Though Klieman admits that her family had little money, she never knew it when she was young because her parents devoted themselves to enriching their prized daughter. From the time she was born, her mother always told her she could do anything—even become president of the United States. Klieman's parents' encouragement and love helped her to become a bright and confident girl who loved to read, dance, and act.
Because she was held in such high regard by her parents, Klieman recalls feeling the constant need to be perfect in every way.
"I think that the best part of it [her parents' encouragement] was that I was given all this self-confidence, but the worst part of it was that I equated being remarkable with being perfect—which of course is unattainable. That impossible goal does do some good things, but I drove myself from the time I was a little kid. You should strive for excellence, not perfection. There's a big difference," she said.
By the time Klieman went off to college in the late 1960s, she was passionate about acting and performance. Once she graduated with a theater degree from Northwestern University in 1970, Klieman was off to New York to become an actress.
"The only thing I ever wanted to do was be an actress," said Klieman.
Klieman and her father had decided that she would give acting a year; if nothing happened during that time, she would consider a new profession. In her 2003 memoir, Fairy Tales Can Come True: How a Driven Woman Changed Her Destiny, Klieman explains her father's position, saying, "He didn't want to see me waiting tables when I was 65, still hoping for my one big break."
A little more than a year after her decision to go to New York, Klieman's acting career still had not delivered a "big break," but she soon had an experience that would trigger a complete life change.
Klieman landed the audition of a lifetime when she was called to read for the role of Apollonia in the future Francis Ford Coppola blockbuster hit The Godfather.
"When the elevator door opened, there weren't a hundred of me—there were like 200 of me. We were all Mediterranean types, five foot two to five foot ten, all looking for this one part," she said of the audition.
"When I got to the back of the line, I looked around and listened to all these people talking about how they had done the road company of Hair, they had been Ophelia (from Hamlet), and they'd done all these great roles, and I realized that all of them were out of work."
Working odd jobs and saving all the time, Klieman did not want to find herself in this rut for 20-plus years. By the time she got home from the Godfather audition, which was over right after a short read-through, she had reached her breaking point.
"I was willing to not succeed. I was not afraid of rejection; I was willing to go forward. But at some point in your life, there comes a time when you say, 'I don't want to do this anymore. I don't need to succeed at this anymore. This is crazy,'" Klieman writes in her book.
"I really did not know what to do with my life," she said. "If you've had a life dream from the age of four to the age of 23, this is a shock to you."
After she immediately returned home to Chicago, Klieman sought guidance from one of her most admired professors, Franklyn Haiman. Klieman met him when she took some of his classes in college, and according to her, despite the fact that she was a theater major, she "never felt more alive than when [she] was taking his class."
Haiman told Klieman that she should consider going to law school since she had done so well in his First Amendment class.
"My response was 'Well, girls don't go to law school,' and he said, 'No, but women do,'" said Klieman. And that's where Klieman's legal career path was born.
"He really dramatically transformed my life," she said of Haiman.
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"I worked like a dog in law school," she said.
Because of her strong performance background, Klieman knew from the beginning of her legal career that she wanted to be a trial lawyer. She even made it to a national moot court team because the whole courtroom presentation concept just clicked for her.
As she approached graduation, Klieman, who had been an impeccable student with perfect grades, started looking for a clerkship. Despite the fact that one of her professors refused to recommend her for a clerkship, saying she "didn't have the intellectual capacity" to be a federal court clerk, she got a job.
Klieman clerked for the Honorable Walter Jay Skinner of the United States District Court of Massachusetts—a prestigious opportunity for a recent law graduate.
"He [Skinner] was a great judge and took a lot of time with his clerks. He'd talk to us about why he was making certain decisions. He was a great mentor and teacher," she said.
After a year of clerking, Klieman reluctantly joined a very prestigious Boston law firm, Hale & Dorr. Even before she started the job, Klieman knew she was making a mistake because the job would not allow her to pursue her dream of being a criminal defense trial lawyer. Instead, she would be "locked up working till midnight, writing memos, and never doing the work that [she] loved," Klieman says in her book. Klieman attempted to gracefully quit on her first day of work at Hale & Dorr, but the firm convinced her to try the job for a week. Klieman did not change her mind after that first week, and she offered to wrap up projects for the following three weeks without pay, which she did.
Now the hunt was on for Klieman to find a promising criminal defense position. Next, she was hired by future Senator John Kerry to work as a prosecutor in the Middlesex and Norfolk County District Attorney's office. Then, she went to work for future Congressman William Delahunt in another district attorney's office.
"Those were four of the most worthwhile years of my law career," she said of her time in the district attorneys' offices.
During her years in the district attorneys' offices, Klieman also found mentors in criminal defense lawyers Joe Oteri and Joe Balliro. Later in life, another criminal defense lawyer, Bobby Lee Cook, mentored her as well.
"All three of them taught me how to try cases, how to be persuasive, how to be communicative, and how to be ethical and proper," she said. They also taught her how to gain trust and relationships with the court, including the clerks and the probation and court officers.
After her years with the district attorneys' offices, and with the help of her friends Delahunt and Attorney General Frank Bellotti, Klieman put together a proposal to open a criminal trial division at the law firm Choate, Hall & Stewart. The firm bought the idea, and Klieman developed the division for three years. In 1984, she received an offer to be a partner with Friedman & Atherton that she could not refuse. Five years later, Klieman started her firm Klieman, Lyons, Schindler & Gross, where she is of counsel today.
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"It's really important that you're not acting in a courtroom. You should be who you are. You need to be authentic and congruent. What you look like, who you are, and the message you convey has to be one and must be trustworthy," Klieman said.
In addition to touring the country to speak to lawyers, Klieman also has taught various law courses at schools such as Columbia Law School and Boston University School of Law.
In 1994, Klieman was given a second chance at a career in show business. She was invited to appear on Court TV to cover the O.J. Simpson trial but ended up staying on full-time for the next nine years. Klieman hosted a political and legal talk show with Johnnie Cochran called Cochran & Company, the daytime show Closing Arguments, and then Both Sides.
Klieman was skeptical about working for Court TV full-time because she had a firm and a husband in Boston, which would be difficult because the network is based in New York.
"You have to stay there full-time; it has your name on it. It's everything you wanted to do—you're there being a lawyer, entertainer, and educator," said one of her supportive law partners, Steve Lyons, of the job offer. Ultimately, Klieman took the plunge.
"What I wound up with was the most extraordinary job of my life. I would have stayed there until they rolled me out in a wheelchair with the drool going down my face," said Klieman.
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Four years ago, Klieman worked out a deal with Court TV so she could host the show periodically while still living in Los Angeles with her husband, Chief of the Los Angeles Police Department William Joseph "Bill" Bratton. She also appears as a legal analyst for CBS and The Today Show.
Besides periodically appearing on prime-time news shows, Klieman has also made it back to acting. She has appeared on shows like Shark, Las Vegas, and Boston Legal—usually playing lawyer and judge characters.
"It's hilarious because everything I thought I wanted from age four to 23 now happened in middle age," she said.
Klieman's rich career has taught her lesson upon lesson about the dos and don'ts of a legal career.
"You must be trustworthy and ethical," she said. "If you move away from those things, you will ruin your reputation, and it will never be forgotten."
She also emphasized the need to develop a hearty work ethic and drive because the work is demanding.
"You need to work hard, particularly in your early years. Preparation is really everything," she said.
Klieman also emphasized that lawyers need to always strive for a balance of work and other life aspects because, according to her, you cannot be number one at your firm with a healthy personal life—"one thing has to give," she said. "I do believe in life balance—it just took me decades to figure it out."