The Ultimate Guide to Hiring an Executive Assistant 👨‍💼

Hire executive assistant

Hiring an executive assistant is one of the most important things you may ever do in business. After all, this will be your wingman/wingwoman; there with you every step of the way as you cruise towards the work-life balance you dream of.

This is a decision that will impact your business for years to come. It is therefore not something that should be taken lightly or rushed.

Yet, as entrepreneurs, we sometimes tend to hire candidates out of necessity due to lack of time. We often hire reactively and out of scarcity, rather than proactively and from abundance.


In this article, I am going to give you as much knowledge and direction as I can to make your job of hiring an A-Player executive assistant as painfree and successful as possible.

Let’s begin…

Hiring and executive assistant

Step #1 – Define Your Ideal Executive Assistant

The key to a successful hire is all in the preparation. How have you prepared for your recruitment drive? If the answer is ‘I’ve put some ads on some job sites’, then it’s time to revise your approach.

It is important to first make a very detailed description of the responsibilities and functions your EA will need to do regularly, and what qualities and experience the ideal candidate will possess.

Ask yourself what experience they should have? What personal qualities? Do you need a part-time virtual assistant, or a full-time assistant who is all yours? Do you need someone who will simply help manage your calendar? Or do you want an assistant that will perform deep financial analysis then find some new recipes for you to try for dinner? 🍜

Executive assistants have many functions:

  • Make and take calls
  • Chat support
  • Manage calendar and set appointments
  • Write documents and reports
  • Data entry
  • Take minutes during meetings
  • Research projects
  • Manage filing (both physical and digitally)
  • Arranging travel and accommodation
  • Personal tasks (from collecting lunch to taking your dog to the poodle parlor) 🐩

It is no good waiting until the interview to see what your candidates can bring. You need to have a clear description of what success looks like before the person gets close to walking in the door. 

After all, how do you know what you are looking for if you don’t know what the job actually is?

In short, be crystal clear on what you want to achieve and it will make your hiring process more effective.

This is also the ideal time to ensure that the repeatable tasks in your company are outlined in effective SOPs, so when your new hire joins your team, they are ready to rock.

Step #2 – Create an Applicant Tracking System

Feeling overwhelmed as the 87th resume hits your desk? Where are other business owners finding the time to read all these? 😩

Hint: They aren’t. They are most likely using an Applicant Tracking System (ATS).

Used by a reported 99% of Fortune 500 companies, an ATS is software that uses algorithms to collect, process, and store applications before you or your hiring manager sets eyes on the most suitable candidates.  

In advanced ATS systems, you can set up an automatic rejection process to weed out those candidates who applied on a whim or are not worth processing for other reasons. More basic systems may not have this function. However, they will still make it easier to process, store, progress, and search for candidates.

There are many levels of ATS software that will suit different companies, budgets, and volume of applicants. Here are three options that can help you manage your candidate pipeline:


Part of the Google Drive catalog of tools, Google Forms allows you to create a simple landing page with the ability to collect data from candidates using either drop-down menus or open answers. The data is stored and can be exported for your analysis. It’s basic, but it’s free and it will do the job for many small businesses.


If you want something more comprehensive and semi-automated, then I recommend using a project management platform like ClickUp (which is also free to use). You can set up an application form, filter candidates, and move them through the application process in stages, while using the platform as a communication tool. 

Check out this article from ClickUp on how to use the platform specifically for recruiting. (I also recommend Airtable, which is another powerful digital workspace that functions in a similar way to ClickUp).


There are several top ATS platforms, including Taleo and Workday, although if you are serious about hiring, I recommend Greenhouse. This dedicated ATS software is used by both SMBs and enterprises, and will help you optimize your hiring and onboarding processes with a complete suite of software and tons of automation. 

Truth be told, this option will be overkill for many small businesses. It also comes with a very hefty price tag! However, this is a great call if you want blissful automation and the best hires.

Step #3 – Go Fishing in an Incredible Candidate Pool

Posting a good job ad using recruiting sites like Indeed, Monster, and LinkedIn will give you a great chance of attracting some real A-players to your job opening.

However, there are also several dedicated EA hiring platforms that help connect busy entrepreneurs like yourself with experienced assistants. These should not be overlooked!

In addition to offering full-time executive assistants, several platforms now offer virtual assistants (VA).

These assistants have already been screened and judged to be at the top of their game. This option allows you to enjoy the benefits of an EA, but without paying for a full-time employee. Instead, you can use them on an hourly basis whenever you need them.

I suggest checking out some of the following EA hiring platforms:

Magic – Magic is an excellent starting point for part-time virtual assistants. Rates are flexible, from just $10 to $35 per hour, making it accessible for the vast majority of small business owners.

Virtual Guru – Virtual Guru offers three packages tailored for solopreneurs and small organizations (up to 15 hours a month), then small businesses (20 to 95 hours a month), and finally corporate clients who need 100+ hours a month. Hourly rates start at $29.

Persona – Persona is ideal if you want a full-time assistant who works 40 hours for you – and only you – each week. The benefit of this is that you aren’t competing for their attention, although you will spend $3,900 a month. The platform uses highly-vetted candidates from around the world and promises to ‘match you to a great assistant within 48 hours’.

MyOutDesk – This is another popular virtual assistant platform that serves some big corporate names. VAs are hired on 40-hour week terms. You can select from 3, 6, or 12 month plans (costing $1988, $1848, or $1788 per month respectively).

Double – Double is a useful service that matches executives with virtual assistants (among other professionals – from marketing to finance). Here, the emphasis is on quality. In fact, the company claims that ‘Only the top 0.5% of applicants become Double assistants.’ For the privilege, there is a $300 onboarding fee, although hourly rates for the first month are at a discounted rate of $45 per hour. This rises to $55 per hour from the second month onwards.

Delegated – Delegated provides a pool of college-educated US-based virtual assistants that are specially trained to work with small businesses and executives. Expect to pay $48 per hour and commit to one of three plans giving you 25, 50, or 75 hours of assistance per month.

Upwork – Upwork is a little different as it is not solely catered towards EAs. In fact, you will find everything from writers to designers available for hire. You prepare a job description and set your specifications (including hourly rate, hours required, and so on), then sit back and watch a plethora of suitable VAs reach out. Upwork is very flexible, and will often give you exactly what you want. While hourly rates start from as little as $5, expect to pay around $30 to $50 per hour for somebody worthwhile. TIP: Look for ‘Top Rated Plus’ candidates, who will have excellent experience and feedback.

C Suite Assistants – C Suite Assistants is a renowned agency that specializes in pairing executive assistants and personal assistants to C-Level executives across the United States. You will ultimately end up with an excellent match! However, this is a higher-end service and only likely to be suitable for larger businesses.

Step #4 – Streamline Candidate Outreach

As you work through the hiring process, you will need to communicate with your candidates. After hiring and firing many, many employees, I noticed how much resentment I had towards the whole hiring process. This was largely down to the time it took and the stress it added to my day.

Therefore, making the process as simple and painless as possible is crucial to your success in the hiring process, not to mention your enjoyment. Because this process should be enjoyable for you!

So, how do you streamline this process?

Unless you are using an advanced ATS like Greenhouse, or one of the dedicated EA hiring platforms listed above, then I suggest you template, template, template. TEMPLATE!

Firstly, I recommend using a platform like ClickUp to keep correspondence with all candidates in one central location. Then create a series of email templates for each stage of the hiring process.

For example, you’ll need an email template to inform candidates that they have been successful in the selection stages and it’s time for their first interview. (TIP: For scheduling interviews, I wholeheartedly recommend Calendly). The same goes for when it’s time to inform them that they have reached the second and third interview stages.

Create templates before you begin candidate outreach. Create templates for each stage and each outcome of the recruiting process. It is a small investment of time at the start, but your ROI is huge as you will be rewarded with a more relaxed journey when the recruiting process gets underway.

Step #5 – Interview Until You Find Your A-Player

Here comes the fun part! You have a shortlist of candidates who have successfully navigated your sifting rounds and have booked time for an interview. Now you get to actually meet your next potential EA. 

Off the bat, I recommend conducting at least THREE interviews:

Interview #1

Often a telephone or video interview, this first interview is your chance to get a first impression of those who have, so far, only performed well on paper. It will also give you the opportunity to weed out anyone whose goals don’t align with those of your company.

A great question to ask is, “What are your career goals?”. This can be very telling. If someone says, “I want to be a lawyer,” and they are applying as an assistant at a marketing agency, it’s probably not going to work out in the long run!

Interview #2

Usually conducted face-to-face (or via Zoom if long distance), the second interview will allow you to refine your shortlist by comparing candidates.

I recommend digging deep into their past jobs one by one, in chronological order. Ask them about their working relationship with their former bosses and how their former boss would rate them on a scale from 1-10 based on their performance.

You want candidates who speak well of their former employers (unless they were actually terrible!) and you want them to be confident in saying their employers would rate them 8-10.  You’ll also want to inform them that you will be speaking with each one of their former employers. This will ensure that they give you honest answers.

Interview #3

With your shortlist down to a handful of the top candidates, the third interview gives you the opportunity to test your candidate on the specifics of their job in the company.

For example, if your executive assistant is going to be focused on scheduling and calendar management, you can ask them in-depth questions about how they succeeded and failed at this previously.  

Does conducting three interviews feel unnecessary? Think again!

Consider the cost of hiring the wrong person. Having the wrong person can not only impact the morale and productivity of the team, but it can set you back financially. As the late CEO of online clothing company Zappos, Tony Hsieh, once estimated, bad hires had cost his company over $100 million! 🤯

Step #6 – Welcome to the Company!

Congratulations! 🎉 The hard work you put into the preparation and interviewing stages has resulted in you finding your new executive assistant.

Before you start throwing tasks at them and take a step closer to unplugging, there is more to do as you welcome your newest asset to the company. You need an onboarding process for new employees.

To make this as painless and actionable as possible, I suggest creating a spreadsheet with your process. Here’s an example of what a basic onboarding process looks like for new employees in my company:

As you can see, this is a simple but important checklist of vital events that must happen before they are truly onboard and ready to begin making the impact you deserve.

Naturally, your onboarding process may look a little different to mine. However, this will give you a rough idea of the steps involved.

Step #7: Develop a Routine with Your New EA

If this is your first assistant, it can be challenging to know how to work with them properly. Our tendency is to expect this new person to think, act, and behave like us.

But it’s important to remember that this person is there to support you, not BE you

Don’t forget what I mentioned about creating repeatable tasks for them to do – don’t underestimate the power of SOPs. You shouldn’t be expecting this person to take over everything you do. Make sure you document what they are really good at doing during the interview process and assign them projects that play to their strengths.

Yes, they should be adaptable. But you don’t want someone who has no financial experience managing invoicing if they made it clear that it isn’t their strength.

However, just because it’s not their strength doesn’t mean they cannot improve. Consider sending them on a course or offering them some books to read to learn new skills. If they are the right hire, they will jump at the chance to learn new things.

The Next Steps

We have covered a lot together in this article, although it only scrapes the surface of the process. I plan to go more in-depth with some of these steps over the coming weeks to really help you nail the hiring process.

The best possible advice I can leave you with is to make sure you stay connected to your new hire and block out regular time for one-on-ones. This will allow you to get honest, open feedback on what’s working for them and what’s not. Communication is the cornerstone of a healthy working relationship!

On the subject of one-on-ones, if you want some guidance on the hiring process or have any further questions, book your free strategy call with me. I will run you through all you need to know! Reach out at

Questions? Comments? We’re here for you at!

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