Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Event Planning

Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Event Planning

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 actresses Anna Deavere Smith and 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.

Event planning is its own animal, but an important skill for assistants to adept. Patrick Healy finds the most effective approach to event planning is to visualize how the guest experience will unfold. “Any event you plan for your boss is a direct reflection on your boss. If the guests are not having a good experience, it’s going to reflect negatively on your boss.” Therefore, when it comes to strategy, he suggests, conjecture each element, plan ahead, and keep a cool head.

The Scenario

Patrick has planned many events from intimate family dinner parties, to Oscars’ after parties and large fundraisers. His approach has always stayed consistent: plan for guest experience above all else. Stay true to this even when outside factors are added to the equation.

Several years ago, I planned an event for an employer in their home where a VIP politician was the guest of honor. I found myself not only managing the usual caterers, wait staff and household staff, but this event had the added element of the secret service and the staffers.


Most importantly at that event, I had to ensure the details were flawless for the VIP guest; for example, how they would arrive, how they would be greeted by my employer, how they would enter the dining room, and how and what they would be served and how they would exit.


There were so many elements to this event that were out of my control, making anticipating the guest experience even more important. But as the stress mounted, I made the decision to keep cool and not let it get to me. That decision too is a conscious one. You must choose in that moment to be the cooler head.


At another event, there was to be a photo line with my employer, because many people want their picture taken with a notable person. But in addition to the details of this event, I also needed to know where and how that was happening for my boss and for the guests. In that event, every guest touchpoint had to be accounted for – always keeping in mind the touchpoints for my employer as well. Again – having anticipated all of the elements of the event – a cool head won the day!


Probably the most important thing of both events was my ability to keep a cool head and whatever problems arose, I addressed them fully and quickly. Planning for all contingencies for that particular event proved incredibly difficult but in the end, the events went off without a hitch. I also received my reward for my work in several ways – when my employer personally introduced me to the VIP politician praising that the entire event could not have happened without my efforts and in the framed photo of me with my employer!



Advice from the Pro

Patrick has conquered event planning by, among other things, visualizing guest experience from the moment they enter the door by analyzing each touchpoint of interaction. When a guest walks in the door, what is the first thing they will see? Will there be someone there to greet them or check their name off a list? Will there be name badges? Where is the coat check located? Will there be someone to direct them on where to go? Someone to show them where the restrooms are located?

Patrick emphasizes that inevitably there is always something that goes wrong or something that occurs you didn’t plan for. Anticipating these happenings is the greatest challenge of event planning.

I am a type-A personality and I like to have everything thought-out, I like to think through every scenario and have options at my disposal. That said, inevitably something always goes wrong. A few years ago, I hosted a dinner party for an employer that was planned for a certain number of guests, there was even a well-planned seating chart. Thirty minutes before the event starts, a guest called my employer to ask if they can bring three additional people to the event. Of course, my employer didn’t want to say they couldn’t so I had to come up with a solution and quick.


The concept behind what I call ‘fluency of thought and flexibility of action’ is to think through every possible option and scenario and have contingencies in place so I can move into action on a plan if something goes wrong. How you move through that barrier is key.


In my case, I happened to have a colleague who is an assistant at a house down the street. I called him and asked if his employer had any additional tables/chairs that I could borrow for the evening. Fortunately, he did and sent a few waiters down the street and they picked them up and brought them over.


Now, they weren’t a total match for the chairs I rented but they worked and in my obsessive need to be prepared, I had already ordered extra china, linens, and flatware for the evening. In the end, I had enough room for the additional guests and added the borrowed table to the end of the tables and no one was the wiser – not even my employers. Thank goodness for a strong network of fellow assistants!

In every scenario, Patrick reminds to plan and act in the likeness of your employer. “It takes a lot of emotional intelligence to be in this job. As previously mentioned, one component of this job is keeping a cool head. The other is knowing when to assert yourself into a situation and when to blend into the wall. How do you develop that emotional intelligence and how do you grow that? That’s the larger question.” Patrick further explains:

In events you plan for your boss, knowing when to tiptoe away and when to assert yourself is key. Again, these events are for your employer, not you. Care must be taken to ensure that they are the center of attention and remain the life of the party. I always try to speak to my employer first and ask how involved they want me to be once the event begins. If I’m not able to have that conversation, then I try to gauge that in the beginning of the event.


I always walk around an event and watch. Watching is key. I watch how the staff is doing, I watch how the guests are enjoying themselves, and I pay attention to my employer(s). I make eye contact with them – see that they know I’m there for whatever they need and see if they respond. If you know your employer well enough, you can know if they are good or not.


If they seem to be well, I might make myself invisible and step away and re-check in later or if they seem to need something or a guest needs something, I move in quickly to remedy the situation. I am always moving at events. Between moving between the staff and the guests, an assistant planning an event is the main hub on the wheel. Remaining cool, reading the room, and having the ability to move quickly to address problems or issues is paramount.

When it comes to event planning, no component is trivial. Walk through each guest touchpoint. Prepare for every detail. Whether it’s a party at your boss’s home or at a remote venue, it is important to have a plan A, plan B, and plan C in place for every detail of the event. Put yourself in the shoes of the guest. Anticipate what could be missing or what could be added. Conjecture each element, plan ahead, and keep a cool head.


Technology to the Rescue


Patrick suggests developing a strong network. As shown in the examples above, having a group of peers in the industry to help you problem solve and/or connect to other service providers is key. As a member (and current President) of New York Celebrity Assistants, a non-profit organization of other celebrity assistants in and around New York, it helps Patrick immeasurably to be able to reach out to colleagues when he is in need of a great, verified contact in a pinch.

He, in turn, gets great satisfaction in helping other assistants as well when they are in need, “There are lots of other similar groups around or start to make those connections yourself and expand that network!”


Patrick Healy spoke on a panel at the Executive Leadership Support Forum: New York City on Inside the Professional Life of New York Celebrity Assistants, and shed light on experiences, lessons learned, and similarities and differences from the corporate executive assistant role. For more information on how the Executive Leadership Support Forums can provide you the professional development to succeed within your career, visit: www.q1productions.com/execsupport


Hear more from Patrick Healy:

Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Developing a Plan C During Travel
Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Developing a Plan C When Scheduling
Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Project Management