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How I Came To Selling

This is how my journey as a salesperson (and later teacher, coach, and consultant) began.

My mother was a teacher. Her parents were both teachers. 

My father was a successful and prominent attorney. His father was a self-made man who died wealthy. He made his money as an accountant. He made his wealth investing in real estate, Broadway shows, and stocks and bonds.

So, there was nothing in my background suggesting that I would become a peddler (and then a peddler of peddling!).

When I was a kid, I thought I wanted to be a big game hunter and a fireman. I didn’t know any of the former or the later, so it’s unclear where those ideas came from. Later I wanted to be an architect, or possibly a lawyer. At least I knew one of them.

I had no clear aim upon high school graduation other than to get out of town. When forced to declare a major, I settled on political science. It seemed more serious than English or History. 

Halfway through college I turned 18. This was in the early 70’s, which meant I was soon in receipt of a draft card with a troublingly low number. Viet Nam beckoned. 

By the time I finished college, and thus my draft deferment, the helicopters had all gone home and there was no more non-war to fight. By that time, I no longer wanted to be an attorney. I still had no idea what I would do with myself.

My First Sales Job

Through an odd set of circumstances, I got offered the chance to be the assistant manager at a backpacking shop. This was at a time when backpacking had become popular, largely in response to the emotional overhang of the big oil shocks of the early and mid-seventies. 

It was a funny choice for me. I didn’t know anything about down vests, backpacks, or hiking boots. I also didn’t especially like being outdoors. 

But I needed a job. 

My father was beside himself.

On my first day, my manager handed me a stack of blank 3×5 cards and a pen. He told me to write down the key selling points of everything in the store. 

I wrote hundreds of cards. That was my first sales training.

The truth is, I had zero sales skills. I was usually polite, but not always. I didn’t know to ask questions beyond, “May I help you?” I mostly threw up what I had memorized about the products and hoped they would buy.

I can also remember being completely intimidated by our higher end gear. For example, we had a tent that cost something like $400. That was half a month’s salary for me. It felt impossibly rich to me, so I couldn’t imagine that anyone would think otherwise. 

One day a guy walked in, pointed at the tent, and said he wanted it. Really?  I wrote up the order, took his money, and thought I was the prince of sales. 

Imagine that. I had sold a $400 tent. 

I quit the backpacking business to help renovate houses in a “transitional neighborhood.” I had no idea what I was doing when I started, but I was getting $9 an hour under the table. 

I learned the trades.

I lived at home.

My father was beside himself.

A while later, I moved to Hawaii to start a coffee company with two college pals. It went on to be very successful. I went on to do something else before it got that way. 

My First Real Sales Job

The advertisement in the newspaper promised professional sales training and the chance to make $70,000 in your second year. In 1981, coming from a string of $800 a month jobs, that seemed like an impossibly large sum of money.

The hiring seminar was intoxicating.  All those attractive, self-confident people. All dressed in nice conservative suits. All talking about all the money they were making. 

I went to work there the next Monday. 

I was told how to dress. I was given a pitch to memorize and a slick pitch book to whip out in front of prospects. I was assigned a territory and sent out to cold call. More than forty years later, I still remember parts of the pitch.

My first job was selling something called a “needs analysis.” Basically, I was an appointment getter for someone else. When HE sold a seminar, I got paid.

I’d get up in the morning, put on a white shirt, striped tie, three-piece suit, and a pair of wingtips. I carried a briefcase. I was 24.

Driving to my territory, I would stop at a public restroom to throw up. That done, I’d park my car and proceed to walk into small business after small business. With business card in hand, I would ask in my most confident voice, “Hi, is the owner or manager here?”

If I was lucky, they thought I was a salesperson. In retrospect, given how I was dressed, FBI, IRS, or INS would have been as good a guess.

This was tough going. This was not fun. I set zero appointments that first week. 

A Big Lesson

One day, something happened that changed my approach to selling forever.  

I was walking down the street. Coming the other way was one of my fellow cold-calling colleagues.  He actually looked happy. Almost crazy happy. 

I asked, “What happened,” “Where he could get some,” and hoped that it didn’t cost too much.

My colleague told me the day before he had gone “O” for “6” – not one appointment set.  This felt familiar.

Today, he’d gone back to those same people and said something like this: 

I was in here yesterday.  I didn’t feel very well and didn’t do a very good job.  I wasted your time and my employer’s money.  I have a small favor to ask . . .

What was the favor?  

Can I try it again?

That day he went six for six.

It turns out a little bit of “not okay” can radically shift the buyer/seller interaction. 

Motivation and (some) Ability Are Not Always Enough 

I gutted out the learning curve and wound-up establishing records for the number of appointments set. In a hiring class of twelve, I was the star. One of the few that lasted more than a few weeks. 

The problem was the guy following me. 

He didn’t sell diddly. So, I didn’t make diddly. So, they promoted me. Now I was the guy selling seminar seats behind someone else’s appointments. 

Unfortunately the company decided to change the compensation plan. Now it was paying the appointment getter $10 for each appointment set. Good for them, but not for me. 

Instead of qualifying the buyer, they just gave up the game and begged the business owners to see me so they could get paid. I was starting from scratch. I just didn’t know it.

I sold my tail off and got nowhere. After three months I had made $1850, a step down from what I had made hawking sleeping bags. 

So, I quit. 

Facing the Music

Was it me or the system? Was I a failure—as a salesperson and/or human being—or was it the company and its process? Did I screw up, or was I set up to fail from the start?

Those questions set me on a journey that continued in different ways for more than forty years. I would never again put myself in a situation where I was so without the resources I needed to be successful.

I vowed to become an expert on why people buy and what people like me could do to help that process along. It began with reading every book I could find (this was the 80s) on sales, influence, persuasion, and self-esteem. I bought cassette tapes (still the 80s). I went to every seminar I could by all the sales luminaries of the day. 

The material I found most interesting came from academic sources with no obvious connection to sales. I came to regard these sources as the real bedrock material. Some examples . . .

  • Jung, and his acolyte Joseph Campbell on archetypes and journeys
  • Everything I could find on neurolinguistic programming (NLP) and Transactional Analysis
  • Sun Tzu, von Clausewitz, von Moltke, and Rommel on (military) strategy 
  • Cialdini on Influence and Rogers on diffusion of innovation
  • Porter on value chains, Hammer on reengineering the corporation, and Christensen on innovation 

More than reading it, I was crazy enough to try it out in a sales call. 

Looking back, some of what I said and did was pretty crazy. Some of it I wouldn’t touch today with a ten-foot pole.

And you know what? In the process of all this reading and trying, I learned how to sell. I cashed big checks. I won big assignments. I made a difference.

I don’t believe the old saw, “Those who can’t do, Teach.” I think it’s the other way around. The best way to cement what you know is to try and teach it to someone else.

So, I did.

I started first by writing and delivering sales training. I wrote something like 30 different programs and delivered them at some of the biggest companies in the world.

Later I became a consultant on sales and marketing. 

Finally, I became an executive, board member, and venture capitalist.  

Over the decades, tens of thousands of people have learned and used my ideas on selling, influencing, persuasion, and decision making. Decades later, I still get calls decades from people wanting to tell me what a difference I made.

I can’t promise you everything I have to offer will make you a better salesperson, but I think it will help.