Five Keys to Getting (and Keeping) a Great Executive Assistant

When Eugene Nizker, then CIO of Custom House Currency Exchange in Vancouver, first met Jessica Raichl, he doubted her ability to be a great assistant. For one thing, she seemed young for the responsibilities of the job (she was 24). For another, when faced with her trademark energy and optimism, he thought she was “putting it on.”

In fact, she turned out to be the real deal. Raichl won him over in the interview, and although they both left the company toward the end of 2006—she for a temporary stay in China with her husband, he to become an executive at PRJ Group—Nizker would be thrilled to hire her back. Four years later, he speaks of her in glowing terms, and it’s not hard to understand why. Even her photo and e-mails pulse with enthusiasm and motivation. His team “loved her”—she executed her day-to-day duties and more, often working 10-hour days. She found frugal ways to acknowledge everyone’s birthday, ordered out food unasked when the team was working late, protected Nizker’s time and protected the department from the cops (more on that later).

“Indeed, my assistant was the face of the entire division,” says Nizker. “The amount of energy and enthusiasm in this young lady is unbelievable.”

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Great assistants take pride in anticipating what an executive needs before he even needs it, in being organized and reliable so that the department runs seamlessly, and in being just the right mixture of friendly and protective. For their part, great bosses are equally protective, providing generous amounts of appreciation, opportunities and training.

Thomas Jarrett, CIO and secretary of the Delaware Department of Technology, has also been blessed with a wonderful assistant. Dawn Hill, Jarrett’s executive secretary, was working in the governor’s office when she heard that a new department was being created. Jarrett was charged with dissolving the old Civil Service IT department and rebuilding it from the ground up. “It was literally like starting a startup company within state government,” he says. Building a department from scratch, an IT department that would be run like a business, with a team that was performance-based and a compensation schedule set by Jarrett and company. An unusual situation and challenge to be sure. Jarrett’s assistant would have to help him build a department from scratch, and since he came from the private sector, helping him and his department build relationships throughout the state government would be critical. He or she would also need knockout interpersonal skills, availability 24/7, the ability to accomplish secretarial duties while helping to build relationships with everyone from the governor to legislators, judges, representatives of the school systems and so on.

Because a newly created department was clearly an exciting opportunity, and because the compensation would be competitive, Jarrett had no shortage of interested candidates, but Hill was the only one he spent two hours talking with. She was motivated, enthusiastic and proactive—she had done her homework on what the job would mean.

That was in 2001. Five and a half years later, Hill is a key member of Jarrett’s senior team. She had a tall order to fill and she went beyond it. Hill is also now a BlackBerry go-to person. Many of the legislators who have trouble with their BlackBerry bypass the help desk and reach out to Hill, whom they know will walk them through the problem gently.

A good admin is hard to find. “Executive assistants are one of the hardest positions to fill,” says Jill Cotter, sales planning and support manager at Manpower. They must be computer savvy and know multiple applications; manage technical issues, e-mail and scheduling; create presentations; exhibit the right (and varying) level of formality with people from all levels of the corporate structure and anticipate the needs of their executives. “A lot of people we place can really run the ship,” she says. But lucky for busy executives, it’s not the spotlight they crave but the satisfaction of organizing, of coordinating, of making things happen behind the scenes.

The actual title can vary by company and scope of responsibility—executive secretary, executive assistant, administrative professional, administrative assistant. But whatever they are called, assistants in a very real way represent you and your organization. “One person wrote to me, ‘Your assistant was the first person I saw when I interviewed and I have to say, your company has the right face,’ ” says Nizker. That’s just one reason it’s so important to find the right person and do everything you can to keep him or her. The question is, How?

1. Be the kind of boss you’d be excited to have. The overarching answer to having great staff is not found in a weekend management seminar or article on how to sift through resumes, it’s this: Be respectful, appreciative, honest and open, and encourage others to be the same—even when that’s difficult. “If I’m frustrated, he’s the first person I go to,” Hill says of Jarrett. He listens and empathizes as well as he talks. This openness even extends to those rare occasions when he’s been the source of that frustration. “I probably couldn’t have done that with others,” she says.

Hill can’t say enough about her admiration for Jarrett: “He’s an extraordinary human being.” About Nizker, Raichl says, “Eugene truly cares about the people he works with.” When Nizker learned that Raichl’s time was being “abused” by another department, he was quick to play protector and put a stop to the situation. “He’s a great leader, communicative and his door is always open,” she says.

Genuine concern for and appreciation of others is clear when speaking with Nizker and Jarrett. Says Jarrett: “Lots of people think it’s mystical, but you reap what you sow. If you’re respectful and open and honest, for the great majority, that will come back at you.”

2. Be specific about the job requirements and the working environment. For hiring managers, it’s critical to spell out job responsibilities very clearly, says Cotter. Don’t just say “computer skills”; say exactly which ones you expect and highlight emphases of the job. If a focus of the assistant role will be to create presentations or schedule events, point that out. The executive assistant has many skills, says Cotter, but every job varies in terms of its focus.

Nizker has a long list of well-articulated requirements. “When I started thinking about the role of assistant, I saw so many diverse qualities I was looking for, so I decided to write it down,” says Nizker. This resulted in “Candidate Parameters,” his matrix of skills, broken down into such areas as organizational skill, planning, Microsoft Office, writing skills, some human resource duties—even creating and maintaining a user group. He also created three writing tests, each designed to ferret out particular skills:

• Letter to the company introducing a monthly newsletter from the tech division.
• Letter to a governmental body asking for a deadline extension.
• Letter to a vendor expressing disappointment in the current level of service, but with which the company wanted to preserve a relationship.

Jarrett’s process is less structured. He looks for demonstrations of initiative, and spends time understanding the background of candidates. But he does have clear expectations of what his assistant’s job would entail, and he discusses those expectations with candidates.

Also be specific about the work environment, what the pace is, what human qualities are valued and what the general atmosphere is like. “I find it very important that the team has a good culture, moral and work ethic,” says Raichl. Also, be clear about time expectations. Needing to be available on weekends, for example, may not faze one person but would put others off immediately.

From the assistant’s point of view, what should you be looking for? “The number-one quality a successful admin or executive assistant should possess is his or her ability to match the executive’s judgment and be able to anticipate what the executive or team require before they realize it,” says Raichl.

“I like to think I can handle myself in any situation,” says Hill. “I’m always going to have a positive attitude even when I’m frustrated,” she says. She also points out that it is key for the assistant to be “a people person,” especially the ability to blend with different kinds of people. One critical area: The assistant must have the right balance of friendliness and firmness. Because of Jarrett’s busy schedule, “there’s a lot of days I say no to a lot of people,” says Hill.

Saying no and making everyone love you at the same time is tricky. Nizker notes how important it for the assistant to have just the right amount (and kind) of protectiveness. He freely acknowledges that Raichl protected him so well that he rarely knew what she was shielding him from. Back to that police situation: When Raichl fielded a call from the Vancouver police saying they needed to ask questions of one of the IT staffers, she would not let them come. Instead, she arranged to meet them rather than have them come to the office.

Jarrett says of his assistant, Hill: “Peers and vendors chuckle at how protective she is, but having said that, they rave about how if you ask her to do something it will get done.”

3. Pay attention to your gut. It’s important to balance the professional and administrative skills with a personal connection that will make or break the relationship.

Nizker says that when he met with Raichl, she had “this light in the eyes, she was emanating it.” The chemistry between the assistant and his boss is “mandatory,” says Raichl, an opinion shared by everyone interviewed for this story.

“I hire people on gut instinct and it has served me well,” says Jarrett. He spends time understanding background, skills and such, but beyond that, he adds, “it’s the thing of someone sitting in front of me, and [whether] I get a feeling of comfort. It’s all about the connection.” Still, a lot of feeling is based on tangible qualities. For example, Jarrett recalls that Hill had the right skills, she showed enthusiasm, and she had done her homework on what the job would be. “If you’re staring back and not saying much, it’s pretty much over,” he says of a candidate’s lack of enthusiasm and initiative.

In interviews, Cotter recommends asking questions about qualities or skills you consider crucial, as well an eliminating question. Go beyond yes/no or rote questions. Ask story-based questions, which are useful in illustrating character. For example, ask the candidate to tell about a time she dealt with a setback or went the extra mile. In any interview—by phone or in person—these kinds of questions help you determine if you can work well together.

4. Create a work environment of trust and possibility. “Stability, room for growth and challenge are the main factors” that Raichl looks for in her career opportunities. Nizker provided the environment for her to stretch and learn. “I told her in the very beginning that she will have a lot of freedom and she will have to use it wisely.” She quickly proved herself.

Nizker says he provided coaching and mentoring. “Whether I received a new task that I am unsure about or needed advice on how to handle a certain situation, I never felt awkward asking no matter how silly it may seem,” says Raichl. “Eugene is approachable and takes the time to listen.”

The same can be said for Jarrett. He says “a good employee’s job is to want to get better; our job is to make them successful.” When Hill became interested in the more technical side of BlackBerry use—to help her state government colleagues when they have problems—Jarrett encouraged her and arranged for training. Now, in many cases “legislators call her directly” when they have problems with their BlackBerry.

5. Don’t take assistants for granted. And then there’s appreciation—lots of appreciation. Raichl says of Nizker, “a job well done was always acknowledged.”

Cotter, the Manpower staffing manager, recommends publicly calling out assistants for a great job whenever possible. (Both Nizker and Jarrett, for example, nominated their admins for CIO’s Best Admin contest, in 2006 and 2004, respectively.) Public acknowledgement is especially important for a role that, by its very nature, tends to be behind the scenes. It can be easy to forget how an assistant can be the glue holding everything together. Cotter also recommends offering training as a reward.

Beyond these overt gestures, what distinguishes both Jarrett and Nizker as bosses is a deep-rooted recognition of the value of their assistants.

Says Jarrett, “In the end, the big thing for me is that [my staff] wants to be here.” So how do you keep a great admin? “That’s easy,” says Nizker. “Trust, and let them fly.”

Send feedback to Associate Online Editor Diann Daniel at ddaniel@cxo.com.