Advice From the Best Salesperson I Ever Met

The Evolution of the Salesman 

My Grandfather, the Salesman 

My grandfather died in 1987 from complications of lung cancer. He was 63 and I was 8. As the years go by, the memories of my grandfather and the times we spent together fade but the feelings of those memories remain. In many ways, these feelings have come to shape who I am and who I continually aspire to be.

He was a WW2 veteran, a Lieutenant in the Arlington Fire Department, a father of five kids and sole provider for his family. (Remember when single income families were a thing? Me neither.)

He had to take multiple jobs during his life to make ends meet. One of these jobs was as a furniture salesman at a store in town. (Remember when you could actually work in the town you lived in? Me neither.)

My grandfather didn’t fit the classic stereotype of a salesman and I always found that strange. I couldn’t picture him “selling” anything to anyone. It wasn’t until later in my life that I figured out how a guy who was as stand-up as they come, as authentic as they come, could save someone in a fire on Tuesday and sell them a dining room set on Wednesday.

Who is your stereotypical salesman? 

When you ask people to conjure up an image of a “salesman”, you’ll typically get one of a few images:

1. Alec Baldwin in Glengarry Glen Ross: A completely ruthless a-hole who cares about nothing but making the sale. Someone who berates his subordinates into submission and compliance

2. Michael Douglas (Gordon Gekko) in Wall Street: A character who made the phrase “Greed is Good” part of the mainstream vernacular

3. Volcano Insurance Salesman in Family Guy: The Volcano Salesman who targets the "right" customers 

Volcano Salesman Success

In Peter’s defense, the Volcano Insurance Company’s Marketing Department may have properly identified Peter as a target persona given his previous tendencies…

Peter Griffin’s poor money management skills aside; its important to note that this is how our society actually depicts SUCCESSFUL salespeople. Whenever unsuccessful salespeople are depicted, they are positioned as down on their luck, sympathetic characters who lack a backbone and are always one commission check away from financial ruin.

Take Gil here from the Simpsons…

When Gil meets Homer at the car lot, he confirms everything one would think of when envisioning a down on his luck salesperson.

Someone eager to sell and willing to settle at all costs. 

Is it funny? Sure! But this clip tells us three key things about the overall perception of salespeople; They are dishonest, unfair and will do anything to be on top. 


1. ​“They can’t be honest”. As Gil is firing up his routine he mistakenly tells Homer the truth. Gil is a good person and, because he’s a good person, he blurts out something that would be in Homer’s best interest. That’s viewed as a BAD thing when it comes to “making the sale”. What’s even worse, Gil quickly pivots and goes back to the talk track, almost mad at himself for disclosing information that’s helpful to Homer’s buying process. Gil submits to the pressures of the culture of “salespeople” and compromises his values.

2. ​“They can’t be honest”. As Gil is firing up his routine he mistakenly tells Homer the truth. Gil is a good person and, because he’s a good person, he blurts out something that would be in Homer’s best interest. That’s viewed as a BAD thing when it comes to “making the sale”. What’s even worse, Gil quickly pivots and goes back to the talk track, almost mad at himself for disclosing information that’s helpful to Homer’s buying process. Gil submits to the pressures of the culture of “salespeople” and compromises his values.

3. "To survive in sales- you have to be an alpha”. Gil then picks up the phone and calls his wife to tell her how he ALMOST made a sale. He finds his wife having an affair with another man whom he knows about but, because Gil’s wife and the man both think Gil is a beta, she passes the phone to him! Unbelievable (and, in a way, totally believable)

What are your customers thinking? 

When you consider that some thematic variation of this lineup is what the public at large has come to think of salespeople, it’s really no surprise that the average customer is 57% through their buying decision BEFORE they engage with a sales rep (Google and CEB).

If we consider what Google tells us to be true, then what does it really mean?

  • Perhaps that the average customer prefers to conduct their independent buying research before they reach out to a salesperson?
  • Possibly that the average customer may not trust a salesperson or, at the very least, they want to avoid the pressure of the “sales process” before they are ready?

I would contend it’s much simpler than that… For whatever reason (perception or reality), the majority of people don’t want to be “sold” – they want to “buy.”
People want to walk towards the light they don’t want to be dragged by a salesperson or a sales process.

The Game of Customer Acquisition Has Changed

In today’s hyper-competitive marketplace, the direct + indirect costs to acquire customers are continuing to rise. Outside of cases where there is an entirely new market being created or a new market segment is forming, the laws of supply and demand dictate that this trend will only continue.

The cost of customer acquisition is constantly rising and as a result, more companies are striving to evaluate the different components of that make up this cost:

  • Digital Marketing Advertising Dollars
  • Traditional Marketing Advertising Dollars
  • Cost of Marketing Technology Platforms
  • Internal Marketing Human Capital
  • External Agency/Vendor Fees
  • Sales Expenses (Travel, Entertainment, etc.)
  • Sponsorships
  • Events/Trade Shows
  • Sales Compensation
  • Sales Technology Platforms
  • Sales Concessions (i.e. what the sales team needs to do to get the customer at a lower price, for the long term, with less/no margin, etc.)

As the tactics marketing can use to engage customers continue to expand (and fragment), as the technology choices multiply, so, too, do the ways companies can waste money TRYING to acquire sales-ready leads on autopilot.

The New Customer Is Shaping New Strategies

The customer of today hates being sold and, that’s why, she has learned to do her own online research. Customers know exactly what is available to them on the market.

The customer of today is:

  • Well-informed
  • Distrustful of institutional sales tactics
  • Well-read
  • Intolerant of quality which does not match their expectations

The customer of today knows who your competitors are. At the same time, the marketplace is often so saturated that your competitors will gladly buy market share at a loss to box out direct competitors.

With that being said, outside of situations when a new or growing marketplace is paired with a company who is the clear (or only) choice for customers who want to buy, the customer holds all the power.

There are simply too many companies forcing too much information to a pool of people who are becoming increasingly indifferent to the noise.

“So, what do we do, JP?”

What's Next? 

Keep Reading! 
Advice From the Best Salesperson I've Ever Met, Part II

In Part II, uncover the secret to becoming a successful salesperson to get closer to your customer than ever before! 

Change is inevitable. Progress is a choice.
Have the Courage to Prioritize Progress.