For 26 years, Debbie Gross made it her business to know everything about John Chambers.
As the Cisco CEO’s chief executive assistant (CEA), Gross was much more than Chambers’ “right-hand woman” or “girl Friday” or any of the other cutesy clichés that fail to capture the immeasurable value of administrative professionals who ensure their company’s seemingly effortless efficiency. Over the years, Gross had proven herself wholly indispensable, serving as the liaison between the hard-working head honcho and his professional circle.
So it was no surprise Gross was in the room as Chambers dictated her nomination for the Admin Awards’ coveted Colleen Barrett Award for Administrative Excellence, describing her as “an example of what administrator excellence is all about both internally and externally, in the valley and all over the world.”
What was surprising, at least for Gross, is that Chambers had come to know her accomplishments just as well as she knew his. In the midst of that realization, the tears began to flow.
“We worked so hard and fast together every day,” Gross says. “One of the things that he said was how productive and effective I was at making him productive and effective.”
In their time together, which came to an end in 2017 following both of their retirements, Chambers couldn’t say enough about Gross’ talent, routinely proclaiming that “I couldn’t run Cisco without her.”
His heartfelt words and description of her cutting-edge work in the CEA role – including her development of Cisco’s administrative training, mentorship and rewards programs – led to Gross’ win at the 2016 Silicon Valley Admin Awards, where her revolutionary work shone a light on CEAs and the incredible feats they accomplish every day in offices around the globe.
Because while it’s true that Gross didn’t invent the title of CEA, she did exemplify it, embracing the role’s most important qualities: advocacy, drive, vulnerability, teamwork.
“When I won, I said ‘This is mine to earn,’” Gross says. “I just really came to a major awareness that I have changed the way people look at this job, the ways administrative professionals focus and work at Cisco. Outside of Cisco, I was teaching and speaking and sharing the vision of how we can be so much more than we think we can be. So to me, that award is everything. It’s a little shrine in my office.”
The road to CEA
When Gross showed up to interview for the executive assistant position at Cisco in 1991, she was one of 17 applicants. She had seen the job posting in The San Jose Mercury News, and decided to take a chance – after all, she had previously worked as an executive assistant for a PC board provider and in office management at a tech company.
At the time, Chambers had only recently joined Cisco himself, as senior vice president of worldwide operations. The tech company was still relatively small, about 560 people, but the work load was sizable. Chambers needed an assistant who could help him maintain his work/life balance, and Gross stood out from the pack.
“He knew right away, within the first 30 minutes, that I was the kind of person he was looking for,” Gross says. “There’s a lot of average out there, and I never thought of myself as average.”
In 1995, Chambers was promoted to president and CEO of Cisco. Gross felt a title change was in order for her as well – not only had the company expanded significantly in the past four years, but so had her day-to-day responsibilities. In addition to ensuring Chambers’ daily productivity, she also had become the leader of Cisco’s global administrative team.
Following a conversation with fellow members of the Silicon Valley Catalyst Association, who were all working at the CEO level, she began to question her title.
“We all thought, ‘We should be calling ourselves chief executive assistants,’” Gross says. “I thought, ‘I am working for the CEO, I am at a senior level and I am doing things that EAs in our company are not doing.’”
So she went to Chambers with a simple request: Change my title from executive assistant to chief executive assistant.
“He had a big smile on his face, and said he loved it,” Gross laughs, “but it didn’t come with a raise. He did recognize that it would distinguish me from the crowd.”
Defining the CEA role
Even though Gross’ title change was initially spurred by the fact that she was an EA to a CEO, she says there are far more important factors to the job than who your boss is.
“I gave John the reasoning behind why I earned that title — and it takes a specific type of person to earn it,” Gross says. “You have to build excellence in your skillset, have a mind for business, be strategic. As a result, we become valued and indispensable, and our executives see us as business partners.”
Part of the way Gross established herself as indispensable to Chambers in the CEA role was to anticipate his professional needs, whether that meant preparing him for events or ensuring that scheduled phone calls or face-to-face meetings were always merited. In her two decades as a CEA, Gross became nearly as legendary as her boss. Other CEOs took note of her trailblazing work – how she meticulously prepared Chambers for every briefing, conference, sporting event and sales pitch, gathering details on everyone in the room or on the golf course.
“John wanted details, he always asked a ton of questions. I learned very quickly that I had to have a lot of answers for him,” Gross says. “I developed templates that had specific areas of information that I knew John wanted, whether it was customers’ existing revenue, biographies, how a person pronounces their name. John was stickler for how he interfaced with people. Sales people hated me because I wouldn’t let them get near John unless they had great information to share. As a CEA, you have to develop templates and processes that allow you to be effective when people are asking for your exec’s time. You don’t want them spinning their wheels when they could be doing something else.”
Effective CEAs also should have a healthy sense of curiosity, Gross says, not just providing answers but also asking questions to better understand their boss, their company — and by extension, their own role.
“John would be very open in educating me on his thought process,” Gross says. “As a result, it allowed me to not only make good decisions for him, but allow me to communicate for him as him. I had to be John or act on his behalf. Knowing how John thought was invaluable for me in bridging that gap. Healthy curiosity is important. Always think about the ‘why.’”
Additionally, Gross says, a great CEA does more than just support their CEO — they establish themselves as leaders within their company.
“I truly cared in a bigger-picture way about the administrative community,” Gross says. “I actually can’t say that I signed up to be a leader; leadership became part of my DNA. I was an advocate for the administrative community. I wanted fairness in terms of promotion, pay, contractor vs. full-time employee. I built teams that provided awards and recognition and mentoring when new people came in. Changing the profession, and others’ worldview of it, became a mission for me.”
So what to do if you think you’re ready for the transition to CEA? First off, Gross says, you shouldn’t be afraid to ask.
“If you don’t have the courage to ask, you’re not ready for the title,” Gross says. “If anyone wants to rise to that level, they have to come prepared to ask for it. If you don’t ask, you don’t get. Tell them why you deserve it. It’s like you’re training to fly a fighter jet — a lot of people won’t make it. But those who do will fly that jet and become the elite of the elite.”
Sharpening your skills
After nearly three decades in the business, Gross is practically a superstar among EAs. She sits on the Advisory Council for administrative programs at UCSC Extension and hosts in-person sessions and webinars for Office Dynamics. She also just launched her own website, debbiegross.com, which offers workshops on topics ranging from creating successful business partnerships to communicating with confidence.
“I’m a trainer for administrative professionals,” Gross says. “I want to see them up-level their skills. I’m all about building exceptional business administrators. If you teach administrative professionals how valuable they are, and once they can recognize and add that value, they become true business partners.”
Gross advises EAs and aspiring and current CEAs to always look for avenues to better themselves, whether through conferences, in-person workshops or webinars. Some of her favorite resources include Office Dynamics and the American Society for Administrative Professionals (ASAP).
“Office Dynamics offers free webinars, online training, and in-room training, and ASAP has free webinars and online training. Both of those organizations are two of my top picks, and they hold annual conferences,” Gross says. “Make it part of your plan to go to a conference. Get over the cube wall and see what’s going on in the big picture. You come back with so many new ideas and so much motivation — these conferences are so energizing.”
She also advises staying up-to-date on trends within the industry, and to be aware of your own strengths and weaknesses.
“Get a mentor or coach, read inspirational books, go online, go to in-room classes,” Gross says. “Do an assessment — develop a plan to address your weaknesses. Work on building excellent communication skills. There are tons of resources out there. And know what’s going on in the world. That’s what’s going to affect you. What your exec is interested in is what’s going on in the world. It’s a much bigger-picture role.”
And while Gross is a wealth of knowledge when it comes to the CEA role, her main piece of advice for surviving and thriving as an executive assistant is to cultivate the skills that make you stand out from the pack.
“There’s going to be a time when AI will come into play and replace the tasks that some administrative professional are doing today. But admins who are doing the strategic thinking and building relationships are not going to be replaced,” Gross says. “It’s up to all of us to change the perception of how we’re viewed, who we are and how we operate.”
Top 5 qualities of a CEA, according to Debbie Gross
- Driven – “What you’re doing should make you relevant and valued.”
- Team-oriented – “Don’t ask your assistants to do anything you wouldn’t – or aren’t – doing.”
- Advocacy – “I had a lot of administrative professionals in my community, and I wanted to be an advocate for my community.”
- Curious – “I had to ask questions. I wasn’t good at that in the beginning, but over time, I realized I had to not just have the answers, but ask the questions, too.”
- Great communicator – “How you communicate, whether personally or professionally – you have to take that to a higher level.”
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