strong implication question isn’t manipulative; it’s honest. If the gap between “As-Is” and “Should Be” is small, they might handle it internally—and you’re not needed.
But if speed matters (competition, market shifts, deadlines), the cost of delay becomes the real problem. Example prompts include: “If things stay the way they are, will you reach your targets fast enough?” and “What happens if you don’t meet your goals in the timeframe needed?”

Do now: Add one time-based implication question to every first meeting and don’t leave without an answer.

What are “Change” questions, and how do they expose your true opportunity?

Change questions ask the make-or-break: if they know where they are and where they need to be, why aren’t they there already?
This is the critical question, because their answer often explains exactly where you can help—capability gaps, political blockers, lack of resources, or the inability to execute fast enough.

Then you push (professionally) with the implication: will the inability to make necessary changes damage the business?
Markets wait around for no one, and “no action” isn’t free—there are opportunity costs, and you need to highlight them so they choose to fix the issue.

Do now: Ask: “What’s stopping you from being where you need to be?” then follow with: “What’s the cost of delaying this?”

What are “Payout” questions, and why do they help you close?

Payout questions surface what’s personally at stake for the buyer if the project succeeds—or fails. “What is in it for this buyer personally, if the project goes well?” is not a fluffy question; the company expects results, and the buyer is under pressure to produce outcomes.
When you understand what’s at stake, you can frame your solution around what matters to them, not just the organisation.

There’s also a high-skill implication question here: what happens if they can’t produce the results the company expects? It must be done diplomatically, but it’s powerful: “In the worst case scenario, what would be the personal impact for you, if this issue cannot be fixed fast enough?”
This is how you shift from vendor to ally.

Do now: In any deal with multiple similar vendors, ask one personal-stakes question and listen carefully to the emotion in the answer.

Conclusion

A questioning model isn’t a script—it’s how you access the private information you need to diagnose the situation and decide how (or whether) you can help.
Without intelligent questions, you’re operating in the dark, you don’t know what they need, and the result is “no sale.”

Quick actions (next steps)

• Build your questioning cadence into your CRM notes (As-Is → Should Be → Implication → Change → Payout).

• Create a “time-based implication” library for your industry and rehearse it.

• Add one diplomatic payout question to your late-stage meetings to separate yourself from commodity vendors.

FAQs

A sales questioning model is a structured question flow that keeps the buyer journey on track and leads to a purchase outcome. It prevents “winging it” and protects you from getting pulled off-course.

As-Is questions establish the baseline so you can measure the gap to the desired future. Without the baseline, you can’t diagnose properly or quantify value.

Implication questions work best when you include time, because delay has real downside and opportunity cost. Buyers rarely have unlimited time, even if the problem is “solvable eventually.”

Payout questions reveal personal stakes, which is often what drives action when solutions look similar. Ask diplomatically and position yourself as helping them succeed.

Author Credentials

Dr. Greg Story, Ph.D. in Japanese Decision-Making, is President of Dale Carnegie Tokyo Training and Adjunct Professor at Griffith University. He is a two-time winner of the Dale Carnegie “One Carnegie Award” (2018, 2021) and recipient of the Griffith University Business School Outstanding Alumnus Award (2012). As a Dale Carnegie Master Trainer, Greg is certified to deliver globally across all leadership, communication, sales, and presentation programs, including Leadership Training for Results.

He has written several books, including three best-sellers — Japan Business Mastery, Japan Sales Mastery, and Japan Presentations Mastery — along with Japan Leadership Mastery and How to Stop Wasting Money on Training. His works have been translated into Japanese, including Za Eigyō (ザ営業) and Purezen no Tatsujin (プレゼンの達人), among others.

Greg also publishes daily business insights on LinkedIn, Facebook, and Twitter, hosts six weekly podcasts, and produces YouTube channels including The Cutting Edge Japan Business Show, Japan Business Mastery, and Japan’s Top Business Interviews.