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

Few are the executives with very little on their plate. Most—actually, all—whom we have worked with not only had overflowing plates but several such plates on the table, not to mention a platter or two. One of Steph’s clients could easily be described that way. His business is one that ebbs and flows seasonally, with summers being the slowest period with the fewest number of projects going on. However, that principal took on a new kind of project over the summer, which kept everyone in hyper-mode.

Knowing he was adding more to everyone’s responsibilities during a time when they usually had less, he tried to compensate by being more hands-on. However, what he considered “hands-on” was what his staff considered “micromanaging.” Not only was he involved with every aspect of the project, but his attempts to be useful and supportive were actually disruptive.

As everyone’s stress level increased due to his interference, a parallel uptick in mistakes became evident. Not realizing the true cause of the stress and errors, he doubled down on his efforts to “help.” Soon, that included reading all communication regarding the project. Yes, this added hours to his days at the office and amped up his levels of frustration while decreasing his (and everyone else’s) effectiveness.

His micromanaging reached a peak one day when he called Steph to admonish her for being “too polite” to a representative of a company they were partnering with to complete part of the project. He let her know that, in his experience, people who are polite the way she was are often interpreted as passive-aggressive or sarcastic.

Steph was taken aback. She explained to her principal that she’d built a relationship with that particular rep and that they had a very friendly and polite rapport. She tried to assure him the rep did not interpret her through such a negative lens. He refused to let it go, so Steph apologized and let him know she’d be more careful in the future and try to refrain from being “too polite.”

The result of her executive’s request wound up causing Steph to be less productive. Emails that would typically take her a minute and a half to write now took over five. Phone calls she’d never hesitate to make or answer gave her pause while she reflected on how to get into the mindset of being anything other than too polite. Worse, the whole experience eroded her self-confidence. A person’s optimal communication style is subjective; micromanaging such things makes everyone wonder what else is being observed and criticized.

In the end, the company completed the project. They did a satisfactory job, but the executive was not thrilled with the outcome. Everyone on the staff was exhausted, burned out, and morale tanked to an all-time low—just in time for fall, their busy season.

It did not have to end that way. The executive could have kicked off the project by letting everyone know he was there if he was needed and that he trusted the team to get the job done. Even better, if he had been able to let himself partner with Steph instead of micromanaging, he may have seen better results from the project because she was a key player in it.

Establishing a level of trust will enable your EA to unleash what we call their EA superpowers. At that point, you will notice a shift in what they do for you—a shift for the better—and a shift in your relationship. You will have more confidence in each other because when you trust your EA, your EA will trust you to have their back, which is what they need to really go the extra mile for you. The benefits from such a relationship are plentiful! Executives will be more effective, efficient, and organized.

It sounds so perfect, executives may just want to jump in and trust 100 percent from the start. However, full trust means:

  • You hand over your credit card information so your EA can make purchases and travel arrangements and pay bills.
  • You will provide your EA with your social security number so they can complete forms.
  • They may have access to your most important financial information.
  • You will need to be comfortable letting them handle those times when business life and personal life bleed into each other—like when someone must communicate, nicely, with an ex-spouse to coordinate schedules around children.
  • You will need to be comfortable with them communicating with your most important business relationships.

That kind of trust is intense. It’s like jumping off a cliff: there is no way to guarantee that nothing bad will ever happen to you or the information you shared with your EA. However, if you don’t take that risk, your performance, results, and ultimately, your income will be hampered.

For more advice on trusting your team, 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.