This article is adapted from The 29-Hour Work Day.
Ethan had a very interesting experience when he worked for a CEO of a billion-dollar company. His principal wielded power in a rather odd way: he liked to keep his direct reports and everyone else working with him “guessing.” That means, he kept them on their toes, perpetually worrying whether they would be the next one handed a pink slip and told to pack their stuff. Frequently, without any warning, people would be fired.
One day, after supporting that CEO for two years, Ethan was on the receiving end of the pink slip. It came completely out of the blue. Never, in the two years of working with the man did Ethan receive an indication that his support was insufficient. In fact, Ethan had heard from other executives in the company that he was doing exceptionally well.
It’s not fair to put anyone in Ethan’s position. It’s also not fair to yourself or your company to allow someone to continue working for you without knowing whether they are meeting your expectations—it is equally unfair to neglect to give them a chance to do so through training or instruction.
That kind of relationship with your assistant—or any direct report—is doomed to fail from the start. Instead, you must learn to partner with your executive assistant. The following are some of the strategies that we have found to be the most productive and that lead to the highest level of efficiency and performance.
One of the first things to do, right off the bat, is to copy your new assistant on every single email (within reason, of course; highly personal or confidential correspondence that does not relate to the company does not need to be shared). By doing that, they will get some context, as well as a feel for your rhythm and the people you’re emailing most.
In addition to that, send out an introductory email to everyone in your company and your VIPs outside it that welcomes, in an enthusiastic and heartfelt way, your new EA into the fold. Along with sending the email, encourage all of your direct reports to take fifteen or twenty minutes to meet with your new EA.
To help spread awareness of the new EA to people outside the office, some principals include their assistant’s name and contact information in the signature line of their emails. Not only does that immediately show your EA and everyone you know that you have a high level of respect for them, but it helps train people that there is a system. Before they go to you for every question, they can check in with your EA.
When it comes to training your EA, again, an outgoing one is ideal to train the incoming one. If you do not have one, then it’s up to you to train the new EA. You should have a few guideposts to get you started, one of which is that inventory of things you don’t want to do—the reason you hired that person to begin with.
Start with that list. Show your new EA what needs to be done and how you have done it to date. Setting up their email account in a way that gives them access to your contacts and calendar will help them tremendously. That way, they can proactively get you up to speed with whom you are meeting with (if necessary), what they do, and why you are meeting with them.
If you have a file system in place already, review it with your new EA. If there is not one in place, suggest your EA use her inbox as a task list. Immediately establish feedback meetings, where you can check in to see what your EA is working on and what you need done that day. Then, ask if they understand how to do what needs to be done. Show them if necessary.
We are astounded every time an executive tells us, “Oh, I know I’m a micromanager. I’m working on it.” In this instance, “working on it” is not good enough. If you have the self-awareness to know you are micromanaging, then stop doing it.
As the principal, you will naturally share as much as possible with your assistant because that person is there to help you. The more information they have, the better equipped they will be to use their superpowers to magnify your performance.
Micromanaging does the opposite of its intended effect. It inhibits superpowers and prevents your EA from mining their previous experience for innovative ideas that could be of benefit for you. You have no idea what your EA may have learned in the past, what they’ve had to research, or what kind of projects they’ve been part of. And that means you have no true idea of what they can bring to your table.
Accountability Versus Criticism
We’ve witnessed executives harshly reprimanding their EAs, and even bullying them, and can honestly attest that such tactics are not sustainable for a long-term relationship. There should be no keeping score, no gotcha! attempts to find an EA doing things wrong, no testing them to prove something, no adversarial approaches to enforce behavior. That is not what partnership is about. Partnership is about collaboration, not confrontation.
The idea that you can belittle or berate your assistant à la the movie Swimming with the Sharks is being thrown by the wayside due to a couple of factors. First, the #MeToo movement empowered women, who make up 98 percent of assistants, to stand up to management and not take abuse.
Second, the combination of assistant plus technology plus emotional intelligence/art of hospitality expands the meaning of executive assistant to encompass business partner, chief of staff, project manager, assistant/scheduler, and personal assistant if the principal is open to treating their assistant as such.
Feedback and Reviews
Related to holding your EA accountable is the concept of providing constructive feedback. It is so valuable for your EA, they will be eager to hear it. Feedback can begin almost immediately upon hiring. Begin with daily meetings to go over what they did and how it went. Once you realize you have little to talk about, you can move those check-ins to weekly meetings, then monthly, then quarterly.
Those meetings give your EA an opportunity to see how you do things and what your processes are. They can also open a dialogue for your EA to provide feedback on how to improve things. Because your EA is coming in with fresh eyes, they may notice things that you gloss over.
One thing that is imperative to remember when providing feedback is that, in addition to being honest, you must explain why an issue is an issue, why it matters that it is done correctly. That is one of the ways you can bring a heartfelt, personal touch to the conversation. Knowing what that reason is can soften the review process and make it about the company, and not so personal. That, in turn, might make the review process go a little easier.
There’s No Magic Wand
Many times, adversarial relationships between principals and their EAs arise because an assistant is forced to deliver bad news that something is unavailable or not possible, thus disappointing an executive with unrealistic expectations. Sometimes executives think their EA’s superpowers mean they can wave a magic wand and make anything happen.
While EAs often can do what appears to be magic, sometimes restrictions are placed on all of us that no amount of magic will undo. To make the principal-EA relationship work, you must establish a partnership.
A principal cannot expect an EA’s superpowers to be of optimum use unless the proper amount of time is given to the assistant for continuous onboarding, as well as for letting your assistant into your thought processes and priorities.
For more advice on partnering with your EA you can find The 29-Hour Work Day on Amazon.
Ethan Bull is a co-founder of ProAssisting, a next-generation remote executive assistance firm for business owners and C-suite executives. With a background in hospitality and expertise in the EA space, Ethan has held a variety of senior positions, including Director of Administrative Services and senior EA to the president and CEO at Rochester Regional Health.
Stephanie Bull is ProAssisting’s co-founder and the former EA for J. Crew’s CEO and the CEOs of two multibillion-dollar hedge funds. Before developing ProAssisting, Stephanie proved herself an expert in the field and a vital addition to the C-suite by fulfilling a variety of roles, including chief of staff, estate manager, and investment liaison.