Guide to Finding the Right Executive Assistant for You and Your Organization - Senior Executive
Executive Assistants 8 min

Guide to Finding the Right Executive Assistant for You and Your Organization

Executives who are involved in the recruiting and onboarding of their EA are better able to ensure compatibility and build a strong working relationship from day one.

by Kimberly Valentine on November 9, 2021

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  • Define your executive assistant’s responsibilities in the job description

  • In interviews, ask how candidates balance their executive’s tasks and their own

  • As offices reopen, expect more competition for top EA talent

Hiring an executive assistant can ease the load on the executive and contribute to a company’s growth and increased efficiency. An executive assistant (EA) may carry a range of responsibilities, including keeping executives on track with their short- and long-term priorities, establishing relationships with various departments and stakeholders, and serving as a key resource for the facilitation and development of company projects.

The value proposition of executive assistants: They are “able to leverage their abilities and their strengths to help the executive buy back time,” says Hilani Ellis, a veteran executive assistant and founder of Exceptional Admins, a staffing firm specializing in administrative roles.

When looking to fill the role of an executive assistant, it’s important to understand that there is no one-size-fits-all job description — the role should be adapted to the needs of each company and, particularly, the executive whom the EA will assist.

While Ellis believes more and more executives are approaching the executive assistant role as a true strategic business partner, traditional stereotypes still exist. “In society, the profession has evolved from secretary to executive assistant. However, the professional environment is stuck in between that evolution,” she says.

When hired appropriately, however, skilled EAs can be business leaders and deft project managers. “I would say most senior executive assistants are already operating at a chief-of-staff level,” says executive assistant Donielle Markel, who has more than a decade of experience working with CEOs of Colorado-based technology, advertising and real estate companies.

As offices begin to reopen after nearly two years, recruiting firms such as Robert Half are seeing an increasing need among clients for administrative assistants and EAs, says Stephanie Naznitsky, executive director of Half’s administrative practice group. It’s created a war for talent, and executives will need to examine the level of responsibilities assigned to their EAs and develop ambitious career-advancement paths to attract the best candidates.

“It’s great to see so many executives involving their assistants in the operational side and the strategic side of the business,” says Linda McFarland, a senior executive assistant to C-level executives at major Silicon Valley technology companies.

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How to Craft a Job Description for Your Executive Assistant Role

Organization and communication are the core strengths to look for in your next executive assistant, Ellis says.

To establish a list of duties that an executive assistant can take off an executive’s plate, Ellis encourages executives to create a document with two columns. “Column one is defining the tasks that they do day-to-day that keep them on purpose to their own mission and goals,” she says. “The other column is the tasks that cross their desk that take them fully off purpose, as well as tasks that they procrastinate doing or they find themselves frustrated doing.”

The second column will likely reflect duties best assigned immediately to your new executive assistant.

Think long-term as well. What skills and functions do you anticipate needing from your executive assistant in the future as your role and your company grow?. “Every executive has a unique set of expectations based on their priorities, and those will evolve over time,” Naznitsky says. “Not only do you want to evaluate what skill sets you’re looking for today, but what their opportunities for development and growth will be in the future.”

Also, consider the boundaries of your working relationship with your next executive assistant. Will your EA have access to your email? Have the authority to respond on your behalf? To sign documents on your behalf? Not all executives are comfortable granting this level of access and authority. “I typically live in the CEO’s sent box the first year to see what and how they communicate,” Markel explains.

What about personal tasks, such as picking up the dry cleaning or booking personal travel? Consider whether you intend to ask your EA to carry out such tasks, and be transparent about it.

How to Interview and Assess Candidates for Your Executive Assistant Role

During interviews for your executive assistant role, you should not only evaluate the skills and experience of candidates — but also their potential working relationship with you and your unique approaches and demands. Some executives are more visionary, high-level thinkers who may operate best without a lot of structure, McFarland explains. Other leaders may be more detailed and prefer a lot of information with clear processes in place. Discuss your respective work styles during the interview to affirm whether the EA can meet the unique needs of the executive.

Ask one key question, Ellis suggests, to determine whether an executive assistant candidate will adapt to your needs: “Tell me how you would envision our first 30 days unfolding.” She says there are three things an executive should listen for in an answer: 1) how the executive assistant plans to observe; 2) if the executive assistant plans to meet with major internal and external stakeholders; and 3) if the executive assistant plans to attend one or two high-priority calls. Each should be with the intention of learning more about the business and where the executive assistant is needed.

Ask one key question to determine whether an executive assistant will adapt to your needs: “Tell me how you would envision our first 30 days unfolding.”

Hilani Ellis, FOUNDER, EXCEPTIONAL ADMINS

A wrong answer, she explains, would be that the executive assistant wants to improve processes right away. This approach is likely to create friction with an executive. Instead, seek an assistant who is “not looking to change things at the beginning but would be excited to enhance processes later on,” Ellis recommends.

To evaluate for critical communication and organizational skills, Ellis suggests asking candidates how they take notes and how they organize their own tasks on top of their executive’s.

To evaluate a candidate’s work style and enthusiasm, Naznitsky recommends asking candidates how they’ve worked with different departments at previous employers.

How to Onboard and Build the Right Relationship With Your Executive Assistant

Naznitsky recommends creating 30-, 60- and 90-day plans to acclimate a new executive assistant with an organization’s policies and processes and to meet others within and outside of the company. An EA should know from the beginning what his or her day-to-day responsibilities are — and be aware of any wild cards that might alter routines on any given day.

Connect your new executive assistant with other EAs at your firm to serve as mentors, Naznitsky suggests, to share institutional knowledge and offer a comfortable environment to ask questions. EAs should also be encouraged to build relationships with their executive’s direct reports, McFarland says.

Just as with other team members, “you want to get to know [your EA’s] strengths and areas of opportunity,” Naznitsky advises. “You can lean into those strengths and also identify how they want to be challenged as well in their future.” As your new executive assistant is getting acclimated, make the time to show appreciation for the milestones he or she is meeting, particularly if he or she is showing proactive thinking, Naznitsky says. Set aside time to ask for feedback from your executive assistant, and assess whether he or she has all the tools necessary to succeed.

“An assistant can be really helpful when they understand how an executive operates,” says McFarland. In order to gain that understanding, executives must carve out time during the onboarding period to share knowledge with new executive assistants.

“My preferred approach is just a good-old-fashioned deep dive,” Markel says. “I just relish in a good-old, half-day whiteboard session with my CEO. I want to learn the business, the operations, who the key players are.” She prefers to ask about the organization’s mission, vision and values because she finds much more color in a CEO’s direct answers. “It helps me really wrap my brain around what drives my CEO or my executive and how best to support them.”

Establishing a strong relationship between an executive and an EA can be more challenging in a remote-first environment, but certainly not impossible. Adapting, pivoting and communicating are core skills of an executive assistant; it may just take a little longer to learn each other’s workflows. Weekly one-on-one meetings and brief daily check-ins can ensure both parties are on the same page.

“It’s really about keeping your EA in the loop of everything that is moving through the company, and asking them to be creative,” Naznitsky says. Her executive assistant, Lani Sykora, knows her schedule and, therefore, knows when and how to communicate appropriately throughout the day’s workflow, even though they’re not in the same office.


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