Debbie Gross: A Career Road Map

Executive Assistant to former CEO of Cisco, John Chambers, shares her career road map

Debbie Gross, former executive assistant to former CEO of Cisco, John Chambers, didn’t start her career as an executive assistant. Like Debbie, many executive assistants started their careers in other industries. Also like Debbie, many find that once they are in the career, they want and know they could do more in the role. How does one take their career to the next level? Just as Gross didn’t begin her career as an executive assistant, she also didn’t end her career as one either as she is now a teacher and a coach in the administrative profession.

Although there isn’t a tried and true roadmap that guides a professional through their executive assistant career, Debbie shares her career journey to help set others up for success, too. Through an interview, she revealed with us how she got to where she is today and how you too can reach your full potential and find your passion.

What were you doing before you became an executive assistant at Cisco?

I wasn’t always an executive assistant. I started my career selling ads in a little advertising magazine called Potpourri. It was a paper that was thrown on people’s door steps and eventually filled the bottom of bird cages. It was my first real job and I was good at it. I was there for four years. It was my late twenties and I felt like I was on top of the world. BUT, there’s always a catalyst or a voice or inside all of us that calls us to bigger and better things, the key is to pay attention to it. At this time in my career, a young man came into our ad agency and walked up to my desk. He was placing an ad for a sales rep to help him sell medical supplies in the Bay area. When he noted what he would offer to pay that person to do the job, that voice in my head said, you can barely make your rent as it is now, this is something you should take a chance on. Life is about taking chances and taking risks. I ultimately quit my job and my comfortable little space, to go to work selling medical supplies.

How long did you work as a sales rep for medical supplies?

Not long. I realized, within the first two weeks of working there, that I had basically jumped off a cliff. I didn’t know what I was doing, had no knowledge of the medical field and I was truly unhappy in this new role. Taking a risk, while it didn’t pan out for me, did make me realize that I needed a role where I had skills and some expertise. At that point, I was interviewing and ultimately hired on with a small Japanese company as a customer service manager. I had two people reporting to me, and for 6 years, I was back in my comfort zone and doing fine! This happens to people in the course of their careers; they get into a comfortable place and as a result that they don’t seek out or make any changes. Many administrative professionals stay in their comfort zones and don’t branch out, they become afraid of making changes.

How did this position lead you to become an executive assistant?

One day, the very person I had trained who left that company, called to tell me she was now an executive assistant for a Silicon Valley startup, and asked if I would join the company as they had another opening for an executive assistant. Initially, I was incredibly resistant, that is, until she told me her salary. When she told me what she was making, the voice in my head said, Debbie, with the 2% increases you get per year you will never meet your financial goals if you stay in this role that you are in. The voice inside my head told me it was time to make another move.

I went to interview for the executive assistant position at this new start up. The interviewer explained the responsibilities of the executive assistant role and I realized I was already doing much of those same responsibilities in my customer service manager role. During the interview, they made me and offer I couldn’t refuse. Here I was leaving a company I had been with for six years to take a completely new risk with a completely different job title and responsibility.

I started working for two executives, and as anybody knows, startups are very risky. Within the first six months I was there ― and I was starting to really like what I was doing ― the funding ran out and the startup went under.

What did you learn from your experience with that start up?

Because I had taken that risk, I realized that I loved being an executive assistant. To top it off, the executive assistant role was higher pay than what I had experienced in other roles. Through my experience with the start up, I learned not only that I wanted to remain an executive assistant, but that I wanted a career with a stable company. While sometimes scary, every time I have ever taken a risk I have learned a lot more about myself and where I want to be.

What was your next career endeavor after your experience at a start up?

I searched the newspaper for opportunities. Finally I got a call from a company called Cisco. Never turn an interview down. If you get the opportunity to interview, do it. You learn something and you get better interviewing, which is a critical skill. I had interviewed with a handful of companies, but I was in search of the right fit. With Cisco, I interviewed the recruiter more than he interviewed me. I wanted to get in with a good company, so I asked many questions. One day after I interviewed, they asked me to come back and interview again. That’s when I met John Chambers, who was at that time, the Senior Vice President of Worldwide Operations. Something clicked and we had a thorough and long interview. He asked me how he would keep me motivated in this job. I said, “Well, money, but secondly, just to be appreciated.” After that conversation, before I even made it back home, he called and made me an offer and I was ecstatic.

I started working for Cisco in one of their three existing buildings in Menlo Park, Ca. In the first 2-3 years of working there, I was just trying to get it right. John has tremendously high expectations and runs a million miles an hour. I wasn’t used to working at that pace and he was changing things all the time. I had to learn how to become flexible and to not expect the days to go the way I wanted them to go. But I knew I was at the right the place.

You’ve built quite a legacy at Cisco, all while supporting John. What programs did you put in place at Cisco and how did you acquire those new responsibilities?

Although I knew I was in the right place at Cisco, and I was happy, the voice in my head told me I could do more. I walked into John’s office and asked if I could start partnering with him more. I explained this would entail attending meetings and traveling with him. Essentially, I wanted to start shadowing him and learning all I could. John said, “Debbie, I hired you to be my executive assistant. I need you to be my eyes, ears and feet on the ground. I don’t want you with me. I want you at your desk, keeping me informed and helping me run this company.” That’s when I realized, the importance of my role in being his Executive Assistant.

I decided in order to move forward, maybe I could do more within my own Executive Assistant’s role and still be supporting him. At that point, I launched the very first internal executive assistant staff meeting with the 13 Cisco executive assistants. It opened a huge number of doors for myself and for the other executive assistants. We started working on initiatives that we felt would really benefit Cisco and the administrative community. This is when I began to see that there was no limit to what we as a team could do or what I could do as an executive assistant. I feel our true abilities shine when we move beyond what we’re expected to do and explore our own potential. I feel some executive assistants experience a resistance to move beyond their traditional responsibilities. It’s called Leadership which is so much more than coming, doing the job and then going home. Leadership, to me, means stepping up and going beyond expectations.

Through the internal executive assistant staff meetings I started at Cisco, we created the Reward and Recognition committee, a mentoring program, and conducted annual all-hands administrators meetings. Then, just two years ago, I became aware that a lot of our administrative professionals were actually working remotely and were very isolated from the Cisco culture. In response, we created a team called G.R.A.C.E., which stands for Global Remote Administrators Connecting Effectively, to bring together remote Cisco executive assistants quarterly to share best practices, challenges and opportunities unique to being remote. All of these initiatives became a part of Cisco’s legacy. We did something that no other company has ever done all because we saw there was no limits to what we could bring to our administrative community and our company.

You’ve taught numerous classes at Cisco, then at UCSC Extension, and now for Office Dynamics. How did you break into teaching?

Back when we were lifting these initiatives off the ground, I started becoming very comfortable in my stride (again in my comfort zone). At this time, we were constantly hiring. HR came to me and asked if I would feel comfortable getting in front of a class of administrator new hires and teach them about Cisco company culture. Although I was excited for the opportunity, I had never spoken in front of a group before and I was terrified! Again, the voice in my head told me to just try it. Cisco got me a coach to help me learn to present. I came prepared for the first class with some great exercises and slides. The administrators in the room were getting it and heads were nodding and we were having fun! When I walked out of that room, I was walking on air. I had never felt that way in my entire career. That was the turning point for me in terms of finding my passion, and it was all because I took a risk and faced my fears. Shortly after that, I became certified to teach a program called Star Achievement. At Cisco, I taught three levels of that program and it just continuously fueled my passion for teaching, all while still supporting and learning from John.

Then, I was asked to join an Advisory Council for administrative training programs at UCSC extension. I attribute that opportunity to my network. Something I’m always trying to press upon administrative professionals the importance of nourishing and broaden their network. Your network can bring amazing people and opportunities your way. I’m now a founding member of an organization called SVCA, which stands for Silicon Valley Catalyst Association, with EAs that support CEOs in the Silicon Valley. It’s because of that group that I got into a conversation with UCSC Extension to create administrative training programs like no other ever created, focused on communication and project management. I’m a guest lecturer on a number of different topics for that curriculum.

What advice would you give to seasoned executive assistants?

You have to pay attention to the voice in your head and your heart.

If you’re going through a period of frustration, aren’t happy in your career, or feel like you want to do more, that’s your inner voice saying to pay attention and take the necessary risks. Step out of our comfort zone. You aren’t guaranteed any sort of result. But by taking a risk, you’re still doing something entirely new and different. Through that process, that’s how you find passion have the ability to take your career to a whole new level.

Passion is a mindset. You have to say “I can” instead of “I can’t”. There are certain philosophies to making your career the best it can be. Don’t be afraid to try something new, don’t limit yourself and realize that sometimes you will make a mistake, but that’s how you learn. By following that voice in my head and my heart, I went from working at a small company as a customer service manager, to being the executive assistant to a worldwide known CEO and then to finding my passion and my calling in training and coaching administrative excellence to others.

Typically, EAs support their executives, but they cannot see beyond that. There are so many other things they could be doing to help their organizations and their administrative community. I say look over the cube or office wall. Seek out a direction that will help you grow. Maybe it’s taking on a new project that you haven’t done before, or maybe it’s finding a mentor (or two) who can help guide you.

Here is are some things I recommend:

1. Become a master communicator. Develop communication skills as this is vital in communicating with your executive and with other stakeholders throughout your career.

2. Build relationships. I don’t think EAs fully understand the value of networking. Go to administrative conferences to meet others who are similar to yourselves! Engage with people who have different perspectives. If you want to expand on your career, reach out and meet people.

3. Step out of your comfort zone. Don’t limit yourself! There’s no manual that tells you how. It’s all about finding that out on your own. You can stay in a box where you are comfortable but you may miss amazing opportunities. When you step out of your box and your comfort zone, you will find unbelievable things happen.

What advice would you give to newer executive assistants?

1. Find a mentor. If you are looking to take the next step but aren’t sure how, find a mentor. When you start out in your EA career, there are things you aren’t going to inherently understand, for example the political landscape of your company. Find a mentor and absorb all knowledge you can from them.

2. Know the business.

Pay attention to the business that you are in. Don’t miss the opportunities because you aren’t paying attention and learning about the business. Your job is much bigger than you think, but you have to see that. Read Wall Street Journal or USA Today. Read what your executive would be reading.

3. Have executive presence.

Dress the part. Look the part. Enter a room with executive presence. Be the brand. Even if your dress code is business casual, be smart business casual.

Any last words of advice?

If you are an administrative professional, love what you do. Realize that no one does it better than you because you love helping people! A true EA loves what they do and will continuously learn new things and develop themselves to their fullest potential and bring passion to the role!

The Executive Leadership Support provides innovative tools to aid assistants in their daily tasks. Through interactive discussions and team building activities, attendees gain crucial skills alongside fellow executive assistants. To learn more about supporting more than one executive, managing and motivating an admin team, or other high-level topics for those supporting the c-suite, attend an Executive leadership Support forum near you!

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