Beyond giving us valuable information . . .

1)    A good question can draw someone inward and . . . cause them to reflect, consider, and even do so subconsciously through (get this) the awareness your question has created.

2)    Good questioning allows you to take control of a situation . . . without being controlling! There’s a huge difference between the two, no?

3)    Good questions create higher quality communication. Higher quality communication fosters superior relationships. Want superior relationships? Start by asking a better question! Works like a charm in one’s personal life too!

4)    Good questions lead the recipient on a path of self discovery. You could tell someone something and perhaps they will consider it. If they discover it . . .  They own it!

5)    Good questions create high levels of rapport. Perhaps Voltaire was spot on when he said “Dude, that was a righteous question” or even infinitely more spot on when he said “Judge of a man not by his answers, but by his questions” What do your questions say about you?

6)    A good question changes the lens in which a person sees their world. Note: That’s some pretty deep sh*t right there . . . I’m not going to lie!

7)    A good question, asked of the wrong person, is just as ineffective as a poor question asked of the right person. We were taught, early on in sales, to go to the highest level of decision maker. What if we ask a brilliant question of this high level individual, but they are several layers removed from feeling the impact?

8)    A good question, at the front end of a response can offer the clarity and context needed for you to offer a meaningful response. It will also buy you time to craft your response.

9)    Good questions focus not only on discovering “ the pain”, they focus on discovering the opportunities your client/prospect desires!

10)  A good question can move someone off the fence of indifference by igniting emotional buy in!

Now here’s the toughest question of all, and in order for you to answer it, you’re going to have to ask your ego to leave the room!

Are the questions you’re asking, helping you not only gather information, but accomplish some of the things I’ve just listed?

I’m going to talk (quite a bit) about asking better questions, including 5 lethal types of questions you need to add to your arsenal, in Session 9 of our Rock Star Academy program.

There’s only 3 days left if you’d like to take full advantage of the $200 savings (and the early registration freebies).

For more information, Click HERE.

Rock Star Academy Early Last Chance


Are You Making Any Of These Questioning Mistakes?

by Paul Castain on June 17, 2016

The questions we ask can make or break the deal.

Execute properly and you pave the way for a higher probability sale. Execute poorly and you disconnect!

Here are several of the mistakes you need to avoid, at all cost!

1)    Failure to establish the proper 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. Let’s be clear. We need to be respectful and control the meeting without being controlling (there’ s a huge difference) but by the same token, would you go to a Doctor’s office and say “Put away that Stethoscope Doc. It’s my bladder so I just need you to work up a quote on surgery?” Selling should never be different. If someone is rushing your due diligence to the point that you know that this will be a “screw you” down the line, get the screw you today instead and insist (respectfully) that they allow you to be the professional you are.

2)    Allowing Your Needs Analysis To Take On A “20 Questions Guessing Game” Vibe. Maybe it’s the impatient New Yorker in me coming out, but why get into this “Is it animal or mineral” BS? I like to cut to the chase and ask a question at the start of my needs analysis that goes like this “Granted I called you . . . what prompted you to take this meeting today?” It gives me a direction to go in 9 out of 10 times and saves everyone the annoyance of questions that have nothing to do with “where it hurts”.

3)    Asking a crappy 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. So how does one ask a better question? By mentally firing yourself from your industry and rehiring yourself in theirs! If you were the person buying what you sell, what would piss you off? I would imagine it could be things like quality, deadlines, surprise costs, poor communication, managing multiple vendor relationships, internal customers, dealing with sales people, navigating around internal external buying policies, how to sell a change to the internal team, cost containment etc. On a more positive note, there are things all businesses want such as more customers, more market share, more profit, happy customers, employees and shareholders, lower turnover, better image and brand awareness, increased efficiencies, quicker to market launches, innovation etc. What questions can you ask to get them thinking about this? This is the stuff they want fixed! Want to take this over the top? Think of one killer, “knock you on your ass” question. I’m talking about one question that flaws the prospect and makes them think “Holy schnikees. Nobody ever asked me that before. The insurance industry has the ultimate “If something were to happen to you, could your family meet its financial needs?” Whoa! Way to stun me long enough to make me listen to you dude!

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. Personally, I like to ease into my questions by starting with more situational types of questions and then increasing the intensity at a pace dictated by my read of the prospect.

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

6)    Asking a clichéd question: Example “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?” Don’t get me wrong, I could think of worse things to ask a prospect, but why sound like every other sales person who sits in the hot seat?

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 “go there”. My best suggestion here (aside from being flexible enough to allow a “discussion” to occur) is to memorize by the topics your questions fall under. This way when a conversation goes from something that’s a deadline issue to a communication issue, you know how the questions execute out of sequence.

9)    Not asking continuation questions and racing to your next question. The best information you can get is usually when a prospect is encouraged to continue or expand. You can facilitate that by simply following up their answer with: “Tell me more” “can you give me an example of that?” “what happened as a result?” and even using some strategically placed (get this) silence. People have an innate need to fill silence. Let it be your prospect. One disclaimer: If you wait too long you might get  a “Bless your heart” and a pat on the head.

10) Making “I wasn’t listening statements” after they answer your question. Examples: “Fair enough” “Interesting” First of all, what the hell are you saying to me? When someone says “Interesting” I feel like you are doing some amateur psychoanalysis and you just concluded I was a bed wetter or something. Are you judging me? “Fair enough” WTF is that? Is that you feeling I was defending an opinion that you don’t agree with? Was that your reentry back into our conversation after an outer body experience and it came down to either saying that or shouting out some other random word like “DAISEYS”  Either way, congrats, you are conditioning me to not give you as much on the next question. Gold star, Rain Man! Here’s an idea. Don’t know what to say after someone responds, thank them for their answer and move on.

11) Asking questions that are so full of prefacing and tangents that they confuse the prospect. I’ve witnessed a bunch of those in my career. The best was when the prospect just stared at the sales rep when he finished and said “I have no clue of what you said, or where you are going with that last question. Was it a question?”

12) Making the Needs Analysis an interrogation instead of a conversation. I offered to help someone the other day with a challenge they were having. I came prepared with a page and a half of ideas. I didn’t get a chance to help this person because they just kept peppering me with questions. At one point I resisted the urge to ask her if I should get my attorney. The cure (in my opinion) is to use different types of questions and to make the exchange conversational and collaborative. Otherwise you are encouraging the prospect to shut down on you.

13) Failure to validate feelings. When someone tells you about a challenge or an incident, don’t race to the next question, acknowledge and validate. This goes back to something I say all the time in this blog “Everyone has a story and wants to be heard” How about a little “I give a damn? How about an “I’m sorry to hear that” or “that would bother me too, and what a testimonial to your professionalism that you kept a cool head” Remember: race to your next question too quickly and you might brand yourself as insensitive and cold. The best part, is that they might not even be able to articulate that. It may hit them as more of a “gut feeling”. When that happens, classic fight or flight kicks in and we simply avoid.

14)  Pre Supposition Questions (aka putting words in the other dude’s mouth) Example “Tell me about the challenges you’re having with your current vendor” Meanwhile, nobody said anything about challenges.

15)  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 course.

16)  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. Besides, doesn’t asking a very specific set of questions, that demonstrates that you did your homework help out in the rapport department?

17)  Committing Any Combination of the 4 Dickish Sins: Interrupting, talking over, finishing thoughts, rushing the prospect’s answer.   I know someone who has this annoying habit of saying “right, right, right” when you are answering their question or just making a statement they want you to cut to the chase on. Don’t ever do that to your prospect or you will be (once again) conditioning them to not give you the details you need. The best way for you to avoid interrupting or talking over is to simply pause after they answer the question.

18)  Disrespecting the word “Why”. The word “why” can serve you, and in many cases it can hurt you in that it might make the other person feel they have to defend their position. Try changing “why” to “what” as in “what prompted you to take that position” or “what were the events that led to those feelings”  The “what” question gets you into mechanics and processes which can be far more productive. Don’t get me wrong, I love to get to the emotions and the feelings. That’s why I phrased this one “Disrespecting the word “why”.  I can’t emphasize it enough that if we aren’t careful, we literally condition prospects to be guarded! Not a good place to be hombre!

19)  Considering a Needs Analysis A One Time Thing: I hope you highlight this one. I see so many people who conduct a brilliant needs analysis, win the account and then never do it again. Things change my friend. Statistically speaking, just in the time you spent reading this post, something has changed somewhere.

Immediate Action Item: Starting thinking of a needs analysis as the annual check up at the Dr. Schedule a “check up” with your clients, and every prospect that you haven’t done a needs analysis in the last 6 months.

I won’t lie to you, there’s a lot here to digest. My suggestion is that you print this out, and commit to “owning” these tips . . . one bite at a time!

Your closing ratio will go up dramatically when you do!

But Wait, There’s More . . .

We have an entire session, of our upcoming Rock Star Academy program, dedicated to asking AWESOME questions!

Click HERE to learn more and to save $200 during our early registration promo!

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The Average Sales Rep Won’t Bother To Do This

by Paul Castain on June 16, 2016

The average sales rep won’t bother to take a look in the mirror!

Whether its because they’re always running, running, running or

Maybe they lack the balls, or worse yet;

Maybe they’re kidding themselves into thinking that they have it all figured out!

And that, ladies and gentlemen, is why the average sales rep;

Remains AVERAGE!

Earlier today, I shared a really cool FREEBIE, to help you take a in the mirror, at your selling skills!

It’s a new and improved checklist, that you can download for FREE, by clicking HERE.

Take a few minutes to rate yourself and then email me (, if I can help, in any way.

But don’t put this off by giving me that “I’m busy” BS;

It’s limiting your options and;

Keeping you AVERAGE!

And when you’re ready to join a bunch of other “humble students”, Click HERE to learn about our Rock Star Academy program!

PC-Rock-Star-Academy - Copy


FREE Download: The Sales Rock Star’s Checklist

by Paul Castain on June 16, 2016

checklist june 2016

Whether you’re somewhat new to sales, or you consider yourself a seasoned pro, it never hurts to take a look in the mirror every once in a while!

To help you take an honest look at your sales skills, I’ve put together a new and improved checklist, that you can download for FREE, by clicking HERE.

Take a few minutes to rate yourself and then email me (, if I can help, in any way.

And feel free to pass this along to your coworkers, your LinkedIn network and all your aspiring sales rock star friends!

So go ahead, I triple dog dare ya, to complete my Sales Rock Star Checklist!

Save $200 and Get A FREE Webinar


You’ll save $200 and get a FREE Quick Start webinar when you enroll in our Rock Star Academy program by June 21st!

Click HERE for the details!

The early registration bonuses go away shortly!

learn more June 2016


Castain Training Systems 2016

I can tell you that Castain Training Systems is a different type of sales training company all day long but;

If I don’t demonstrate that difference, the PERCEPTION is that;

We’re just another “Me too” training company.

Please allow me to get a little more personal;

How about you . . .

Is it possible that YOU’RE approaching, and nurturing potential clients, in a way that makes you seem like a “Me too” solution?

Now if you are, in fact, a “Me too” company, then;

By all means keep doing what you’re doing but;

If you truly believe, that you and your company, bring something special to the party;

Then stop acting like EVERYONE else!

For Those Who Want To Leave The “Me Too” Club . . .

Starting July 21st, I’m going to take you “backstage” and share the step by step system my clients and I have been using to grow our sales.

I’m going to provide you with templates for email, phone, voicemail, social networking, networking, handwritten notes and asking for referrals.

I’m going to share actual examples (no theory or philosophical crap on my watch).

And I’m going to deliver this in a way that changes your opinion about “sales training” for the better!

So without further ado

Please allow me to present . . .


Part I (The “Concert”)

  • Session 1: 20 Ways To Create Opportunities.
  • Session 2: Meticulous Pre Call Planning.
  • Session 3: How To Get Your Email Open, Read and Responded To
  • Session 4: A Cure For The Common Cold Call
  • Session 5: How To Sell MORE Via Your Social Network
  • Session 6: How To Network Like A Pro (And ROCK Your Referrals)
  • Session 7: How To Break The 8 Second Attention Span Barrier
  • Session 8: A Complete Comnunication System To Get You In The Door (And Exit With A New Client)
  • Session 9: How To Take Control Of Your Prospect/Client Meetings
  • Session 10: How To Position Yourself As The Logical Choice
  • Session 11: How To Close MORE Deals (And Win Back The Ones You’ve Lost)

Part II (The “Encore”)

Most training ends right about here. Wouldn’t it be beneficial if there were some additional things in place to help drive the content home? That’s why I thought I’d offer my aspiring sales rock stars, an “ENCORE”!

Once you complete the 11 sessions, I’m going to send you a weekly email, for 3 months, reinforcing and expanding upon the course material.

I’m going to send you 5 eBooks complete with ideas and exercises to help you ROCK your new skills!

At the end of the 3 months, I’m going to send you a special 60 minute review webinar.

What You Get, Pricing, Etc . . .

(11) 60 minute training sessions


10 Email Templates

“Warm Calling” Template

3 Voicemail Templates

5 Social Networking Templates

Prospect Meeting Template

Follow Up Template

Requesting A Referral Template

Requesting A Testimonial Template

Recordings of each session (Always sent within 24 hours of the live session)

Email access to Paul Castain during entire time of the program

3 months of reinforcement emails from Paul (Emails begin after the 11th session)

5 eBooks (Sent out at various times during 3 months following 11th session)

Special Reinforcement Webinar (Sent at the end of the 3 months of reinforcement)

Early Registration Bonus

Register BEFORE June 21st and get a bonus, “Quick Start” webinar (and worksheets) so you can immediately begin your rock star training!


Enroll BEFORE June 21st and your investment is only $999
Enroll AFTER June 21st and the investment is $1199 And no “Quick Start” webinar for you :)

Special Discounts (and Extras)

I discount (even on top of the early registration discounts) when you enroll 2 or more in this program.

I’m also offering some cool extras like the all caps AWESOME Sales Manager’s Guide to this course! It has ideas on how YOU can help your team OWN the lessons in the program. Ideas for sales meetings, quizzes etc.

Email me for special pricing (and extras) when you enroll 2 or more

Due to the time commitment involved, I will only be offering this program once to twice per year and this will be the last time that I offer it in 2016.

So if you’d like to develop some serious sales chops (and you’d like to cash in on the early registration bonuses) hit that button below, and let’s get this party started!

Rock Star Academy Early Registration 1

You don’t have to have a PayPal account to pay with PayPal. Simply select “Pay with a debit or credit card or Bill Me Later” after hitting the “Buy Now” button! Email me if you prefer to pay by check. 

Running Tight On Money?

You might be able to finance this purchase through PayPal!

Here’s how!

  • Check out with PayPal and then choose PayPal Credit.
  • Answer 2 quick questions and accept the terms.
  • You’ll know within seconds if you are approved.
  • Look for your PayPal Credit statement notification via email.

My Risk Free Promise

If at any time you feel that I have not delivered what I have promised, then I want you to call me personally, directly, at this number (631) 455-2455 and I will personally make it right! If for some reason you are not satisfied, I will personally offer you an immediate refund. Please feel secure in the knowledge that you have zero risk in trusting me with your personal development!

“Hunt and close deals better!”

I love all the specific examples you shared, and how you pulled it all together with the communication mapping and time management techniques to help me hunt and close deals better!

Tanya Ramakers, Jonas Software

“Worth the investment!”

The topics were bang on and the curriculum flows through the sales process. The investment is certainly worth it and I refer to my notes at least weekly!

Rock Star Academy Early Registration 1