Roberta G. (Bobbie) Stempfley joined the Carnegie Mellon University Software Engineering Institute as Director of the SEI's CERT Division in June 2017. Stempfley previously served as director of cyber strategy implementation at MITRE Corp. and as acting assistant secretary and deputy assistant secretary, Office of Cyber Security and Communications, Department of Homeland Security. In addition to her work at DHS, Stempfley previously worked in the DoD as CIO of the Defense Information Systems Agency and as chief of the DoD Computer Emergency Response Team, which she established. Stempfley received her bachelor's degree in engineering mathematics from the University of Arizona and her master's degree in computer science from James Madison University. A recipient of many awards, she was recognized by CyberScoop as among the Top Women in Cybersecurity, by Federal Computer Week in the Fed 100, and by Information Week as one of the Top 50 Government CIOs.

Kasha Gauthier: Describe your career and work briefly.

Bobbie Stempfley: I’ve been a public servant working in IT, focused on the application of that information and technology to National Security missions for about 25 years. I’ve done this through my work first as a civil servant for the federal government at DHS and DoD, and now at research and academic organizations. My specialty is leading organizations and groups, helping them solve problems like communications and interoperability of systems. I’m currently at Carnegie Mellon University Software Engineering Institute where I am the Director of the SEI CERT division.

What have been some transition/decision points during your career that you’ve faced?

Reflecting on my career, I’ve needed to drive my own changes in my life. What that often meant is that major changes in circumstances or life have presented me with transitions. Having children was one example, another was when I made the decision to leave an agency I’d been at for 14+ years, even though I’d attained a senior position, I needed to create my own opportunities to make sure I continued my growth. Sometimes it’s been because I’ve stopped learning in a job. For example, I thoroughly enjoyed my job at DHS, so when I decided to leave, someone said “what about where you are isn’t good enough/high enough?” But I had stopped learning and growing, so I had to make a tough decision to move on. I had to be brave enough to move from something I was successful at to something else unknown. Sometimes life presents these opportunities, and you have to adjust to them, and sometimes you choose those moments for yourself. It’s important to look at them and consciously make the decision, because if you don’t examine it and just keep going mindlessly, that in itself is a decision.

How do you find the courage to leave a job where you have been successful, and what resources/tools did you use to help you determine what path to take?

I try to live and teach others not to just search for the “right” answer. I accept that I am going to make mistakes, and know that I will be able to recover, walk back, or walk around those mistakes when they happen. What I was actually seeking was a “good enough” next step or “not wrong” next step, not the “perfect” next thing. I can find a really good thing or even a good next thing that could grow into the perfect next thing.

This approach also keeps me from measuring what I’m doing against the perfected or beautified view of what that job would be. Everyone is measuring what they know, and assuming the next steps will be without foibles, and that’s not the way it is, every place has its positives and negatives. I have made mistakes and made the wrong decision, and have had to walk back from it. For example, I had a job where I was feeling a little stagnant, I wanted to be more involved in the technology. I got excited by a job opportunity to do more of that type of work, but forgot during the interview process to also test that the organization was a right fit for me. I allowed myself to take a job that had a lot of positives, but their values didn’t align with mine. They really valued individual contributions above all else, and I value helping people and teams be better versions of themselves. In the end, I began to recognize this dichotomy and I changed my circumstances. But there were still a lot of things I gained from this so-called “mistake!” I made new relationships, built a ton of new skills, and had a lot of successes. It was an important lesson that I need to remember what I value, and measure that as much as anything else when I’m making my decisions.

Is it really a “mistake” then, or is it just part of developing the bravery/wisdom to be able to take the next step in your journey?

It was a mistake in that I had enough indicators early on that it wasn’t the right fit, and I ignored it. But it wasn’t a mistake in that I learned so much and made so many relationships. So yes, in that sense, everything is building on the journey. I always say “bloom where you are planted,” but you also need to know yourself well enough to know when you need to be moved and planted somewhere else. Where I was, there was only one outcome, I needed to be someplace where values aligned. That meant either they needed to change their values, or I needed to change mine. When it became apparent neither one of those was going to change, it was time for me to move on.

I love this plant analogy; how do you know when to transplant yourself?

It’s a gut feeling that something’s wrong. I start recognizing I’m uncomfortable, unhappy, bored, feeling stifled (whatever it is in the specific situation), then it becomes, “ok, what is it that I like about this situation, and what don’t I like.” At that job I just mentioned, I didn’t recognize at the time that is was about values. I can only see that in hindsight. I just had a gut feeling something was wrong. Once I noticed, then my “TJ” kicked in (Myers Briggs personality type- Thinking/Judging). I started looking around and talking to people about the possibilities. Once I start that, it becomes a practical matter. I will study, analyze, consider, create a plan etc. to avoid making one of these big changes, so I just have to make a deadline for myself. I might revisit it in 45 days to see what I’ve learned and see where I’m at with the process, whether that means either staying put and keep exploring, or I’m ready to move on. There have been times that what came out was taking cooking classes because I wanted to explore and grow in a different way than a job could do for me. At other times I did leave the job. The exploration process is really important to me.

That is really interesting. It reminds me of the time I had a gut feeling something at my job was wrong, but couldn’t put my finger on it. So I began tracking a smiley (good day) or a frown face (bad day) at the end of each day. After 30 days, I had recorded more bad days than good — the data helped me validate my gut — this job was not providing me satisfaction anymore.

That’s right- it’s also not easy to make that change once you realize it’s time. The decision to make a change was gut-wrenching. Bravery didn’t just come. I don’t like change. Our family’s schedule is often built around jobs and their place in our lives, who takes the kids to trombone and dance lessons, etc. The ramifications of such a change are widespread. You just have to gear up for a change that big. I also now know I need energy reserves for that process, to be attuned to my environment, look at data and make intellectual decisions. An important part of making these changes is to recognize how to build those reserves, whether before or after you move. Regrow the reserves, whatever that means to you.

What you’re describing is resiliency, which studies now show is a huge factor in success, and a trait that girls today often have lower levels of. How have you developed this resiliency and confidence in yourself to keep going, even after a “mistake,” or to trust yourself to make a big change?

The most important thing is to learn from everything. I know about myself that I am the least satisfied and the most unhappy when I am not authentic to myself. I do analyze and overanalyze. But I have long been of the belief that I am responsible for myself and my choices. I choose not to allow myself to wallow too long. I really believe there is something good to be had in every situation. Sometimes you have to look really, really hard to find the positives, but you have to make that choice. I can’t get stuck, I need to be the best example of the kind of person that others look to me to be, whether it’s my kids, my mentees and mentors, or the people that work for me.

What would you like to see happen, or what solutions have you seen, that will help us move towards greater diversity (gender diversity specifically).

This is such a hard problem, and I wish there was an easy solution. But of course, if it was easy, it would be solved already! One of the things I try to perpetuate is to ask people to question their assumptions about other people and their circumstances. For example, let’s not assume the only woman in the room is the admin assistant. Let’s make sure every person in a meeting has the opportunity to participate and engage. A practical example of this is to adjust a room’s configuration to try to build engagement and a level playing field between participants, or invite people to the table. I also actively invite people in to the conversation, even if it might be a situation they’re not entirely comfortable in. I read the room to sense if someone has something to say or is getting interrupted. And let’s do everything we can to increase the number of diverse candidates that are considered for positions. 

I’ve raised three children; two girls and a boy. It’s not just about teaching our girls, but also about teaching our boys. As a mom I have an obligation to both, but I don’t think there’s enough emphasis on teaching both genders about what equality looks like and how to be a part of it. There’s a ton of emphasis on teaching girls to be confident, but we also have an obligation to teach our sons what an equal world looks like.

These are very individual fixes, and one of the reasons it’s such a hard problem is there are no institutional fixes yet, so each person needs to do it individually.


Kasha's Takeaways

Bobbie’s story really affected me on a few levels. First, she’s very accomplished, but refreshingly humble about her career success. She leaves room for mistakes and learning, and doesn’t allow herself to rest on her laurels for too long. It’s rare to see a senior executive in Infosec with such a holistic and intuitive approach. Similar to Sandy in our last story, Bobbie is both analytical and highly emotionally intelligent. It strikes me that her keys to success apply far beyond the Infosec industry and career management. Here are a few of my takeaways from Bobbie’s story:  

  • There is not always an external trigger to make a change. It’s up to you to manage your career. It starts with being authentic to yourself, knowing your values and what you need to thrive and grow.
  • Learn to recognize when something may need to change, and have a process to explore what that gut feeling means. It may help to gather data, talk to others, research other opportunities, and set deadlines to check-in on yourself.
  • You always have a choice. Don’t allow yourself to believe your mistakes define you — try to be the best example of the kind of person you want to be. 
  • There are not a lot of institutional fixes right now, but there are lots of actions we can each take to promote and model equality in our workplaces. 
  • One of the most important places we teach and model for the next generation is as a parent. Let’s help both our girls and our boys see what a diverse, equal environment looks like, and why it’s important.