2 min read

4 Best Open Ended Sales Questions To Ask

The best salespeople ask questions. They don’t just try to sell benefits, they dig into their prospect’s pain points and understand what’s holding them back from buying. In this post, we give you three of the best open-ended questions that will help you close more leads.

Open Ended Sales Questions

1. What’s your biggest challenge you need to solve this quarter?

Ask them to name their biggest challenge:

  • What’s your biggest challenge you need to solve this quarter?
  • Can you tell me about that?
  • How does your current team handle it, and what could a team with our product do better?

2. What would stop you from moving forward today?

This question is designed to help you understand the prospect’s perspective and what they are thinking. Prospects will be more likely to buy from you if they trust you, feel that you understand their problems and that you have the best solution for them.

The key here is to avoid any language or phrases that may make a prospect defensive, such as “your time is valuable” or “I know I’m asking a lot of questions.” Instead focus on showing empathy with this question by using phrases like:

  • “I can see why this would be important for your business”
  • “It sounds like it was a big decision”

You want to create an environment where they feel comfortable expressing themselves while also understanding why it was difficult for them in the first place.

3. What other companies are you comparing us against?

It’s important to know what other companies your prospect is considering so you can better understand how your product or service differs. In addition, this information can help you differentiate yourself from the competition.

To ask this question and use the answer to your advantage:

  • “I’d love to learn more about how much research you’ve done on other options. Can I get some examples?”
  • Follow up with “Why did you choose those over us?”


It's important for the prospect to understand that they have a problem that you and your company are uniquely positioned to solve.

One study from Brevet shows that only 44% of sales reps follow up with a prospect only once, before they give up.

And after just four follow ups, 94% of sales reps give up completely.

That's why salespeople should clearly define the next steps with the prospect during the call (and actually have the prospect voice it).

Asking questions will help you dig into your prospect’s pain points.

Asking questions is one of the most powerful ways to get your prospect talking about the problems that are keeping them up at night. By asking questions, you can find out what they want, need and think. You’ll also learn a lot more about how they view your company and product/service offering.

This process goes both ways—if you ask questions and take notes on what people say (or even better – record it), then review those notes before meeting with them again in person or on the phone, it will allow you to build up a better picture of their pain points than if you had just assumed how they felt based upon past experience with other prospects or customers.

Remember, the goal of these questions is to help you understand what your prospects are looking for and how they’re approaching their decision-making process. As a result, they can give you more insight into whether or not your product or service is really going to solve their problems. If it isn’t right now, maybe it will be in the future as you continue to develop new features!

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