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How Assistants Can Deal With Difficult Bosses

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Calling all Administrative, Personal, Executive, whatever-other-title-they-can-think-of Assistants: Is your boss unruly? Do you need strategies to keep them in check?

Over the course of my life, I have held numerous assisting positions in numerous different fields. You can throw Receptionist gigs under the assisting title because they usually get tagged to help out with these duties, too. I’m not saying that there is a problem with assisting someone – the title of the job is literally the job. But what about when you’re working for someone who is scatter brained, impulsive, disorganized, and generally makes you wonder how they even got their job in the first place? As Jack Klemeyer pointed out in a post about workplace relationships, “The Three R’s” can really get in the way of productivity:

  • The first R is RESENTMENT – which is any negative emotion towards any person, place, thing, condition, circumstance, thought or idea.
  • The second R is RESISTANCE – defined by the withholding or withdrawal of any of your resources, potential, gifts, talents or positive expressions.
  • The third R is REVENGE – the process or desire of making another person feel your pain in some way, in any way.
  • How can you be expected to help this person stay on track with their daily duties? You may feel like a nanny with an out-of-control toddler on the loose. It’s not easy to talk to your manager about your issues that you face on the job – they ARE the issue. Before the “The Three R’s” wreak havoc on your work life, check out some of my tips below!

    difficult boss

    © Flickr user seanhagen

    Get Your Answers From Them In Writing

    I am a huge fan of texting and emailing. Why? Because they leave a trail and that trail can save your butt. If you’re working for someone who is forgetful and disorganized, you need to up your organizational game. Create folders in your email account that are specifically for conversations you have with your boss. You could even go so far as having folders for every week. If you had a conversation in person, just send an email to them as a follow-up, that you want to make sure you are on the right track with their requests.

    Don’t Give Them A Bunch Of Options

    Try to think of this person as they are, and not what you wish they would be. They are easily distracted and hard to nail down for answers. So instead of presenting a plethora of options for things, give them a “this or that” to choose from. Two options, no more, no less. If they ask why there aren’t more, you can tell them you went ahead and narrowed it down for them already. Not only does this make you look like you’re ahead of the curve, you’re also saving yourself loads of time waiting for an answer.

    Rely On Your Co-Workers

    Chances are that other people know how your boss is. They’ve likely had their own run-ins with them in the past or are even currently working with them. Don’t resort to gossip, but keep your eyes open for who goes in and out of their office. Run your thoughts about something by those who have worked with your manager. Something as simple as having casual conversation in the break room and mentioning something you’re working on. People like to feel needed. Turning to someone for advice is a good way to build relationships and also put your own mind at ease.

    Don’t Be Afraid To Throw In The Towel

    Last but not least, if all else fails, start looking for a new job. There’s nothing wrong with giving up on someone who can’t be helped. Sometimes, especially in positions where you are assisting, the combination of personalities just doesn’t work. They may find someone to work for them that has no issues with their style of work and that’s great. That doesn’t mean you’ve failed, it just means that someone else’s skill set can handle that type of crazy. So keep your resume looking pretty!

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    Alyssa Shea

    Alyssa Shea

    Alyssa Shea transplanted from Illinois to South Carolina. She loves to write, read, and spend time with her dog and her family. Alyssa is very active on social media. She has been part of the AccelaWork team since 2013.
    Alyssa Shea

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    • robbyslaughter

      Great points, Alyssa! As someone who has both been an assistant and a person *with* those who assist them, you are on it 100%. Thanks for sharing your wisdom!

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