As an executive, your day is necessarily more reactive than you’d like it to be. No matter how much you plan your day, you’ll spend some percentage putting out fires or addressing issues that were not originally on your agenda.

Your executive assistant, therefore, must operate proactively to keep everything “on the rails” for you. He/she must proactively anticipate needs and address them before they become problems.

Nevertheless, seasoned managers all know that no amount of upfront vetting guarantees a good hiring decision.

There is no test, set of interview questions, or background checking process that will give you a definitive “crystal-ball view” to help you determine whether a person will be great at their job. You can never know for sure if that new hire will be a good cultural fit for your company and stay focused long enough to add value.

That’s why every hire is such a risk.

When looking for a first-rate executive administrative assistant, however, there is one key attribute you can size up: whether or not a person is inherently proactive.

No other attribute is more important for an executive assistant.

Whether you choose to hire a virtual assistant or an in-house assistant, you want someone that’s proactive. So, how can you determine if an assistant will be proactive?

Below you’ll find 3 ways to find out in advance.

Again, you won’t be able to predict if your future executive administrative assistant will be proactive. But, you can size up whether or not your candidate is proactive by nature.

Here’s how to do that:

1 Avoid asking a candidate whether he/she is proactive

That’s a useless question, as the candidate will always say “yes” and immediately invent a few examples. Instead, watch for certain behaviors, and provide opportunities for your potential new executive assistant to exhibit that behavior.

The best way to provide those opportunities is to require several interviews on different days instead of just one. Along the way, watch for positive signals by asking yourself the following questions:

  • Was the candidate early, late or just on time to the first appointment? Being on time, especially to an initial meeting to a place you’ve never been, requires proactive thought. You need to remember to leave time for parking, elevators, etc. If remote, did the candidate get on the conference bridge in advance? Did he/she trouble shoot any connectivity issues in advance?
  • Did the candidate have a printed resume on hand in case you did not have yours ready? If the assistant is remote, did she email you a resume in advance without you having to ask?


When candidates for any position within any company arrive at an interview (whether remote or in-person), they should be well-versed in the products and/or services that you offer. It’s fairly simple to vet this out, since leading questions like, “what do you like most about our company?” are sure to elicit either blank stares, semi-intelligent fumblings, or eloquent answers.

Here are a couple more questions to consider: 

  • Did the candidate learn something about you and/or your company’s history and/or current newsworthy information in advance?
  • Did the candidate have questions ready in advance of you asking if he/or she had any questions?

3Take note of how the candidate follows up with you

Every human resources department the world over will tell you that the #1 best practice for post-meeting follow-up is…following up

  • Did the candidate follow-up with a thank you note shortly after the interview?
  • Did the candidate come back to you in a politely persistent manner when you failed to quickly get back to him/ her on next steps?

A proactive temperament is the most important attribute for an executive assistant. It is actually much more important than the second most important attribute, which is attention to detail. Some may think that attention to detail is most important, but that’s wrong.

A one-off spelling mistake will often go unnoticed. A double booking creates issues, but issues that can be resolved when spotted and when the executive assistant thinks in proactive ways.

But an executive assistant who never makes a spelling mistake or who never double books a calendar entry is fairly unhelpful if he/she is not thinking about what is coming up next.


Luckily, compulsively proactive people tend to have strong attention to detail. Regardless, an executive should concede a detail mistake once-in-a-while for an executive assistant who is always resolving tomorrow’s issues today.

Taking the steps above will help you assess if your candidate for executive administrative assistant has that proactive temperament.


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