Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Project Management

Fluency of Thought and Flexibility of Action: The Assistant’s Guide to Project Management


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 will be a distinguished speaker at the Executive Leadership Support Forum: New York City, June 28-29, 2017.

Whether you aspire to bulk up your resume, or you are looking to expand responsibility within your current role, project management is an essential skill to growing within your career. Patrick recommends three steps to mastering project management: Always volunteer, start small, and finally, expand your scope into to more comprehensive projects.



See where you are needed. Patrick reminds that as a business partner to your boss, often you can see first where projects need an extra hand. In some instances, your boss might not even be aware a project is falling through the cracks. Point out when a leader is needed and ensure your executive, you are available to help.

If there is someone already assigned as a project leader, Patrick recommends still volunteering to co-pilot. “The only way you are going to get heard is if you raise your voice. Get your foot in the door and show your worth.”

Executive assistants are often underutilized. Stepping up and taking on new responsibilities and projects will not only build trust with your executive, but it will also help you expand into a respected member of the leadership team. Volunteering to spearhead a project provides you the opportunity to gain experience in new areas, while building your leadership skills.


Start small

Breaking into project management can start with small tasks. Patrick explains,

It may be as simple as updating your executive’s rolodex. That’s a project where you can say, ‘this is something that needs to be done because your contacts have not been cleaned up since 2007. Some of the people have not been at that company for a while, how about I just go through them and update them for you?’ Start there. Start small. It’s usually the first thing I try to do in any job – whether it’s a celebrity or a CEO. It’s a perfect way to (a) show initiative to your boss; (b) start the job off knowing everyone’s number and email are correct and; (c) get to know and start to create relationships with all of your boss’ friends, family and colleagues. Already on day one you are engendering for yourself an idea of how everyone fits into your boss’ life – who is important and why – and that knowledge is key to your success.

When you step up and create a system that is helpful for your executive, you pave the way for larger responsibility.


Expand your scope

When taking on larger projects, anticipation and careful planning, once again, play leading roles. It’s prevalent to implement best practices to safeguard all bases are covered. At the start of a project, ensure you have all project details and familiarize yourself with all stakeholders involved.

Communicate with team members who will have a hand in the project. Schedule a brief kick-off meeting with project team members to confirm all expectations are understood and define project milestones.
Ask questions. Get to know everyone involved and ask questions. Even if they seem mundane. This not only helps you to define all parameters and limits but also shows to your employer that you are seeing the whole picture.

When delegating tasks, ensure involved parties are clearly aware of their responsibilities. Assist with project flow by keeping your team updated with milestones and important information. When conducting meetings or providing updates, concise is key. Last but certainly not least, communicate hiccups or deadline changes. Changes happen and deadlines are not always met. Secure enough time to cushion changes nearing the end of the project. Again, it’s all about being flexible in all your actions and having plans in place for all contingencies.


Technology to the Rescue

Notes/Voice Memos. Nothing is easier on the go that being able to dictate something that is on your mind or quickly typing something into your phone and every phone – iPhone or Android – has something like this built in so no need to download!

Asana. Allows you to manage and communicate with multiple teams on multiple projects. Create task lists (and more importantly check off what has been done!), get reminders, and add files to the tasks and it’s a great app so it’s on your phone!

Having a system in place for stepping into leadership is key. By implementing best practices, tips and advice, project management can be an exciting next step to evolving your resume or growing within your current position.

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:


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