How to Ask the Right Questions for Sales Success 

how to ask the right questions for sales success

We have all had that moment where we get introduced to a customer to discuss what exactly their needs are. Here you are faced with someone who has an idea for the betterment of their business, whether it be time or cost-savings, streamlining their processes, or unifying various system functionalities into one solution, but they do not necessarily know how to communicate or envision this.  

The options and ideas are sometimes a little daunting with the idea of having everything under one roof, as it were because customers always have a question they often do not want to ask.  This is an example of one I have heard many times before: “What if the system is down? Can I still access the other systems?” The reason why it’s great to have these kinds of questions surface from your customer engagement is so you can ensure that you address all their concerns and issues while instilling confidence in the outcomes of the project. 

How to Improve Your Sales Engagements 

This is when the right questions must be asked. There is no blueprint or stencil for this as many customers are part of different business sectors. While there is training for successful sales strategies, many of the techniques and methods are getting a little outdated, and are no longer applicable (as the world has gone vastly digital) and face-to-face engagements are no longer the norm, in a typical sales strategy. Asking the right questions can make all the difference.  

1 – Keep it simple, ask clear and concise questions.   

What do I mean by this? Make sure the questions you pose are to the point and not open to misinterpretation. Ensure that questions are related and that they follow a flow or a form storyline. Jumping from one side of a customers’ business requirements to the next and back again will confuse, and maybe even lead to a customer losing faith in your capability to deliver a complete, and functional solution. If you address the right questions, this will enable you to assess the KPI’s or the expected outcomes your customer has, so you can resolve and remediate any issues and doubts that may arise.  

Some of the basic questions asked to customers are:  

  • “Will customers need access to the system to capture information even if there is no connectivity?”  
  •  “If the system is down, how long would be acceptable until it is up again? What are the assurances that the customer would want?” 
  • “Is client data to sit in-country or can the data sit outside of SA? Are there any rules around where data must sit?” 
  •  “Is there a mobile requirement? Do they have any systems in place we have to integrate to?”  

These could be a little daunting to answer as a customer might feel as though they are being cross-examined for answers in your sales engagement.  

2 – Be Intentional, Ask Actionable Questions  

I recently came across a quote from a book called “A Beautiful Question?” and it has stuck with me for a while now. The quote is not about philosophical or spiritual questions we all have heard before, but more about what we can do to act on the questions we have. The Quote is as follows: “A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change”. So always ask what actions you are driving with your questions and are they adding value to the expected outcomes. 

The best questions engage the client without you having to make assumptions about their knowledge and needs. 

3 – Have Objective Discussions  

The best course of action in my opinion is to let the customer tell you a story. Let them guide you through what they want, what they need, and what they currently have.  This will in turn allow you to raise the questions above, but not in a manner where the customer feels they are being interrogated.  But rather, that they are part of a discussion where you are applying thought, insight, and care to their needs. 

Be open to the idea that a customer isn’t ready to go with the whole “enchilada” and that perhaps they are looking to take a phased approach to a complete solution, I know how exciting it can be to capture a customer’s interest, but we must remain objective and focus on their goals. 

4 – Be Open to Customer Ideas  

Customers generally don’t want to get too technical and often have ideas and thoughts that could lead to significant differences, in how a salesperson approaches the sale of a product or service. Be open to ideas, thoughts, and plans raised by customers but be sure to explain the “why and why not”. If you feel what is needed falls outside of your offerings there is nothing wrong with saying no to a customers’ ask…  It is always better to give your customer a realistic expectation of what is possible in their timeframe and budget. It’s not all about the information, it’s about the “customer journey of information”, this is something I feel we should all, as sales team members focus on. 

When all is said and done… Listen, assess, question and address. You’ll have happy trails with many sales! 


Questions can stimulate fruitful discussions that empower sales to deliver to the customer, at their best. If a sales agent is informed and understands what a customer needs, they have higher chances of succeeding at building relationships and generating profits. Asking clear and concise questions, asking questions that enable action to be taken, being objective and open to customer ideas will often lay the foundation for a successful sales engagement.  

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