Former assistants turned star CEOs weigh in: Is your assistant ready for the C-suite?

By Bonnie Low Kramen for Smart CEO | April 4, 2016

Can you picture your executive assistant as a C-suite executive? If you didn’t instantly say “No way,” this could be an exciting idea worth exploring.

Ursula Burns

Take Ursula Burns. She worked as an EA at Xerox, and now she is the first African-American female CEO of a Fortune 500 company. When Burns started as an intern at Xerox more than 30 years ago, she had no idea that she would someday end up running the company: “I just chose to work. The best way to get the best out of people is to not force them to be something other than they naturally are. Where you are is not who you are.”

Then there’s me. For 25 years, I worked as a personal assistant for actor Louis Zorich and his wife, Oscar winner Olympia Dukakis. After Louis and I had successfully collaborated on purchasing not one but two homes abroad, he quipped, “Bonnie, I really think you could run a company.” He turned out to be absolutely right. I founded my own company, and today, I consult with, speak to and train high-level executive and personal assistants all around the world.

My work began as Olympia’s assistant, filling needs such as organizing her busy schedule, arranging cars and hair stylists, and handling correspondence. At first, I didn’t even know there was a name for my role. When Olympia said she wanted me to handle the purchase of a house in another country, my response was, “I’m not sure I know how to do that.” She just said, “Of course you do. We’ll figure it out together.”

Bonnie Low-Kramen (center) with Olympia Dukakis and Louis Zorich

In the aftermath of her Oscar for Moonstruck, Olympia decided that I should handle pretty much anything and everything that she did not have to do, so she could be free to do the things that she wanted to do. My skill set expanded as the demands increased. It was never dull, that’s for sure.

Olympia would tell people that we worked “with” each other, rather than I worked “for” her. She insisted that everyone in her life — without exception — respect me for the role I played.

As a busy CEO, I strongly recommend you take a fresh look at the assistants in your company. They are the backbone of your business and the right arms to their managers. Plus, they are already on your payroll, and they sit 10 feet away. Their skill sets certainly include being highly organized, resourceful and detail-oriented, but beyond that, you may very well have a few individuals who aspire to higher things — such as a position in the C-suite.

C-suite EA or C-suite VP?

Consider that you might have a mid-level assistant who is fully capable and ready to support a CEO or VP executives. With mentoring, coaching and specific professional development, you may be grooming your next chief of staff.

It also could be that a C-level executive assistant is ready to be groomed as the next SVP or beyond. That too will take mentoring, leadership training and sponsorship, but know that these go-getters do not need much to take flight. These are not people who need their hands held. Mainly, they need to believe that you, the CEO, believe in them.

Whoopi Goldberg and Tom Leonardis

What are the signs an EA is ready?

One of the signs is that the EA is a sponge for knowledge about the principal and behaves like a stakeholder in the brand and the company.
Take Tom Leonardis, who started out as Whoopi Goldberg’s personal assistant and producer 22 years ago — with no end in sight. Tom is now president of Whoop Inc. and has been nominated for both an Emmy and a Tony. He has met the Queen of England and enjoyed many events at the White House with the Clintons and Obamas.

“I move mountains and watch Whoopi’s back. We are a rare breed who can make the move into the C-suite. I pinch myself every day,” says Tom. Whoopi Goldberg adds: “Tom and I have had a partnership for almost 22 years. He’s the adult in the relationship.”

Another sign an assistant is ready to move up: She is fearless and possesses advanced emotional intelligence, which manifests itself by people relating easily to her, including board members and staff at all levels. She is a people magnet, the go-to person, and acts as Information Central. She asks to attend meetings where she can contribute and “lean in” to the discussion as a seriously respected participant.

Going above and beyond

Still another sign is that she goes above and beyond by coming in early and staying late when necessary, volunteering for unpopular and low-profile assignments, and doing all of that cheerfully and with a positive, can-do attitude.

In addition, she may become the go-to person for technology training and advice. That describes Vickie Sokol Evans who worked as a legal and executive assistant before deciding to be the person teaching others how to best use the technology that they have at their fingertips. Vickie is now CEO of the Red Cape Company, the one Bill Gates’s team hires to train them on the latest best practices in Microsoft productivity.

“No matter what industry I was in, I could see the ways technology and automation could make things so much better for assistants in offices,” she says. “I had mentors who independently told me that I was destined for bigger things. They planted seeds of confidence in me so that when it was decision time, it was an easy transition for me. Now I have an assistant and a team of my own. Without a doubt, my experience as an executive assistant prepared me for running my own company.”

Your future C-suiter is a team player and goes the extra mile by offering to mentor colleagues and peers. Sometimes, she even creates an internal assistant network to provide networking and training between assistants. She is not afraid to voice a dissenting opinion and will offer valid, rational and relevant points of view.

This is precisely what Victoria Darragh did at Hays Recruitment in London. Victoria raised the bar at Hays by creating a successful conference for personal assistants. She traveled the world at the request of other companies who wanted to replicate what she had done at Hays. Now Victoria is CEO of EPAA, the Executive and Personal Assistants Association in the UK, and she is an in-demand speaker and consultant.

Pulling back the curtain for CEOs

Know that it is not always easy to spot the potential superstar on your assistant team. The fact is that 95 to 98 percent of all executive assistants are females. In general, women are not quick to tout their achievements or voice strong ambitions, due to early socialization which taught them that expressing their achievements can be viewed negatively. They prefer their leaders to notice these achievements on their own, rather than needing to point them out.

Furthermore, most women feel that they need to possess 100 percent of the skill set for a position before they feel confident applying for it. (In general, men don’t feel like this.) That means it’s up to you to encourage assistants to speak up. Have a serious one-on-one conversation with them. Literally say, “I really want to know what you want and what you think.”

I am thankful every day that Olympia Dukakis saw something in me that even I didn’t see, and she insisted on knowing my opinions. It took some firm urging, but it did not take long before I believed her, and then she could not keep me quiet. Once a CEO opens that door, some pretty great things can happen.