Winning Every Negotiation Makes You... Poorer.
- Jul 18
- 1 min read
There’s a strange little paradox in the world of negotiation that nobody likes to talk about:
The strongest negotiators often make less money.
Yes, you read that right.
You see, if you're too sharp, too unyielding, too perfectly “tactical” — congratulations! People will quietly start avoiding you.
Vendors ghost you. Partners tiptoe around you. Clients pick someone “easier.”
Because while you might win the battle (with surgical precision), you're scaring everyone away from the war room.
Business, after all, isn’t about winning deals.
It’s about making them.
Let me put it another way:
If every negotiation ends with you sipping champagne and the other side sobbing into their calculator…
You won’t be invited back to the next party.
There’s power in being formidable.
But there’s gold in being approachable.
The goal isn't to be the wolf.
It's to be the person everyone wants at the table — even if they know you'll ask hard questions. Because you're fair. Because you're human. Becase you're in it for the relationship, not just the scoreboard.
So if you pride yourself on being "the toughest negotiator in the room"...
Ask yourself:
Are people still inviting you in?
Because if they aren't - you’re not negotiating anymore.
You're just performing a solo act no one paid to see.





