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Meet former FBI Special Agent Gina Osborn

Gina L. Osborn is an expert in navigating Chaos, Crisis and Change. Having responded to catastrophic terrorist attacks and cyber hacks as an FBI Special Agent and chasing Cold War spies in the U.S. Army, Gina knows that crises can be managed, chaos can be controlled, and change is inevitable. Gina serves through speaking, coaching and hosting executive round tables, VIP Days and Masterminds. She provides tools and techniques to eliminate self-imposed obstacles, stop tolerating the intolerable, have the courage to lead authentically and create clarity and confidence to become UNSTOPPABLE. She also hosts Behind the Crime Scene – A True Crime Podcast. She can be reached through her website at

1. What inspired you to join the FBI? How did your career begin?

When I was growing up, I wanted to be a writer. I also dreamed of being an international woman of intrigue working as a CIA Operative. It was the 1980’s, the decade of the spy. I was fascinated with the Cold War. All I needed was a sense of adventure and a four-year degree.

In my second year of college, I was a cocktail waitress wondering how I would afford to go to a four-year university. A young man sat down next to me in the library and began to tell me about the U.S. Army’s Counterintelligence Program. He told me I could chase spies across Europe while earning my college degree. The next day, I went down to the Army Recruiter’s office and enlisted.

It was a dream come true. I spent six years in Belgium and Germany working the highest profile espionage cases through the end of the Cold War and the beginning of Desert Storm. The most noteworthy espionage case I worked on was the U.S. Army Specialist Albert Sombolay. After months of investigation, I was present when he was arrested for espionage and aiding the enemy. He was sentenced to 34 years in prison.

After six years in the military, I wanted to continue my career in law enforcement. I joined the FBI as a Special Agent in 1996.

2. How did you navigate working in such a male dominated environment?

My parents divorced when I was a child, and my mother raised my sister and me. I never heard “It’s a man’s world.” In our home, there was no mention of a “glass ceiling.” The three of us mowed the lawn each week. If my feelings were hurt because of what someone said, my mother told me what other people thought was none of my business. I was raised to believe I could achieve anything through hard work and determination. Gender had nothing to do with it.

When I joined the FBI, only 14% of FBI Agents were women. I learned early on the FBI didn’t hire me because I shared the same characteristics as a man. They hired me for what I brought to the table: my counterintelligence experience, problem solving skills, good judgement, and I could professionally represent the brand. At no time during my 28 years in law enforcement did I ever feel the need to give up my femininity or sideline my personality to “fit in.” The higher I rose through the ranks, I realized that embracing my skillset made me a more effective and authentic as a leader.

I also learned early on not to take things personally. I’m very passionate when working with my coaching clients to reinforce this lesson. Taking things personally is a major defining factor in how we handle chaos and crisis. If we are constantly being offended or hurt by what other people may say or do as though we are the center of the universe and their intent is to take us down, we are creating unnecessary obstacles that detract us from accomplishing our goals.

3. What did you love most about your job?

I loved helping people and making our communities safe. My first job in the FBI was working Asian Organized Crime in the Little Saigon District in Orange County, California. My first case involved Thai women being brought into the United States and forced into prostitution. That led to investigating violent crimes, such as murder-for-hire, extortion, gang shootings, to name a few. The Asian gangsters targeted their own community. Arresting violent criminals and taking them off the streets was very gratifying.

When I became an Assistant Special Agent in Charge, I led over 100 special agents, task force officers, computer scientists, intelligence analysts and forensic examiners working in the largest cyber and computer forensics program in the FBI. I loved creating an environment where my people had pride and ownership in their work and had everything they needed to do their jobs. I found that encouraging ownership in our program increased morale, creativity and productivity.

In my final years before I retired, I loved coaching and developing the leaders coming up behind me; teaching them how to effectively navigate major cases and projects in extremely chaotic situations. I often stretched them to their limits so they could grow. I also allowed them to make mistakes so they could learn to be better FBI Agents, leaders and humans.

I love that I continue to be in a position as an Executive Coach to help female leaders in transition to navigate chaos, crisis and change, identify their strengths and encourage them to have the courage to make mistakes and learn from them.

4. What challenges did you face in law enforcement?

The greatest challenges I faced came from being exposed to the worst society has to offer. I worked cases involving organized crime, terrorism, espionage, crimes against children and cybercrime. I’ve responded to kidnappings, terrorist attacks and catastrophic computer hacks. What offsets the darkness law enforcement often has to endure, was the hope I witnessed in the aftermath.

As the host of Behind the Crime Scene – A True Crime Podcast, I recently interviewed Erin Runnion, the mother of five-year-old Samantha Runnion who had been kidnapped and killed in 2002. I was working in the command post the day Samantha’s body was found. It had been a case I hadn’t forgotten after all these years and was apprehensive about interviewing Erin. I couldn’t imagine the pain she must live with everyday after losing her little girl. Erin attended the trial everyday and sat in the same courtroom with the monster who killed her daughter. I asked her, “How did you get out of bed everyday and have the courage to do that?” Erin told me Samantha had the courage to fight till the end of her life. Erin said she had to have the courage to make sure justice was served so this could never happen to any other child. Erin went on to create the Joyful Child Foundation to teach children how to be safe.

After facing all these challenges, I learned that crises can be managed, chaos can be controlled and change is inevitable. This is so important to remember, especially in 2020 and why it has become my mission to speak on this topic to help people turn chaos into calm.

5. After six years in Army counterintelligence, 22 years in the FBI catching terrorists and cracking down on cybercrime, you decided to quit and follow your passion of writing. What gave you the courage to do that?

After 28 years in law enforcement, it was time for me to retire. My passion for writing was stronger than ever, and I knew I could continue to serve as a positive influence on the world by sharing my stories.

It was daunting to leave the security of working for the federal government, but I believed enough in my abilities and my passion that I would find my niche. I was invited to speak at conferences where I could share my stories to inspire other women. I created a podcast where I can share the heroic stories of others in law enforcement. I’m writing a book on navigating chaos, crisis and change to become unstoppable. I also coach executives in transition to use some of the skills that helped me at the FBI and after leaving the agency to redefine themselves and think about the usefulness of their skills in new ways.

6. And what would you say to someone who is terrified of taking a leap into a new career or industry?

Do it! Is it scary? Yes. Will it be easy? Probably not. Achieving greatness is never easy. I tell my clients that you have to do the work, but you don’t have to do it alone.

Once you identify your passion and purpose in life and surround yourself with a supportive network, what are you waiting for?” I am not sure what motivates each person to start working on a goal or a dream, it’s different for all of us, but one motivating factor for most of us is that time is finite. We only have so much time, so you must get to it, the sooner the better.

While I was playing with the idea of retiring, I saw a painting of a women wearing a beautiful ball gown and white gloves leaping off a cliff. She was lovely, poised, and she seemed to float instead of fall. That inspired me to make the leap.

My favorite quote is “She who attempts the absurd can achieve the impossible.” I believe that every day as I find success serving others through my writing, speaking, coaching, and podcasting business.

7. Are there any particular female role models or mentors who have acted as a source of support or inspiration for you?

My mother was my first female role model. She showed both my sister and me how to not just survive but to thrive. When my dad left in 1974, mom hadn’t worked outside the home in more than 13 years. Before I was born, she was a hairdresser at the Disneyland Hotel. Now she was faced with having to keep a roof over our heads and food on the table. She took a risk. She went into real estate knowing we’d have to live off of commission only. She’d wake us up every Saturday morning to pass out her marketing materials in her sales area, which was a lower income neighborhood in Orange County, where houses sold for $35,000. I watched her work hard, fight for her clients, and take ownership of her job to ensure every deal went through, and she looked great going it. In her first year, she sold over $1 million in real estate. Watching her whip the world was magic.

My other role model was Army Chief Warrant Officer Connie Huff. She was the case agent on the Albert Sombolay espionage case. While I was in the military, there weren’t a lot of soldiers who looked like me. I rarely saw women in leadership roles. When Connie showed up, a confident woman taking charge of a team full of triple A personalities who were mostly male seasoned investigators, I was in awe. Connie was smart, capable, and attractive, which could be extremely intimidating to men back then. However, she had the ability to listen to ideas, and make everyone feel like they had an ownership role in the operation. Connie made informed decisions, but they were her decisions to make. I learned that a woman could be a strong, effective leader using skills like communication, collaboration and empathy. Connie respected every member of the team and treated each of us like we had value. As a leader, I would have followed her anywhere.

8. Could you tell us about ‘FBI Cyber G-Girl Academy’? What do you hope to achieve?

In 2014, it was the first time in history the Los Angeles Division of the FBI had four female Assistant Special Agents in Charge. I led the Cyber and Computer Forensics Programs and created the FBI’s Cyber G-Girl Academy, inviting my female executive counterparts to join me as role models for nine to 11-year-old girls.

The purpose of this program was to encourage girls to pursue Science, Technology, Engineering and Math (STEM), improve internet safety skills, make good decisions, and encourage them to explore the idea of becoming an FBI Agent. I also wanted to expose the girls to strong, female role models to enforce the message that women can achieve anything they set their minds to. In 2017, I partnered with the Girl Scouts of Orange County and the Discovery Science Center to turn our half-day program into a week-long camp. FBI Los Angeles continues to host 40 Girl Scouts each month at the Orange County Regional Computer Lab as part of the Cyber G-Girl Program.

9. One of The Female Lead’s key themes is ‘find strength in setbacks’. Can you tell us about a particular obstacle or challenge that’s affected your journey and how you overcame it?

My dream when I enlisted in the Army was to earn my degree and work for the CIA. After almost six years in the military, I had my college degree in hand and applied. I had all my Army counterintelligence training and experience. How could they not hire me? I received preferential treatment in the application process and was interviewed. I nailed it, or at least I thought I had. A month or so later, I received a thanks but no thanks letter. I was absolutely crushed. I tried my hand at travel writing and was a big flop. I took more writing classes but never got traction in Hollywood. I sold timeshares and worked at a vitamin company. I applied for every other government agency, but they were all under a hiring freeze. During that time, I had to reinvent myself. But most of all, I had to believe that through the rejection and failure, the right thing was going to come along. Somebody once told me that it doesn't matter if your ship comes in if your port isn't built to dock it. Once I pulled myself out of my pity party, I worked each day to remain shape, stayed up on current events, and took more writing classes. I had to build my port believing I would need it someday. Three long years later, the FBI hired me.

10. Another theme is ‘Dare to be Different’ – how have you used your differences to help or guide you?

One of my favorite keynote speeches I present is called, “Lead like a Lady.” People don’t know how to interpret that title coming from a woman who spent 28 years in law enforcement. The theme is to encourage women to lead authentically and present themselves unapologetically.

As I look back on my career, the times that make me smile most were when I “Dared to be Different.” In the Army, my First Sergeant made me do push-ups every time he caught me wearing red lipstick with my battle dress uniform. I used to love it when people told me I couldn’t do something. That was always my invitation to prove them wrong. There were many hills along the way I was willing to die on to support my people or principles. Excellence is derived from originality.

11. Looking at how far you’ve come and everything you have achieved – if you could go back and tell your teenage self something what would it be?

Entering a male dominated profession, I started out feeling compelled to be perfect. In my mind, there was an unwritten rule I had to work harder, be smarter, run faster than my counterparts or else they would view me as “a weak sister.” It was a game I would never win because nobody can be perfect all the time. As time went on, I became comfortable in my own skin and abilities. I gained a sense of humor and learned to embrace my weaknesses, accept my flaws and eliminate the limiting belief that I had to be perfect to be great at my job. If I could go back and speak with teenage Gina, I’d tell her..

You don’t have to be perfect. It’s your imperfections that make your extraordinary.”


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