7 Tips For Being the “Boss” of Your Boss

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7 Tips for Being the Boss of Your BossBy Kristina Schneider, Executive Assistant

An executive assistant is probably one of the most important support staff members that any busy professional could possibly have, regardless of his or her profession. One of the things that we hear all the time from our boss, Phil Kavesh, is that his executive assistant is actually his boss. Of course, this doesn’t give us, as executive assistants, the same kind of “power” that a normal boss might have over an employee. What being the boss of your boss means is that you are supporting your boss and directing his or her daily work life so that he or she is merely the “actor”, working as smoothly, efficiently, and productively as possible.

Utilizing the experience I gained in the better part of the last 11 years supporting Phil Kavesh as his “boss”, I present to you the 7 steps that every executive assistant and executive should take in order to reach this “assistant-boss” level.

Tip #1: Communicate Expectations

If you’re an executive assistant, your boss already hired you for a specific purpose. But all executives have different personalities, working styles, and expectations about what he or she wants from an executive assistant. So, the first step in better understanding what your role will (and won’t) be is to communicate with your boss about what expectations he or she has for you. Frankly, some bosses don’t want a certain level of hand-holding or assistance that other bosses may require.

Additionally, from the very outset, it would be helpful to communicate about what kinds of tasks you will be expected to handle. In particular, if any personal tasks will be handled by you. An executive assistant may have some personal tasks that they will take on, but it is important as an executive assistant to know whether or not those personal tasks are expected of you, what priority they will have, and how you feel about taking on those personal tasks.

Tip #2: Create a Calendar Template

One of the most essential tasks that any executive assistant manages on a daily basis is the boss’ busy and constantly moving calendar. In order for any executive assistant to do this task effectively, it is helpful to have a general idea of how the boss wants his or her calendar laid out. This calendar template is intended to be more of a guideline for you to use about your boss’ scheduling preferences.

Here is a sample of what a calendar template for an estate planning attorney may look like:


9am                Meeting with Associate Attorneys

12pm              LUNCH

1pm                Client Appointment (appointments may be either in person meetings or phone calls)

2:30pm          BREAK

3pm                Work Time (Projects, Marketing, Reviewing Files/Plans, etc.)

4:30pm          Meeting with Executive Assistant


9am                 Client Appointment

10:30am         Client Appointment

12pm               LUNCH

1pm                 Client Appointment

2:30pm           BREAK

3pm                 Client Appointment

4:30pm           Meeting with Executive Assistant


9am                 Client Appointment

10:30am         Client Appointment

12pm               LUNCH

1pm                 Client Appointment

2:30pm           BREAK

3pm                 Client Appointment

4:30pm           Meeting with Executive Assistant


9am                 Client Appointment

10:30am         Client Appointment

12pm               LUNCH

1pm                 Client Appointment

2:30pm           BREAK

3pm                 Work Time (Projects, Marketing, Reviewing Files/Plans, etc.)

4:30pm           Meeting with Executive Assistant


9am                 Client Appointment

10:30am         Work Time (Projects, Marketing, Reviewing Files/Plans, etc.)

12pm               LUNCH

1pm                 Client Appointment

2:30pm           Meeting with Executive Assistant

3pm                 Leave Office

Obviously this sample calendar template above is very structured and may not even seem possible. I realize that it appears to not allow any room for a variety of appointments and commitments that come up on a boss’ busy calendar. However, having a template of what your boss would like his or her typical workweek to look like, including preferences for arrival times, lunchtime, breaks, departure time, and the time of day he or she wants to work on certain tasks is all part of being an effective executive assistant. Having this template and pre-blocking these times on the calendar will help you better manage the calendar and your boss’ scheduling needs, while also eliminating the chaos and stress that comes with a calendar filled with no structure at all.

BONUS TIP: Create a fundamental, non-negotiable rule that you, the executive assistant (and ONLY YOU!) have access to modify, change, add or remove things from your boss’ calendar. All appointments and calendaring needs for your boss should go through you, because you’re the one responsible for supporting your boss and managing the calendar and there is absolutely no way that can happen if others have access to modify the calendar. By the way, this includes your boss! The boss will always be able to access his or her up-to-date calendar by going onto your computer system or using a phone app (like Google Calendar).

Tip #3: Schedule Regular Check-In Meetings

As you can see with the sample calendar template, there are daily meetings scheduled for the boss and executive assistant to meet. It may not need to be 30 minutes or even daily, but a regular time for you to be able to meet with and check in with your boss is very important to you being able to be the boss of your boss. This helps to avoid countless interruptions throughout the day from both you to your boss and your boss to you.

Tip #4: Be Your Boss’ Gatekeeper

This may be extremely difficult to do depending on how much control your boss is willing or unwilling to give up. It’s important that executives are doing tasks that are maximizing the highest and best use of their time. Unfortunately, we see all too often that attorneys are handling a variety of administrative tasks that would be best handled by an executive assistant. This includes anything from answering the phones, checking e-mail, making copies, pulling files, managing the calendar, and even sifting through the mail! While all of these tasks are important, they can all be handled by someone else. Unfortunately, you cannot do your boss’ principal job and meet with clients or provide clients legal advice. Anything else that can otherwise be handled elsewhere should be delegated to you (or someone else in the firm) and the more you can function as a gatekeeper and protect your boss’ valuable time, the more productive he or she will be in doing the things that bring the most value to the firm.

Tip #5: Strive to Be a Step Ahead at All Times

As an executive assistant, it’s your job to strive to be a step ahead at all times. That means that you should be more prepared for your boss’ day than he or she may be.

One easy way to do this is to make sure that you have anything that he or she will need to complete the tasks for the day already pulled, placed in chronological order (ideally in files or some other organized fashion), and ready to go so that when that day comes, you’re prepared. The day before, you should print a copy of your boss’ calendar out and make sure any appointments (including phone calls) are confirmed. Then, check off all of the files and items that he or she will need to make sure that your boss is prepared for the day.

Tip #6: Don’t Be Afraid to Be Firm with Your Boss

In order for you to be the boss of your boss, it is important that you try and remain firm with your boss. This doesn’t mean you get to be unprofessional and insubordinate to him or her. What this means is that you shouldn’t be afraid to speak up when your boss may try and have you schedule something or change something that would otherwise contradict a project or priority that he or she has communicated to you.

This tip is a tricky one, because every boss is different and may react differently to resistance. But, it’s all about how you approach your boss. Make sure that you’re clear that you’re trying to achieve the same goals and help your boss keep on tasks to the priorities that he or she has provided you.

Tip #7: Be Open to Learn a New Way of Doing Things

First, if you haven’t already done so, check out my other article on how to build trust and rapport between boss and assistant. This article has a number of tips on how both you and your boss can start to work better together, because in order for you to be your boss’ boss, he or she needs to be able to trust you.

Also, if you think that you might benefit from getting some additional training on how to better organize yourself and support your boss, you might want to check out a number of our previous articles, as well as our Executive Assistant Training.

Last, but certainly not least, in order for this type of working relationship to work, your boss needs to be open to it. If you don’t think that your boss would be open to giving up some of the control needed to allow you to be his or her boss, you may want to discuss the possibility of your boss attending one of our 2-day Ultimate Level programs, which will help with this issue and much more! (See www.theultimatelevel.com for more information.)


As you can see, communication between boss and assistant is the key to making all of this work. Communicating about his or her expectations, calendaring needs, priorities and goals, etc. Additionally, communication about what you need in order to do your job and support your boss’ goals is also necessary.

It might not happen all at once and it does take some time to develop the trust and rapport needed between assistant and boss to reach this type of working relationship – – but, it can be done. And when done properly, the result is pretty amazing and rewarding – – for both you and your boss, as well as the company!


By popular demand, we are now offering Executive Assistant Training for Executive Assistants! During an Executive Assistant Training Session, we will be able to cover an array of best practices for Executive Assistants and assist your Executive Assistant with advice on the following areas:

  • Calendar Management
  • Prioritizing Tasks
  • Managing Interruptions
  • Handling Difficult Clients
  • Organizing Your Office Space
  • Writing Proper Business Correspondence
  • Maintaining Confidentiality
  • Hiring and Training Other Staff
  • Developing a Procedures Manual
  • And much, much more!

Think about it…if your Executive Assistant was able to free you up to get more done and functioning at the highest and best use of your time, how much would that be worth to you? If you could meet one more client each day, would that be worth it? If it took some stress off your plate so you could sleep at night a little easier, would it be worth it? If you said yes to any of these questions, then sign up your Executive Assistant for our Executive Assistant Training today! >>MORE INFO


Kristina Schneider is the current Executive Director of The Ultimate Estate Planner, Inc. She graduated with a Bachelor’s Degree in Business Administration from Pepperdine University in 2004 and was hired right out of college to work for the Law Firm of Kavesh, Minor & Otis, coordinating and facilitating Philip Kavesh’s “Missing Link” Boot Camps while also providing administrative support to Mr. Kavesh as his Executive Assistant for over 7 years. With a combined almost fifteen years of administrative experience and her direct experience working at Mr. Kavesh’s law firm, Kristina has been able to assist numerous estate planning professionals through The Ultimate Estate Planner, Inc. And, equally as important, she has assisted the executive assistants and staff members of many of these estate planning professionals to provide better service and support.

You can reach Kristina at (424) 247-9495 or by e-mail at kristina@ultimateestateplanner.com.


Image courtesy of jesadaphorn at FreeDigitalPhotos.net

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