Beauty fades. Good negotiation skills are forever.
Judge Judy Sheindlin spent over 25 years presiding over televised legal arguments. On her syndicated program “Judge Judy” and later streaming programs, Sheindlin was firm as she looked to make sure litigants weren’t, as she liked to say, peeing on her leg and telling her it was raining.
Behind the scenes, Sheindlin was also negotiating her own contracts. By the end of her run, the television judge was making a reported $47 million annually. On the “Good Hang” podcast, Sheindlin shared her best negotiation tips.
It starts with knowing your worth, something Sheindlin said women specifically often struggle with.
“I quickly understood that I could go anywhere,” she said. “You want to continue making what you make. I’m going to teach you how to be a partner rather than an employer.”
Sheindlin recounted the stories of her contract negotiations. Every few years, she and the company’s president — who changed over the years, she noticed — would sit down at the steakhouse The Grill on the Alley, where she would hand them an envelope with her desired conditions.
She’d advise the company president: “Don’t open it until you get home. Let’s have dinner first and then tomorrow you’ll tell me yay or nay.”
During her final negotiation, the president attempted to give her an envelope back with his own conditions. She rejected it; for Sheindlin, it was one-sided, not a back-and-forth.
“I said, ‘I’m not taking your envelope, because if I take your envelope, it’s a negotiation. And this isn’t a negotiation,'” she recalled.
That led Sheindlin to her second tip: make yourself indispensable.
“You don’t have to be a television personality to make yourself indispensable,” she said. “Doesn’t matter what you are. You have to be aware of that, how you fit in. Can somebody else that they find do what you do?”
That doesn’t mean you should shoot for unjustified sums. When Richard Lawrence’ Rebel Entertainment Partners attempted to sue CBS over Sheindlin’s reported $47 million pay package, claiming that it was excessive, the court ultimately found that there was no bad faith in the salary number.
Sheindlin’s advice was simple: “You can’t have unreasonable expectations.”
The television judge also said she benefited from an unpretentious attitude. That much is apparent on the show, with Sheindlin’s no-nonsense approach to litigation.
“I don’t consider myself an artist, so it’s easy for me to get down and dirty,” she said.
Sheindlin also said she doesn’t have an agent or a manager. Her self-reliance goes hand-in-hand with her final piece of advice: negotiate for yourself.
“It’s much harder for the company who needs you to turn you down in person than it is to turn down some intermediary that is dealing for 50 people,” she said.
While Sheindlin officially left “Judge Judy” in 2021, she hasn’t stopped working. She continued presiding over cases in “Judy Justice” on Freevee, and her current show, “Justice on Trial,” is streaming on Prime Video.
What does Sheindlin think was her biggest career mistake? Turning down a cameo in “Legally Blonde.”
Correction: September 3, 2025 — This story has been updated to reflect that “Judge Judy” was a syndicated TV show, not a cable TV show.
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