• The Sales Jam
  • Posts
  • Not Asking These Questions Will Cost You the Sale

Not Asking These Questions Will Cost You the Sale

Today we’re looking at questions that’ll have prospects eating out of the palm of your hands. We’ve got some goodies on AI integration and what that means for winning GTM strategies in 2024! 

In Today’s Jam

  • Sales Tip of the Day: Open Up Tight-Lipped Prospects

  • The Sales Lab: Not Asking These Questions Will Cost You The Sale

  • Weekly Poll

  • Sales Q&A: Most Powerful Questions to Ask Customers?

  • Top 5 Sales Negotiation Techniques

  • Sales Scene of the Week: Talk About an “Innovative Sales Strategy”

Forget the Forms AND Capture 40% of your traffic!

  • Capture emails for 40% of your anonymous traffic

  • Add them to your retargeting audiences

  • Grow your list way faster 

  • Email irresistible offers to users browsing your site

  • Send more abandoned-cart emails when they don't purchase

  • 100% CAN-SPAM Compliant

The Sales Lab🔬: Not Asking These Questions Will Cost You The Sale

Let’s face it: People fumble a sale for many reasons – failing to understand the prospect’s problems, not focusing on benefits, poor product knowledge, you name it. 

Another major challenge that underperforming reps have in common is asking bad questions. Or in some cases, not asking any questions at all.

Imagine trying to close a sale by reeling off about how great your product’s features are then waiting for a prospect to whip out their wallet and part with its contents at the drop of a dime.

Good luck.

No, really.

Not only do we know that some sellers aren’t asking the right questions. We also know exactly what those ‘right questions’ are. 

And today, we’re breaking them down 👇

“What’s Stopping Your Company From Growing Right Now?”

Simple as it sounds, this one is a game changer.

It opens the door for prospects to get specific. Is their main issue a financial one?

Maybe it’s a people pain, an issue with hiring or retaining top talent in the company.

The key is to learn the biggest pain point and tailor your pitch to it from there. The pain points you’re looking for can fall under the following: 

  • Financial

  • Talent

  • Process

  • Productivity

“How Do You Plan to Solve This?”

The purpose of this question is simple: Discover how knowledgeable the prospect is.

In the event that the prospect shrugs and goes: “I don’t know”, you now have the opportunity to insert your product as the solution. 

If the prospect is knowledgeable then things get interesting.

After all, the problems still exist which is why they’re talking to you.

This means their knowledge of the issue and possible solutions isn’t enough to free them of this particular pain which is where you come in.

Once the prospect shares the needed information on why the issue hasn’t been resolved, you can tailor your pitch to what they’ve shared.

“What’s The Deadline You’re Working With?”

Or you can ask, if they have a date they’d like to see a change implemented.

If the prospect tells you: “I don’t know. We’re not really working with a deadline right now.” 

That’s a major red flag.

If the company doesn’t have a set deadline to solve a problem, there’s no way the problem is that big a deal.

You now know to help your prospect see the size of the problem, financially or otherwise, to create a stronger desire to take action.

On the other hand, should they give you a specific date, this indicates that they are actively seeking to solve their problem and are a qualified potential customer.

“What Does Your Team Think About [X] Problem?”

Similar to the deadline angle, this question can help you figure out where you can find common ground for moving the deal forward.

If a prospect is telling you they have a problem but their boss, or the rest of their team isn’t pushing for that thing to be fixed, this gives you information to ask follow-up questions.

Keep in mind that the boss is also a decision-maker. So if the person who has to greenlight the sale isn’t already trying to solve this problem, why is that?

The more quickly you figure this out, the more quickly you can put the right information, demo, or data together to paint the larger problem so it can be shared with the team, boss or company as a whole.

What's your current role?

Login or Subscribe to participate in polls.

Sales Q&A

Most Powerful Questions to Ask Customers

It’s Time For That Dream Sales Job…💼

Looking for a new job opportunity in Sales? Search for the latest and greatest jobs here.

Looking to hire someone with great Sales experience? Post your job on The Sales Jam Job Board, here.

Game Changers of the week🔥

Top 5 Sales Negotiation Techniques

The Future of Sales Ecosystems with Barrett King

New Breed’s Senior Director of Revenue, Barrett King, comes aboard the Sales Strategy and Enablement train to take a deep dive into the integration of AI within partner relationship management. Interestingly, this episode touches on AI’s part in increasing scalability and efficiency in GTM strategies for 2024.


Robert Cialdini’s “Influence” takes a deep look at how our behaviour and how this can influence those around us, particularly in business i.e. sales. If you haven’t read a ton about how our behaviors can turn the tides of a business exchange, this might be a good place to start. Be on the lookout for the occasional fluff associated with many of these books. 

Sales Enablement Summit

Enablement experts will be showing at the 2024 Summits, giving you access to case studies, best practices, and other industry secrets to help you take your game to a whole new level. Don’t miss it.

Sales Scene of the Week🎬

Nothing beats knowing your customer…

What did you think of this newsletter?

Login or Subscribe to participate in polls.