Paul Castain's Blog

17 Questioning Mistakes That Can Kill Your Deals

Posted January 25, 2018

Image result for harold and kumar interrogation

The Needs Analysis is no doubt, a critical step of the sales process. Execute properly and and you pave the way for a higher probability sale. Execute poorly and you disconnect!

Execute poorly on a regular basis and;


Here are several questioning mistakes to avoid at all cost!

1)    Failure to have the proper communication environment. This includes everything from not having enough time, to allowing people to tell you “we know exactly what we want so you don’t have to ask us those questions” etc.

2)    Allowing Your Needs Analysis To Take On A “20 Questions Guessing Game” Vibe.

3)    Asking a sh*tty question. This includes everything from questions that you could have answered yourself by taking a time to research (How many locations do you have? etc) to weak questions that don’t serve you or the prospect.

4)    Asking a good question at the wrong time. When we jump right in with a more intimate question, a prospect might think “Who the heck is the person to ask me that? I don’t know them or trust them” and then they shut down on you.

5)    Answering your own question. Don’t laugh. It happens more than you think!

6)    Asking a clichéd question. Examples “What keeps you up at night?  “On a scale from 1-10 how is your present service?” “What would it take to make them a 10?”

7)    Asking a set up or “salesy” question. These are the questions that they see coming from like a hundred miles away. My favorite “If I could show you a way to blah, blah, would you seriously consider blah?” I think the 80’s called and wants their sh*tty question  back!

8)    Being so attached to your questions on paper that you don’t follow up on the answer or allow the conversation to naturally go to different places and topics.

9) Demonstrating that you weren’t listening.

10) Asking questions that are so full of prefacing and tangents that they confuse the prospect.

11) Making the Needs Analysis an interrogation instead of a conversation.  

12) Failure to validate feelings. When someone tells you about a challenge or an incident, don’t race to the next question, acknowledge and validate.

13)  Conclusive Questions (aka putting words in the other person’s mouth)Example “Tell me about the challenges you are having with your current vendor” Meanwhile, nobody said anything about challenges.

14)  Allowing Unproductive Tangents. Part of your responsibility as the professional is to facilitate a process without being controlling. If the conversation is going in a direction that isn’t beneficial, then you need to get things back on topic.

15)  Failure to Customize Your Questions based on your Pre Call Planning findings. Don’t be this creature of habit who must ask the questions they always asked. Better to have your arsenal, and choose your weapon and even create your weapon based on the situation at hand.

16)  Interrupting, talking over, finishing thoughts, rushing the prospect’s answer.

17)  Considering a Needs Analysis A One Time Thing

Here’s the deal . . .

We’re going to be talking about how you can use BETTER questions to;

  1. Take BETTER Control Of Your Meetings (WITHOUT Being Controlling or Manipulative)
  2. Gently Guide A Prospect INSTEAD Of Having To “PITCH” Them
  3. Create A Dialog That Is Focused MORE On VALUE Than Price
  4. Create More Of An “Objection Resistant” Interaction With Prospects
  5. Close MORE Business

This all takes place on February 8th at 11:30 am during our How To Ask AWESOME Sales Questions webinar.

Here’s what I’ll be sharing;

  • How To Create An Arsenal of AWESOME Questions (You Know, The Ones Your
    Competitors Fail To Ask)
  • Five Types Of Questions With Examples
  • The One Type Of Question That Helps You Take Control
  • The One Type Of Question That Dramatically Increases Your Credibility
  • Three “Questioning Flight Plans” That Can Help You Get BETTER Results
  • How To Create A Conversation Instead Of An Interrogation

February 8th at 11:30 am EST.

Can’t Make It?

Sign up anyway and you’ll get the replay later that afternoon. View it at your leisure!

What Do You Get?

(1) 90 Minute Webinar With Action Based Tips and Tactics


Webinar Replay In Case You Can’t Make It or You’d Like To Go Back For Seconds

Bonus PDF (Sent The Following Week)

How Much?


Click HERE to register and to secure your spot!


There’s going to be 90 minutes of tips, tactics and most of all;

I’m NOT going to be regurgitating any of that “ask open ended questions” and “look for the pain” stuff you’ve been force fed since Day 1 of your sales career.

I’m including worksheets so you can follow along, the replay of the webinar (in case you can’t make it or you just want to view it again), a bonus PDF and;

You’ll have access to me not only during the webinar but;

After the webinar should you have any questions about the content I shared.

So, if you’d like to join us live (or if you can’t make it and would like the replay) CLICK HERE to reserve your spot.

You’ve worked REALLY hard to get in front of the opportunities you have so;

Let’s do something to help you bring MORE of those deals across the finish line.Click HERE and let’s get to work!

… and never miss a beat!
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Castain Training Systems
(631) 455-2455
Paul Castain, Founder & CEO

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