Advice From the Best Salesperson I Ever Met

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.

The “Salesman” Stereotype

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

There’s 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

There’s Michael Douglas (Gordon Gekko) in Wall Street

A character who made the phrase “Greed is Good” part of the mainstream vernacular

Then there’s the Volcano Insurance Salesman that sold Peter Griffin:

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.

Is it funny? Sure! But this clip tells us three key things about the overall perception of salespeople:

  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 fair players”. He goes into the office to put a car next to his name on the leaderboard and what happens? An alpha male comes over, takes the keys out of his hand and takes the sale away. The other salesperson doesn’t have much screen time but it’s clearly suggested that Gil is weak and he is strong. It’s implied that he has no respect for Gil and has no clue that Gil compromised who he was as a person, on that parking lot, to sell to Homer in the first place.

    And, in case you’re not looking at the Simpsons like I am, we have subtle hint #3 at the salesperson stereotype.

  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).


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).

Salesmen Stereotypes

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.

And, assuming the sale does occur, there are multiple costs involved to retain these customers:

  • Order Fulfillment Technology Platforms
  • Shipping Technology Platforms
  • Customer Service Technology Platforms
  • Customer Service Human Capital
  • Client Relationship Management Costs
  • Operations/Organizational Support Costs
  • The Actual Cost to Produce Goods or Deliver Services

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?”

I think we have to start by agreeing what makes up the most effective salespeople in today’s marketplace.

If we agree that the vast majority of people do not want to be “sold” but instead want to “buy”, it stands to reason that the most effective salespeople are those who enable the customer to make the purchase and effectively facilitate this buying process. In addition to that, they are able to zone in on the exact problems and profile the prospective customer by leveraging their experience and skills.

When someone is successful at any type of sales position, there is this tendency to label that person as one of the “successful” sales types we described above. Often the label is followed by the suggestion that the salesperson has some type of “power” over people.

For example, I have participated in Fantasy Football + Baseball leagues for 15 years. Whenever I would approach an owner of a team for a trade, I would get some variation of the following:

“JP, don’t think I am going to fall for your JEDI mind tricks like everyone else….”


Now, I realize it’s Fantasy Sports but what this situation really illustrates is a traditional sales objection.

So, how do I overcome that objection?

I focus on how I could help solve their issue (roster need) without focusing on what I gain.

Why? Because how I benefit is the least important factor in the discussion.

Overcoming the image of the Alec Baldwin salesman can only happen through helping the other owner and their team solve their problems.

…And I can tell you this works like clockwork. Every time. Once we focus on their solution, the other person quickly dismisses the original objection.

The “Secret” of the Successful Salesperson

So, why does this little “trick” work?

It’s simple: Everyone has problems…

People will naturally gravitate to someone they perceive as trustworthy, capable of resolving their problems and willing to make acquiring the solution easy.

The complexity and cost/benefit of solving the problem at hand vs. the perceived talent/ability of the problem-solver determines how much inconvenience the person will put up with.

Therein lies the true talent of the most effective salespeople, because…

  • The most effective salespeople understand their customers by listening to them
  • They walk into sales meetings knowing how to read the attire, posture, body language, non-verbal cues of the people in the room and establish hierarchy + communication style
  • They research their prospects in advance to profile their personalities and understand the perceived biases around the problem set or the proposed solution
  • They are incredibly polished in their appearance and communication style
  • They understand the stigma of “sales” and dispel that notion through actions
  • They prioritize the pain points of the customer against the perceived benefit of their solution

….and they do all this in an instant.

The best salespeople solve problems. That’s the big “secret”.

The natural byproduct of this problem-solution approach is revenue.

Stop “Selling”. Start Problem Solving.

The most critical step towards improving the performance of your entire sales organization is changing the culture. It starts with rebuilding the entire sales process based on the specific needs/wants + desires of the specific types of customers you’re targeting.

The goal is no longer to “make the sale”.
This requires answering some important questions like:

“Who do we want to sell to specifically?”
“Why do we want to sell to them?”
“How and where do we stack up well against competitors?”
“Where do we foresee further expansion/contraction/stagnation?”


By asking these questions and promoting internal consensus, both Sales + Marketing can prioritize the market segments and niches which are most critical to the organization’s Sales plan.

This strategic focus allows both of these internal organizations (Sales + Marketing) to dive deeper into the nuances of the buying process and how it applies to the target customer types.

Understanding the different “players” involved on the customer side, their relative role in the process and the application of your product/service in their lives, enables you to effectively pre-answer objections while satiating the needs of the different types of customers during the research phase.

Whether you’re catering to the needs of the decision maker, the sales enabler or the researcher, you will be able to facilitate the buying process naturally because your marketing strategy will be relevant and customers will notice.

Companies leave money on the table when they leave it up to the customer to connect the dots as to how he or she benefits from the product/service and how the company is different/better.

I Think I Know My Customer vs. I Know My Customer

If Sales + Marketing join forces, they can identify the target markets with specificity and validate internal assumptions about what the customer values with actual customer insights. That’s the reason why “Voice of the Customer”, “Persona Development” and “Buyer’s Journey” exercises are very sought-after services today in the digital space.

The process typically involves:

  • Interviews with current customers (in relevant target segments)
  • Interviews in focus groups (lookalike interview segments)
  • Interviews with prospective customers
  • Interviews with former (lost) customers

The questions asked during these interviews have to be open-ended and geared towards (in)validating the internal assumptions gathered by Sales + Marketing. The process relies on qualitative saturation and provides clear priority in terms of content, tactics and advertising.

While this process solidifies joint direction for Sales + Marketing in any organization, organizations that are SMART companies can implement the findings into their sales process immediately while also using them as fuel for sales enablement materials.

I Think I Know My Sales Team vs. I Know My Sales Team

The challenge for marketers has now grown beyond lead “quality”. Marketers need to understand what happens after a lead enters the sales funnel. This means that Sales + Marketing have to align strategically on WHO they are targeting and validate what they KNOW about how these target customers buy.

But it doesn’t end there… The organization needs to consider WHO the leads are going to and HOW they will be guided through the sales process.

That’s why, when I discuss how Sales + Marketing can work more effectively together, I start with the following analogy:

“If you take 10 salespeople…”

  • 2 are top performers
  • 2 are in the process of being fired
  • 6 are in between

“Of those 6 salespeople in between….”

  • 2 are on their way to becoming top performers
  • 2 are on their way to being fired
  • 2 will never be good enough to get promoted or bad enough to lose their job.

There are many variables involved and many reasons why the salespeople in your organization fall into these buckets. The factors range from things the salesperson cannot control (sales territory, market segment, competitors) to things they can and should control (appearance, preparation, inherent skill, effort level).

With that said, it’s not simply about WHO your sales people are. Too many companies focus on changing who their salespeople are (remember Gil?), instead of acknowledging the truth about sales:

If a sales process of any kind makes a customer feel or do things which are unnatural to them and/or not in their best interest that process will fail more often than it will succeed.
So, too, will sales strategies of any kind that make the salesperson feel or do things which are unnatural to them.

“Wait a minute, JP. You’re saying that most salespeople aren’t soulless monsters who would stab their colleague with the 2nd place set of steak knives they just won from Alec Baldwin?”


That’s why, rather than focusing on changing people, the SMART companies of the future will focus on understanding HOW the attributes of the individuals within their sales organization (style, tone, demeanor, strengths) align with the buying processes of the various target audiences.

For example, if a salesperson is not someone who is high-pressure by nature and focuses more on the functionality of a product, then their “sales persona” is likely to match with a “buying persona” where the customer values reliability and cost of integration over all else.

By matching these internal and external personas, Marketing + Sales will remove one major reason for failure.

Actual Intelligence Is a Prerequisite to Artificial Intelligence

The tools which Sales + Marketing teams leverage for success are only as good as the logic behind how they are configured.

To use these tools at full capacity, Sales has to first tag the attributes of their salespeople and match them with a perceived target market. Only then can MarTech platforms be configured to automate and route leads to the right salespeople.

As you can see, the (re)configuration of the software platforms comes only after:

  • Internal Alignment between Sales + Marketing + Target Audiences
  • Creation + Validation of Specific Buyer’s Journeys
  • Joint Sales + Marketing Customer Acquisition Strategy
  • Internal Sales Persona Modeling
  • Matching the Internal Sales Persona + External Buyer Persona

Nowadays, it’s more important than ever to measure ten times to cut once.

Companies that cannot align philosophically cannot align tactically. Companies that cannot align tactically cannot configure technology to enable measurement.

Artificial Intelligence will not replace people. At least not in the foreseeable future.

Actual Intelligence (that is possessed by people) needs to enable Artificial Intelligence to add value. Or, to return to our examples, matching Gil to the customer that appreciates someone who tells them the truth can turn Gil into a “sales” leader.

Advice From the Best Salesperson I Ever Met

My own path to SMARTech Convergence caused me to finally realize why my grandfather could save someone in a fire on Tuesday and sell them a dining room set on Wednesday. The truth was very simple:

He didn’t sell.

He was the same guy, in the same town, working and living alongside the same people for 50 years. People in his town respected the man and who he was. Whether he was on a fire truck or in a showroom, he was always perceived as Harold.

WHO he was in the eyes of people who knew him didn’t help him get the “sale”. My grandfather provided a comfort level for people who knew him to buy the things they wanted or needed. He helped them buy things they felt good about. And they trusted him. They knew that, if Harold recommended it and sold it, then it must be good.

Today sadly; most of us don’t work + live in the same town. The world we live in is immediate, and impersonal. Extended work days and two income households rob most people of the interpersonal relationships that people had during my grandfather’s time. All of that is not to mention that he (to the people who he came into contact with) was one in a million.

So; you are probably guessing that my grandfather is the best salesperson I ever met. I’ll admit that the first draft of this article had a simple sentence that followed this..

“He isn’t. I am.”

My point was that I am the best “salesperson” I have ever met because I don’t sell things, I solve problems. But I realized after the fact that in writing it like that; I broke my own rule. If you are solving problems, you never personify it. The methodology above is devoid of ego (even unintentional ego). The best salesperson anyone has ever met is themselves, so long as you focus on what’s right for the other party.

In my entire career, I have never knowingly steered a customer down the wrong path. But I will tell you that every time I was attempting to provide a solution for a client that worked for them, but (for whatever reason) my company needed the revenue- I lost the deal. Nobody likes to lose, especially when external forces influence how a “salesperson” acts, no matter how just the cause. People are so much smarter today than they have ever been and the slightest desperation they sense- the walls go up.

Why? Simple. They have been preconditioned by everything you’ve read above to be looking for the catch. The adage “if it sounds too good to be true it probably is…” is alive and well.

Any success I’ve had in business stems from the removal of variables that can lead to failure (here’s a hint that your biggest variable is staring back at you in the mirror). In the absence of things that will lead to failure you often find success. Success in anything means you solved a problem or achieved a goal. The best salespeople you know solve problems and consistently exceed + overachieve. It’s so simple you’d wonder why sales training companies still exist.

The scariest thing to do is to abandon the sentiment that “business as usual” can no longer work. The companies that embrace SMARTech Convergence will be in a position to front-end the “sales process” with meaningful marketing content to satisfy the 57%+ of the public that does their own research in advance of filling out a form or calling “the sales line”.

When Marketing front-ends the needs of the customer to educate, the sales process becomes less stressful on both sides, and the 6 sales reps out of 10 which are neither the top performers or the soon to be unemployed have a better chance than ever to close more deals, more quickly.

Customers that come in by way of a SMARTech Strategy have been exposed to a unified message, an easy sales process and are less likely to leave given that SMARTech Convergence is predicated on the idea that the reasons customers choose you is the reason why they stay with you (and vice versa).

“Sales” doesn’t have to be the dirty word it has become. The reps that have given the industry (and their Managers) a bad name are being worked out of the marketplace through attrition and/or customers who are intolerant to their tactics.

So stop selling, start solving problems and start winning the hearts + minds of more customers than you ever thought possible.

Change is inevitable. Progress is a choice.
Let’s get started today.