Sales Engagement

Interesting Sales Engagement Questions to Grab Your Prospects’ Attention

Seek first to understand and then to be understood - Stephen Covey

In the current fast-paced landscape, customers and buyers are busier than ever. Therefore, sales representatives must employ strategies that will make their prospect push their priorities, emails, meetings and notifications for the moment and dedicate that time to listening to the sales pitch. 

Sounds like a diabolical job? Well, if you take the same old approach as every other SDR, likely, you won't get the results. 

The reign of the fancy, overly persuasive sales presentation is over.

Sales engagement questioning is now a delicate blend of art and science. With the right sales engagement questions, you cannot just transform a prospect into a customer but also make them brand advocates. 

But there is a technique to ask sales engagement questions to grab your prospect's attention. And that's what this blog is about! 

So, let's get started!

Sales engagement questions-applying new techniques to the primitive process

It is no surprise or unknown fact that the sales process encompasses a very professional and relationship-based experience for both representatives and customers. When sales representatives ask questions, it should feel like a natural part of the conversation flow rather than a desperate attempt to sell the product. 

As a sales representative, your job is not just to ask questions to your prospects but also to focus on the answer your prospect is providing. Your prospect's answer can reveal critical information. 

Sales representatives can harness the power of two fantastic strategies that could help them achieve successful deal closures. 


Active Listening

  • Active listening represents a scientific technique where you carefully listen to your prospect and also observe nonverbal movements and vocal inflections. 
  • With active listening, you can provide feedback to your prospects by paraphrasing their responses. This technique has demonstrated positive outcomes in therapy, counselling and dispute resolution. 
  • Active listening gives a message to your prospects that you are actually listening and understanding their needs rather than blatantly practising product placement. 
Active Listening Image (Source)

Solution Selling 

  • Solution selling represents a selling technique where sales representatives leverage a problem-led conversation instead of a product-led one. 
  • With this technique, sales professionals actively listen and understand a customer's pain points and decide which products or services will be best suited to resolve their issues. Here, sales representatives avoid pushing the entire product range. They focus on a single product providing the best solution. 
  • Presenting a highly specific product or service feature represents an important approach instead of a predefined generic sales speech. 
Different Buyer Personalities & How to Sell To Them

10 attention grabbing and impact-making tricks during sales engagement questioning phase

The initial sales call lasts for just a few seconds-- approximately 30 to 40 minutes, to be precise. So how do you grab your prospect's attention and make an impactful impression quickly? 

Use your time wisely.

As mentioned previously, the first engagement with a prospect is unlikely to be a long one. Therefore, instead of overwhelming your prospect with excessive information, tailor a smart yet insightful message that perfectly suits the scenario. 

For example, present a quick one-line introduction about a single topic related to your product. Then ask for another 2 to 3 minutes of extension that will give you enough time to request a follow-up meeting. 

Prepare and set the agenda.

Establishing a detailed agenda and expected topics for a sales engagement tool can help your prospect comprehend what you're offering, translating into success. It also offers a framework to keep the conversation within a reasonable time frame. 

Make Sales Engagement Questioning Fun

Get started with Sales Simplify Platform

Don't be predictable and put your product in the limelight from the beginning.

From a sales representative's perspective, delivering a product-centred pitch is extremely important. But if you start with your product at the very beginning or if your prospect senses a sales pitch coming, you will get tuned away immediately. 

Begin the conversation with a subject that relates to your prospect, not your product. Practically initiating a call this way keeps an element of unpredictability, helps to establish a natural conversation flow and immediately grabs their attention. 

For instance, Here's what you shouldn't do--- "I saw your company interested in Y, and we offer the perfect solution." 

Instead, you can say, "I saw your company interested in Y. How do you plan on implementing/ doing it?" 

Leave your product out of the conversation in the beginning to grab their attention. 

Build report

The primary aim of the conversation is to get your customer comfortable. Prospects are more likely to trust and purchase from you when they like you or feel connected. And smart sales engagement questions can give your prospect the right impression.

Imagine yourself in the role of a student and be curious.

This is a part of active listening. 

In the initial sales call, curiosity is given more value over credibility. When you approach your prospect with a curious mind, they quickly assume the role of a teacher and become interested in continuing the conversation with you. 

And how exactly do teachers engage with their students? They are generally calm and forthcoming. But when sales representatives become subject matter experts, the prospects have nothing to contribute, translating into no engagement and consequently no sale. 

Here are some interesting questions that can reflect your curious mind: 

  • I was going through your portfolio, and ABC piqued my interest. Could you explain….? 
  • On your company's LinkedIn page, I noticed an XYZ update. Could you please help me understand more? 
Sales engagement statistic

Remember, silence is good.

After asking questions, you might notice a period of silence. Embrace silence because it is a positive indicator on the first call. In most cases, the prospect wasn't expecting or ready for your call. Therefore, you need to allow yourself time to think before responding to your queries. 

Trying to interrupt the silence with another conversation starter will break their focus. Consequently, they might not be interested in continuing the conversation further. 

Maintain the conversation balance 

In a healthy, interactive conversation, every participant should be playing an active role. A sales engagement questioning phase is no different. 

High-performing sales representatives maintain a balanced ratio between the prospect and themselves. This balance helps to position the questions organically during the engagement process, enabling them to weave naturally into the talks.

Tips to plan a sales engagement flow

Take small steps and focus on one thing at a time.

While engaging with your prospect, limit yourself to achieving one goal at a time. Here are a few sales engagement questions or closing statements that you can utilize: 

  • Do you have any marketing or business material where I can learn more about your organization? 
  • Does your financial department play a role in the vendor approval process? 
  • I found the slide take you presented at the event extremely insightful. Can you kindly let me know where I can get a copy of that deck? 
  • When a new product is introduced, can you help me understand what the implementation process is? 
  • What factors does your business consider while selecting a product/service? 

These questions will help you to gather the information that can prove to be beneficial during the product demo stage. 

Close the deal through natural flow

Through a series of sales engagement questions, you can move your prospects into the closing territory. This is where you need to utilize your closing finesse. 

Statically lay out the questions that will lead to a purchase for another meeting with a wider set of stakeholders to move the sale towards completion. 

If you have gathered the right information through sales engagement questioning in the previous phases, you will have more confidence and can present the right data to close the sales process. 

Plan your sales engagement workflow before making your initial call

Before starting your first phone call with the prospect and presenting your sales engagement questions, it is vital to have a clear pre-strategized outreach workflow. 

This will help you plan and distribute your sales engagement question throughout the process.

With sales engagement platforms such as Sales Simplify you can easily prepare a sales engagement questionnaire using the notes section. Add new notes or take a look at your previously added one. Get everything under a single, centralized location:

Notes addition feature for keeping track of sales engagement questions

Types of Sales Prospecting Questions

The way and technique to ask the question are equally critical as what you ask. Therefore maintaining a good balance of open and closed-ended questions can help you gather IEA vital information and data points to plan your sales pitch for product demos.

  • Closed-ended: Close-ended questions can be answered with a binary answer. In simple words, open-ended questions generally get a yes or no response. For example, "Did you find our product impressive/valuable?" If the prospect answers "no", your entire engagement process can come crashing down. 
  • Open-ended: Open-ended questions represent queries that will have an elaborative response. Open-ended questions cannot be replied to with a simple "yes" or "no". For example, what were the features of our product that you found impressive or helpful?

Open-ended answers will typically give you more data and information about their prospect that you can utilize throughout your sales engagement process and strategize the best way to close the deal. 

Best sales engagement questions- samples

There are several types of sales engagement questions you can ask depending on the stage of your sales cycle

Opening questions

Establishing and nurturing a relationship requires a warm and personal touch. Therefore, your prospects will instantly lose interest if you directly cut to the chase and try to close the deal. 

When engaging with a prospect, ensure to warm up with some personal questions and get them talking about themselves. Here're some examples: 

  1. How is your day going?
  2. What are your plans for the upcoming holiday or weekend? How was your holiday?
  3. I noticed we have a mutual connection [contact] on LinkedIn. How do you know them?
  4. Tell me briefly about your background in (industry).
  5. Are you planning to attend any conferences or trade shows this year?
  6. How is your (personalized downloaded resource/template) working for you? I hope it helps with your business!

With sales engagement platforms such as Sales Simplify you can keep a track of all the questions during a sales call through a notepad feature. 

Image for note feature for streamlined sales engagement questioning

Insight Discovery Questions

To get an insight into what your prospect wants and where their decision can be headed, you need to know their present thought process. 

Asking insight discovery questions provides you with a great perspective on what services or products your prospects are currently using and what challenges they're currently struggling with. 

Some sample questions can be: 

  1. When was the last time you selected this solution for XYZ's purpose?
  2. Which provider are you currently working with? 
  3. What are the positive factors about your current provider? 
  4. Did you have a changing business need? If yes, why? 
  5. Is there anyone else you want to be included in the discussion? 
  6. What is your thought process about other solutions you're considering?
  7. What is the most deal-closing element of a provider for you? 
  8. (Highlight prevalent challenges in the prospect's industry) How are these challenges affecting your business?
  9. What are you hearing from your influencers about your current challenge? 
  10. What's your opinion on improving the existing system/solution? 
  11. How critical is exploring new possibilities for your business?

Business pain point questions

Finding a pinpoint with prospects is struggling. This will help you find the best approach to provide them with a solution that truly impacts their life in a positive way.  

Sometimes a solution might be a great fit for the business. However, the implementation and learning curve creates a bottleneck. 

Remember, no solution is perfect. Understanding the effects can be a great motivator to change.

  1. What challenges are you facing with the current solution? 
  2. What roadblocks are your current solution introducing to your business plans? 
  3. How are you presently addressing (service) problems? 
  4. Has the lack of a solution to the challenge affected your employee turnover?
  5. How much time/resource do you allocate to tackle (common industry challenge)?
  6. What's the effect on your customer attrition rate due to this particular challenge? 
  7. How did the revenue generation react to this pain point? 
  8. What revenue projections could you expect by implementing a better solution?
  9. What new features/functionalities might give you better results?
Tips to plan a sales engagement flow

Objective identification question

Having a good knowledge of your prospect's business objectives opens up an excellent avenue to respond to their requirements—immediately and in the long run. 

Therefore, preparing objective identifying questions is an optimal way to understand and get insights about your customer's long-term plans and requirements.

  1. Why are you planning to embark on a purchasing process?
  2. If you're planning to implement a new solution, what would you like to see achieved at the end of this process?
  3. What is your stakeholders' expectation from this process? 
  4. What are your next quarter and next-year business goals? 
  5. How much easier would it be to achieve your goal if you had a better solution in place? 
  6. What additional revenue-generating goals could you set with a new and more effective solution in place? 
  7. What's holding your sales team back from reaching your business objectives? 

Prospect qualifying sales engagement questions 

Before you move to the closing territory, you need to check the budget and qualifications of the client. With prospect-qualifying sales engagement questions, you can subtly signal the requirement to discuss the pricing objective. 

  1. Have you established a budget for this new tool/service/technology implementation?
  2. Are there any additional elements you want me to demonstrate to help you understand the value of what I'm proposing?
  3. What is your budget planning process for similar projects? 
  4. What vital details stakeholders/management will require to sign off on this expenditure?
  5. Do you feel the requirement for another meeting with the stakeholders to provide information to any interested parties? 
  6. Is there any additional information, guides, decks, data points or material I can provide for discussions with other relevant parties? 
  7. What would you like to happen to make the implementation of this solution a priority?
  8. What would a successful result look like to you? 

Deal closing questions

These questions are specifically reserved for the deal-closing stage. With these sales engagement questions, you can get a better idea of when and how the deal will close and what the chances are of it being successful. 

  1. What's your tentative timeline for making a purchase decision?
  2. I've shared some calendar slots for you to choose from, and we have availability on (range of dates). What works for you?
  3.  For a solution within your existing infrastructure in your desired time frame, it is advisable to have a contract in place by (date). Is this attainable?
  4. If all the criteria outlined have been fulfilled, how comfortable would you be to proceed?
  5. Are there any queries that I haven't already covered?
  6. What information can I provide your finance team?

How to handle objections during a sales engagement questioning session?

Here's the hard truth: even with the right set of sales engagement questions, you can't expect to close a sales deal smoothly. 

There might be some hiccups and challenges down the road. Objection handling is one of the most critical aspects of the sales engagement process that'll help you improve and stay motivated!

Let's take a quick look at how you can handle the most common objections during the sales engagement

We already use [your competitor] / We've already signed a contract with [your competitor] 

  • That's fine! (your competitor) has some remarkable features. How's that working out for you?

This pattern-interrupt question can get your prospects talking about any issues and give you ideas as to how to position your product/service.

  • Not an issue. What if you plugged us in along with your existing to turbocharge your workflows / boost the overall effectiveness of your current stack? 

Such suggestions are rare and can help you win a deal. 

  • We do integrate with (existing product/service). We have customers migrating from XYZ service to our product due to (point out the challenges). Could you please explain any such issues you're experiencing?  
  • I completely understand. What do you like most about the current solution, just so I can be better informed?
  • That's great! Is there anything additional you wish the (competitor solution) could provide? 

Ideally, your solution might provide some perks that their existing solutions don't. 

  • What's the length and tentative ending date of your contract?

You can prepare a customized re-invigoration sequence further down the line. Remember, building relationships is as vital as closing sales. 

We're happy with the way things are/We're doing great in this area / We have everything we require

  • That's great. Can you let me know how you are achieving that? I talk to a lot of (prospect's job roles), and most struggle with (mention a challenge). How did you achieve it specifically?

This isn't a priority now

  • If you could please tell me what would make it a priority?
  • I get that. What about (another business cycle/quarter)? What would make it a priority, then?
  • So what are your present priorities? If you could brief me about them, maybe there's a way I can help.

It's too expensive / I don't see the potential for ROI

  • Our customers achieve (practical and attainable ROI) on average. What ROI would help you to try it out? 
  • What kind of ROI are you targeting?

I'm not interested

  • What factors would it take to interest you?

Call me back in 3/6 months

  • No issues. What changes are you expecting by then that might help you consider our product?

Send me an email

  • Is there anything specific information/content you'd like me to send in that email?
  • Sure. Is there anyone else I should copy on that email? 

Frequently asked questions

What is sales engagement? 

Sales engagement is a continuous process of enhancing the communication between you and your prospect. The sales engagement questioning process boosts meaningful, two-way interactions that generate more information about the deal.

What is sales engagement compared to sales enablement? 

Sales engagement involves empowering sales reps to easily interact and communicate with prospects by providing sales automation tools. Sales enablement typically deals with the internal processes that help create a workflow for the sales team, such as training, coaching, etc. 

How do I track all my prospects' responses? 

Consider integrating a sales engagement platform that automates and streamlines your sales engagement process and gives you an overview of the entire process. 

Streamline your sales engagement questioning process with sales simplify

When used correctly, open-ended sales engagement questions are an effective way of interacting with your prospects. 

Ready to start using open-ended questions in your sales engagement process? Sales Simplify is a sales engagement solution explicitly engineered to help enterprises reach out to leads in an efficient and streamlined way.

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