say something that makes you feel uncomfortable…

The year was 1991, I was a 19 year old boy trying to become a man. I took 6 months off universtity to sell insurance …I wanted to make money.

I had initially, pitched my father to let me come and work for him and sell insurance at his agency, but he said no … first, I had to go and work in Florida for the son of his previous boss whom my Dad said was the best. Once I worked a month or so in Florida, then maybe my Dad would let me come and work with his agency.

After passing all the tests to get my insurance license – I jumped at the chance of going to work for my father’s previous boss.

I lived in Jacksonville, Florida — my office, the office where I reported to work was in St. Petersburg, Florida (about 6 hour drive) … so one Monday, I woke very early and drove to attend the weekly meeting, but more importantly to meet the person that would “train” me on how to sell insurance.

Reflecting back … I was just a little boy who had absolutely no idea of the “real world.” The first day in that office was like the first day in the rest of my life — There I sat in a big open room with tables and chairs .. with 50 – 100 or so “insurance sales men” almost all of them in their 30s and 40s … a few well into their 50s. It seemed like everyone was smoking and talking very loudly as if they were drunk.

Naively, I eagerly sat like a boy at his first day of school ready to go, without a seconds doubt or worry that I would be successful … after all, my father was the best, therefore, I would be the’s easy, right??? Wrong…

I had no clue of what it was like to actually work – I had zero understanding of the value of money. Up until my new adventure selling insurance (or attempting to sell), everything had come very easy for me because my parents had given me the world– up until that day in the smokey insurance office, I had never had a job.

Reflecting back, I think everyone, assumed that because my father was one of the best in the company that I knew what I was doing; but I had no idea.

The guy that was put in charge of training me, was in his mid 30s …

My training started that Monday afternoon, after the meeting — the training program was fairly simple, I would spend the week with the sales agent and go to all his sales calls and learn the game from watching him … and then I would be ready to go out the following week on my own.

On that Monday afternoon, the agent and I set off for the week in his car … within 15 minutes I understood that the guy training me was a loser. Within 15 minutes of meeting me, he was boasting about all the “crack cocaine” he had smoked the night before ….crack!? I was shocked.

I got zero training from this agent during that week … in fact, after that week, I don’t think he lasted 2 months at the company before he quit — he was an absolute loser.

However, I naively set out on my own the following week … trying to sell. I had no idea what I was doing, but my father and all the people that worked for him made it look so easy, therefore, I expected it to be very easy. It wasn’t.

….upon reflection, I was a little boy lost in a man’s world.

During my sales calls, I made a lot of friends — but I did not come close to selling one client. I was terrible.

After a few weeks of absolute failure … at my fourth Monday meeting, I went up to the number one sales person in the company, a 25 year old, short, cocky kid who drove a ferrari …his name was Mark Gable.

He knew my father, so I went up to him …”hey Mark, I’m Scott Ragsdale … Joe Ragsdale’s son … I want to learn how to sell …. but I am terrible — will you please train me.”

In life — there are instances that are stuck in our minds forever, moments which we never forget …this conversation is one of those moments …

Mark Gable starred at me for a few seconds … and said, “you want me to train you … ok, but first you have to do something that makes you feel uncomfortable during the sale …come back to me next monday …tell me what you did or said and if I think it was something that made you feel uncomfortable ..I will train you….now get outta here…” and he turned and walked away …

I responded immediately — “what do you mean???

Mark turned back around and said, “What I mean is …say something during your pitch that makes you feel uncomfortable …example, tell them to go get their check book because you are busy … I don’t know … but you need to come back to me next Monday and tell me what you said…” and he walked away.

The conversation with Mark lasted, maybe 3 minutes …. but my drive back to Jacksonville was at least 6 hours and during the whole 6 hours … I kept thinking …”what does he mean??? say something that makes me feel uncomfortable..” ???
I sincerely had no idea … but I thought about it for the whole drive …

and like magic, as I am pulling into the drive way of my house (my parents condo)… after driving 6 hours … it clicked …

“I need to say something that the sales person before me doesn’t say … I need to control the sale … I need to assume the sale … I can not be scared to ask for the deal.” BAM. I got it.

The following week – My father by now had become concerned at my failure, so he moved me to Nebraska to get proper training and support at his agency — and he organized for his best agent, Bruce Chapman to train me … and Bruce gave me great training … we practiced the pitch and practiced and practiced … and practiced.

Bruce taught me the product. He taught me the sales pitch and every aspect of the pitch — and in the back of my mind, I had a secret weapon ….the understanding of the principle: “to say something that makes me feel uncomfortable.”

I put my new secret weapon into play from that first Monday … in the middle of my sales pitch, once I felt that I had them buying, I would interupt the pitch and ask, “do you like donuts? there would always be the same shocked very akward look on their faces as they eagerly told me “yes!” I would reply, without feeling the slightest bit uncomfortable, “good, because when I bring you these policies that you are buying right now … I am going to bring you donuts…now please go get your check book, I have another appointment in 30 minutes….”

I started saying lots of things in the sale that made me feel uncomfortable (at least in the beginning … but then it became natural)

It worked. Suddenly, I started to sell.

So there is no misunderstanding — the person that taught me how to sell was my fathers agent, Bruce Chapman … he trained me well and I learned how to pitch and sell insurance because of him. There is no way I would have succeeded in selling insurance had it not been for Bruce and my fathers training and support.

However, the understanding of “why” one must say something that makes them feel uncomfortable during the sale, or in negotiations for anything has helped me succeed – and I apply this principle to everything in my life.

As silly as it might seem, this new found understanding also helped me pick up girls …

I am definately, no Brad Pitt — but (before I got married) I applied the same princilple (saying something the sales person before me was too afraid to say or ask — asking for the date and not being scared to lose or get told “no”) … I started picking up lots of beautiful women.

This principle can be applied to any negotiations situation … even when you are on the opposite side of the fence, when you are the one being sold to .. whether you are buying a car, house, even a suit … the person before you will 9 out of 10 times be too scared to ask/demand for a better deal … the person before you will be too scared to negotiate the price down …the person before you will be too scared to lose the deal …by not fearing being “uncomfortable,” you can negotiate a lot better deal.

During your sales pitch — whether to a prospective client – or a beautiful woman, do not be afraid to say something that makes you feel uncomfortable.

When you say something that makes you feel uncomfortable … example, “the event is being closed in 30 minutes. I will get you the contract, you need to sign and fax it back to me within 15 minutes … whats your fax number …” you have to be 100% confident in what you are saying ….you CAN NOT suddenly change because the person you are speaking to does not like what you said.

When you see that gorgeous woman sitting alone at the cafe … all the guys are looking at her, but no one has the guts to pitch … you must be 100% confident in your pitch and whatever uncomfortable thing you say that will break the ice … or you will get blown out. Who cares if you get blown out — as long as you pitch.

The secret is “confidence.”

Some mediocre sales people often come across unconfident and scared to lose the deal. It’s as if they say:

“you dont want to attend an expensive conference do you????”

or …

“you don’t want to go out to dinner with me, do you ….?”

When you say things that make you feel uncomfortable — you must be confident and stick to what you have said … you can not suddenly change … or you will lose control, thus the deal.

Those 3 minutes in 1991, I am sure Mark does not even remember — however, learning & understanding this principle has had an incredible impact on my life.

Although I only worked for a few months as an insurance sales man before I went back to University — the challenging experience of selling insurance woke me up …. and my adult life began …

I am grateful to my father, Bruce Chapman and to Mark Gable … all three of them, without knowing, during those few months back in 1991 had a big impact on my awakening.


One thought on “say something that makes you feel uncomfortable…

  1. I truly enjoyed reading this blog! i’ll start using the “do you like donuts? in my pitch next time.