Working With An Executive Assistant
One of the most common pieces of advice I have given to leaders I have mentored or coached is to hire an Executive Assistant. These leaders are almost always founders who have accomplished much, but then find themselves overwhelmed as their successful enterprises grow to bigger sizes. Usually, my advice is met with acceptance but also with reluctance, as these leaders express hesitation to hire an Executive Assistant when they are unschooled in how to work with one. I put this short guide together to help leaders overcome their reluctance and hire an Executive Assistant.
I. Orientation to working with an Executive Assistant
Many people would think of an Executive Assistant as someone you can delegate lower order things to -- they are the person who does your busywork, thereby freeing you up for higher order responsibilities. I argue that this orientation is flawed, and it will lead you to neglect the significant opportunities available to you if you have an Executive Assistant. Instead, it’s best to think of an Executive Assistant as someone who helps you to be more effective with your time.
What does it mean to think of an Executive Assistant’s role as helping you to be more effective with your time? You could start by imagining the many things you might do on a normal day. You probably would conduct meetings with the people who directly report to you. You might need to make a significant decision about resource allocation or finances. You could be spending time reviewing organizational strategy or positioning and identifying pivots or modifications. For all of these examples and more, you can be more effective in the same amount of time (or less time!) with an Executive Assistant’s support.
Consider a meeting with a direct report. Do you normally have an agenda ahead of time such that you can reflect on it in advance of the meeting? Do you usually have real-time data from the direct report’s areas of responsibility to review ahead of time? Do you always have inputs from the person you are meeting with so that you know their frame of mind going into the meeting? In my experience, the answer to these questions has usually been “no.” It would have been nice to have all of this information in advance of the meeting, but I mostly never had enough time and I never felt on top of my schedule enough to where I would be preparing for tomorrow’s meeting today. An Executive Assistant can change that.
II. Job Description
Bearing the general principle in mind, here are some key responsibilities that would form the core job description for an Executive Assistant:
Preparing you for meetings by putting together an agenda ahead of time and circulating it to attendees; gathering pertinent data and other significant information and delivering it with time for you to digest it; soliciting inputs from meeting attendees that you might use to revise the agenda, tone, or content of the meeting.
Maintaining up to date and comprehensive data covering all operations you oversee, and most importantly drawing out trends, critical developments, or flags that demand your attention; compiling and presenting dashboard-level summaries of the data.
Since many interactions with subordinates will take the shape of them requesting that you make a decision or that you delegate decision-making authority, an Executive Assistant should be tasked with preparing any such requests for your review. This might include identifying needed supporting data or key background information, all of which will enable you to make an informed decision faster and with more confidence.
Ad hoc research projects that involve gathering and then organizing large tranches of information and summarizing findings, all in support of major organizational decisions. For example, you might be considering a large expenditure on multi-year polling to establish and then track the name recognition, favorables, and intensity of enthusiasm for your organization’s signature programmatic initiative. Much publicly-available polling data likely already exists and could be used in decision-making, and an Executive Assistant could gather that information so that you can make use of it in creating a plan and budget for your own polling.
Of course, an Executive Assistant should also have responsibilities that would formerly have been up to you to complete. By assigning these responsibilities to an Executive Assistant, you can devote more of your time to duties that cannot be delegated.
Schedule and calendar management, including scheduling new events and meetings, rescheduling as necessary, and preparing attendees by circulating agendas, logistical information, and any needed documents.
Financial management, such as purchasing supplies and equipment, reimbursements, and accounting oversight.
Note-taking during all meetings, distribution of notes post-meeting, and assignment of responsibilities once a meeting has been completed.
Logistical arrangements, such as scheduling Zoom meetings, booking flights, renting cars, or booking hotel rooms.
Keeping a to-do list and scheduling time for each to-do item to be completed.
Attending meetings, conferences, or other gatherings that would be a lower priority for you to attend; producing summary toplines and detailed notes for your review.
Handling incoming requests ranging from sharing a file to writing a letter of recommendation.
III. Best practices
Keeping in mind the orientation that an Executive Assistant should help you to be more effective with your time, it logically follows that a successful working relationship with an Executive Assistant requires that they understand your definition of “effective.” By that I mean that your Executive Assistant needs detailed knowledge of your goals and priorities, and as much as possible they should be trained to evaluate a situation as you would. You can do that by devoting time early in the Executive Assistant’s tenure to explaining your decision-making process. Each call or meeting the Executive Assistant attends is a window into your thinking, and you can expand that window by debriefing afterwards to review your thought process.
One of the best ways to accomplish a mindmeld with your Executive Assistant is to meet with them regularly. I recommend that you begin each working day with a short meeting of around 15 minutes with your Executive Assistant. Standing agenda topics would include:
Priorities for the day/week/quarter.
Reviewing the schedule for today and tomorrow, and identifying any necessary preparations that the Executive Assistant will need to complete.
Discussing any upcoming to-do list items.
Adding categorization, prioritization, and deadlines to new to-do list items.
Requesting information.
Once a week, I recommend holding a longer meeting that would be sure to cover:
A complete review of the to-do list and scheduling for when items will be finished.
A presentation by the Executive Assistant intended to draw attention to major findings or developments as reflected in dashboard data. In other words, this is the Executive Assistant’s opportunity to make sure you are aware of critical information.
Managing your to-do list is an important responsibility for your Executive Assistant. There are two benefits to be gained: not losing sight of tasks, and freeing some of your attention away from keeping track of all of them. I would suggest a process like this for setting your Executive Assistant up manage your to-do list:
The Executive Assistant should add to-do items into a spreadsheet or other document and assign them a priority level and due date.
There are two ways you can add something to do the to-do list. You can do it directly by sending your Executive Assistant a note or communicating verbally that a task should go onto the to-do list. Or you can copy your Executive Assistant into an email thread. The Executive Assistant should be trained to recognize when they are being notified of a to-do list item in this latter fashion.
In some cases, there may be intermediary steps to take before you can complete a to-do list item. These steps should be enumerated in the daily meeting where you review new to-do list items.
Using the prioritization, due date, and knowledge of your schedule, the Executive Assistant should schedule the to-do item for a specific date in your calendar.
You will communicate completion of your to-do list items to your Executive Assistant via your daily or weekly meeting.