Nancy Shilepsky's Legacy

“The most important thing about how I’ve succeeded in my career is that I would rather jump out that window than lose,” says Nancy Shilepsky, a founding partner of Boston’s Shilepsky O’Connell. She is sitting in a conference room on the 16th floor of an office tower overlooking a glass atrium. It would not be a soft landing. “I’d rather die than lose,” she continues. “It’s the only secret to success that I know of.”  

Apparently, it’s a good secret. Since she began her career 30 years ago, she has prevailed in precedent-setting cases, served the legal community in an array of capacities, and appeared often on lists of ‘best” and “most influential” employment lawyers.

Shilepsky, 55, co-founded the firm in 2005. The 11-lawyer boutique firm was created to concentrate on the emerging field of executive advocacy while representing employee rights in such matters as discrimination and wrongful termination. The former category is the firm’s bread and butter, the latter has brought Shilepsky some of her highest-profile cases, so it’s the perfect setup to indulge her trio of passions: winning, fairness and crafting a good deal.

Those passions converged in Bowman v. Heller, a prominent 1995 case regarding sexual harassment and free speech in the workplace, which pitted her––successfully––against Harvard law professor Alan Dershowitz. “I’m at this firm less than a year and all of a sudden I have this case with Alan Dershowitz,” Shilepsky says. “He was a total gentleman.” 

The case involved a woman––Shilepsky’s client––who sued a male co-worker after he created fliers featuring the woman’s head pasted over a naked model’s body. Dershowitz argued that the images were protected expression. “He was wrong on this one,” Shilepsky says. “[In] the interface of discrimination law and the First Amendment, the line does not get drawn where he was wanting to draw the line.” The Massachusetts Supreme Judicial Court ruled in her favor, but sidestepped that issue, and the U.S. Supreme Court declined to hear the case.

More recently, Shilepsky has worked on cases involving what she calls the “glass ceiling for women with children.” Surprised to find herself agreeing with former chief justice William Rehnquist, she quotes his opinion: “The fault line between work and family [is] precisely where sex-based overgeneralization has been and remains strongest.” Punching her words for emphasis, she continues. “It’s what is dramatically used to hold women back because the prejudices regarding men with children as employees and women with children as employees are 180 degrees opposite.”

Many of these cases settle out of court and usually with confidentiality, so Shilepsky can’t talk specifics. That, she acknowledges, limits their impact. “I have called those settlement agreements the licensing fee, all too often, to continue bad behavior.” But being a test case is tough––“You want a paycheck or you want a lawsuit?” she asks rhetorically––and she suggests that even settlements kept from the public can do some good by educating employers one at a time.

However, Shilepsky did get an opportunity to fight employment discrimination publicly in Tan v. Stonehill College. Her client, Dr. Soo Tang Tan, was a mathematician, born in Singapore and of Chinese heritage, with a Ph.D. from UCLA and several textbooks to his name. He was a full professor—and the only non-white faculty member—in the math department at Stonehill College in Easton, Mass., when he learned that, after nearly 20 years of employment, he was being paid less than some associate professors, a startling anomaly in the academic hierarchy. 

“He was devastated when he saw what it said about how they had valued him,” says Shilepsky. “One of the things that came out was that it was assumed that because he was Chinese, he would be good at math. That’s called stereotyping. Racial stereotyping is often unconscious, but even unconscious stereotyping is actionable under a law. The problem is proving it.”  

Shilepsky describes that process as a kind of intellectual tennis match, turning her head as if following a ball being lobbed back and forth. In the end, she maintains, the college had no case. “We came to refer to it as the ‘But-he-drives-a-Taurus defense,’” she says, amused that the argument got reduced to which professor drove what make of car. “The college’s list of excuses collapsed under its own weight.” In 2001, the Massachusetts Commission Against Discrimination agreed, awarding Tan $150,000 in emotional damages in addition to back pay. The case went on to set precedent three years later when the state Supreme Judicial Court ruled on appeal that MCAD was empowered to award damages without a jury trial.   
Shilepsky didn’t set out to be a lawyer. She grew up in Westport, Conn. Her mother’s family were orthodox Jews, her father’s political activists, so they split the difference and raised their children with great respect for civil law––“as the substitute for Torah, I guess,” Shilepsky says. Along with that respect came her mother’s determination that one of her children would be a lawyer. She, however, wanted to be a writer, so they made a deal: “She’d leave me alone in college if I went to law school.” Shilepsky immersed herself in creative writing at Tufts University, then took the LSAT. 

After graduating from Boston University School of Law in 1978, she bounced around various legal-aid services, not enjoying the work much, until one day she found herself in the bowels of a law library. Shilepsky was working at a law collective when she signed on to write a brief opposing summary judgment in a breach-of-employment-contract case. This was in 1984, “back when you actually did research in law libraries,” she says. “It was just down there in those books, chasing the cases, analyzing it, [that] my brain came alive in a way it had never been alive.” Shilepsky’s voice goes soft, as if still amazed by the turn of events. “And I fell in love with employment law.” The summary judgment was denied, she was hired to work on the trial, they won, and she was hooked.   

Employment law was a field wide open to women, who tended to come to it on the plaintiff side and from a racial- and gender-justice perspective, while men typically concentrated on the more remunerative management side. “The reason so many women of my generation succeeded in [employment law] was because it was seen as civil rights work, God’s work,” Shilepsky says. “No one ever expected it to become as lucrative a profession as it became.” But things changed as people began switching jobs more frequently and workplace regulations proliferated. “What happened over time is that both sides, employee and employer, have lawyered up. That’s not a bad thing. Like any other contract, it’s important that people understand the terms of what they’re getting into.”

For her executive clients, those contracts fall into three categories: in-deals, which cover the myriad details involved in hiring, compensating and moving top executives; out-deals, which concern an executive’s separation from a company; and retention deals, which include all the things that keep an executive with a company.  

Shilepsky is drawn to the complexity of the in-deal––everything from negotiating stock options to getting a kid into the right school to balancing a spouse’s career. “This is a prenup,” she says. But companies have their ways of doing things and a slew of regulations to abide by; her role is to negotiate an attractive deal for her client while respecting the company’s culture. It takes analysis and diplomacy.   

In contrast, out-deals appeal to her because they can offer a really good fight. Although Shilepsky characterizes employment law negotiations in Massachusetts as generally civil and constructive, conflicts still arise. “I am probably never happier than when I am in the heat of battle,” she says.

The size and focus of her firm allow her to sidestep the conflicts that can arise within large law firms.  “I am so proud of this group and what we do,” Shilepsky says. She holds out her coffee mug to show that below the large print of “Shilepsky O’Connell” a string of other names circle the sides. “You’ll notice we have a lot of names on our firm. Although that goes against all marketing advice, it was because I understood that this line of people here”––she traces the smaller print––“that’s my legacy.”