5 Tips for Asking your Prospect Better Questions

From Sales Development Expert, Walt Gerano

You don’t want to look, act, or sound like every other salesperson when asking your prospect questions. There is an art and a science to being masterful at asking your prospect better questions and building a strong, credible relationship with them. Watch below to learn 5 tips for asking meaningful, exploratory, and courageous questions. 

Find out more below:

5 Tips for Better Questions from Anthony Cole Training on Vimeo.


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Video Transcript: 


Now I am sure that you do not want to look, sound, or act like the salesperson no one wants to meet with – you know, the one that shows up and throws up.  The salesperson who asks the canned questions and then talks too much instead of listening?  


There is an art and a science to being masterful at asking questions and building a strong, credible relationship with your prospect.  Now even though many of you think you have this skill of asking questions nailed, it would be interesting to have a microphone hooked up to you during your next sales call to find out if you really ask meaningful, exploratory, and yes, courageous questions. 


Here’s a tip:  Think ‘Presidentially’ with your questions.  It is probably the single most important piece of advice we can share with you when you are meeting with the executives of a company or with a head of household.  Think about the things they think about and worry about.   


Executives, owners, and heads of households usually think about the bigger picture, longer-term issues such as the wellbeing of their enterprise. So, ask them questions about that.  What you sell is just a part of the overall picture.  Instead of focusing on a specific loan need, investment strategy, or benefit coverage, think broader and ask questions like:


  • How does this impact growth? 
  • What is the effect on turnover? 
  • If you had to find the money to cover this loss where would it come from? 
  • How does this investment affect your longer-term retirement goals? 


You get the idea.  Really seek to understand the challenges facing your prospect, not just the specific product need you might be able to solve.  This separates you from the other salespeople talking and pitching product solutions.  You will be solving business problems instead! 


So, what about when your prospect asks you questions like:  How big is your companyWhat kind of service guarantees do you provide? What other companies in our space do you work with? 


Here’s tip #2:  These questions are not their real questionsGet beneath their question by asking:  Joe I want to make sure I address the right concern or question you have, when you ask ‘how big’, what is your concern relative to ‘how big’.  The prospect will now give you a more accurate answerfor example – I want to make sure that you have the resources to take care of our entire footprint. 


Questions like these will drive a much deeper conversation. 


Here’s tip #3 and a rule of thumb for questions:  Follow the leader (your prospect). Too often salespeople have their list of questions and are prepared to ask those questions.   They want to follow the script but the problem is the prospect doesn’t know their lines.  You have to follow their lines or lead.  Here is an example: 

  • You ask a question – how concerned are you that you won’t be able to come up with the cash to take advantage of the market opportunity? 
  • The prospect says – very concerned 
  • You ask – Tell me more about ‘very concerned’ what specifically are you concerned about? 
  • The prospect says – my concerns are xy & z 
  • You ask – why does xy and z bother you?  what is the impact? 


This is how to get to the bottom of the real issues that need to be solved not just the surface issues. 


Let’s say you have uncovered a prospects motivation to take action and you know that they have a real pain that is costing them.  Hidden in the conversation though is another pain.  The pain of change.  Tip #4 – The key thing to remember is that there are two pains at work – the pain of not changing and the pain of change.  The pain of not changing has to be substantially greater than the pain of change.  So, with that in mind you have to ask about the pain of not changing: 

Here are some examples: 

  • How long has this problem been going on? 
  • What happens if you don’t fix it? 
  • What is the cost to you, the company, your family, or your community? 
  • Who in your organization is impacted by this change and how will you handle that? 


Tip #5 – Occasionally your prospect will want to transfer the pain: 

“Well if we don’t do this then the company, the department, the marketing group, etc” will… Transferring the pain to someone else makes it easy for your prospect to ignore the problem.  This is why you have to make it personal. When you ask the question:  What happens if you don’t fix the problem and you get a transfer answer you must re-ask the question.  I’m sorry Sally what I meant to ask is this:  Why is this a problem for you specifically if you don’t fix it?  


So, there are 5 tips you can use today, to get better at discovering what is really bothering your prospect.  Go give them a try right and see how they work for you.