In commemoration of March as Women’s History Month, we found some time to connect with five leaders here at Hillard Heintze who are women and asked them about their perspective on their careers and their views on women and their role in advancing our purpose: protecting what matters here in the U.S. and worldwide.

Debra Kirby is the Chief Legal Officer at Hillard Heintze. She has been a lifelong champion for change and improved policing practices in the U.S. and in Ireland. She retired as the highest-ranking female in the Chicago Police Department, having developed expertise in labor management; officer-involved shooting investigations and policies; criminal investigations; large-scale demonstrations and emergency preparedness; and, internal affairs and accountability.


Deb, let’s start with your career. How did you first get into this area?

I always wanted to have something to do with addressing injustice. Early on, I wanted to be a lawyer – and, actually, I was able to become a lawyer while I was employed by the Chicago Police Department (CPD). The agency provided tuition reimbursement, which was great. That was one of the reasons I went to work as a police officer.

However, I found being a police officer to be a fabulous and interesting job, and instead of becoming a “true lawyer,” I continued to work with the CPD, and still using my legal training, until at one point in my career I was appointed the general counsel of the Department.

What is your professional background?

Most of my career has been with the CPD — almost 28 years. I rose through the ranks from a police officer to a Chief. I did a lot of different things in my career, including establishing the domestic violence response plan and protocol for the department. I identified ways in which investigative units could more directly engage with the community as part of community policing programs, and I did a significant amount of work around policing integrity and internal investigations. I was also in charge of the 2012 NATO Summit in Chicago. At the time, it was the largest federally designated National Special Security Event to be held on U.S. ground.

When I retired from the CPD, I went to work for Ireland’s An Garda Síochána — a national police service. This includes all law enforcement actions from local policing, through federal and international policing, similar to our FBI and CIA, all in one entity. Its Department of Justice and Equality was recruiting and called at just the right time. I was looking for my next challenge.

It was a great opportunity. I’ve always enjoyed living and working in other cultures. I was there for a year-and-a-half. Key reports that I contributed to in the time I was there include those on crime investigations and investigations into child sexual abuse.

When the contract ended, I went hiking in the foothills of the Himalayas and decided I needed to find a job. I came back, and at that time Hillard Heintze had engaged in a significant piece of work with the Department of Justice and I was hired as part of that team.

What is your role at Hillard Heintze?

I was hired as Vice President to work in the Law Enforcement Consulting practice, and from there was promoted to Senior Vice President. Now I’m the Chief Legal Officer. I feel the work I’m doing here is the closest thing to restorative justice work in the private sector, while still applying a commercial approach, which is unique. Being able to come in and identify, as an independent observer, the challenges facing a client – and then help that client find ways to improve and sometimes even transform its mission, culture and relationship with its community – is probably one of the more rewarding aspects of my work at Hillard Heintze.

What is the valuable skillset you bring to clients?

My range of experience is very unique in some ways. I have an undergraduate degree in finance. I’ve worked in all areas of the police department, developing a range of skills. The strength that I bring is the ability to provide insightful analysis. As I once said during an interview, I’m a problem solver. That’s what I’m most successful doing – identifying and improving processes that help clients achieve their goals.

What accomplishments are you most proud of?

I am a third-generation female police officer. My grandmother was a matron with the CPD, and my mother entered the force after I was already in the department. I was in the first big class of graduating women hired by the CPD in a long time.

The real reward I’ve seen is that a lot of the work I’ve done remains in place. At the time we did the domestic violence review, we really contributed to the safety net for the women who are victims of domestic violence in Chicago. Many aspects of that program still remain.

Later in my career, the NATO Summit demonstrated the professionalism and capacity of the CPD to deal with a national event in a manner that prepared for future events, which included both of the national conventions. The officers within the Department really set the standard. It’s not so much me individually, but the team of people I worked with that made that happen.  That’s very personally rewarding.

What advice do you have for young women starting in their careers?

I’ve spoken to a lot of women of different ages and the ability to be comfortable with saying “This is my choice and this is how I’m going about it” requires a level of self-confidence. You can’t control other people’s perceptions; you can only control your own actions and goals. The standards for measurement of success for men and women aren’t consistent. Women have to own that and define for themselves their own measure of success. What I choose as my yardstick may not be the right one for someone else, but that doesn’t diminish either of us.

The important thing is to make sure you have a voice at the table and be able to influence those things that matter — what matters to you is defined in different ways. It’s been my experience that competency overcomes a lot of the perceived challenges of gender inequality. Distinctions between genders remain, but I haven’t found it to be a direct impediment to me or my ability and capacity to do the job. Women need to embrace that strength going forward.

I also think women in my position need to be more comfortable and capable of mentoring women coming up through the ranks. As someone told me once, “I want to be challenged by those I’m mentoring, because I want that person to someday have my job.”

This interview has been edited for length and clarity.