Outrageous Boss Requests: Where Do You Draw the Line?

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File papers: check. Create work flow chart: check. Develop a marketing plan: check. Pick up dog from groomers, get baby from doctor and drop off prescription medication at pharmacy...check? Everyone needs additional help from time to time, including your boss. But how much is too much when it comes to asking a favor from an employee?

"Everyone's bound to get an unusual work request now and then. In general, it's best to try to be helpful rather than saying something's not in your job description. However, you should avoid doing something if it's clearly illegal or unethical," says Robert Hosking, Executive Director of OfficeTeam.

But what if your boss doesn't stop asking you for tasks outside of your workflow? "If you find that you continually receive wacky requests that are outside of your job description, it may be worth discussing it with your boss," says Hosking. "It's important to be clear about expectations and priorities. You might consider revisiting your job description with your manager to ensure your responsibilities are up-to-date and you'll be evaluated fairly against that description when it's review time."

When in doubt, connect with HR. They'll act as a mediator and help to resolve any issue--like these particularly unusual ones.

Breaking a Sweat: "I had a boss who made me play racquetball with him. I didn't mind the exercise, but he would make me go towards the end of the day. I would still have a bunch of work to do, he would go home and I would have to go back to the office. So on those days, instead of leaving at 7:30, I would leave it 9:30, because the two-hour break to play caused me to fall behind on work that needed to be finished," says Aron Susman, Co-Founder of TheSquareFoot.

Hustling for Beiber: "I was interning for Island Def Jam during college, in the International Marketing department. Justin Beiber was in the office, and my boss asked me to go to Pinkberry to pick up a frozen yogurt in December," says Alex Marshall of TheSquareFoot.

Facing the music: "About a year ago, our former VP found out that I play in a band and she asked if she could sing for us. I realized she was serious when she sent an email to my personal account, asking when we could 'jam.' I avoided her email for several days and when she finally confronted me about it in person, I said that it must have gone to my junk folder. Luckily, she left the company before I ever had to give her a solid answer," says Brandon Seymour of Beymour Consulting.

All the right moves: "I worked for a very large multinational company and we were at a trade show and had a hospitality suite. This was when the Wii game system was just coming out and my job was to teach all of these company [employees](mostly men) we were trying to schmooze how to play the Wii games like baseball and tennis. I had to demonstrate but not only did I have to demonstrate I had to basically play cheerleader for these guys and clap and cheer for them (also requested) to make them feel good. It was quite a scene. I didn't even get to eat. I have an MBA and was a marketing person so this to me was over the top (not to mention pretty sexist)," says Margo Schlossberg.

Do you want fries with that?: "Each year we had a press preview event, at which I played a critical role in organizing handling the media invites, setting up the event and more. The night of the event the director of this event came up to me and told me to go to the food concession and to work there - cooking chicken fingers. That was 15 years ago - I will NEVER forget the feeling of doing all the work and then being hidden away cooking food all night for the media I'd invited at the event I'd organized, but I sucked it up. Needless to say, it was a long summer and when it was done I was more than happy to take on a corporate job where there wouldn't be any need to cook 1000s of chicken fingers," says Maggie Patterson, Communications Strategist for MaggiePatterson.com.

Do you hear spirits?: About 7 years ago I was working in a small Criminal Law Office in Queens, NY. My boss was a partner and I was a junior associate. On the day we were going to court to file our motion my boss insisted we drive to Jamaica, Queens, to see a Haitian voodoo priest perform a ritual and bless our case. I totally refused to go but he insisted. When we arrived I waited in the car while he actually went in. I do not know, nor do I ever want to know, what happened inside that day but the ruling that came down was in our favor. So glad I never went in as I believe in Karma and do not like meddling with the forces of nature," Matthew Reischer, CEO of LawyerReviews.com.

Orange is the new black: As part of a pitch for winning the advertising budget of a new client, a holiday travel brand, our boss made us put on lots and lots of fake tan, and believe me, we all looked horrible! But, we won the client in the end as they loved our crazy dedication," says Nathalie Gaveau CEO of Shopcade.

Lastly, here are some pointers from Roy Cohen, esteemed career coach and author of The Wall Street Professional's Survival Guide:

"When you refuse to go above and beyond or outside to get the job done, someone else most likely will. Although it is impossible to always be available, when you never demonstrate your flexibility and availability you become less relevant regardless as to how outlandish the request may be. A word to the inflexible: Being on the job doesn't necessarily mean being at work. A lot can be accomplished from home and before and after hours."

Don't just say no: According to Roy, "If you really cannot honor a request, there are many less adversarial responses than just saying no outright. But at the end of the day, if you are feeling constantly put upon, maybe this is a sign that you are on the wrong career path. Here are two responses, both of which demonstrate a willingness to compromise and should be conveyed with good humor:

  • "I am just now finishing up a project on deadline. If this request is urgent, I can set the project aside. I am happy to do so. Please advise."
  • "I need to leave the office by 6 today due to a previous commitment. If I could get out of this commitment, you have my word that I would do so in a heart beat. Is it possible to come in early tomorrow morning? I am happy to come in as early as you need me."


Always set up boundaries: "Boundaries are critical to ensure that you don't establish a reputation for being indiscriminate in where and how you invest your time, energy, and support," says Roy. "When you say yes to every request, you potentially end up getting dumped on--and not for the right reasons. Your boss and your colleagues will see you as a patsy, not having enough backbone to say no when appropriate."

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