Oh, executives – what can I say? We want what we want when we want it. So what could possibly be frustrating about finding and hiring a bright, tolerant, mind-reading genie of a gatekeeping mini-me assistant? Easy peasy, right? Ha. No; so wrong & here’s why:


In an age of instant and uber connectedness, it’s easy to get lost in the notion that everything should and can happen immediately. It’s true, for the sake of money and time, I can now hire an AI (artificially intelligent) assistant to schedule my meetings and negotiate my calendar. However, after testing nearly every AI solution on the market – it turns out that I don’t have the time or money to spend finding a way to automate things instead of doing them.

Say what?

The world moves fast, but people-skills – those move slowly. Preferences and formalities are learned with precision and care. So no matter what an AI assistant can offer me, more work is always required of me. But… isn’t that why I signed up for the assistant?

For some of my contacts, it’s quickest to pick up the phone and call. Others respond best to an email followed-up with a text message reminder indicating that an email has been sent. One of our Board members is most responsive via a social media platform.

How do I know all this? My brain (or that of my assistant) identified efficient patterns and intelligently integrated them into how my team gets things done. When the pattern changes, as it often does, we simply adjust our sails so we always remain on course.

I’m sorry Amy and Alexa, but you have nothing on EM’s Chief of Staff, Ariel.


So, despite what popular culture is feeding you, a good (human) assistant is indispensable. They handle contractual obligations, act on the unexpected variable and proactively anticipate a litany of unspoken expectations.

With Ariel at the head of EM’s ship, I receive everything I ask for and some things happen without me ever asking. For example, a selection of dinner reservations to offer when I mention that my family’s visiting from out of town, or parking instructions and costs dutifully integrated into my meeting directions.

I know what you’re thinking – and yours won’t be the first offer we’ve received to steal her away. All I can say is: good luck.  

Finding Ariel didn’t happen overnight and it’s safe to say that I went through a lengthy list of mediocre assistants before she arrived. So, why is the ideal so hard to find? Contraction and action are hiring elements that can be standardized; an assistant either has the skill-set or doesn’t. But proaction – that is something personal to each executive assistance relationship.

What does that mean? It means that the level of proactivity an executive welcomes, requires and discourages is relative to the assistant standing in front of them AND the preferences he or she has developed via experiences with past assistants.

Right here, readers, is where compatibility between the Executive and Assistant makes its first big play. I like Ariel, so whether or not she knows how to do something immediately is largely less relevant than whether or not I’m willing to give her the opportunity to try.


Ah, prioritizing. It’s a necessary evil and an elusive one. The tasks that shout the loudest aren’t always the most important ones to accomplish – they might just be the most annoying. It’s imperative that an assistant knows and learns how to prioritize and remains steadfast in the art of gatekeeping. Learning to say no and applying the boundary with a skillful hand is something we require from our EMbassador Assistants and you should, as well.

There’s no such thing as successful multitasking. There are people who skillfully prioritize, execute and repeat, and there are people who don’t. Which kind do you want on your team?

TL;DR? Executives face 3 major frustrations that translate into 3 non-negotiables when hiring an assistant:

(1) Time; this relationship is between two people. An executive must be willing to spend a little time interacting with an assistant now if he or she wants to effectively save a lot of time later.

(2) Compatibility or synergy – whatever you want to call the spark of intuition that says – yes, I can relinquish my need to control things to this assistant and allow them to be proactive for me – this Spidey Sense is an indicator of success. Stop ignoring it.

(3) An effective gatekeeper who can and will set boundaries for you and with you is someone who can and will prioritize. Be grateful for the skill they bring to their craft and be mindful of the boundaries they set – chances are they’re set to increase your long term success.

Interested in finding a great assistant or a great assistant position? Executives click here and Assistants click here to join the wait list for EM’s compatibility survey.

Wishing you all the best!



Jenny Kitchen

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