Why Great Salespeople Ask Better Questions

 The best salespeople don't necessarily have the best answers. They know how to ask the questions that uncover the answers. 

You walk into a customer meeting.
You have prepared your presentation.
You know your product.
You know your pricing.
You have rehearsed your pitch.
Then the customer says:

 "Tell me what your solution can do."
Most salespeople start talking.
The better response might be:

"Before I do that, can I understand what you're trying to solve?"
That small difference can completely change the conversation.

 The problem with asking the obvious questions
Most salespeople have a list of questions.
What's your current solution?
What are your requirements?
What's your budget?
When are you looking to implement?
Useful questions.
But they often produce information, not insight.
A stronger salesperson tries to understand what is happening behind the answer.
For example:
"We're looking to replace our current provider."
Instead of immediately asking:
"What features are you looking for?"
"What changed that made you consider replacing them now?"
Now you've opened a completely different conversation.
The requirement is the same. The reason behind it is completely different.

1. Ask about the problem before the solution
One of the first things a salesperson needs to establish is whether the customer actually sees a problem.
Because if the customer doesn't believe there is a problem, why would they spend time solving it?
Ask:
"What isn't working today?"
Then go one level deeper:
"What happens if you don't fix it?"
And deeper still:
"Why does this matter now?"
The answers tell you whether you're looking at a genuine business priority—or simply a nice-to-have.

2. Ask what changed
Timing matters.
A company can live with the same problem for three years and suddenly decide to act.
Something changed.
Finding that trigger can tell you more than another 30 minutes of product presentation.
Don't just understand the problem. Understand why it became important now.

3. Ask who else is involved
Enterprise buying is rarely a one-person decision.
There may be:
Users. Influencers. Technical teams. Procurement. Finance. Legal. Business leaders. Decision-makers.
And each one may look at the same purchase differently.
So don't just ask:
"Who is the decision-maker?"
Ask:
"Who else will need to be comfortable with this decision?"
That's a much more useful question.

4. Ask how the organisation actually buys
This is one of the most important questions in enterprise sales.
You might have a great product.
You might have a great champion.
But if you don't understand the customer's buying process, you can still lose the deal.
Find out:
How does the organisation move from identifying a problem to selecting a vendor?
You are not simply selling to a company. You're navigating a decision-making process.

 5. Ask what they need to believe before they can say yes
This is where selling becomes interesting.
Different people need different reasons to support the same decision.
The CFO might need a business case.
The CIO might need confidence in the architecture.
The risk team might need security and compliance information.
The CEO might simply need to understand the strategic impact.
So ask:
"What would you need to see or understand before you could recommend moving forward?"
Now you're not guessing what the buyer needs.
You're asking them.

6. Ask questions that make the buyer think
They help the customer see something differently.
For example:
"What happens if you continue with the current approach for another two years?"
Or:
"Which part of this problem creates the biggest impact for the business?"
Or:
"If you could fix only one part of this today, which one would you choose?"
These questions move the conversation from:
Product → Problem → Impact → Decision
And that's where meaningful sales conversations happen.

 The AB Formula Framework
Ask. Listen. Understand. Guide.
ASK
What is happening?
LISTEN
What is the customer actually saying?
UNDERSTAND
What is the problem, impact, urgency and decision process behind it?
GUIDE
What does the customer need to do next?
That's the difference between questioning a customer and helping a customer think.

 The Last Formula
Before your next enterprise sales meeting, don't prepare only your presentation.
Prepare five questions you genuinely need the customer to answer.
And don't ask them because you need information for your CRM.
Ask them because the answers will help the customer make a better decision.
Because ultimately, great enterprise sales isn't about having the most convincing pitch.
It's about helping the buyer understand their own problem better.

— Akshay Balchhandra
The idea of understanding the buyer's decision journey is also central to modern B2B selling. McKinsey — Follow the customer decision journey if you want B2B sales to grow