The Assistant’s Guide: Navigating Situations When You’re Out of the Loop

Executive assistants are business game changers, always making the impossible possible for their executive. When organizing solutions for leading assistants’ top challenges, we turn to celebrity personal assistant, Patrick Healy. Healy has 13 years’ experience as a veteran assistant and has supported several spotlight figures, including actress Olympia Dukakis. He is currently the President of New York Celebrity Assistants and was a distinguished speaker at the Executive Leadership Support Forum: New York City.

Being out of the loop is the hardest and often the most frequent situation to navigate in our job, because if you don’t know anything about the person or the situation, and you are just going in cold, you have to figure out really quickly how to make things happen and find ways to uncover the information that you don’t have. These are the most challenging category of situations to maneuver. 

The Scenario

Out of the loop scenarios all fall upon a very broad spectrum. Most commonly, they come in the form of a task that is asked of you and you are lacking information exchanged or understanding the parties involved. Patrick Healy provides a simple example:

I had an employer who sometimes would put a meeting in his calendar himself, for example ‘Breakfast with Joe’. Now, that’s not the strangest thing in the world nor is it uncommon but as his assistant it was my job to understand everything in his calendar and my first thought is who in the world is Joe? And where is breakfast? Maybe it’s a personal meeting, but maybe it’s not. If my Principal comes back and asks for me to send Joe a document or even call Joe to tell him that he’s late, then I’m asking myself again, Who the heck is Joe? Joe Who? Do I have his business card or contact info? Does Joe know where this breakfast is taking place? Did they make a reservation? Does my boss know how to get there?

The toughest scenario an assistant is tasked with is to navigate what you don’t know. Patrick asks, how do you leverage your resources and, more importantly, communication to fill in the gaps? 

I’ve had all sorts of strange, vague “out of the loop” requests in my career as I’m sure many of you have. One that remains forefront in my mind is “I saw a dress in a window. I want you to buy it for me.” Pretty vague, right? So how to you proceed? Well, in this case, I first asked questions. What city were you in? What day did you see this? Do you remember the name of the shop? The neighborhood? The color of the dress? The style? She didn’t actually remember the name of the shop or the neighborhood but I had the city and a day of the week and the color of the dress. I then went back to her calendar to investigate where she was over the past 3-4 Thursdays to determine an approximate neighborhood and where she could have been walking that she might have passed a shop window. Then I used Google Street View to “walk” along those streets to see if I could see a dress shop or a shop in which I thought she might shop.


If only Google Street View was in real-time, I might have been able to spot the dress! But, alas. By this time, I had narrowed it down to about 5 shops that she could have passed. I then called each shop and asked if they happened to have a red dress in their window on that Thursday that she passed by the shop. Low and behold, 3 of them did! I asked them all to send me a picture of the dresses in their respective windows and was able to present all three dresses to my Principal for her review. As luck would have it, one of these dresses was the one! WHEW! I was able to call back that store and get the dress in her size and have it shipped to my Principal’s house.



There are so many ways that you can figure out details and navigate the things you don’t know, but it’s all specific to each situation. If your boss is going into a meeting and you don’t know who they are meeting with, how are you able to prepare them for that? If your principal needs you to get ‘Mary’ on the phone – how are you to know about whom he/she is talking? If your boss asks you to join them in a meeting that’s not in their calendar, how do you know what you are walking in to? Patrick suggests:

    • Ask questions. As soon as you realize you are out of the loop on a meeting, encounter, or project, start doing research and ASK QUESTIONS.
    • Reacting in proximity to the situation. Arm yourself with all of the information you can find on your own. Then, communicate with your executive to ensure there isn’t any additional information you are missing. Only then can you move forward putting the pieces together and effectively solve the issue at hand. 
    • Context. Adding any sort of contextual information to the calendar invite can help remind you and your Principal of important details regarding an appointment. Or do you have emails in your inbox that you can search through to find any information about this person or situation? 
    • Communication and the ability to be resourceful. Take the time to use resources at your disposal to find answers to the questions revolving around the situation. Have you looked through your executive’s contacts? Searched people on Google? On LinkedIn? Did they attend undergrad together? Are they related? Or, is the respective person working for a business within the industry? Take the initiative to conduct your own research first.
    • Google. Don’t underestimate Google and the power of a good search engine and the subtlety of a good researcher. 


  • Anticipation. It’s crucial to have information ready at your fingertips to provide your executive. If they schedule a meeting, it’s very probable they won’t remember all the details of the meeting closer to. In my opinion, it’s your job to have that information ready for them at a moment’s notice.


Technology to the Rescue

There is really no easy technological fix for this kind of thing unfortunately. In order to effectively solve these kinds of challenges, you’ll need resourcefulness and tenacity – two things that technology can’t do for you – yet another reason why I am not threatened by virtual assistants! It’s vital to have access to your employer’s contacts and calendar and to effectively use Google and your own context and resource clues to help identify and clarify the missing information and target your efforts to obtain said information.

The Executive Leadership Support Forum is a leader in developing professional skills for executive assistants. Patrick and other expert instructors guide interactive discussions on the most critical topics facing EAs and administrators.

If you have not attended an Executive Leadership Forum in the past, we hope to see you at one of our upcoming forums in New York, Seattle, Minneapolis, or Dallas. If you have attended one or more Executive Leadership Support Forums, we encourage you to describe your experience in the comments below. The Executive Leadership Support team is endlessly thankful for all of the past, present, and future attendees.

Patrick Healy is one the distinguished presenters of the Executive Leadership Support Forum Series. For more information on how the Executive Leadership Support Forums can provide you the professional development to succeed within your career, visit:
To hear Patrick Healy’s insight on managing travel, visit his last installment, Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Developing a Plan C During Travel.