Top 10 Challenging Questions to Pose During a Sales Call

I have always believed that asking the right questions is crucial when it comes to making a successful sales call. As a sales professional, I understand the importance of engaging my prospects and uncovering their real needs and pain points. That’s why today, I want to share with you my top 10 challenging questions that I find highly effective during a sales call. These questions are designed to probe deeper, challenge assumptions, and ultimately, close more deals. So, join me as I reveal my go-to questions that are guaranteed to take your sales conversations to the next level.


In the world of sales, connecting with prospects and understanding their needs is essential for success. However, feeling disconnected from a prospect can hinder a sales call and make it challenging to build rapport. In these situations, it is important to pause and ask hard questions to understand the hesitation and address any concerns that may be holding them back. By asking straightforward questions and genuinely caring about their opinions, sales professionals can gain valuable insights into their thoughts and feelings. In this article, I will share the top 10 challenging questions to pose during a sales call, which can help salespeople overcome obstacles and close the sale.

  1. “What are your main concerns about this product/service?”
  • By asking this question, you can identify any specific concerns the prospect may have.
  • This will allow you to address those concerns and provide them with the necessary information to alleviate any doubts they may have.
  1. “What is holding you back from making a decision?”
  • Understanding the factors that are preventing the prospect from making a decision is crucial.
  • It could be financial constraints, fear of change, or uncertainty about the product/service.
  • By identifying these obstacles, you can tailor your approach to alleviate their concerns and help them move forward.
  1. “Can you share any previous experiences or challenges you’ve faced with similar products/services?”
  • This question helps you understand the prospect’s past experiences and any challenges they may have encountered.
  • By addressing their previous concerns, you can build trust and assure them that your product/service is different.
  1. “How do you envision this product/service fitting into your business?”
  • By asking this question, you can understand the prospect’s vision and goals.
  • This insight will help you propose a tailored solution that aligns with their specific needs and objectives.
  1. “What are the key factors you’ll consider when making a decision?”
  • This question helps you understand the prospect’s decision-making process.
  • By knowing the key factors they consider, you can provide the information and reassurance needed to meet their criteria.
  1. “What are the potential roadblocks you foresee in implementing this solution?”
  • Identifying potential obstacles in advance allows you to proactively address them.
  • By showing that you are prepared and experienced in handling challenges, you instill confidence in the prospect.
  1. “How does this decision align with your long-term business goals?”
  • By linking your product/service to the prospect’s long-term goals, you emphasize the value and potential return on investment.
  • This question showcases how your offering can support their strategic objectives.
  1. “What is the timeline for implementing a solution?”
  • Understanding the prospect’s timeline allows you to manage expectations.
  • It also enables you to propose a plan that aligns with their desired timeframe.
  1. “How involved do you anticipate your team being in the implementation process?”
  • This question helps you gauge the level of commitment and support from the prospect’s team.
  • It allows you to provide appropriate resources and clarify the collaboration required for a successful implementation.
  1. “What would be the impact of not taking action and maintaining the status quo?”
  • By highlighting the consequences of inaction, you create a sense of urgency.
  • This question encourages the prospect to consider the potential benefits and risks associated with their decision.


Asking challenging questions during a sales call is crucial for understanding a prospect’s concerns, addressing obstacles, and building rapport. By genuinely caring about their opinions and showing willingness to level with them, sales professionals can strengthen relationships and increase the chances of closing the sale. By incorporating the top 10 questions mentioned in this article, you can gain valuable insights into the prospect’s thoughts and feelings, tailor your approach, and effectively move the sales process forward.


  1. Should I ask all of these questions during a single sales call?
  • It depends on the conversation flow and the level of information shared by the prospect. Adapt your approach based on the specific needs and interests of each prospect.
  1. What if a prospect feels uncomfortable answering some of these questions?
  • If a prospect feels uncomfortable answering a question, respect their boundaries and move on to another topic. Focus on building trust before delving deeper into sensitive areas.
  1. How can I ensure my questions come across as genuine and not intrusive?
  • Ensure you ask your questions with empathy and active listening. Use phrases like “I’m genuinely interested in understanding” or “I want to make sure I address your concerns fully.”
  1. What if a prospect avoids answering difficult questions?
  • If a prospect avoids answering, delicately rephrase the question or ask follow-up questions to encourage their response. Try to understand their hesitation and address it accordingly.
  1. How can I overcome objections raised by these challenging questions?
  • Listen carefully to the prospect’s objections and concerns. Address them directly, provide relevant information, and show how your product/service can overcome those objections.
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Namaste~ My name is Ace and I found these contents SUPA~ Valuable! I apologize for the quality of the transcript... (In case you are curious I used YT EVO plugin to automatically pull these amazing contents) Enjoy!

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