Most people don’t lose negotiations by being too aggressive. They lose them by starting too early.
Before you have an offer, you aren’t in a negotiation. You’re in an audition. And the instincts that win a negotiation can lose you the audition.
Conventional wisdom says to show strength. Anchor high. Make it clear you have options. That works once the other side has decided they want you. Before that moment, every condition you set is one more reason to choose someone else. Until they’ve picked you, they hold the power, and nothing you say changes that.
Consider Shedeur Sanders.
Sanders played quarterback at the University of Colorado. His father is Deion Sanders, one of the greatest athletes in American history (he played in both the NFL and Major League Baseball) and now Colorado’s head football coach. In his final college season, Shedeur threw for more than 4,000 yards and 37 touchdowns. The scouting reports called him accurate, poised under pressure and a good reader of defenses. They also said he held the ball too long, took too many sacks and might not have NFL-level arm strength. Most projected him as a late first-round or early second-round pick. But that’s a very respectable place to be.
Deion sold him as a top-five pick. In interviews before the 2025 NFL Draft, he suggested he wouldn’t let his son sign with certain teams even if they drafted him. The family chose not to hire an agent. They built a lavish draft-day room, complete with a giant screen and Shedeur’s personal branding, ready for the TV cameras.
Meanwhile, the teams were doing what teams do before they invest millions in a quarterback. They were interviewing.
The New York Giants held the third pick. Their head coach at the time, Brian Daboll, was known for handing quarterback prospects the team’s playbook, quizzing them on it, and planting deliberate mistakes to see whether they catch them. By most accounts, Sanders hadn’t studied enough, and he didn’t catch the mistakes.
Then came the draft.
Round one went by without his name. Then round two, round three and round four. He went 144th overall in the fifth round, to the Cleveland Browns, a team that had already drafted a quarterback. His contract was four years and $4.6 million, with a $447,000 signing bonus. A first-round quarterback typically signs for somewhere between $13 million and $45 million over those same four years. Sanders reportedly earned about $6.5 million from endorsements in his last year at Colorado. He took a pay cut to turn pro.
Some people blamed racism. But the first player taken in that draft was Cam Ward, a Black quarterback. Something else was going on.
The Sanders camp treated the pre-draft process like a negotiation, with leverage, conditions and terms. But nobody had offered anything yet.
The teams weren’t counterparties. They were evaluators. And evaluators don’t have to beat your demands. They just have to pick someone else.
When I was a young lawyer looking for my first job, I interviewed at law firms. In one interview, I was asked, “What are your strengths?” Before I could think, I laughed.
Big mistake. I didn’t get the job.
The interviewer inferred a lot from my reaction. They were trying to figure out if I was right for their firm. They had the job. I wanted it. That meant they made the rules, not me.
Forty years later, I still have to play by those rules.
When a company has a big insurance fight, it will often meet with a few law firms before it picks one. I don’t like these meetings. My firm is small, and the company usually picks a bigger firm. Sometimes they even take our ideas and give them to the firm they hire.
But I still show up ready. They’re about to trust someone with a lot of money. Of course they want to check us out first. And if I skip these meetings, I’ll never land the big one.
I make sure to ask one question: “What are you looking for in the firm you pick?” Then I show them how we fit. If you don’t ask, you’re guessing. If you ask, they tell you how to win.
The moment an offer arrives, the balance shifts.
They’ve spent time and credibility choosing you, and walking away now costs them something. That is when your leverage is real, and that is when you negotiate.
To Shedeur’s credit, he reported to Cleveland saying he was there to work and wanted to win a championship. That’s exactly the posture that would have served him before the draft.
Think about the pitch you’re preparing, the job you’re chasing or the partner you’re courting. Are you auditioning, or are you already setting terms on a deal no one has offered you?
Remember: negotiation is life.
– Gene
