How Executive Assistants Can Deal with Difficult Bosses


Bosses — like the rest of the workforce — are human, which means they have their shortcomings. They may be forgetful, late, or picky, but for the executive assistants who support them, these idiosyncrasies can make the workday challenging.

However, there are times when the term “challenging” falls short. Some bosses are better described as “difficult,” which can make the workday extremely frustrating for their executive assistants.

How can an assistant deal with a difficult boss? Complain to HR? Change their LinkedIn status to “Open To Work?” Jessica Vann, founder and CEO of Maven Recruiting Group, suggests executive assistants take a different approach to difficult bosses.

“If you are dealing with a boss who is difficult, you need to get curious and explore what is driving the difficult behavior,” Vann says. “Get invested in discovering what their flash points are and what triggers the difficult attitudes or behavior. Once you figure that out, you will have a chance to proactively manage it.”

Maven Recruiting is a nationally recognized recruiting firm that specializes in connecting high-leverage executives and personal assistants to the nation’s most prominent companies and individuals. It has been recognized by California Best Startup as one of the most innovative corporate training companies. For those interested in ongoing training and development for their executive assistant career, Maven offers e-learning courses, including a soon-to-be-released course on being a strategic executive assistant, as well as group and individual coaching. 

“You need to make that difficult boss your muse,” Vann explains. “If you don’t really study up on them and take the time to investigate and explore what drives them, then you are most likely doomed to continue facing that difficult behavior for as long as you have the job.”

Seeing the person behind the problem

When dealing with difficult bosses, it is easy to become fixated on the behavior that makes them difficult. They are simply seen as the too-busy executive, the non-responsive executive, the no-boundaries executive, or the perpetually-late executive, and while those who work for them bristle at their behavior, they fail to see the mindset that drives it.

“At the end of the day, it is the assistant’s job to understand the executive,” Vann says. “What is their operating style? Are they entrepreneurial? Are they an innovator? What mindset do they bring into the office each day? To do their job well, executive assistants must know the answers to these questions.”

Seeing past the problem to the mindset of the person allows assistants to develop a deep understanding of the executives they are supporting, the type of support they need, and the things that can trigger difficult behavior. 

“If you understand how the executive relates to their work, how they relate to the world, how they like information framed, and what their vulnerabilities are as a leader, then you can tee up your own style of support to be more nuanced,” Vann says. “Simply understanding expectations and needs can make a difficult boss easier to work with.”

Conveying the downside of the difficulty

Sometimes, difficult bosses do not understand how their behavior is impairing the work of their assistants. For example, the non-responsive boss often does not understand how much extra work her assistant must do to obtain the information necessary to do their job effectively, and the perpetually-late boss does realize the scheduling mayhem that results from his habits. 

When these issues result in unsatisfactory performance, it creates a situation that is triggering for the boss. In these cases, it is critical to communicate how the difficult behavior is affecting the assistant’s workflow and, consequently, the executive’s overall productivity.

“It is a matter of helping the executive to connect the dots,” Vann says. “Convey the consequences of their lack of engagement or failure to provide the necessary resources. Help them to see how they are a party to the outcome and — more importantly — how better support will ultimately benefit their success. Ideally, this results in the executive becoming more involved with and invested in the outcome.”

Once assistants understand their executives’ values and goals, they can relate their bosses’ difficult behavior to those things. They can explain how the executive’s difficult practices are not serving to advance their agenda.

“Often, the behavior that makes for a difficult boss comes from a place of feeling misunderstood,” Vann says. “Making a commitment to know a boss’s values and goals and clearly communicating that you are committed to supporting them can be extremely helpful in creating a healthy, productive partnership.”

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