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Ethan Bull 9 min read

Even the Best Executive Assistants Make Mistakes

Even the Best Executive Assistants Make Mistakes 

This article is adapted from The 29-Hour Work Day.

You probably don’t have enough hours in your day and important things are falling through the cracks. Executive assistants can be the answer to most, and possibly all, of these issues. But the role of a great EA isn’t easy either. They have to use superpowers, like ESP, to anticipate their principals’ needs in advance, or omniscience, to take more control over day-to-day details. 

Naturally, you do not want someone who makes many mistakes, but “to err is human,” as Alexander Pope once said. Mistakes will happen. How your EA handles them is what matters. A good EA holds themselves accountable and is genuinely remorseful when they make a mistake. You want someone who will care about your business as much as you do, and one of the ways they will express that is in the way they handle mistakes—being mortified, remorseful, and fixing them as soon as possible is the right way.

When it comes to mistakes, there are also some lessons that principals should keep in mind. If you want to develop a strong partnership with your executive assistant and effectively weather any storms that may arise, read on to learn how you can keep your bond tight in the face of mistakes.

Mistakes Aren’t an Excuse to Micromanage

Something we have repeatedly witnessed is that when an EA makes an honest mistake, many principals use it as an excuse to micromanage, which is almost never the right way to handle the situation. 

In the grand scheme of things, most mistakes can be fixed with a simple adjustment. It is better to let the mistake be part of the growth process so the EA can learn from it and become better at their job, than to micromanage it, which will inhibit growth and improvement.

When an EA makes a mistake, you may be justified in being angry. And your assistant will need to create a system or tool to make sure they never make that mistake again. But berating your assistant or micromanaging won’t fix the problem. 

Instead of micromanaging, the executive can encourage growth by asking, when things are calmer, how they can prevent the mistake from happening again. Perhaps they could create a table that listed frequent travel destinations and her preferences for each one that he could check prior to finalizing any reservations.

Not All Mistakes are Actually Mistakes

Some principals perceive any deviation from perfection as a mistake, which is true only if something goes wrong. And other principals assume there is only one way to do something and doing it any other way is a mistake, which, again, is not a mistake—unless something goes wrong. 

When an EA takes a different approach to manage a situation or uses a different phrase in communication than you would, that does not mean the EA blundered. It means they are a different person than you. Spending time to explain how you would handle it or having a discussion about the difference between the two styles is counterproductive and, worse, could undermine your EA’s self-confidence going forward. 

The same could be said regarding demanding perfection with every action. Your concerns should be: Did the job get done? Is everyone satisfied? If the answer is “yes” to both, no mistakes happened.

And when you do hold an EA accountable, be sure you’re right—remember your EA is great at documenting!

No Surprises

You should have an open line of communication with your executive assistant, which includes having regular opportunities for constructive criticism and feedback. Being candid is always the best approach with feedback, as well as with reviews. 

Despite your EA loving to get feedback, most likely they will dread the review process. Everyone hates the review process—both the reviewers and the reviewees, which is why we stress that they should be held in less formal settings than an office. Reviews should be a time to kick back and have a couple of laughs about the year—however, they should also conquer the serious turf of where improvements need to happen as well as areas of strength.

The last thing a review should be is a surprise for the reviewee. Stephanie had a principal who gave two reviews a year. With each one, the principal opened with, “If anything comes as a surprise to you, then I’m not doing a good job.” But he was great at his job, and consequently those reviews never held any surprises. When he wanted to see improvement, he was straightforward about it, explaining what he wanted to see and why. Stephanie always knew where she stood with the man and where she stood with the company. Having that kind of open relationship led to an optimal working environment, in part because expectations were clear and understood.

Everyone Makes Mistakes

The key point to remember is everyone makes mistakes. The ideal way of handling them is to ensure something was learned so the mistake doesn’t happen again. 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. Ideally, the relationship between a principal and an executive assistant is a partnership, and keeping assistants on their toes isn’t what partnership is about. Partnership is about collaboration, not confrontation.

For more advice on finding the right 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.

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Ethan Bull

Co-Founder of ProAssisting

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