It was the latter half of the 1990s, more than a generation after the women's movement had begun and long after business casual dress was common in many workplaces. But some taboos die hard.
"We all still wore suits, with pantyhose and skirts that hit just at the knee -- not above, not below -- and mostly silk blouses that tied at the neck," recalls Lisa Pattis, a former Sidley & Austin partner who is now executive vice president and general counsel at Wintrust Financial Corp.
But one particularly cold winter day, Pattis' mentor at the venerable law firm showed up in a pair of tailored black pants with a jacket.
"She didn't get everyone together for a meeting about it, she just did it," Pattis recalls. "It was a cold winter, and we had been working late and walking to the train in stockings. We all went out that weekend and bought pantsuits."
Pattis' mentor, the rebel in the pantsuit, was Christine Leahy.
Now senior vice president, general counsel and corporate secretary at CDW, the Vernon Hills-based technology vendor, Leahy is still breaking new ground.
Since leaving Sidley and joining CDW a decade ago, Leahy has built the company's legal team from scratch, started its women's leadership development initiative and helped take the company private while still maintaining enough financial and legal disclosure to get it back on this year's Fortune 500 list.
She's one of 10 executive committee members -- four of them women, three of them named Chris -- guiding the $9.6 billion firm.
"She's beyond being a very good general counsel," said Tom Richards, CDW's president and chief executive. "The things she does to keep her team engaged reeks of someone with leadership skills all over the place."
Walking through a customer demonstration center in Mettawa recently, Leahy, 48, talks about CDW's technical capabilities, from traditional networking and data recovery services for government and business clients to protecting a hospital's patient data in the cloud. She emphasizes how important it is to her that the legal department be seen as part of these operations, not an obstacle.
"People see us (CDW) as a reseller offering tech-agnostic advice," she said. "Now, with cloud computing, we're dealing with new providers and how to ensure CDW's position" in the competitive mix.
Richards, who is leading the company's push into new information technology services, calls it a key strength that Leahy is able to articulate the company's legal issues, from supplier contracts to data security measures, in the context of the overall strategy.
"She makes sure everybody stays focused on the bigger business issue, and I value that a great deal," he said.
Business has, indeed, been improving at CDW after hefty losses during the recession that in 2009 prompted the first layoffs in company history.
It was a rough ride after private equity firm Madison Dearborn Partners paid about $7.3 billion to take CDW private in 2007 in a leveraged buyout, only to see business begin to collapse the following year as companies slashed IT spending.
CDW snapped a string of net losses in 2011 as the economy improved, and Moody's Investors Service in April upgraded the company's debt rating. The agency noted the company's improved operating performance, market share gains and the expectation that the company will further cut its massive debt load, which was a whopping $4.6 billion in 2007, according to the credit agency.
The improvement has spurred speculation about another public offering.
"Every company that goes private eventually deals with an exit strategy," Richards said. "Is the possibility that we become a public company again on the list of options? Absolutely, it is."
Leahy would be a key player in that effort when it comes to pass, and Richards has made it clear she has the chief counsel job as long as she wants it. But is she aiming for a front-office job?
"That's a really good question, and my boss has been asking me that," Leahy said of Richards. "Here's the thing. I've never been a person who sits down and plots my life. What I do think about are the environments I like to be in. I love being part of an organization with clarity around a cause.
"Could I see myself running a business? Absolutely. Running a nonprofit? Absolutely," said Leahy, unknowingly imitating, in a separate interview, her boss' syntax of posing a question and then affirming it.
For now, significant day-to-day challenges remain, however.
The company has lots of competition from other resellers, and as cloud computing solutions become easier for users to handle on their own, CDW will have to scramble to stay relevant, said Andy Hoar, a senior analyst with Forrester Research.
Stephen Baker, senior industry analyst with NPD Group, thinks the company is finding a niche in providing clients broad access to cloud-related services, but he agrees with the concerns about competition.
"It's a crowded space, so margins are always going to be tight," he said.
And that's precisely where Leahy wants to step in and make her mark: on the bottom line.
By inserting herself and her legal staff onto projects early, Leahy has helped minimize exposure to costly overruns on contracts, said Chris Rother, senior vice president of public and advanced technology sales and a 21-year CDW veteran.
"She asked me early on if one of her team members could sit in on my team meetings," Rother recalled. "At first I had to calm everyone down about it, but now he's part of the process, and as we develop a contract with a customer, we don't have a long delay while it's reviewed by legal."
When the company was launching a new unit to go after health care clients in 2006, Rother said, Leahy helped set up the sales organization. And today with new cloud-based services, Leahy has been instrumental, she said.
"The way we go to market is changing so much, and she's providing a lot of advice for building out those strategies," Rother said.
It was that attitude that led CDW Chairman John Edwardson to hire Leahy away from Sidley in 2002 after she had worked on a secondary share offering as company founder Michael Krasny was reducing some of his stake.
"When I was interviewing for my job as CEO, I was interviewing with the corporate secretary, who was Tom Cole, managing partner at Sidley," said Edwardson, who started in 2001. "I had known Tom before, and as we were wrapping up our conversation he said, 'One last thing. You know CDW has no legal department, right? I will only recommend you if you promise to hire a general counsel, because they need one.' "
Not long after that -- in fact, it was at the closing dinner meeting after the share offering -- Edwardson asked Leahy to think about joining the company.
"Instead of giving me 15 reasons why we couldn't do something, Chris' approach to the problem was to figure out what it would take to make it work," Edwardson said. "We had never had a legal department before, and I wanted someone who was constructive and wouldn't turn leadership off."
Cole said he wasn't surprised by the move.
"She can convey the right advice the right way, without shirking from doing it. Any CEO should want that," he said.
Once she arrived at the company, Leahy said, Edwardson had her spend a month getting to know 65 key people around the company, a daunting time commitment, but one she says paid off.
"I now knew 65 people and they knew me, so from that moment on I could hit the ground running," she said.
Leahy has also led or been involved with many of the company's efforts to boost women and minorities in the executive ranks.
The company has informal networking and social groups and a formal diversity process when it comes to promotions and hiring, said Dennis Berger, senior vice president of Coworker Services, CDW's human resources department.
Hiring managers are evaluated on the number of women and minorities they bring on their teams, Berger said, and those numbers are figured into their annual performance reviews. But the company stops short of tying hires directly to bonuses, he said, because of concerns about that practice distorting the process, he said.
In other realms of her life, Leahy led a Children's Home + Aid fundraising effort that tripled results from the previous year, ran a couple of marathons and is the mother of twin teenage girls.
And yet she bristles a bit at the suggestion that perhaps she does, indeed, have it all.
"That concept means different things to everyone," she said. "I'm at a point where I have a very fulfilling life: a great marriage, two wonderful kids, a job I adore. But there have been sacrifices."
Leahy and her husband, Adam Weinberg, spent six years in a commuter marriage and delayed having children until their careers were well established. When they did start a family, they spent six weeks in a neonatal intensive care unit after their twin girls were born prematurely. The twins, Annika and Samantha, are now 13 and healthy.
During her college years, she had to withdraw from Brown University for a semester while she worked two jobs to save enough money to complete her undergraduate degree. She's the middle child and oldest daughter in a family with five children, all of whom went to private colleges.
Those years of tight cash flow fueled her desire for financial independence, she said.
But the setbacks never seemed to really get to her, said her husband, a former William Blair & Co. executive now taking time off between career projects to spend more time with the girls. The couple met in a political science class at Brown, where Weinberg played tennis and Leahy played lacrosse and field hockey until work required more of her time.
Playing competitive sports also helped shape her work ethic, she said, recalling a time when she played lacrosse with a broken nose to finish a championship tournament with her team.
"She has a way about her, an approach to life that anything can work out well. I don't think she allowed herself to think about negative outcomes when the girls were in the NICU," Weinberg said. "I've seen her go a couple of days without sleeping when she was working on transactions at Sidley and CDW, but I've also never seen her let her children or family members down."
Her secret? It's not multitasking.
"I think the girls are proud of their mom, and when I'm with them I try to be entirely present," Leahy said. "They were 4 years old, and I remember clear as day they were talking to me about their day at preschool, and I was sorting the mail. It hit me that here were my cute little kids telling me about their day, and I'm doing this at the same time. I still sometimes have to step away (from family time) to take the occasional phone call, but if the default habit is to be engaged with them, it's OK.
"There have certainly been trade-offs, but it's like that Sheryl Crow song: It's wanting what you've got, right?"
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Christine Leahy, senior vice president, general counsel and corporate secretary, CDW
Family: Husband, Adam; daughters Annika and Samantha; golden retriever/cocker spaniel/poodle mix puppy, Wilson, in Glencoe.
First job: Worked in high school in Princeton, N.J., as a waitress for a catering company.
Education: Brown University (English major); Boston College Law School
Civic connections: Board of trustees, Children's Home + Aid; member, Economic Club of Chicago and The Chicago Network; planning committee, Annual Corporate Counsel Institute, Northwestern University School of Law.
Reading: "The Outside of August," a novel by Joanna Hershon.
Her 2011 Chicago Marathon time: "I think it was a little over six hours! At mile 17, I found out I had a raging infection in my toe. But I wasn't going to give my colleagues back at the office any fodder -- 'You couldn't finish because your big toe hurt?' -- so I was determined to get over the finish line."