Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Developing a Plan C

During Travel

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 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, June 28-29, 2017.

Patrick shares his insight, advice, and technology must-haves for the top six scenarios assistants navigate. The first, and in his opinion, most important for fluency of thought and flexibility of action, is travel. Travel will never be completely within an assistants’ control, and therefore, requires a thought-out approach to logistic piloting. When it comes to managing a travel itinerary, it’s crucial to have a proven and visual strategy in place for a Plan A, Plan B, and Plan C.

The Scenario

Navigating travel logistics is an art form and takes time and skill to perfect. Getting to a place where planning and executing travel for your principal becomes second nature takes time. Does travel ever go off without a hitch? Patrick shares a relatable scenario and his advice for navigating rough patches in travel management:

Recently, it was raining in New York and my boss’s international flight was delayed by an hour and a half. My boss initially only had a 3-hour window to collect his suitcase, get through customs and immigration, walk to a different terminal, and then re-check in and get on his connecting flight. Due to weather delays, that 3-hour window got shortened by half. Even so, he could have just barely made the connecting flight, but when he checked in at the desk, the airline wouldn’t let him on. He called me and asked what he should do. As I often do, I had a plan B and plan C on hand ready to use. I quickly had a back-up flight ready to go, had contacted the airline, and contacted the desk attendant. The attendant got him the tickets quickly and notified the gate that he was on his way, he got on the next flight, and was on his way to where he needed to go with minimal disruption to his day.

Patrick reminds, “You can’t control many things if they are flying commercial. You can’t control if the plane has mechanical issues or if there is a weather delay. In my opinion, the most important component of managing travel is to always anticipate the worst outcome and have your plan ready to put to work if you need it.”


Advice from the Pro

The key to managing successful travel is to constantly ask, what is the worst possible outcome for every travel variable? Patrick does this by visualizing travel start to finish and asking that question for each component of a travel day. Essentially, analyze all of your variables and be realistic about probable elements of travel.

For example, Patrick reviews, “I try to put myself in my Principal’s shoes – asking how they will experience their travel from start to finish. What are the possible pitfalls and how can I remediate those pitfalls before they experience them? For example, what if the car doesn’t show up? Okay, that’s easy: I’ll hail him a cab. What if my boss misses his flight? What’s the worst possible outcome from that? There are no other flights that day. What’s the worst possible outcome from that? There are no hotels. And what’s the worst possible outcome from that, etc?”

Arm yourself with all the information you need to manage details and logistics at your fingertips. As soon as you have booked your boss’s travel, track their flights so you have up-to-date information on delays and gate information. Patrick suggests having least three back-up flight options ready in case any issues are experienced with the initial flight. In addition, know which terminal and gate where your back-up flights are located just in case they have to change to a different terminal at the last minute. Last but not least, communicate with all parties involved. Correspond any delays or travel updates to your boss’s driver, their greeter, other assistants they will interacting with once they arrive, and the person whom they are meeting with at their destination.

“Frankly, sometimes it doesn’t work out. Sometimes, you just have to go to plan B and say, well, the next flight isn’t until tomorrow morning so now what’s plan C; either we have to charter you a plane or we book you into a hotel and you stay there for the night. You always have to be thinking, what are the next steps? Hence the fluency of thought [having thought through every scenario] and flexibility of action [putting those plans B and C into place easily].”


Technology to the Rescue

Patrick Healy suggests the mobile app and web-based platform, FlightAware. FlightAware provides live flight data, airport delays, weather maps, flight planning, flight routes, and much more. You can even track the previous flight to see where the aircraft is coming from if your principal’s flight is delayed. He also loves SeatGuru, another app and web-based platform that has the seating maps of every commercial airline and aircraft so you can accurately and comfortably put your boss in the best possible seat for their preferences.

“Anticipating what is going to happen is key when managing travel and these apps really help me do that,” Patrick says. FlightAware and SeatGuru help assistants see in real-time what is happening without actually having boots on the ground.
Travel isn’t predictable and never offers the comfort of complete control. By implementing best practices, tips and advice, navigating travel will become easier, less stressful, and a more enjoyable component of your job.

Executive assistants must be on top on their executives plans at all times. The Executive Leadership Support Forum provides attendees with top level strategies for organizing travel itineraries. These strategies cut down on time and streamline logistics to keep executives on schedule.
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 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 will be speaking on a panel at the Executive Leadership Support Forum: New York City on Inside the Professional Life of New York Celebrity Assistants, and will 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.elsforum.com/events