dealing with a demanding boss

Demanding bosses can be, well, demanding. They are often difficult, sometimes lack a filter, and never back down with what they want, when they want it. But, just like any other boss type, there’s a method to their madness, and an effective way of dealing with them. It’s actually pretty easy, as long as you know what to do.

Be Efficient

In today’s technology-driven world, efficiency is king. Everything needed to be done five minutes ago, every email is high priority, and there is no such thing as “putting it off until tomorrow.” So how does an executive assistant deal with all of the demands? He/she learns to be as efficient as possible. There are many ways of becoming more efficient, like grouping similar tasks together, organizing your workspace, or even turning off your cell phone. Whatever works for you, do it.


If you work for a demanding boss, chances are they are constantly two or three steps ahead of everyone else, which means you need to be four or five steps ahead of him/her. As a gatekeeper, an important skill you must learn is how to anticipate your boss’s needs. The low-hanging fruit of anticipating your boss’s needs and requests is taking note of his/her routine. If they consistently leave at 4:45 on Fridays, give them any items to review by 3:00 so they have enough time to do so before they go and are not in a rush. If they get coffee from the break room each morning, ensuring they have a fresh pot brewed upon arrival is a good way to save them an extra 5 or 10 minutes in the morning.

Know their Expectations

Similar to anticipating needs, it’s important to understand your boss’s expectations. Perhaps he/she is a stickler for promptness? Don’t be late. Maybe his/her biggest pet peeve is misspellings? Spell check everything. No two bosses are alike, so what may have been no big deal to a previous employer could set your new one off in the wrong direction. A great place to start with expectations is your job description. Many employers will use the job description as a base for employee reviews, so if you’re ever in doubt of what you should be doing, or what your boss expects of you, refer back to that J.D.

Understand their Priorities

It is important to thoroughly understand a company’s mission and values. Similarly, it is important to understand your boss’s mission and values, as these things become his/her priority. If one of the responsibilities endowed to your boss was to cut company spending, consider this heavily when making any purchases on the company’s account. If they are expected to improve employee retention rate, make an extra effort to be courteous to employees you come in contact with throughout the day. Positivity breeds positivity, and while your cheerfulness may not ultimately impact whether an employee stays or goes, we can most certainly guarantee no one will say they quit because the boss’s assistant was too nice to them.

Get Feedback

Feedback is not reserved for negativity! Positive feedback and constructive criticism are just as important to growing your relationship with your boss (and growing personally and professionally). When in doubt, ask! Make it a point to check in with your boss twice a month to see how you’re doing, if there’s anything you can improve upon, or any other tasks that he/she may need an extra hand in. This type of behavior shows that you are not only committed to being successful as an employee, but that you are committed to contributing to your boss’s success, and, ultimately, the success of the company.

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