Hiring and Retaining the Perfect Executive Assistant

— Sep 9, 2018 —

As an executive, are you scrambling to keep things together on your own? Maybe your workload has finally increased past the point where you can handle it all yourself. Or maybe everyone in the C-Suite is getting overloaded.

It might be time to hire an executive assistant.

According to Jamie Resker, president and founder of Employee Performance Solutions, “If a manager is doing a lot of travel or is getting bogged down by lots of low-level coordination, hiring an executive assistant could free them up to focus on revenue-generating techniques.”

Lots of people resist hiring an executive assistant until they’re completely overloaded; so by the time you decide to hire, you might feel like you can’t wait another day. But before you hire the first competent applicant who walks through your door, remember that your assistant can be one of the most essential members of your team. They will likely handle everything from scheduling to financial documents to acting as the face of the company, and the right person can make all the difference.

You need to think not just about hiring a great executive assistant, but one who fits in. They need to be your right-hand man or woman—someone who will stick around, and with whom you can develop a true rapport. When you’re hiring an executive assistant, slow down and take the time to do it right.

Joan Burge, author of Become an Inner Circle Assistant, says that, “People think it’s a simple thing, that it’s no big deal to hire an assistant—but that’s a problem….You have to put time and effort into it if you want to get the right person. The idea should be to get a very good match, a person who will stay and grow with you.”

A note of caution: be careful that you’re hiring for the right position. Executive assistants, personal assistants, and office managers have much in common, but their job responsibilities do differ, and using the correct job title in the job description will attract the right pool of applicants.

Hiring a personal assistant is a whole different “beast” from hiring an executive assistant, because the former will handle significantly fewer business matters. An office manager will focus on responsibilities surrounding the office, likely overseeing other administrative staff. Here, we discuss executive assistants, though many elements of the hiring process will be similar across positions. If you are looking into hiring a personal assistant or office manager, you can look at these tips for hiring an executive assistant, and use executive assistant interview questions and answers as a guideline to start your search.

Hiring a Great Executive Assistant

Defining the Job

You don’t just need to hire the perfect executive assistant—you need to find the perfect assistant for you. When compiling the job description, be thorough and honest about everything you need.

Your assistant may end up doing any of the following, and more:

• Handling your schedule, and making changes as circumstances necessitate
• Making travel arrangements
• Preparing financial statements, handling invoices, preparing expense reports and meeting agendas
• Running point in your absence
• Acting as the face of the company in varied interactions
• Using various software programs, such as Microsoft Office, Adobe, Concur, Quickbooks, SalesForce, and Social Media
• Screening phone calls and visitors
• Organizing inbound communications, such as emails and paper mail

The more comprehensive the list of tasks in the job description, the less likely you’ll end up with a disillusioned assistant who expected something totally different.

If your assistant will be working with more than one executive, discuss these responsibilities with them. Figure out how your new hire’s time will be allocated. Make sure that everyone who will be assisted by this new hire is part of the executive assistant hiring process.

Be specific about what you’re looking for, from prior experience to personality traits. Let potential applicants know what the company’s culture is like, and what you are like. Don’t waste your time or theirs by pulling punches when it comes to stating exactly what you need.

How do you find your executive assistant? You need to decide if it is important to you to cast the widest net possible. Also, how quickly do you need to hire? To cast the widest net and for the speediest hire, make use of several approaches all at once.

You might make use of your personal and professional networks. Someone within your company or who knows you well can recommend candidates who fit into your culture. You may try posting the job on your company’s website, or on other job search sites, but don’t be surprised if you are inundated with unqualified resumes. For this to work you need an internal person with the time to screen resumes and do initial interviews. To save time and be sure to get the best talent in the market, you may also consider hiring a staffing firm that specializes in the placement of Executive Assistants, such as C-Suite Assistants.

The Executive Assistant Interview Process

The interview process for your assistant should be thorough. It may seem at this point that you just need to get someone on board to help you out, but the key to employee retention is hiring the right person for the job in the first place, so take your time.

If conducting the search on your own, you may begin with a phone interview, and then move on to multiple in-person interviews. If you are using a staffing firm, they will save you valuable time, by screening potential candidates on your behalf to make sure the candidates are a total fit in terms of skill set and personality and also that they are within your compensation range. A good staffing firm will also test the candidates’ computer skills, spelling and grammar; and assess their emotional intelligence. By the time you receive resumes from your trusted recruiting partner, you should be ready to look the resume over and set up an in-person interview.

Executive Assistant Interview Questions and Sample Answers

When conducting interviews, you will want to choose interview questions that help you make sure your candidate possesses the following:

• Organizational aptitude
• Ability to multitask
• Discretion with private or proprietary information
• Capacity to diplomatically screen phone calls / visitors
• Problem-solving abilities
• Software expertise

Ask story-based questions. This allows the interviewee to take charge of the conversation, and avoids simple “yes” or “no” answers. You want to see their personality come through in their answers.

Here are a few sample executive assistant interview questions and answers to help flesh out whether a potential assistant is right for you. Listen to the way they tell their stories. Are they concise or do they digress and tell stories that wander? Do they take credit for everything or blame others for failures? Do they anticipate and take responsibility? Try to imagine them as your spokesperson.

Q: “In your previous position, can you give an example of a time when scheduling had to be changed last minute, and how you dealt with that?”
A: The candidate should show an ability to be flexible, creative, and think on his or her feet to minimize inconvenience.

Q: “A frustrated client wants to speak with me, but you know I am in meetings all day and will not have the time. How will you address this situation?”
A: The candidate should show strong emotional intelligence, and an ability to diffuse the situation while respecting both the client and the executive’s schedule.

Q: “How do you handle multiple competing deadlines? Give me an example.”
A: The candidate should show multitasking skills, the ability to prioritize effectively, and coolness under pressure.

For more great executive assistant interview questions and answers, check out this article on indeed.com.

When you’re creating a list of executive assistant interview questions (and analyzing their answers!) look for a combination of competence and values-fit.

Last but not least, don’t fall off at the end of your hiring process. Once you have made your final decision, begin the reference checking; either conducting them yourself or through the agency. Speak to at least three references, including one former boss. Get that job offer out as soon as you possibly can. Your prospective new hire is probably polished and talented, so he or she will be in high demand. Don’t drag your feet and risk losing an excellent employee to a competitor.

Retention: Keeping the Executive Assistant You Hired

If you did a thorough job in your hiring process, you’ve already done half of the work when it comes to retaining your assistant. They are perfect for you and your company. You just need to make sure both of you remain happy, and that they continue to feel like they are getting what they need out of this position.

In particular, pay attention to:

• Communication
• Trust
• Boundaries
• Career Development

An Open, Trusting Relationship

Communication is key. Schedule regular check-ins so that you have a set time to go over anything that’s on either of your minds, outside of your busy day-to-day hustle.

Positivity is also important. Remember that when things are running smoothly, it’s because your assistant is on the ball, and express your gratitude.

Beyond simply communicating, it is essential that you develop an honest relationship based on openness and trust. As time goes on, your assistant will be able to anticipate your needs, so don’t be afraid to give them more responsibility. Trust is earned, so make sure to give it once it has been.

Lastly, set boundaries early on. Make sure that your assistant knows at what time of night you will not contact them unless there is an emergency. Even if your brain never strays from work, they deserve to have some time on nights and weekends to unwind. The same goes for vacation and sick time. Don’t let your assistant burn out.

Career Development

Chances are, if you’ve got a great assistant, they aren’t satisfied unless they’re learning and growing. Find out what areas interest them, and support their continuing education. If you work in a large company with more experienced assistants, set up a mentorship with someone they could learn from.

With the right person, open and honest communication, boundaries, opportunities for development, and appreciation expressed when it is due, you can hope to keep your amazing executive assistant for years to come. And if you need help hiring the perfect executive assistant, turn to a trusted recruiter like C-Suite Assistants, specializing in the placement of Executive Assistants since 2003.

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