Mastering Sales Questioning Techniques: A Comprehensive Guide for Success

The importance of asking the right questions during sales conversations with potential buyers is pivotal to maximising sales success. Without asking the right kinds of questions you may not be able to fully discover your buyers pain points and needs. This guide covers all you need to know about owning a sales conversation through a variety of questioning techniques and methodologies.


The importance of asking the right questions during each sales conversation you hold with potential buyers is pivotal to maximising sales success. Without asking the right kinds of questions you may not be able to fully discover your buyers pain points and needs, which can leave you in a position that doesn’t allow you to present your products or services in the best possible light.

As business growth consultants, we know the importance of asking the right questions and when to ask them. Your sales successes are heavily dependent on your ability to ask questions which seek out useful information that will put you in the optimal position to generate and convert leads successfully.

In this guide, we will be using our 10+ years of experience in B2B sales, working with clients ranging from large-scale enterprises with 200-+ salespeople to micro and SME businesses to help you with the types of sales questions you should be asking, how to prepare yourself, common mistakes to avoid and overcoming some frequently encountered sales challenges.

Types of Sales Questions

In the beginning it can be hard to identify the type of questions you should be asking; should you be asking questions that have only one answer? Could they be questions that require some opinion from the individual? There are numerous question types you can use, and every great salesperson uses a combination of the following types:

Open-ended questions

Designed to encourage buyers to provide more detailed and informative answers an open-ended question is more invitational to share thoughts as opposed to just providing a yes or no answer. These types of questions are great for gathering valuable insights that will help you to better understand your buyer’s needs. An example of an open-ended question in a B2B sales conversation would be: Can you tell me more about your company’s current challenges or pain points?

Closed-ended questions

Given the name, a closed-ended question is the opposite of an open-ended question, whereas the open-ended question is designed to gather a more detailed response a closed-ended question is asked when you are looking for specific data or details such as budget allocation or deadlines. Though these types of questions are good for clear and concise answers they are typically not a good idea to use at the start of a sales conversation as they don’t encourage buyers to elaborate on their needs.

Probing questions

Useful for finding out a buyer’s needs and motivations, probing questions are used to probe the buyer to generate more information from them. The desired outcomes of probing questions is that the buyer uncovers their purchasing motivations as well as helping you, the salesperson, overcome any sales objections they may have. Probing question types are great for helping you to tailor your approach to the buyer’s specific needs.

Hypothetical questions

Great for exploring scenarios, future planning or envisioning possible benefits of your product or service with the potential client, hypothetical questions allow the client to think creatively about their decision making. This question type can allow you to hypothetically place yourself within the client’s business which allows you to steer the conversation toward the future of your yet to exist B2B relationship. As you can imagine, with enough hypothetical questions you are allowing your potential client to imagine the roles and responsibilities that you will be taking on once the deal has been secured.

Leading questions

Leading questions can play a valuable role within a sales conversation in that they can be used to guide buyers towards a desired conclusion or response. While there is a need for these question types they should be used sparingly as too much or incorrect use can be seen as unethical and some people may feel that they are being forced down a route as opposed to nurtured. Leading questions should be used as a tool to facilitate discussion and understanding rather than as a means of manipulation.

Alternative questions

At Firestarter, we believe in the power of questions that offer choices to stimulate decisiveness. For example, asking prospects whether they prefer the red or blue option can propel the conversation forward by implying that the decision lies in the details rather than whether to make a purchase. This approach alleviates the pressure of the decision-making process and helps prospects focus on their preferences. Remember to use these questions strategically, striking a balance between offering choices and maintaining a collaborative atmosphere.

In the initial phase of a sales conversation, your objective is to identify pain points. This will enable you to tailor the conversation around those specific issues, showcasing how you can effectively address and resolve them. Whichever sales question types you decide to use, it is important to understand how, when, and why you are asking these questions. Think about your aims and the desired outcomes you would like to gain from each conversation, don’t ask questions that result in little to no information.

Preparing your Sales Questions

To effectively prepare your sales questions, it is crucial to thoroughly understand your target market and industry, conduct research on buyers and their businesses, identify common pain points and challenges, and anticipate objections and concerns. By gaining a deep understanding of your target market and industry, you can ask relevant and insightful questions that address the specific needs and trends within that industry. This knowledge also demonstrates your expertise and positions you as a trusted salesperson.

Researching buyers and their business can help you gather valuable information that can be used to tailor your questions to their specific situation. This personalised approach shows your genuine interest in their business and helps establish rapport and credibility. By identifying common pain points and challenges that your prospect relates to, this enables you to ask targeted questions that address these issues. By making pain-point selling work for you, you are able to demonstrate your understanding of their challenges and position your product or service as a solution.

Anticipating objections and concerns beforehand allows you to be prepared with well-crafted questions that can overcome objections and address concerns effectively. This level of preparation demonstrates your professionalism and helps build trust with buyers.

10 Must-ask Sales Questions to Help Identify Buyers

As discussed, there are 5 types of sales questions that you should be asking, each with their own benefits. Although there is no definitive “best” ratio, it is important to focus on asking the right questions at the right time that allow you to gather information, build rapport, and guide the conversation effectively. Here are 10 must-ask sales questions to help you learn more from your buyer:

  1. Could you tell me about your business?
  2. What issues are you looking to address?
  3. What’s holding your team back from reaching your goals?
  4. Where do you see the biggest opportunities for growth?
  5. Who would be involved in the decision-making process?
  6. What budget do you have for this/to fix this/to purchase this?
  7. What alternative (internal/external) solutions have you considered?
  8. How important is this to you? Where would it rank on your priority list?
  9. What are the biggest challenges/areas that you think need the most focus in the next 12 to 24 months?
  10. Do you work with any external partners already? – if so, in what capacity?

These questions cover areas such as their business details, challenges, goals, decision-making processes, budget, priorities, future focus areas, and more. By utilising such questions, you can engage your buyer and understand their needs which will allow you to align your solution to their specific requirements.

Common Mistakes to Avoid

When leading a sales call, the thought of the conversation not going exactly how you want it to can be daunting and often off-putting to sales reps. Often the gap between a top-tier performer and a mediocre salesperson is in the way they conduct their sales conversations.

Asking leading or biased questions

Inexperienced sales reps can fall into the trap of leading prospects down a path to a certain answer, these types of questions are classed as leading or biased. As mentioned previously these types of questions can be unethical and are often spotted by anyone who has ever been on a sales call, this can be quite evident within young or inexperienced sales reps. You want to come across impartial and honest, by limiting leading or biased questions you avoid the prospect jumping to the wrong conclusions or answering in a manner where they feel pressured.

Overwhelming prospects with too many questions

At Firestarter, we understand the importance of striking the right balance when engaging with prospects, you want to ensure that you gather valuable insights without overwhelming them with an avalanche of questions. By asking too many questions you run the risk of coming across as self-centred or even incompetent as it can give the impression that you require lots of attention to carry out your role. Below are a some tips that can help you:

  1. Come prepared with a well-curated list of questions. At Firestarter, we emphasise the significance of thorough preparation to ensure that you have a clear understanding of your prospects’ needs and pain points.
  2. Streamline your questioning strategy. At Firestarter, we advise our salespeople to cross out questions that have already been addressed during the discussion. This mindful approach ensures that you don’t repeat inquiries, preventing the prospect from feeling frustrated or disengaged.
  3. Ask the right questions in the right order. Mastering the art of asking the right questions in the right order can significantly impact your sales success. By strategically structuring your questions, you can guide your prospect on a journey where they convince themselves that your solution is the ideal fit for their needs. The goal here is to empower the prospect to make an informed decision by guiding them through a thought-provoking journey. Remember, the power lies in letting the prospect convince themselves. By skilfully asking the right questions in the right order, you can lead them to a point where they genuinely believe that your solution is the right one for them.

Failing to Actively Listen

Let’s face it, even the most seasoned sales professionals can sometimes find themselves in sales situations where they forget to engage their ears. But why does this happen? Well, as humans, we’re wired to focus on our own thoughts, opinions, and objectives. Our brains can become so preoccupied with formulating responses and showcasing our knowledge that we unintentionally neglect to fully absorb and understand what the prospect is saying.

Because of this we may miss cues, overlook subtle objections, or fail to grasp the prospect’s true needs and desires. By being as present as possible and listening with intent you can then help yourself in rectifying and clarifying points made helping you to ask good follow-up questions.

Overcoming Challenges in Sales Questioning

Encountering difficult or resistant buyers is a common challenge that every salesperson will come across time and time again. At Firestarter, we believe that turning these challenging situations into opportunities is key to achieving sales success. By using the questioning techniques discussed previously, you will start to see in your sales conversations which of the “gentler” questions allow you to navigate your way through resistance but ultimately establish good rapport and build stronger relationships.

Buying decisions are as much about the individual’s circumstances as the business need. This is where the challenge of not adapting your questioning techniques to match an individual’s circumstances can slow the sales process. To overcome this challenge here are some Firestarter hot tips:

  • Learn personality types – Frameworks such as DISC or Myers-Briggs personality test are great ways to familiarise yourself with the various types of personalities. You can learn to understand general traits, preferences, and communication styles by studying each type.
  • Observe and listen – One of the best ways to learn about your buyer is to simply observe and listen, by using open-ended question methods you can initiate the buyer to talk in depth about their pain points and challenges they may face. This is a great method to allow you to Observe their body language, tone of voice, and choice of words. This can provide valuable clues about their personality type, communication style and it gives you the ability to adjust your questioning techniques in real-time.
  • Be flexible and adaptable – You should be prepared to recognise that not everyone will respond well to your questioning approach. By having an open mind to being flexible and adaptable you can adjust your style to meet the needs of the buyer. Your tone, pace and level of detail are key elements that will help you adjust your sales questioning techniques accordingly.
  • Tailoring your approach – We find that during sales calls we can usually (and safely) determine the buyer to have one of the following four personalities, analytical, expressive, assertive, or amiable. For analytical personalities ask detailed, fact-based questions that provide logical reasoning and data-driven insights.

Expressive personalities like to tell stories or discuss situations to express their thoughts and emotions, this is where the use of open-ended questions can be utilised. Assertive buyers respond well to concise questions that are direct and focus on results and outcomes. For amiable buyers you should employ a more empathetic and relationship-focused approach, asking questions that prioritise their feelings and opinions.


At Firestarter, we have developed our sales questioning techniques through 10+ years of experience, working with over 200 businesses across various industries. Our team of experts have led large sales operations for national and international brand names, and have extensive experience in sales, sales leadership, and business coaching and mentoring. Our commitment to understanding the power of effective questioning has allowed us to build strong relationships and achieve sales success time and time again.

Mastering sales questioning techniques is an ongoing journey, we encourage you to implement the strategies and techniques outlined in this article into your daily sales conversations. By using a mixture of sales questioning types, avoiding the common mistakes and by tailoring your approach, actively listening, and adapting to different personalities, you can enhance your sales effectiveness and achieve remarkable results.

At Firestarter, we believe that understanding and connecting with individuals on a deeper level, leads to powerful sales conversations and stronger, long lasting client relationships. By mastering your sales questioning approach, you will find it easier to create those connections and establish long-term success.

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