• Home
  • /
  • Blog
  • /
  • TSE 525: TSE Hustler’s League-“Questions Your Customers Want You to Ask – Part I”

Don't miss our weekly sales tips!

Sign up below to get weekly tips from Donald on how to build a healthy sales pipeline and convert 2x as many deals!

The Sales Evangelist

Donald Kelly, TSE Hustler's League Today’s snippet taken from one of our past sessions over at the TSE Hustler’s League is all about asking the appropriate questions to help advance your deal and let you bring more value to the table.

Regardless of what you’re selling or who your selling to, you have to ask the appropriate, value-rich questions. These are questions your prospects would be glad that you asked.  Reduce your talking. Help them feel they’re buying and not you selling. Then price would no longer even be a question.

If you find some of these questions to be missing in your process, then feel free to tweak it and fix it.

Strategies for asking the right questions:

  1. Do your basic research before the call/meeting.

Don’t just wing it. You have to come prepared with information. You can find details about anyone just by going online. Find out about the company in advance and don’t ask questions where the answers are already accessible. Make sure you come as a consultant by showing them you’re bringing intelligence to the table.

  1. Get access to their why.

The more you can get access to what’s really powerful and meaning to them, the more connected you’re going to be. Remember, people do business with people they know, like, and trust.

Bad example:

“How long have you been around?”

Good examples:

  • “I know you’ve been around for 13 years and as an individual solopreneur, why did you decide to get into the x-ray business?”
  • “You mentioned you currently have a system, what would cause you to look at something else?”

Sometimes you may have a solution that they already have. So it’s important to find out what caused the disservice.

  1. If you feel it, say it.

If you feel you have a question you really want to know the answer to, then don’t be too shy to ask it. Ask. Be bold and be open. Remember, you’re here as a consultant. And they will respect you for that.

  1. Acknowledge they’ve also done their research.


“I know you’ve done some research already, what are your must-haves in a new system?”

“I know you’ve probably looked at many different services like ours already or done some research on systems like ours, what are some of the must-haves in your service?”

  1. Dig deeper than just the features or benefits they’re looking for.

Asking these type of questions will let you know whether they like the system or it’s just a legacy system that was in place which they wanted to change.


“What are some of the criteria you’re looking for when selecting a system? Why is that so important to you?”

“Were you part of the original selecting committee? Who is also part of the selecting committee.”

  1. Bring up their band-aids that would reaffirm to them that they need to do some changes.


“What do you do to fix this challenge? What are the band-aids you’re doing? Is that something you’re going to keep doing? How long can you keep doing that band-aid before it becomes ineffective to you?”

  1.   Delve down to their true pain that’s affecting them.

Emphasize how it affects their business by asking, for instance, the 5 why’s. Ask with a why and keep following it up with a why. By the time you get down to the fifth why, you usually get to the true issues.


“How does that affect your business? How much is that costing you?”

Episode Resources:

The Alchemist by Paulo Coelho

Get a free audio book download and a 30-day free trial at audibletrial.com/tse with over 180,000 titles to choose from for your iPhone, Android, Kindle or mp3 player.

Help us spread the word out by leaving us a rating or review on iTunes, Stitcher, or Google Play or whatever platform you’re using.

About the Author The Sales Evangelist

Donald is the host of the popular sales podcast,"The Sales Evangelist". He is the founder of The Sales Evangelist Consulting Firm where he helps small companies develop killer sales process to scale their business and increase growth.

Donald is also an award-winning speaker, sales trainer, and coach. He's a big fan of traveling, South Florida staycations and high-quality family time. Donald has a belief that “anyone” can sell if they have the desire and receives the proper training.

Leave a Reply

Your email address will not be published. Required fields are marked

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}

LinkedIn Prospecting Made Easy!

5 Simple Ways to Landing Appointments on LinkedIn, Even If You Don’t Know Where To Start!

LinkedIn Prospecting on Laptop

TheSalesEvangelist.com needs the contact information you provide to us to contact you about our products and services. You may unsubscribe from these communications at anytime. See our privacy policy for terms and conditions and to learn how we protect your data.