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5 Tips for Asking Your Prospect Better Questions

Posted by Walt Gerano on Fri, Apr 05, 2024

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. Read on to learn 5 tips for asking meaningful, exploratory, and courageous questions.

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 the #1 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 an executive 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 well-being 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:

  1. What is getting in the way of reaching your revenue goals?
  2. How does this impact growth?
  3. What is the effect on turnover?
  4. If you had to find the money to cover this cost where would it come from?
  5. How does this investment affect your longer-term 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 company? What 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 questions. Get 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 size?" The prospect will now give you a more accurate answer – for 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 prospect’s 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 “pain 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 now and see how they work for you.

Do You Need More Leads? –  Free Sales Prospecting eBook Download



Topics: Sales Training, asking questions, motivating sales people, asking sales questions, sales training tips


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    Anthony Cole Training Group has been working with financial firms for close to 30 years helping them become more effective in their markets and closing their sales opportunity gap.  ACTG has mastered the art of using science-based data and finely honed coaching strategies to help build effective sales teams.  Don’t miss our weekly sales management blog insights from our team of expert contributors.


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