The Five Paradoxes of Sales
Why the Most Effective Selling Behaviors Look Like the Opposite of Selling
Sales is full of contradictions. On the surface, the craft seems simple. You have something to offer and someone else might need it. Yet the moment we step into the role of seller, everything becomes blurry. Logic stops behaving logically. Human behavior starts behaving like… well, humans.
And this is where paradoxes appear.
In philosophy, paradoxes come in three flavors.
There are the trick paradoxes that look strange until you decode the illusion, like Zeno’s paradox.
There are the logical paradoxes that challenge our understanding of reality itself. The classic is “This statement is false.”
And finally, the human interest paradoxes. They reveal higher truths through statements that appear contradictory on the surface.
“We are never so alone as in the middle of a crowd.”
“The only true wisdom is knowing you know nothing.”
Or the more playful, “No matter where you go, there you are.”
Sales belongs in this final category. A place where the most obvious behaviors produce disappointing outcomes and the most counterintuitive behaviors produce trust, clarity, and performance.
After thirty years observing how people buy and how people sell, I can confidently say this.
Salesmanship is a human paradox machine.
Below are five sales paradoxes that every salesperson, founder, or business leader should internalize. They appear simple. They are anything but. Each contains a truth that can transform the way you sell, negotiate, and build relationships.
I will explore each paradox in detail in a second post.
The Five Paradoxes of Sales
1. The best way to sell is to stop selling
Everybody likes to buy. Nobody likes to be sold.
People sense pressure instantly. They resist it instinctively. Hard selling, forcing next steps, excessive qualifying… these behaviors create distance rather than clarity.
The paradox is this. The more you try to make the sale happen, the more the other person wants to escape it.
2. The most reliable road to short term results is to focus on the long term
Companies say they value long term relationships, yet they constantly send short term signals. End of quarter pressure, promotions, artificial discounts… all these reveal the real message.
“We want something from you now.”
Buyers pick up on this immediately. Nothing destroys trust faster than a seller who claims customer centricity but behaves with self interest.
Ironically, sustained short term results only emerge when you stop chasing them.
3. The most important thing is sincerity. If you can fake that, you have it made
This line from George Burns is funny and painful at the same time.
You cannot fake sincerity.
You cannot fake genuine concern for the customer.
The only way to look authentic is to actually be authentic. And that is not a skill. That is a way of being. It requires intention, alignment and the courage to serve the customer’s interest before your own.
4. The best way to get what you want is to help the other person get what they want
Reciprocity is ancient. It is embedded in human nature.
People naturally respond to generosity with openness. They respond to pressure with defense.
Give clarity and you receive clarity.
Give respect and you receive respect.
Give value and you receive the right to propose.
It is negotiation theory. It is behavioral science. And it is simply how relationships work.
5. If your goal is the sale, you have already lost
This is the paradox at the heart of modern selling.
Goals matter. But the wrong goal destroys everything. If the salesperson is primarily focused on closing the transaction, the customer feels manipulated and withdraws trust.
The sale becomes uncertain.
When the goal becomes helping the customer make the best possible decision for their situation, everything shifts.
Trust grows. Conversations deepen. Decisions accelerate.
And sales emerge as a natural byproduct.
One could call this the Heisenberg Principle of Sales.
The more you obsess over this transaction, the more fragile it becomes.
The more you focus on doing right by the customer at all times, the more likely you are to win both this sale and the next ones.
What Comes Next
In the next post, I will explore each paradox in depth with concrete examples, stories, and advice you can apply starting today.
Because sales is not a battle of persuasion.
Sales is a mirror of how we show up as humans.
And paradoxically, that is exactly why it works.