42 Open-Ended Questions You Can Ask in Your Prospecting Emails

by Ayhan K. Isaacs in July 13th, 2020
People talking

Questions are a powerful tool for salespeople. By asking questions, you can transform your prospecting emails from an irrelevant pitch into an engaging two-way conversation, one that actually interests your prospect. 

Not all questions are equal though. If you’re not careful, the wrong question can end the conversation before it’s even started. Too often, I see salespeople using questions that can be answered with a single word. 

“Would you be interested in learning more?”

“Do you want to book a meeting to discuss further?”

“Are you ready to sign up now?”

No, no, and no. Even if the answer is yes, these types of questions don’t engage the prospect. They’re simple and can be answered with little thought. That’s why I encourage salespeople to use open-ended questions in their emails. By asking questions that can’t be answered with a quick yes/no, you prompt your prospect to think more about their situation when answering. 

Asking Effective Open-Ended Questions

Simply changing your closed-ended questions for open-ended ones is a great start. However, to get the best results, you still need to carefully choose what open-ended questions you use.  

This is especially true with emails. With a prospecting phone call, you get immediate answers to your questions. You can ask a series of questions throughout the call, adapting your pitch depending on the answers. You can also ask rapport-building questions (“So, what are you up to this weekend?”).

However, with emails, best practice is to keep it to just one question at the end. Asking too many questions means they may not answer any of them. Using that one question to find out about their weekend plans is unlikely to be the best plan. For the same reason, it’s best to avoid pointless rhetorical questions, especially ‘salesy’ or guilt-tripping questions that only motivate a prospect to roll their eyes and delete your email. 

Rather, you need to make your open-ended question relevant and meaningful, one that will both encourage your prospect to give the matter some thought and to provide details you can use in your future emails. At the same time, your questions shouldn’t be so deep that your prospect needs to dedicate too much time or brainpower to answer them. If answering your question seems like too much work for your prospect, they won’t. 

With those principles in mind, here’s a list of effective open-ended questions you can use in your next prospecting email. Use this list as inspiration, a pick and mix of ideas for you to try out. Go through them, choose what's most appropriate for your prospect and your service, then give it a go! 

Open-Ended Questions to Uncover Prospect Problems

Problems are a powerful motivator. We all have them, and we all want to solve them. When talking with prospects, you want to deal with their pain points. To do that, you first need to know what those pain points actually are. Assuming you know what’s troubling your prospect without confirming it can make your whole pitch completely irrelevant. 

Using an open-ended question to find out more about their problems and challenges changes the whole dynamic. Rather than talking about you and your product and its features, you’re now talking to them about something they care about. With an understanding of their problem, along with the implicit promise you can help, you'll get your prospect’s attention. 

  • What {service-related} problems are you currently dealing with? 
  • What {service-related} difficulties have you had in the past?
  • How have you handled {service} problems in the past? 
  • How are you currently addressing {service} problems? 
  • What's holding your team back from reaching your objectives? 
  • What challenges are you facing with your current solution?
  • (After outlining common challenges in the prospect’s industry) How are these challenges affecting your business?
  • How much time/money do you spend on {common industry challenge}?

Open-Ended Questions to Understand Necessary Changes

As much as we hate problems, sometimes the idea of change is even scarier. We all have our comfort zones, and leaving them can be difficult, or even painful. It may not be ideal, but it's what we know, and that's often preferable to the unknown. 

Change is difficult and, if we don't appreciate that, we won’t be able to help our prospect. By asking these questions, you’ll have a better idea of the obstacles your prospect will face implementing change, and you’ll also get them to think more about what's holding them back. 

  • What would it take to change your existing process?
  • How do you manage product changes at {Company}?
  • What would you need to know in order to consider making a change? 
  • What's the decision-making process for something like this?
  • What information would your team need to make a decision?
  • How do you decide that it's time to do things differently?
  • What's your opinion on improving the existing system? 
  • What needs to happen for your company to agree it's time to a different approach?
  • What's keeping things the same at {Company}? 
  • How important is exploring new possibilities for your business?
  • Have you tried implementing a similar solution before?

Open-Ended Questions to Understand Your Prospect Better

Whatever product or service you’re offering, your email should always be focused on your prospect. It's about them, not you. At its core, this means learning more about your prospect. 

As a problem solver, you need to be empathetic. You need to have a thorough understanding, not just of the problem, but also them. That includes their companies, their thoughts, their processes. While you should always have researched the prospect before reaching out, there are some things you can’t learn from a database. Additionally, these questions can help the prospect think more about their current processes and the results they're getting. 

  • Who normally handles this?
  • What solution are you currently using?
  • What solutions have you already tried?
  • How is that working out for you?
  • How would you describe your relationship with your supplier?
  • How does this compare with your existing solution?
  • How much do you currently spend on {service}?
  • What are your priorities for the next quarter? 
  • How important is {solution} to your company?
  • How do you currently train your teams on new products?
  • What features are most important to you?

Open-Ended Questions That Highlight Your Solution

We’ve covered how you can learn more about your prospects and their problems, but ultimately you need to show how you can solve those problems. These questions help you uncover the information you need to deliver a solution that fits their needs. Additionally, they demonstrate to the prospect that you are the ideal company to provide that solution. 

  • What new skills/features/capabilities might give you better results?
  • ​​​​​​​​​​​​​​​​​​​​​​​​​​​​What's preventing you from getting better results?
  • What would need to happen to make this a priority?
  • What would need to happen to make you do something different?
  • What would need to happen for you to sign up for a trial? 
  • What would a successful outcome look like to you? 
  • How would solving {problem} affect your 2020 objectives? 
  • What would your ideal solution include?
  • What if we could demonstrate how {solution} would specifically benefit {Company}?
  • What features do you need from {solution}?
  • What kind of content can I send over to make the decision easier? 
  • How would you use {solution benefits, e.g. an extra 30 minutes a day/$500 a month}?


When used correctly, open-ended questions in your emails are an effective way of engaging with your prospects. Ask them wisely and you'll have a better understanding of your prospect, how they deal with change, their problems, and how you can provide a solution.

Ready to start using open-ended questions in your sales messages? Airborne is a sales engagement platform designed specifically to help agencies reach out to leads with relevant messaging.

Talk to an Airborne Specialist today to get access!

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