If you ask the right sales engagement questions, you can better understand your prospect’s buying journey and tailor your sales pitch and content to their needs.

In this article, I’ll show you examples of real sales engagement questions that you can use in your cold emails, or bring to your next sales meeting. 

They’ll help you learn everything you need to know about your prospect and move the deal forwards more effectively.

  1. What are Sales Engagement Questions?

  2. Benefits of Using Sales Engagement Questions

  3. Use Open-Ended Questions to Get Your Prospect Talking

  4. Sales Engagement Questions to Include in a Cold Email

  5. Sales Engagement Questions to Learn About Their Pain Points

  6. Sales Engagement Questions to Close a Deal

Let’s jump in.

What are Sales Engagement Questions?

Sales engagement questions are targeted questions you use during your sales process to discover key information about your prospect’s pain points, budget, and other factors that could affect the sales process.

Your questions will help your prospects open up, and you can use their answers to qualify or disqualify them from your pipeline.

Benefits of Using Sales Engagement Questions

1. Use Questions for Prospect Qualification

Not every lead will be a perfect fit for your product or service. Your sales engagement questions help you qualify or disqualify prospects from your sales process based on their responses before you spend weeks of your time nurturing them.

For example, if you ask them about the budget early on and they give you a number below your minimum contract value, you can tell them immediately, as well as re-emphasize the ROI of your product or service.

It’s going to stop both you and your prospect from having weeks of discussions, only for them to find out your product/service is over their available budget.

2. Understand Your Prospect’s Buying Process

Sales engagement questions can also help you understand how your prospect plans to approach the buying process.

If you ask the right questions, they’ll open up about:

  • Their budget

  • Their timeline

  • The people involved in the purchase decision

  • What their deadline for the decision is

By understanding these things, you can more effectively address them later in the sales process.

As well as that, data collected by Mindtickle found that the best sales reps talk for only 45% of their average discovery call.

Source: Mindtickle

By asking questions, you keep your prospect talking and you can keep learning about their unique pain points and motivations. 

3. Purposely Keep The Conversation Moving

Your sales engagement questions act as call-to-actions at different parts of the sales process.

  • Your cold email call-to-action will be there to start a conversation.

  • Your question at the end of the first call will be about how you can book a follow-up meeting.

  • Your question after a second call will be about confirming they’re ready to receive a proposal

Naturally, these will vary based on your unique customer and sales process, but the logic is still the same. Every time you interact with a sales prospect, you’ll ask targeted questions designed to move them to the next stage of the process.

Use Open-Ended Questions to Get Your Prospect Talking

There are two types of questions you can ask.

Open-ended and closed questions.

Closed questions are things like “Do you already have a CRM at {{company.name}}?”. They can be answered with a “yes” or “no”. While this can be useful at times, you end up missing out on extra information someone might have been willing to share with you.

Instead, use open-ended questions. These help your prospect think more about their answer and, in turn, help you learn more about their current situation.

For example, rather than using the closed question we looked at above, we could say “How do you handle your sales pipeline at {{company.name}}?”. They’ll be able to share their current process, pain points, and will bring up whether or not they’re using a CRM.

Next, let’s look at some examples of sales engagement questions you can use when talking with prospects.

Sales Engagement Questions to Include in a Cold Email

1. Is this something you would be interested in?

This question will have been prefaced with a short introduction to the problem you can solve.

For example, if you run a lead generation agency, you might have mentioned how many leads you generate for similar businesses per month.

This call-to-action then gives your prospect a chance to tell you if they’d be interested in what you can help them with.

This is a relatively close-ended question, but at this stage, your main priority is to get a reply – so it’s okay to use it. 

2. Is solving [problem] a priority for you?

This question is a simple way to learn if the person you’re reaching out to is going to be interested in your product or service.

If they tell you that solving a problem you can help with is a priority, it opens the door for you to schedule a call, or for them to let you know they’d like to learn more.

Like the previous question, it’s close-ended, but it’s an effective way to qualify or disqualify someone from your sales process without wasting time.

3. Do you have 15-minutes to discuss [problem] next week?

This question is a high-commitment CTA that can be an effective way to move an email conversation straight to a face-to-face or video meeting.

If the problem you’re bringing up in your outreach is a priority to the recipient, they’ll be open to catching up on a call as they can get direct answers.

This ask also shows respect for their time. 15-minutes won’t take up a big chunk of their day, and if it goes well, you can always schedule a longer meeting to discuss how you can help them in more detail.

It can also give you an idea of whether the person you cold emailed is the right person to talk to at a company. If they’re not, there’s a high chance they’ll refer you to the right person to schedule a call with.

Sales Engagement Questions to Learn About Their Pain Points

1. How familiar are you with [topic]?

This question can help you understand a prospect’s understanding of their problem. Some prospects you speak to will have already done deep research into their problem. Others will just be learning about the problem.

You can use their answer to tailor your meeting to their level of expertise. 

If they’re already familiar with the problem and potential solutions, you can get into more detail. If not, you can focus on educating them on their problem and what parts of the problem you can help them solve.

2. How are you currently handling [problem]?

This sales engagement question helps you get more background on your prospect’s current situation. It’ll also help you convey the benefits to them more effectively.

Suppose you’re selling accounting software and your prospect tells you that they’re currently doing their accounting in Excel.

 Straight away, you’ll know that they probably struggle with problems like forgetting to enter data or syncing it with other banking tools. You can then bring up the most relevant benefits of your product/service in the meeting.

This question is also a good way to learn about who at the company is involved. For example, if they tell you that it’s mainly their CEO and CFO involved in the accounting process, you can focus your pitch on the benefits they care about most.

3. What’s the biggest obstacle in your way of solving [problem]?

This question can help you identify the main blockers to closing your prospect as a customer.

For example, they might tell you:

  • We haven’t had the budget until now

  • Our growth rate has made it hard to take a step back and solve this problem

  • We didn’t have a dedicated marketing person who could benefit from a new tool

You can use all of these to improve your understanding of their company and buying situation.

For example, if they tell you that they haven’t tackled this problem until now because they didn’t have a marketing team, you can push to get their new marketing hires on a call with you to help them see why your product/service will be an essential part of their marketing function.

4. What would be the biggest benefit of solving [problem] to your company?

This question helps your prospect see the benefits of working with you from their own perspective.

This sales engagement question helps to eliminate your own bias. If you run a marketing agency, you might enter the conversation thinking that the main benefit to them will be that you can help them generate 200% more qualified leads through ads every month. But, they might then tell you that the biggest benefit will actually be that they can stop worrying about marketing and have a trusted expert handle it for them.

You can continue to use that angle in your future interactions with your prospect and reinforce the benefits of working with you based on what they care about most.

5. What’s the alternative to using our product/service?

This sales engagement question helps you build an understanding of your prospect’s mindset to their problem. It will also help them frame the problem in a way that agitates their current pain points. 

For example, if you’re selling a cold email platform, your prospect might tell you that the alternative would be:

  • Not using cold email as a sales channel

  • Spending hours manually preparing campaigns in Gmail or Outlook

  • Having to pay a freelancer or agency to run their outreach for them

This process will help them see the benefits of your product/service without you even needing to tell them.

You can also bring up these alternatives to agitate their pain points in future meetings and reiterate how your product or service can be a replacement for their current solution.

Sales Engagement Questions to Close a Deal

1. Who else should I send the sales proposal to?

When you’re close to securing your prospect as a new client, you need to make it easy for everyone involved in the purchase decision to access key information.

This question will encourage your prospect to confirm who else is involved in the purchase decision. You can then loop them into your follow-up email to re-confirm what you talked about on your call, and ensure they see the proposal you’ve sent them.

If your email software includes email tracking, you can identify which decision-makers have opened your email and seen the proposal.

If they don’t interact with your sales proposal, you can follow up after a day or two and check in with them.

2. What’s your deadline for making a decision on solving [problem]?

This question gives a sense of urgency to your conversation with a lead.

If they tell you their deadline is 30 days from now, it permits you to follow up promptly after your calls or if you don’t hear back from them for several days.

If they tell you their deadline is 180 days from now, you know you can leave a longer delay between follow-ups because they’re still having internal discussions and it’s not the number one priority for them.

Even if your prospect doesn’t have an official deadline, this sales engagement question can help you set one together, which will help both you and them move the deal over the finish line.

3. Can I follow up with you on this on [date]?

This question works well at the end of a sales call because it sets expectations for when your prospect will hear from you again. When you reach out, they’ll be expecting it and it won’t feel like you’re following up too soon. 

Having your prospect confirm when they’ll hear from you again also sets expectations for what they’ll need to do in the meantime. For example, if they have work to do on their end after the call – such as discussing your product/service with their manager –they'll be more likely to take action if you've set a deadline together.

Wrapping Up

Your sales engagement questions are powerful tools for learning about your prospect’s pain points and needs. You can use their answers to guide them through the sales process and personalize every interaction you have with them.

As well as being helpful for you, the right sales engagement questions will help show your prospect’s the benefits of working with you and help them see exactly how you can help their company.

When you’re ready to start booking more meetings with qualified prospects, you can try QuickMail’s cold email software with a 14-day free trial