Paul Castain's Blog

7 Really Deadly Questioning Mistakes

Posted August 17, 2015

question 5

The questions you ask your prospects and clients can and will make or break a deal but;

Sometimes we just get so caught up in a routine that we fail to question our own questioning practices.

Here are a few mistakes you might be making . . .

1) Focusing ALL your questions on “finding the pain”. Pain makes us change faster than anything and therefore (at the risk of sounding sick) finding pain is great for us sales folk but pain doesn’t always exist. So what happens when you focus your questioning only on pain? You exit that meeting with a whole lotta nothing. Think about questioning areas that aren’t painful that would represent an opportunity. Add that to those pain questions and you have a more thorough exam Dr Awesome!

2) Asking too many questions that are situational as well as “spec” related. Sometimes we can get a bit too focused on things like number of employees, number of users, project details etc. These types of questions are important but they will never jump start the emotions necessary to get someone off the fence of indecision.

3) Getting too intimate, too quickly. I remember sitting down with a financial planner who decided to skip all the foreplay and ask me about my net worth. I think it was an important question to ask but it was poorly timed and it made me uncomfortable. My lack of comfort with the financial planner resulted in me becoming guarded and our meeting being quite unproductive. I like to start with more situational/spec type questions and ease into the questions that are more

4) Asking questions that demonstrate that you didn’t do your homework. When you ask someone a question that represents something you could have found out by taking a 60 trip to Google, you aren’t going to be taken seriously.

Mini Rant: How many times have you been talking with friends, family, coworkers and everyone is trying to remember the name of a song, actor, band, movie etc and all of a sudden everyone’s phone appears and its a race to see who can Google it the fastest.

And yet many will go into a meeting without Googling the most basic of information.

5) Racing to the next question with your needs analysis without digging deeper with the answer they just gave you.

6) Poor listening. Sometimes we’re so used to typical answers to the questions we’ve asked, in a thousand different sales calls that we fail to really listen and even display a degree of empathy for our prospect.

Oh, and by the way, you’re allowed to give a sh*t. Feel free to say things like “Sorry to hear that””Man, that sounds like rough” and so forth.

7) Doing a needs analysis only once. Many of us are all over the needs analysis during the courtship but once the ring is on the finger, we call it “done”. Business moves at the speed of light. Just in the time you’ve spent reading this, something has changed somewhere.

You need to be doing regular “check ups” with your clients. Are you? Because if you aren’t, you’re not only missing opportunities, you’re making yourself vulnerable to a competitor who’s data might be a tad more up to date than yours. Kind of sucks considering you had the inside track, no?

There’s obviously more that we can add to this list, but these are just a few to get you thinking about something, you probably don’t thinking about enough!

Would You Like To Sharpen Your Questioning Skills?

We’re going to be talking about them in greater detail during our August 26 webinar How To Take Control Of Your Prospect Meetings!

Here’s what you’ll discover by joining us . . .

2 Ways To Ask For Access To A Decision Maker Without Insulting Your Contact

How To Stand Out And Force Your Competitors Into Playing A Defensive Game

One Question That Will Change The Trajectory Of Every Meeting

5 Types Of Questions You Need To Start Asking (And None Of That “Open/Closed Question” BS)

7 Insurance Policies You Need To Take Out In Every Meeting

How To Reduce The Probability Of A Prospect “Going Silent”

What To Do When You Find Yourself In A Highly Competitive Situation

What To Do When The Conversation Shifts Prematurely To Price

I’ll be sharing over 20 tips in this 90 minute webinar, all with a simple objective . . .

To Help You Take Control and Keep Control Of Your Prospect Meetings!

Click HERE or the handy/dandy banner below to learn more and to reserve your seat!

Better-Control-2

 

Do NOT follow this link or you will be banned from the site!
SIGN UP FOR OUR FREE TIPS
… and never miss a beat!
Your Information will never be shared with any third party.
Could Your Sales Use A Little LOVE?
LOOKING FOR ANSWERS?
Ready To Hunt For New Business Differently?
It's Time To Bring Prospecting Into The 21st Century!
Not really! Fries are bad for you but my FREE sales tips are actually quite good for you! Join 90,000 of your peers when you subscribe below!
Free Fries!
JOIN US NOW
Join 90,000 of your peers when you sign up for my FREE sales tips!
Your Information will never be shared with any third party.
Not really but my FREE sales tips are just as tasty! So hit that subscribe button and I'll send you some FREE cold email templates!
Free Fries!

Company Contact Information

Castain Training Systems
(631) 455-2455
Paul Castain, Founder & CEO
paul@yoursalesplaybook.com

Copyright Information

© 2025 Castain Training Systems
All rights reserved.

Website Design by VanHove Design