The 6 Questioning Strategies That Separate Top Sales Pros From Amateurs

Most salespeople talk too much and ask all the wrong questions. Sound familiar?

They jump into pitches, rattle off product features and wonder why the prospect ghosts them. It’s not rocket science — it’s just bad sales behavior. Every sales manager on Earth will bark, “Ask more questions!” But no one ever tells you which ones actually matter.

That’s where most training fails... and where the No BS Sales System steps in.

In this post, I’m giving you six sales questioning strategies that cut through the noise, help you discover the truth and — here’s the magic — get your prospect to sell themselves.

Why Better Questions = Better Sales

You can stalk your prospect on LinkedIn, dig up their company’s blog, even Google-stalk their cousin’s dog groomer. But you still don’t know shitp about what they think or feel.

Facts don’t close deals. Opinions and emotions do.

The real magic happens when you stop trying to sound smart and start being curious. Curious about their problems. Curious about their expectations. Curious enough to shut your mouth and let them do the talking.

Here’s how the pros do it.

1. Good/Bad Questions

Want to unseat a competitor? Stop bashing them. Start validating them.

Ask, “What do you like about your current provider?” And I mean it —really ask. Let them brag. Let them talk. Then ask, “What else?” until they run out of steam. When that moment hits, follow with: “If there were one thing they could do better, what would it be?”

Boom. That’s the crack in the armor. 

2. Reversing With Softening Statements

Prospect hits you with a question? Don’t pounce. Change direction.

Try this: “That’s a great question. Why do you ask?” or “Interesting — you must be asking that for a reason.” These keep you in control and buy you time to think.

You’re not dodging. You’re digging. There’s a difference. 

3. Third-Party Stories

Nobody cares what you think. But they do care what someone like them thinks.

Don’t say, “Our service is the best.” That’s amateur hour. Say, “One of our clients said the same thing last year and told us it turned out to be their best investment.” Let your clients tell the story for you. It’s more believable and 10 times more effective.  

4. Assumptive Questions

Most people have no clue what “good” looks like. So show ’em — subtly.

Ask, “When your advisor meets with you quarterly to review your goals, what kind of changes do they suggest?” That’s an assumptive question. You’re planting an idea without sounding preachy or self-serving. 

5. “Let’s Pretend” Questions

When someone says, “Your price is too high,” don’t cave. Don’t beg.

Say this: “Let’s pretend we agree on price — what else would you need to move forward?” Or, “Let’s pretend we can’t give that discount. Is it over?” These reveal the real objections without all the back-and-forth nonsense. 

6. Columbo Questions

This is where you play dumb — on purpose.

“You mentioned turnover. What does that look like in your world?”
“Margins are tight? What are they? What should they be?
“You said their price is too high. When you say ‘too high,’ what do you mean?”

Simple. Disarming. Ridiculously effective. 

Why Most Sellers Get This Wrong

They rush.
They ask vague questions and accept vague answers.
Worst of all? They talk at the prospect instead of helping them process their own thoughts.

That’s not selling. That’s performing. 

Real sales pros ask the right questions and then shut up.

These six strategies aren’t about tricking anyone. They’re about getting to the truth — the truth about what your buyer wants, what’s holding them back and whether you’re the right person to help. 

You’re not here to interrogate. You’re here to connect, to guide and to build real trust.

And hey — this is just one part of the bigger system. Stop winging it and start closing real business. 

Tired of wasting time on bad-fit prospects and dead-end calls? Start learning how to sell like a pro. Schedule a call with me — Walker McKay — and master the skills that actually close deals.

Let’s build a badass sales career. No fluff. Just results.