Dealing with a Difficult Boss as an Executive Assistant or Personal Assistant

Navigating the often turbulent waters of a challenging boss can be a defining aspect of your role as an Executive Assistant (EA) or Personal Assistant (PA). While every working relationship has its ups and downs, there are effective strategies to manage and even thrive under a demanding boss.

Understanding Their Priorities and Perspective

Key to your success in this role is understanding what drives your boss. What are their priorities? What pressures are they under? By getting into their headspace, you can anticipate their needs, making their life easier and proving your indispensability. It’s not about being a mind reader, it’s about being a step ahead.

Facilitating Effective Communication

You’re not a mind reader, and you shouldn’t have to be. It’s crucial to establish clear lines of communication. Ask direct, open-ended questions to understand their expectations. Remember, your role is to make their professional life smoother, and this starts with understanding exactly what they need and want from you.

Educating and Guiding First-Time Bosses

If you’re the first EA or PA your boss has had, they might not know how best to utilise your skills. This is your chance to guide them, demonstrating areas where you can add significant value. Showcase your skills, and teach them how your role can be a game-changer for their productivity and peace of mind.

Setting Boundaries for Work-Life Balance

While flexibility is part of the job, clear boundaries are essential for your well-being. If work is encroaching too much on your personal life, have a candid conversation about your working hours. Yes, some overtime is expected, but you’re not a 24/7 operation. Your time off is just that – yours.

Become Solution-Oriented

Every problem is an opportunity in disguise. Instead of dwelling on issues, focus on finding solutions. This proactive approach not only alleviates current problems but also prevents future ones, positioning you as a forward-thinking and indispensable asset.

Giving the Relationship Time

Remember, Rome wasn’t built in a day. It can take six to eight months to fully understand each other’s working styles. Patience is key. Give the relationship time to develop and look towards the future with optimism. This period of adjustment is normal and necessary for a successful long-term working relationship.

Prioritise Your Wellbeing

Lastly, never compromise on your wellbeing and happiness. If all efforts to improve the relationship fail, it may be time to look elsewhere. Conduct your job search discreetly until you have secured a new position. Your mental and emotional health should always be your top priority.

In conclusion, dealing with a difficult boss requires a blend of understanding, clear communication, boundary-setting, solution-finding, patience, and self-care. 

Remember, you’re not just an assistant; you’re a key player in your boss’s success. And while it’s important to be supportive and flexible, never lose sight of your own value and wellbeing.


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