by | Dec 8, 2021 | Blog, Executive Assistant

As your business grows and responsibilities begin to stack up, it can become more challenging to keep track of your workload. Things start to slip. You may find yourself losing control of your schedule or missing deadlines. Or you spend so much of your day on mundane tasks that there’s no time left for big-picture thinking. If you can relate to these problems, it probably means it’s time to hire an executive assistant to help you out.

When is It Time to Hire an Executive Assistant?

Let’s be honest, if you’re researching how to hire an executive assistant, it’s likely already time. 

If you need more convincing, hire an executive assistant if:

  • Tasks are overwhelming, and you need some help.
  • You spend a lot of your day handling low-value tasks and administrative work rather than making strategic decisions and growing your business.
  • You sometimes miss deadlines or arrive late to meetings due to disorganization.
  • There’s a significant increase in work-related stress.
  • You’re struggling to maintain a good work/life balance.
  • You can afford it.

How to Hire an Executive Assistant

An executive assistant can be an invaluable asset to you and your organization. They handle day-to-day tasks, so you can focus on leading the company. They’ll also be the team member you work the closest with. An excellent EA can be a strategic business partner and a trusted confidant. 

This unique position and relationship means that hiring an executive assistant presents more challenges than many other jobs. Top candidates need to be a good skill and cultural fit. If you find the right executive assistant, they can make your life significantly easier. The wrong EA can do the exact opposite.

The steps below will run you through how to hire an executive assistant that you’ll want to keep around.

Think About What Exactly You Are Looking For

Start by outlining your requirements for a potential executive assistant. You can’t expect to hire an epic executive assistant if you don’t know exactly what you’re looking for.

Write down:

  • The day-to-day tasks you need done
  • What you expect an EA to achieve in the first three, six, and 12 months
  • Necessary skills for the job
  • Education requirements or certifications
  • Desired personal traits and attributes
  • How a candidate will fit with your company culture and work environment

Now you have yourself a job description.

Black woman on her laptop with her iPhone besides

Create a Job Posting

The next step in hiring an executive assistant is to use your job description to create a compelling job posting. While a job description is for your internal use, it’s what potential candidates see on your company’s careers page or job posting sites.

A job posting needs to list responsibilities and required skills. It should differentiate your company from the competition. Hiring is a two-way street, after all. Sell yourself. Tell potential candidates why they want to work for you.

An effective job posting will attract the right candidates and the best candidates.

Narrow Down Resumes

If your job posting was successful, you should start to see resumes pouring in.

Look for candidates whose skills and attributes match your job description. Past executive assistant experience is a huge bonus. Just because a candidate worked as an administrative assistant, doesn’t mean they necessarily have what it takes to be an EA. EAs require greater business insight and problem-solving abilities. Check for proof of these skills on their resume through additional qualifications or activities outside of work.

Ask The Right Questions

Once you have narrowed down resumes, it’s time to interview potential candidates. The interview is a critical stage in the executive assistant hiring process. Be sure to prepare your questions in advance.

The best interview questions for an executive assistant should showcase the broad range of skills needed for the role. The questions should also focus on your specific requirements. Once again, think about the qualities you want in an ideal candidate and make sure your questions fit accordingly. You need to ask the right questions to get the right person.

Possible executive assistant interview questions include:

  • In your opinion, what three words characterize a great EA?
  • Describe a time when you had to reschedule an entire meeting-packed day due to unforeseen circumstances.
  • If you received confidential information from the executive you support, and another executive asked questions about it, what would you do?
  • Tell me about your computer experience. Which applications do you use and why?

Find the Right Personality Fit

The interview stage is also a good time to judge whether a candidate is a good personality fit. You’re going to spend a lot of time working closely with your EA. The two of you must mesh well. You don’t have to become best friends, but you also shouldn’t have personalities that clash and lead to increased stress and irritation. 

Things to consider include:

  • Do their core values align with your own?
  • Would they fit in well with the rest of your team?
  • Would they thrive in your work environment?

It doesn’t matter how impressive a candidate’s resume or educational background is. If the two of you don’t “click,” they probably won’t work out. Cultural and personality fits are vital components of a successful executive and executive assistant relationship.

Involve HR or an Outside Hiring Specialist

If you’re struggling to hire an executive assistant on your own, it might be time to involve your company’s human resources department or use an outside hiring specialist such as a job placement service.

Reasons you might consider using a job placement service include:

  • You are already working overtime and don’t have time to commit to the hiring process.
  • This is the first time you hire an EA and don’t know what to look for in top talent.
  • You’re looking for a specific set of skills and role experience.
  • It’s been difficult filling the position.
  • You don’t know the first thing about hiring and would rather have someone else do it for you.

Specialist assistant placement services such as LifeSquire can remove the stress of hiring and help you find the perfect executive assistant. A recruiter will take the time to find out what you need and use their wealth of experience and expertise to help you find the right candidate as quickly as possible.

LifeSquire Can Help You Hire An Executive Assistant

Hiring an executive assistant is an important task. It shouldn’t be a rushed process. You need to make a thoughtful choice based on skills, experience, personality, and cultural fit. The candidate you pick might not always be the obvious choice. You also need to know what to offer in terms of executive assistant salary and perks to attract the top talent.


If you’re not ready to hire for yourself, Lifesquire Connect can take care of the process for you. We specialize in hiring, training, and placing exceptional executive assistants. Our comprehensive process matches assistants and executives based on skills, experience, and personality to provide the best long-term fit.

Contact us today to find out more.

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