Lead with the best version of yourself.

The Executive Assistant Billet: Keys to Success



By CAPT Kevin Volpe

Congratulations! You have been selected to be an Executive Assistant to a General, Admiral, or high-ranking civilian. You will find this to be one of the most rewarding (and demanding) assignments in your career thus far. Maybe you have served as an aide-de-camp before, or perhaps this is the first time you have worked directly for a General Officer/Flag Officer. Either way, the Executive Assistant job requires patience, humility, and endurance. But you will also draw on all the skills and talents that you have already honed. Here are some tips for success:

Know your boss. Above all else, you need to be familiar with the principal who you are assisting. From a functional perspective, ensure you understand his or her roles, responsibilities, and authorities within the organization. During the interview process or on the first day, ask about their priorities and goals, critical information requirements, and “wake-up” criteria. As the first days and weeks go by, find out how he or she best processes information (e.g. reading vs. listening) and get a feel for their writing style, since you will be proof-reading and editing letters, memos, and ghost-emails. Finally, understand your boss’ personal battle rhythm and energy cycles. What part of the day do they prefer to do routine paperwork, and when do they like to do their strategic thinking?

Remember what got you here.You were selected because your previous performance demonstrated that you have the talents, skills and maturity valued by senior leaders. Just like every previous leadership position, you will be expected to anticipate requirements and protectively ensure their completion with minimal guidance. Like a baseball player making it to the majors, the fundamentals of the game haven’t changed, but the required level of skill and focus has greatly increased.

Get organized (for two). You probably already have a tried-and-true organization system that works for you. I have always preferred David Allen’s Getting Things Done. But whatever your process for managing your schedule, inbox, and to-do lists, it must now accommodate both you and your boss, and take into account his or her preferences for processing information. Maybe you are inheriting a system from the individual you are relieving, and therefore only minor tweaks are required. But if you are starting at the same time your principal taking over their job, you’ll need to build from scratch, and have an iterative feedback process on what works and doesn’t. To the maximum extent possible, strive to make 80% of what you do routine and automated (through checklists, calendar reminders, outlook signature blocks, etc) so that you can focus most of your mental energy on the 20% that consists of pop-up meetings, short-fused taskers, and full-on “clear the schedule” crises.

Master your weapons systems. This is a staff tour, so you are no longer flying an aircraft, conning the ship, or leading an infantry unit. Your primary weapons systems consist of secure phones and the suite of Microsoft office applications, especially Outlook. Learn them well. Even if you are fairly familiar, you need to master them so that actions become second nature. Don’t let the first time you learn to transfer a call occur when you have your principal’s four-star boss on the line. Take online courses on Outlook, Sharepoint and OneNote, to find those hidden gems that will help you automate your routine processes.

Separate the signal from the noise.Your boss is inundated with information: emails, phone-calls, weekly reports, memos, daily intelligence products, read-ahead material, and drive-by updates from subordinates. Even the most voracious consumer of information will not be able to fully process all of it, and you will need a triage system. The “Urgent vs. Important” matrix is an extremely helpful way to categorize information and taskers. This first requires an understanding of your boss’ priorities and goals, as previously discussed. Once you have determined relative importance of the item, you need a method of curating that works for your boss so that he or she can quickly scan their inbox or to-do list and attack the next important item. A word of caution: context matters. Some priorities are enduring, some change daily. One of your biggest challenges will be finding that sweet spot between “Why are you showing this to me now?” and “Why haven’t I seen this before?” This daily battle is not for the faint of heart. From a risk mitigation standpoint, remember that it’s better your boss “have it and not need it” than “need it and not have it.”

Be the gatekeeper. Leaders demonstrate priorities not through words, but in how they spend their time. You know your boss and his or her priorities. You have a solid organizational system to track, rank, and execute required actions and events. Now you need to be ruthless in keeping the schedule focused on what’s important. The lower your boss is in the food-chain, the more difficult this can be, as meetings always pop-up and more senior leaders react to changing priorities (or shiny objects). Regardless, be as assertive as you can – within the bounds of military courtesy and maintaining important relationships – to ensure your principal is focused on the truly important and not the seemingly urgent.

There will always be someone who says, “I just need five minutes to update the boss.” First of all, nothing takes five minutes. More importantly, if left unchecked, such “drive-bys” can consume the day and prevent strategic focus. Unless it is both urgent and important (read: crisis), it should be properly scheduled. Your boss will appreciate you being the “bad guy” and not him. Be careful here though. Your principal may want visibility on all invites and meeting requests, in order to have the final say. Again, know your boss.

Be connective tissue. The Executive Assistant job is all about relationships. Certainly the primary relationship is between you and your boss. But in order to be truly effective, you need to build a network of contacts, and ensure the relationships are more than just transactional. These contacts will include fellow EAs within your organization, support staff (especially IT and comms), and the front office of your principal’s boss. Richard Haas’ compass framework in The Bureaucratic Entrepreneur is helpful for identifying the important relationships to nurture. You must build trust by sharing information, fostering teamwork, and not letting short-fused taskers get in the way of the long-term relationship. With any new piece of information, schedule change, etc., your first though should be, “Who else needs to know this?”

Be discreet. Although it is important to be connective tissue, some of what you hear and read needs to be closely held, not due to bureaucratic “rice-bowls,” but because the information may be pre-decisional, involve sensitive personnel moves, or stay within what I like to call “principal-assistant privilege”. You will see your boss on both their very best and their very worst days, and they will be extremely candid with you at times, because besides being the EA, you also serve as consigliere and chaplain. Such conversations stay behind closed doors.

Your boss’ subordinates will be very respectful and at times deferential to you, even if they outrank you, because you are the gatekeeper. Don’t let it go to your head, and never wear your boss’ rank. Stay humble and courteous. You will often relay your boss’ feedback to his or her subordinates, which can be problematic when they outrank you. I have heard this described as “walking amongst elephants.” Make sure you don’t get trampled.

By all means, be able to make cordial small talk when engaged by a high-ranking officer, but also know when to stay quiet. As a military assistant to the Secretary of Defense once told me, assistants should be like pieces of furniture: they should only be noticed when they are needed.

Keep it in perspective. Yes, this can be a stressful job. Your boss most likely has high standards and a low tolerance for mistakes. And you are definitely going to make mistakes, especially early on. Shake it off, focus on the next task, and remember that unlike other leadership positions you have held in tactical units, there are no lives at stake here. Although it may feel like it, no one is going to die because the most current slides didn’t make it into the read-ahead binder right before the meeting.

Don’t waste the opportunity. Your time as an Executive Assistant will be highly educational. You will be personally mentored by a high-performing leader in your organization. You will be able to review information and attend meetings that peers in other billets cannot. It can be easy to get cynical, and see yourself as a highly-paid clerk or a glorified scheduler. Get past that and make the most of this amazing opportunity.

Any and all opinions are solely my own and do not represent the views of the Department of Defense

CAPT Kevin Volpe is a Naval Flight Officer who previously served as Commanding Officer of VAQ-135. He is currently the Deputy Executive Assistant to the Chairman of the Joint Chiefs of Staff. He is the author of the Father, Sailor, Citizen blog, where this article was originally posted.