By Suzanne Kelly
Editor's note: In the Security Clearance "Case File" series, CNN profiles key members of the intelligence community. As part of the series, Security Clearance is focusing on the roles women play in the U.S. intelligence.
One of the first measures of tradecraft, as any good spy will tell you, is being able to tell when something just doesn't add up. So when Joan Dempsey began ticking off her decades of experience in various roles in the military and intelligence communities, it's tough not to add it all up in your head. With some 25 years in the U.S. Navy, (some of it in the reserves) another seven at the CIA, and some 17 at the Pentagon in a variety of intelligence leadership positions, Dempsey is one of the women in the intelligence community who has been a true pioneer, which of course, also means she has achieved a number of "firsts."
"I was nominated by President Clinton as the first deputy director of Central Intelligence for Community Management," Dempsey says from a high-rise conference room in McLean, Virginia.
She was also appointed by former President George W. Bush as executive director of the President's Foreign Intelligence Advisory Board, chaired by Brent Scowcroft. Add to that, a role as the deputy assistant secretary of defense for intelligence and security in the Office of the Secretary of Defense, and you start to see how Joan Dempsey's career in intelligence spans not only decades, but administrations and agencies as well.
Her early years as a Naval Reserve officer helped open the door to subsequent management opportunities, but the one thing she credits for her success, has been her willingness to take risk.
Dempsey didn't always play the safe card during her career. When she left the CIA to become the deputy assistant secretary for intelligence at the Pentagon, there was a "package" waiting for her. It wasn't a mysterious bundle delivered from one spy to another, but rather a challenge to solve a problem before it became a bigger one. The "package" was a Department of Defense directive on information operations that included developing guidelines for offensive cyber activities before many people even understood what "cyber" meant. As sometimes happens in government, the directive had been issued years earlier, but had gotten snarled in the bureaucracy of process.
"By the time I got in the job it had pretty much stalled because there was so much disagreement over what should be included and how it should be governed and where ownership resided for all of these various things, and it took about a year to get it all sorted out," recalls Dempsey, who says that what she learned as a result of going through that process, she carried through with her on every other challenging intelligence issue she encountered. Within the process of pushing the package through lay valuable lessons in diplomatic leadership.
"Figuring out how to pull levers and get organizations aligned around a course of action is an art," says Dempsey. "If you can figure out how to do it, you can make progress against these really difficult enduring issues and it's not flashy, it's not the kind of thing that people are going to necessarily remember as a something wonderful that you did, but you get tremendous satisfaction in knowing that you were able to make progress in a very challenging environment."
After a government career that spanned decades and saw the assassination of a president, a war in Vietnam, the end of the Cold War and a series of wars in the Middle East, Joan Dempsey was ready to turn in her government badge. But she wasn't ready to hang it up, so six years ago she did what an increasing number of her male counterparts have done over the years since 9/11, and went to work in the private sector. Some may have said it wasn't a particularly good time to become a contractor, given the criticism that the community was receiving over just how it was using its contracted work force, which mushroomed after the attacks of September 11, 2001.
Critics questioned the ways in which contractors were being used and the nature of the work they were performing. But that criticism aside, the reality was that the intelligence community couldn't function adequately under post 9/11 demands without a private, contracted work force.
Retired Gen. Michael Hayden, while calling for a reduction in the CIA's use of contractors while he was CIA director, also implemented a rule that any CIA employee who left the agency had to wait 12 months before returning as a contractor to the CIA. Still, he remains one of the industry's biggest defenders.
"Contractors were essential to our success," said Hayden. "I always considered them part of the resources I could call on. No one could claim that we (the government) had been efficient in our use of them. But that was our fault, not theirs. I challenge anyone who tries to deny that they were effective."
Like others before her, Dempsey fielded some of the questions that many government employees do when they leave government service and enter the private sector, where they presumably get a higher paycheck for their expertise.
"There have been times when I have felt maybe some unfair criticism for the fact that I left government and went into industry, and I think people maybe don't always have a complete understanding of how important the private industry is to supporting both defense and intelligence," said Dempsey, who is now a senior vice president at Booz Allen Hamilton, which has been a contractor to the U.S. government since World War II.
Up until a couple of months ago, Dempsey used her intelligence insights to help the company craft strategy and identify challenges within the intelligence community that she believed the government would need help with. They included cyber security, which FBI Director Robert Mueller predicts will soon overtake terrorism as the number one threat to the U.S.
Dempsey was also key in developing strategy for Booz Allen Hamilton in the areas of quantum computing and parallel processing. She has recently moved to the firm's defense team and now leads the company's largest account inside the Pentagon.
"Under the rubric of, 'If I had only known then what I know now,' I only wish that I had had time in industry at some point in mid-government career," said Dempsey. "I would have been a better senior government official if I had understood better how industry operated and what the government looked like from the industry vantage point."
Her best-kept secret
"I'm pretty good at keeping secrets," Dempsey says as a smile spreads across her face. "The whole Moneypennies thing - people who were there that night would be shocked," says Dempsey as she explains how her support for the CIA Officer's Memorial Fund was the impetus for dressing up and taking center stage in a fundraiser for the community led by actor and longtime intelligence community supporter Dan Akroyd.
"We were the top-rated group, nonprofessional group," says Dempsey, whose band called themselves The Moneypennies and shamelessly belted out Elvis tunes to raise money for the children of fallen intelligence officers.
"I wouldn't go so far as to say I'm a singer; a lot of people will tell you that deciding to keep my day job was the right decision. But it was a lot of fun and it was a very good group," Dempsey recalls.
She also sits on the board of the foundation, which she describes as the most personally rewarding duty she has taken on since leaving government.
"These are anonymous foot soldiers for the most part, and people want to know that their children are going to get an education, they want to know they want them to know that the country appreciates the sacrifice that their family made," says Dempsey, who hasn't lost her sense of adventure since going private. "We played a medley of Elvis songs, high energy, a lot of fun. We wanted to do (the Beatles') 'Back in the USSR.'"
From Arkansas with Love
When novelists sit down to create a top spy, the main characters are typically male and typically hail from some of the world's most glamorous locations; Paris, London, Moscow. The reality, however, is that America's top spies hail from places like Iowa and Idaho. Dempsey was no different.
"I grew up in Arkansas and I'm a product of the Arkansas Public School system," Dempsey said. "I was the little girl who was over in the corner and reading as much as possible."
Far from Bond-like, Dempsey describes herself as an introvert who has had to overcome it.
"I've learned how to act like an extrovert because the job required it, but I didn't ask too many questions," recalls Dempsey.
Dempsey's father served in the U.S. Navy and spent time in China as World War II got under way. He retired in 1957 and went on to teach school until much later in life. When he was in his 80s he went to work as a government contractor.
"He was reading aerial photography for the Department of Agriculture and looking at ... how crops were being seeded in Arkansas and - was the land that was being used as crops being overused or underused," says Dempsey, who has both an older brother and older sister, neither of whom followed the national security path. She acknowledges that the world she grew up in is very different from the world she discovered as an intelligence officer.
"Every generation is unique, for my generation I think fear of cataclysmic nuclear exchange was something that drove us and caused us to think about service to country differently," says Dempsey. "I think the challenges today that the country faces are enormous, with the geopolitical environment, and China as a growing economy, and cyber security and all of these things."
Dempsey now spends part of her energy encouraging other women to study and excel in science and technology. She says it's her best advice for navigating a career path that aligns with the needs of evolving threats.
"I think that's a huge growth area in intelligence, the big data analysis kinds of things, quantum computing which, I mean, we're a few years away from realizing real quantum processing and quantum computing. And I mean these are areas that are going to have profound effect on every aspect of our lives, but certainly on the intelligence.