4 Keys to Unlocking a World-Class Executive Assistant

What to look for when hiring an executive assistant

William Ballard, MBA
Aug 3 · 10 min read
Image Credit: Andrea Piacquadio

I recently read a pretty interesting book by Michael Hyatt, entitled “Your World-Class Assistant: Hiring, Training, and Leveraging an Executive Assistant.” It’s a quick read but well worth it. Inside, it mentioned some very important keys to look for when selecting a “world-class assistant” and so I thought I would share those with you here.

Now, whether you directly hire an Executive Assistant or use some type of agency that provides Virtual Assistant services, these four keys are essential no matter which option you take. However, there are some advantages and disadvantages to both, and we will touch on some of those towards the end of this article.

With that said, regardless of the responsibilities and/or task you decide to delegate, you are looking for someone that can do more than complete the assignments. Skills are important (and it is one of the four keys we will talk about in this article), but they are only the starting point for selecting the kind of assistant that is right for you and your operation.

Your ideal candidate must possess much more than just skills to be a solid member of your team, they must also possess aptitude, attitude, and character — at least that is what Michael Hyatt expresses in his book.

Key #1: Skills

Believe it or not, not all Executive Assistants are created equal. The type of assistant you may need might not be the right fit for one of your colleagues, albeit, they may have the same title.

So, what skills does an assistant really need? Well, that really all depends on the type of tasks you want to delegate to them.

You see, you may need an assistant that is insanely good at scheduling and managing your calendar. Or you may need one who is good at maintaining systems and processes — but not necessarily need them for screening calls, for example.

Moreover, what about those areas of competency that don’t necessarily fall within the parameters of what most people think an Executive Assistant is to do, such as HR support or accounting, or even project management?

Therefore, getting crystal clear in your job description is essential. The type of task you will require them to do is what will, essentially, dictate the skills they will need to possess.

However, then the question becomes, how do you verify that the candidate can do the job? And especially how do you do that when you are considering working with a Virtual Assistant? We will talk more about that later.

Beyond assessing a candidate’s resume, and checking in with references, you can also test for the skills you are looking for. For instance, if one of your tasks is to take control of your overwhelming email inbox, you could ask them to show you how they would organize your inbox according to your priorities.

Or another example could be that if you need them to be able to engage on social media and do some certain tasks of a social media manager, you could have them compose a dozen or so Tweets or Facebook posts to show you a little bit of what they can do.

According to Michael Hyatt, “any skill can be tested.” And if no traditional test exists, he suggests that you create your own based on real-life tasks that you would expect your assistant to be able to accomplish.

Key #2: Aptitude

A brief test assignment or trial run on a certain task should be able to give you an indication of whether or not a candidate has what it takes to accomplish a task, but there’s more to being a successful Executive Assistant than just learned skill. They must also possess the quality of aptitude, which is that natural or innate ability to perform a certain task (or to learn it quickly) without much training or real effort.

Being able to determine a candidate’s aptitude, as best you can, is essential. The problem with measuring aptitude is that it is mainly done with personality assessments. And according to Michael Hyatt, “many commonly used assessments have proven to have a built-in bias based on race, age, or gender.” At Michael Hyatt’s company, he tends to rely on the Kolbe A Index, which up to this point, has never been proven to be biased.

Moreover, the Kolbe A is also different in the sense that it does not assess based on intelligence or personality, but rather on how our minds work when approaching a certain task. In other words, it doesn’t assess based on how we think or feel, but rather on how we go about doing the work.

For example, it will help to determine if a candidate as the aptitude for research, which would require an innate ability for fact-finding. Or perhaps an aptitude for clerical work, which would require an innate ability for data gathering and organizational skills. Or even the aptitude for process creation, which would require the innate ability to follow through.

Key #3: Attitude

Attitude is a bit harder to screen, but just as vital. For instance, you may want an Executive Assistant that will challenge you at times. Let’s say handling your schedule is one of the important responsibilities you have dedicated to your assistant. Well, having an assistant that pushes back and isn’t afraid to tell you no when you are trying to add something to your calendar that ultimately interferes with your main priorities — or perhaps more importantly — takes away from your margin, which is meant to give you more space and time to do what you really love, like spend time with family.

And what if you are looking for an assistant that you can trust, one that can advocate on your behalf, challenge the status quo, and even be able to manage others? Well, when looking for someone like that it would be wise to find someone with some leadership traits. But then the question is, what kind of leadership style are you looking for?

If you are like me, you may admire those that express the servant-leadership style. Some will tell you that it was Robert Greenleaf (who used to work for AT&T) who fathered the concept of servant-leadership, however.

I would disagree. He may have been the one to the coin the name, but the concept of servant-leadership goes all the way back to the time of Jesus and Paul. For instance, in Matthew 20:25–28 it reads:

“But Jesus called them unto him, and said, Ye know that the princes of the Gentiles exercise dominion over them, and they that are great exercise authority upon them. But it shall not be so among you: but whosever will be great among you, let him be your minister; And whosever will be chief among you, let him be your servant: Even as the Son of man came not to be ministered unto, but to minister (serve), and to give his life a ransom for many.”

Moreover, I would say that the best verse about leadership in the Bible would be that of 1 Corinthians 11:1 which reads, “Be ye followers of me, even as I am of Christ.” Notice that the word leadership isn’t even mentioned one time in that verse.

You see, Paul did everything that he could to model his life after the example of Jesus Christ. This is where the concept of servant-leadership really started.

However, Greenleaf did observe that the leadership of his day was mainly interested in power and lording over others rather than serving them, which is why he resolved to do something about it. He took early retirement from AT&T and started writing and speaking out against the more common and accepted top-down model of leadership that he was familiar with.

His work continues to resonate with us even to this day. In fact, The Robert K. Greenleaf Center for Servant Leadership says that a servant-leader “focuses primarily on the growth and well-being of people and the communities to which they belong.”

I say all that to say this: when it comes to your Executive Assistant, what a servant-leader means is someone who is confident, capable, and yet humble. Michael Hyatt put it this way

One who is capable of running a meeting in your absence or confident enough to push back about your overbooked schedule, but who remains humble enough to pick up your dry cleaning or get a glass of water for someone who needs it is a servant-leader.”

Where most people think that an assistant is like a “maid” and suppose to bring them coffee, clean up after them, get their dry cleaning, cook for them, and do all these other types of things have it dead wrong and don’t deserve to have an assistant.

An assistant (and even a maid for that matter) is not your slave. If they do these kinds of things for you it is because they are humble and have a servant’s heart, and they should be shown your appreciation for these things. With that said, this type of servanthood is not a requirement, and certainly should not be demanded. You should consider yourself blessed to find an assistant like this.

Now, how exactly do you screen for something like that? It may not be as easy as screening for skills or aptitude, but it’s possible, nonetheless. It will just take some thorough observation and deep awareness.

Michael Hyatt suggests that the first thing you should do is ask the right questions in the interview. This could be anything from open-ended questions like, “What is leadership?” to more specific ones like “what experiences made you want to be an Executive Assistant?” He then suggests that you have several other people interview the candidate as well.

Lastly, he suggests that you call the people from the list of references, and instead of asking them about the performance of the candidate, ask them what impressions they have about them. Also, describe the type of attitude you are looking for and ask if what you have just stated describes the candidate.

Key #4: Character

Now, the last key that is mentioned in Michael Hyatt’s book is that of Character. I already mentioned briefly about being able to have trust in your Executive Assistant, but here we will go a bit more in-depth with it.

You see, there will often be times when your assistant will need access to “privileged information,” such as financial data, passwords, IDs, credit cards, or even trade secrets. While having a new hire sign a nondisclosure agreement is typically routine and expected during the onboarding process, that doesn’t mean that the threat of legal action is necessarily going to deter a person with poor character. With that said, running a criminal background check is also an important piece of the onboarding process.

Beyond that, when checking in with references, be alert to warning signs about a candidate’s character and trust factor. During the initial interview ask questions that go beyond just the resume so that you can see when signs of one’s character beings to appear.

For instance, Michael Hyatt suggests that you might ask questions like, “When it is okay to break the rules?” Or ask them to give you an example of “when it is appropriate to do this and explain why.” He goes on to say, “the answers to this type of questioning will shed light on their decision making, emotional intelligence, and character.”

He also points out some successful responses that might include, “examples of breaking the rules when someone was in physical danger or had violated ethics or confidentially standards.”

Personally, I’m not sure if I agree with being unethical for the sake of someone else’s unethical actions. It’s like trying to fight fire with fire. We all know what would happen if we tried to do that.

Nevertheless, Michael Hyatt closes out this chapter by employing us to “hire slow.” In other words, he encourages us not to be hasty when hiring a new Executive Assistant.

“Hiring the wrong person is worse than hiring no one. Conduct a thorough search and screening process, and you’re very likely to be happy with the result.” — Michael Hyatt

To that end, I just want to point out a few advantages and disadvantages of hiring an in-person Executive Assistant vs. a Virtual Assistant. For one, by only focusing on hiring an in-person assistant you limit your pool of options, as well as limit the skills that could be available to you.

In other words, where it might be convenient to have an in-person assistant, that candidate might not have the already learned skills and innate ability to do what you are looking for in the sense that a Virtual Assistant might have. Plus, the pool of options is wider virtually than locally.

However, if you need an assistant that is available for in-person meetings and running around doing errands locally, then obviously a virtual assistant may not be the way to go for you. As stated before, it is important to be crystal clear in your job description, as well as to be clear on how you envision having an assistant on your team.

In short, there are advantages to having a virtual assistant just as there are advantages to having an in-person assistant. It’s really all based on what your particular needs are. Are you able to manage your business and operation with having an assistant that works virtually? Or do you need an assistant that has to be present in order to interact with customers or clients?

William Ballard is one of the most sought-after business and leadership coaches in the world. As founder and CEO of William Ballard Enterprise, his core business development and leadership programs are designed to be a catalyst for entrepreneurs and leaders who want to enhance performance and make a meaningful difference in their business, their lives, and the world.


Delicious reads, fresh daily

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch

Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore

Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store