Profiles in Military Service: 
Colonel Holly O'Grady Cook, US Army (Ret.)
By Zach Sanders, GPSLD Intern

Holly O'Grady Cook (US Army Ret.), serves as the Associate Executive Director of Operations in the ABA's Washington, D.C. office. Her circuitous route to that position, however, brought her from the Long Island suburbs, through 23 years in the JAG Corps, to the Pentagon, and only then to the ABA's doorstep. Holly was kind enough to speak about her experiences in the JAG corps and offer advice. The following interview contains helpful suggestions for military attorneys considering a transition to the civilian sector. Check back here often for more tips from attorneys who have successfully made this transition!

Tell me a little bit about where you grew up. How did your upbringing influence your decision to join the military?

I grew up on Long Island in a very close-knit family. We did not have a lot of money but we all went to private grammar and high schools. If we wanted to go to college, we had to pay our own way. I never thought I would join the military when I was growing up or when I was going to school. However, I think wearing a uniform for twelve years of my education, following strict rules my whole life, and learning at a young age that you needed to have a strong work ethic to succeed made parts of being in the military very easy for me.

How did you first get involved with the military and what attracted and motivated you to join? Could you share some of your experiences?

I met my husband Alan on my orientation day of law school in New York. He was a 3L student, and we got married at the end of my 2L year. When he graduated, he owed the Army four years of service to fulfill the terms of his ROTC scholarship, but he planned to serve longer because he enjoyed the legal issues and the opportunities the JAG Corps presented. I finished law school, had a judicial clerkship, and then worked for a labor law firm in Maryland, where Alan was then assigned. Ironically, my firm represented a hotel very close to the ABA's Washington, DC office, so I like to think of my career as having come full circle in that regard. When Alan was reassigned to Arizona, I decided to join the Army as a Judge Advocate rather than taking another state bar exam. He was enjoying his Army career and I have never regretted the decision to join him.

My first job was as a prosecutor in Arizona followed by another prosecution job in Korea. My cases included murder, rape, theft, drug offenses and many other crimes similar to those seen in the civilian criminal courts.  I also worked on labor law and ethics issues Early in my career, I tried to get assignments that allowed me to develop experience that kept me competitive in the civilian legal market in case I got out.

The military community is just a smaller community of what the general public sees, but the difference is that the military justice system has to be flexible and able to respond quickly to allegations of misconduct and accommodate the expeditionary nature of the military. Two to three-year criminal trials could be disruptive to good order and discipline in the units and interfere with accomplishment of the military's mission. For example, one of my premeditated murder cases in Korea took less than six months to get to trial after the victim was discovered. Criminal investigators investigated the crime, identified the suspect who had returned to the United States, brought him back to Korea, processed the forensic evidence in Japan, and we tried and convicted the perpetrator by the end of the sixth month. I also worked at the State Department for two years wearing civilian clothes and providing litigation support for a case in the Hague between the United States and another country—complex civil litigation, document finding, writing pleadings, responding to foreign pleadings, and submitting legal documents on strict deadlines—all skills I could take to the civilian sector.

At the 16-year mark, I really appreciated being a judge advocate and started taking jobs with an "I might as well stay 'til 20-years" mentality. I was offered a supervisory attorney role in the peacekeeping operation in Bosnia and later I was the head lawyer in a combat division in Baghdad during the surge. I cannot think of an assignment I did not enjoy in the Army, although I admit there are a couple I might not want to repeat.

What are some of your fondest memories of your work in the JAG Corps?

The people with whom I got to work. The JAG Corps is a very tight-knit community. Every office I worked in had officers, enlisted soldiers, international attorneys or civilian legal personnel and we all work together and we got to know each other. When I retired, my family sat in the first row of my retirement ceremony at the Pentagon, and my military family sat next to them. I told both of them "thank you"—I couldn't have done what I did for 23 years without the support of both of them. People don't join the military because they have to; it is a volunteer force. People stay because they want to and because they've been selected to do so. I am honored and very lucky to have worked with legal professionals in the military with incredible talent, character, and compassion.

I have also been lucky to see some very cool places. I have lived in Baghdad, Bosnia, Korea, and Germany and traveled all over the world—Indonesia, Australia, Europe and Asia. Living overseas is an amazing opportunity both personally and professionally, and it teaches you a lot about other people and cultures. It also helps you appreciate more what we have at and to recognize how much we can learn from others.

Tell me a bit about the challenges you faced while serving. How did you deal with those challenges?

I think one of the biggest challenges I faced was taking teams of lawyers and paraprofessionals overseas to work in unsettled places and making sure they had everything they needed both professionally and personally. People work very long hours in the military and they are selfless in doing whatever is necessary to accomplish their mission and take care of fellow service members. While doing so, they sometimes put themselves last or do not recognize the impact that the stress in deployed environments can have on them or their families. Some days are more dangerous than others, and friends and peers get killed doing their jobs. One of our paralegals was killed by an IED, one of our attorneys was seriously hurt, and there were many other casualties in our division in Iraq. That is hard to accept and it is hard to explain to families at home, but one thing that is true is that those service members who do not make it home are never forgotten by those lucky enough to serve with them.

It was also challenging to be a senior female officer while deployed in or at schools with predominantly male environments. If the commander had a meeting with all of his staff, and the meetings were offsite, they would ask if I wanted to be flown to the site the day of the meeting on a separate helicopter so that they didn't have to worry about finding a place for me to sleep. I tried always to be flexible with the staff making the arrangements and I always appreciated their efforts. I did not mind being on my own in some environments or being the only woman in others. I always felt safe personally and challenged professionally in the military, and I had fun serving with so many big brothers around me.

I've read a bit about your work with the Response Systems to Adult Sexual Assault Crimes Panel. Can you discuss any of your work with the panel and on sexual assault within the military?

The Department of Defense and Congress have really been committed to improving how the military services address the issue of sexual assault in the military. I was honored to be appointed by the House Armed Services Chairman to this panel and to spend a year working with eight incredibly dedicated panelists looking for ways to improve the process for responding to reports of adult sexual assault in the military and to improving the public's confidence in that process. 

Our panel held 14 days of public hearings, spent weeks travelling to different installations, and reviewed thousands of pages of documents. We listened to the testimony of military leaders, sexual assault survivors, prosecutors and defense attorneys, military judges, academics and subject matter experts, senators and private citizens. We made 132 recommendations for improvements and adjustments to how the military responds to sexual assault allegations, some minor and others more significant, many of which were ultimately approved and have already been implemented. During the year of hearings, I appreciated the very courageous victims who testified to help us try to understand their experience and I watched as some of them gained more confidence in the process.

I am grateful that Congress's continued scrutiny of sexual assault in the military and its commitment to our panel and the subsequent panel that has been meeting during this last 18 months to consider judicial processes has ensured that the Department of Defense has more resources, both in the short term and in the long term, to allocate towards preventing sexual assault from happening and towards improving the services and support to victims when it does. I am proud that my panel gave the Department of Defense and Congress a report that will help better inform decisions to improve victim confidence in the system and victim rights when the military responds to assault allegations in the future and still protect the constitutional rights of those accused of committing such crimes. Much has been done to improve military processes and to curb problems with sexual assault, but recent news reports clearly show that problems still exist and much more work still needs to be done.

What accomplishment are you most proud of from your years of military service? What duties were most rewarding?

I had a great military career and I found all of it rewarding. The Army challenged me to do things I never thought I would have the opportunity to do, introduced me to life-long friends I would not want to live without, and took me to places I did not think I would ever see. It is hard to single any of that out. My favorite part of the job though, was  training and mentoring young attorneys and paralegals as they served in the military and watching them live up to their potential. Practicing law was the easy part. The harder parts that both inspired me and made me smile was watching a legal team in Baghdad find enough plywood, materials, and skilled help during a deployment to build and wire an actual courtroom where we held trials; watching them find unused trailers and air conditioners to build a tax center so deployed service members could file their taxes on time; and seeing lawyers and paralegals take their computers in rucksacks to service members on guard duty in Bosnia so they also could file their taxes on time.

Everyday military legal personnel go out of their way to take care of their fellow soldiers and their families. They do not complain about it; that is just part of the job and they do it with utmost professionalism and competence. While providing top notch legal advice to commanders and staff in the field and at home station is critical to mission success, it is the impact that our legal personnel have on individual Soldiers and the families who are helped that always feels the best. In the legal offices where I worked I tried to take care of my legal teams and to the extent I was successful in that mission, then that is what I am most proud of.

Tell me about some of the people you've met during your many years of service. Did you have any key mentors or people who deeply influenced who you are? Tell me about them.

I have had a live-in mentor ever since law school. My husband Alan, a retired JAG Colonel himself, taught me both legal issues in criminal cases and military issues throughout my career. He also taught me how to write, better than any professor I had in school. Alan has deeply influenced the kind of lawyer and person I grew into over the last 30 years, as has my family during my entire life.

I have also been lucky to have great bosses during my 23 years on active duty. One of my most important mentors was LTG Scott Black who not only understood the importance of career development and satisfaction, but also of personal aspirations and family. While still in the Army, LTG Black helped Alan and me balance our professional and personal interests, and he did the same for me again as I decided to retire from the Army. As a civilian, mentors are just as important to me as they were in the military. At the American Bar Association, Executive Director Jack Rives has motivated and challenged me in my new career, while GAO Director Tom Susman and Bernie Robinson, a partner at The Livingston Group in Washington DC, have generously helped me to understand government policy and advocacy on a whole new level. I can never thank any of these gentlemen enough for their support, but I can pay forward their investment in me by continuing to mentor future leaders in our legal profession. 

What advice can you give for military lawyers who might be embarking on a career change to civilian life?

First, thank you for your service in the military. As you think about transitioning to the civilian workforce, please do not underestimate the value of the skills you learned in the military. Military attorneys, legal administrators and paralegals develop diverse and extensive experience and technical skills in various types of law and law office operations throughout their careers that will serve them well when they transition to careers outside the military. In addition to substantive legal skills, Judge Advocates and paraprofessionals develop leadership, mentoring, and strategic planning skills that set them apart from other legal practitioners. We do not just focus on just the task at hand, but we also look where those tasks fit into the larger picture. We know how to learn and master difficult tasks on the job, many of them at the same time, and we know how to bring projects to completion. We also don't just look at our goals for this year but we also look for opportunities five and ten years out. Transitioning attorneys and paralegals need to appreciate these skills and incorporate them into their job searches. 

Military practitioners transitioning to civilian jobs should remain flexible in their search for their next career and consider various career opportunities besides practicing law. Project management, organizational leadership, compliance, teaching, lobbying, writing, and politics are just some of the potential options open for consideration. Look for training opportunities to learn more about areas you are considering and to update and improve your skills as needed. Focus on translating your legal experience, scope of responsibilities, and skills to potential employers in whatever field you are considering. Not everyone knows how much you have already accomplished while serving in the military and it is up to you to clearly explain it using language people unfamiliar with your military jobs will understand. Let your peers and mentors know you are transitioning and look for volunteer and networking opportunities in areas you think you might like to work – you never know when an opportunity will present itself. Whatever you decide though, make sure to have fun and enjoy your next career. You deserve it.