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10 Questions To Ask When Interviewing An Executive Assistant

Are you thinking about hiring an executive assistant?

Many entrepreneurs start off with someone on a part-time or contract basis as they’re growing their business. As the company gains momentum, the executive assistant can take on a permanent role.

More often now, however, business owners are opting for contract or project-based assistants. It saves the company money on human resources and gives the contractor laser-focus on a specific task.

Regardless, it’s essential to ask the right interview questions and be able to decode the answers.

The Top 10 Executive Assistant Interview Questions and Answers

There are helpful resources on sites such as LinkedIn…I’ve boiled down the content as a quick summary here.

1. Solid computer skills

This is an essential “hard skill” and can’t be underrated. You might have proprietary software specific to your industry. Still, an executive assistant should be well-versed in a broad range of programs on multiple platforms and an affinity for learning new ones.

Ask about their specific skillset, and take a measure of their willingness to master a new program.

2. Understanding confidentiality

Your executive assistant is going to be handling sensitive documents. How will he or she address access? Will they leave confidential reports on their desk or give in to pressure from a superior who demands they have access without checking with you first?

You want a candidate who will err on the side of secrecy. It will be your job to explain the parameters of access on a case-by-case basis so that nobody is denied vital information.

3. Practicing persistence

They’ll be tasked with setting meetings, and some of the participants will be hard to pin down. You want someone who can be dogged in their goal…without being rude.

Use interview questions to have them consider a colleague who has ignored repeated email and phone requests to secure a time and place for a meeting. How will they manage? What advice can you give them?

4. Setting boundaries

Some assistants can become the “Boy or Girl Friday” and have multiple colleagues making requests for their time and support – tasks that are outside the purview of their actual job description. Will your assistant be able to push back and set some parameters for his or her time at the office?

If he or she is managing a deadline for you and another manager makes a request for resources, how will they navigate it?

5. Rolling with the punches

An executive assistant can spend an entire week setting your itinerary, only to have an emergency or cancellation throw a wrench in the cogs. Will they be able to adapt to the shifting parameters with a cool head?

Organizing meetings can be akin to herding cats. Will they be able to seek consensus, or throw up their hands in frustration because someone is “being unreasonable”?

6. Saying a hard “no”

People – clients, suppliers, staff – expect unfettered access to your time, but that’s not practical. Can your executive assistant operate as an effective gatekeeper – or gateway – and turn people down when they make demands on your time?

You don’t want to seem inaccessible, but you have to keep a reasonable schedule that allows you time to complete your tasks. Can your executive assistant create an atmosphere of collaboration without letting everyone wander into your office for a brainstorming session…?

7. Lessons learned

What did they take away from their previous jobs? Successes…mistakes…regrets. A good candidate will be realistic about their prior experience and be able to articulate what they learned.

Don’t be afraid to ask pointed questions about their last job. They might identify weaknesses in their management team that you can avoid going forward…or they might show themselves to be chronically allergic to authority and incapable of taking constructive criticism.

8. Self-awareness

Ask your candidate to sum up the qualities of a great executive assistant in three words. If they know their strengths and understand the job requirements, those three words should come easily.

And, they should align with your company’s values.

9. Understanding the role

Does your candidate understand that they’ll be an extension of you? That they’ll have to anticipate your daily routines and fix things before you even realize they were broken?

All too often, executive assistants are considered paper-pushers who answer the phone and greet people in the office. That’s a vast underestimation.

A great assistant will be like an air traffic controller. They don’t fly the planes, but they know where all of them are at any given time and how to land them safely.

They are vital to the smooth operation of any company, no matter the size.

10. Keeping calm in a storm

Of all the executive assistant interview questions and answers you should seek, an indication of a calm, cool head is paramount. You want to know that your assistant won’t fly off the handle or panic in the face of a challenging work day.

Be sure you have some realistic scenarios for them, and pay close attention to how they respond. Walkthrough some “what if” situations…are their responses deliberate and logical, or are they asking who might be to blame for the problem you’re describing?

A great executive assistant will focus on solutions, not blame.

Do you need a short-term executive assistant or project manager?

It’s rewarding when a company grows enough that you can start hiring administrative staff to stickhandle the details – whether it’s in-house training, trade shows, webinars…

As an entrepreneur and a visionary, you’re not necessarily fond of working down a to-do list. You have ideas about how to keep building your business and need administrative support to make it happen.

If you’re not ready to hire a full-time executive assistant, check out our services. We can execute special projects affordably and effectively.

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