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Questions that Close More Sales

iWish.AI SalesPerson On Phone Taking Notes

A Tale of Missed Connections 

Your well-meaning sales rep starts making dials, armed with enthusiasm but lacking a plan. "Do you want to save money?" They ask. "Are you satisfied with your current service?", “would you like to learn more about our service”. The prospect, overwhelmed by the barrage of yes-or-no questions and sensing no clear intent, crafts a swift exit: "Sorry, I need to go into a meeting. Bye." 

Dead-end questions shut down potential avenues of discussion making conversations feel more like interrogations. Skillful questioning allows sales reps to weave a thread of credibility while creating interest by opening prospects through meaningful dialogue. This allows sales to engage prospects and customers deeply by understanding what’s important to them so they can position solutions that resonate with the prospects’ core needs. 

Mastering the art of asking questions is not just about getting answers; it's about: 

  • Engaging More Effectively: Tailored questions make conversations relevant and engaging, showing genuine interest in the prospect's situation. 

  • Building Trust: Insightful questions demonstrate expertise and build credibility, fostering a trust-based relationship. 

  • Uncovering Hidden Opportunities: The right questions can reveal underlying problems, leading to opportunities for value-added solutions. 

  • Guiding the Sales Journey: Strategic questions steer the conversation toward uncovering the prospect's readiness to buy. 

Open-ended Sales Questions 

Open-ended sales questions are the secret sauce for a richer conversation. Unlike their closed-ended cousins, these questions encourage dialogue, peeling back the layers of a prospect's needs and priorities. For instance, turn "Do you like your current product?" becomes "What do you enjoy most about your current product?". This way you get more juice out of each question, rather than asking multiple questions. 

Practice roleplay is a crucial tool for salespeople to sharpen their ability to navigate real-world scenarios. Simulating sales conversations, reps learn to ask effective questions, uncover customer needs, and adapt to varied responses, enhancing their conversational quality with prospects and customers. This hands-on practice builds confidence and the critical thinking required for successful sales dialogue. 

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1. AI Sales Coach trains new SDRs faster with the conversation skills they need to start setting meetings faster.

2. AI Power Dialer with real-time objection responses guides SDRs during live calls so you convert more conversations into meetings.

3. AI Email Generator scales SDR outbound campaigns with captivating sales emails tailored to your buyers and value proposition increasing open and reply rates.

To learn more about how our AI Sales Platform can empower your SDRs to book more meetings faster, visit us at

10 Examples of How to Convert Closed Questions into Open Questions

  • "Is cost a concern?" becomes "How does cost factor into your decision?" 

  • "Have you used our product before?" becomes "What has been your experience with our product?" 

  • "Do you have budget constraints?" becomes "How do you typically allocate budget for solutions like ours?" 

  • "Are you the decision-maker?" becomes "Can you walk me through your decision-making process?" 

  • "Do you need our service?" becomes "What challenges are you hoping our service will address?" 

  • "Is your current solution failing?" becomes "What aspects of your current solution are you looking to improve?" 

  • "Did our presentation cover your concerns?" becomes "What parts of our presentation stood out to you?" 

  • "Do you want a demo?" becomes "What would you like to see in a demo to ensure it's valuable for you?" 

  • "Shall we proceed with the paperwork?" becomes "What are the next steps from your perspective?" 

  • "Are you ready to buy?" becomes "What information do you need to make an informed decision?" 

Is it OK to Challenge Prospects on Calls? 

It's about asking; asking right and asking enough. That means being tactful in your pursuit so as not to overstep or offend. Do that well and YES you absolutely can and at times SHOULD be provocative in your sales outreach!

As a sales rep, your queries should tease out details of a prospect's business landscape without overwhelming them. Is there a limit to how many questions? Yes and No. The key is to ask as many questions as is necessary without casting a shadow over the conversation, this means not asking more questions than necessary – do more with less.  

Also, the type of sale e.g. B2B vs B2C is important to consider, for example, personal purchases are more sensitive and may not be the right format for a challenge.

Avoid switching between unrelated topics and question areas as this will quickly confuse and exhaust prospects and customers. It makes far more sense to probe deeply into 1-2 areas in a conversation than to loosely cover 10 different areas. Your first questions are the most important to opening the conversation so focus on a good setup, then go deep. For example, probing questions like "What hurdles are you facing with your current process?" or "How does this challenge impact your team's productivity/Results?" help to reveal the raw challenges, needs, and goals of a prospect, steering the conversation towards genuine problem-solving. 

Active Listening and Good Questions Build Rapport 

Good questions show a prospect and client that you are listening, and you care. You can also use questions to show empathy – for example "Tell me about your day-to-day", and “How does your current platform impact your long-term goals?.” Take a moment to reflect on their response before asking further questions and make a point to align any follow-up questions with their unique situation. Be personal and human and you will open more conversations that build relationships. 

Many salespeople talk their way out of sales by trying to over-sell someone who's already decided to buy. Active listening will help you know when someone is ready to buy, once that happens you must focus on understanding how to help them move forward, rather than continuing to sell them which just results in frustration for everyone involved.

9 Question Traps to Avoid 

While this post is focused on asking good questions, I thought it may help to outline some question types that you do want to avoid: 

  • Aggressively leading questions that push your agenda – take a moment to learn about them first. 

  • Multiple questions in one breath - most people will only remember the last thing you said. 

  • Dodge questions with obvious answers – don’t waste questions by asking the obvious (unless it’s necessary to set up a powerful story you have to share)! 

  • Personal questions that are irrelevant to the business/product – if you are selling a product that is DIRECTLY related to the personal question then fine, otherwise just don't do it.  

  • Complicated, jargon-filled questions. A common mistake that salespeople make is to think that their prospects use all the jargon terms they learned from their product training. Nope! Keep it simple, don't use terms you will have to explain. 

  • Hypothetical scenarios - these can easily confuse people and take focus off their present needs. 

  • Questions that question their competence – people don't like it when you do this! 

  • Questions with a negative premise – don't’ start with negatives, but if the prospect takes you there and you have a solution that will help, now is the time to paint the positive picture with your solution. 

  • Any question that you should know the answer to - this is not something that you want to draw attention to. 

Closing with Questions 

As you conclude a conversation your final questions should naturally lead to a clear next step that feels seamless. When you reach the natural inflection point it is time to ask for the next step which can be as simple as, "What would be the best way for us to follow up on the solutions we discussed?", or "What would be a good time for us to walk through a demo of the solutions we discussed?"

If you haven't already uncovered this in your earlier probing, this is also a chance for you to expand your buyer community by asking “Is there anyone else on the team that you think would benefit from joining the next call/meeting”. 


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