Guest post: ILTACON’s Women Who Lead session will stay with attendees long after ILTACON

Kat Freeman, legal technology innovation solutions analyst at Alston & Bird, talks us through ILTACON 2022’s Women Who Lead session, featuring writer and former Central Intelligence Agency officer Melissa Boyle Mahle. The session was described by one female ILTACON attendee as ‘one of the best sessions I have ever been to in my life.’

At this year’s ILTACON, DEI and women in law and legal technology was a theme that was woven into the program agenda, including the Women Who Lead session on Tuesday 23 August.  In De-Coding Your Future – Life Lessons From a CIA Officer (a.k.a. Spy), attendees were treated to an engaging discussion on boosting their leadership skills and career progression with Melissa Boyle Mahle.

Ms. Mahle was recruited by the CIA in the late 1980’s and as she rose through the ranks, she became one of the few female CIA case officers to operate and lead teams in the Middle East.

To start us off, she described one of her first bits of resolve in her career when she was asked where she wanted to be stationed.  Fluent in French and Arabic, her new employer assumed a glamourous post like Paris would be the request, but no, she wanted the Middle East.  The response? “But, we don’t send women to the Middle East? Think on this for a while and let me know.”

Ms. Mahle did just that, but the request was still the same: she wanted to be posted to the Middle East.  This and many previous and future acts of determination put her on a successful path where she was able to cut her teeth with the agency, moving up the ranks to lead operations and teams, gaining trust and respect that did not come easily to women, let alone in a male dominated environment like the CIA.

Towards the end of her tenure with the CIA there was an instance, she told us, when her steadfastness had a negative impact.  In 1996, she was working on an operation to capture Khalid Shaykh Muhammad (the future co-conspirator of the 9/11 attacks) but unbeknown to her, the FBI was working on a similar plan, and when she was asked by her leadership to revamp her operation, she said no.  She believed hers was the best option.  Ultimately, the FBI’s plan was executed, and Muhammad escaped, leaving him free to plot with Osama bin Ladin.

Ms. Mahle came away from this experience realizing that had she been open and flexible to modifications, Muhammad likely would have been captured, thus potentially changing the course of events that lead to 9/11.  How do we find that balance between having the tenacity to realize our career and life goals, and not sabotaging ourselves with inflexibility?

Ms. Mahle was asked how she managed her career and family, to which she replied, “poorly”.  This answer was quickly greeted with knowing laughter from the attendees.  Her life in the clandestine services made work-life balance difficult to say the least, but at the end of the day, she, her husband and her daughter made it all work.  Her mantra of get comfortable being uncomfortable resonated with attendees on many levels.

One of the biggest takeaways from the session was the simple notion of curating your contacts and connections to be meaningful and imminently more useful.  Too often now, as back in the day, we scramble to gather as many LinkedIn contacts (the new business card) as possible instead of being thoughtful in who we connect with.  Will the people we add to our professional and personal networks be supporters and/or advisors or just a name we vaguely remember?

The session concluded with an interactive exercise and reception which spurred more energy and deeper discussions that will no doubt carry on with attendees long after ILTACON.

Kat Freeman has been a legal technology innovation solutions analyst at Alston & Bird since April 2021. Before that she was a senior paralegal at King & Spalding and her paralegal career spans over 15 years.