Biggie Tips For Your Biggie Life

What to Do if Your Boss Asks Something Difficult of You

If you haven’t seen the movie, Horrible Bosses, do yourself a favor and see it. It’s hilarious and very relatable. The reason we bring this up is, as outlandish and foolish as that movie may have been, there actually has been a boss or two who may have asked a little bit more from an employee than what is in the job description.

So, maybe this is happening to you, or you anticipate that your boss is a weird creep. These six steps will help you deal with any weird request from your boss

For this article, we will provide an “extreme” example, in hopes that your situation is less dramatic.

Here is the scenario: You’ve been working at your job for three months. Your boss comes up to you during a break and asks to speak with you privately. You oblige, and go to his office. Your boss comes right out and explains that he’s married. He’s having an affair. Unfortunately, the woman he’s having an affair with is a stage five clinger. He needs to break it off. And he’s calling on your services to handle his “dirty laundry.”

Since you’ve been working for the company, you’ve enjoyed the experience. You don’t want to ruin your employment. What do you do in a situation like this, or something similar? These six steps will help you deal with a weird request.

Related: How to Get Out of Work Without Getting Into Trouble

1. Take Several Deep Breaths, Take Your Time

The first thing to do is, don’t overreact right away. This can be worked out in a way whereby everyone wins… except the mistress.

Take your time before giving an answer. Let your boss know that this is a lot to take in. Let him know that this difficult request from him/her shouldn’t be given an immediate answer, and that you need time, thus giving you time to consider your options.

2.  Assess The Pro’s And Con’s

After you’ve told your boss, “you’ll think about it,” the next step is to consider your advantages and disadvantages resulting from the weird request from your boss.


  • You’ll seem like a team player.
  • There could be a financial benefit in it for you.
  • It’ll show you that you have “bravery” and composure.


  • You say no, he threatens to fire you, and does fire you.
  • You get assaulted by the mistress, who spits on you and cries making you feel awful.
  • The wife scolds you for taking participation, and the rest of your employees think less of you for your lack of scruples.

Weigh out your pro’s and con’s, and think long and hard. You have an 8 hour day for good reason. Use it.

Related: 6 Traits that Separate Leaders from Bosses

3. Refer to A Friend For Advice

Now, if your boss isn’t a friend of yours on Facebook, you can take it to Facebook and perform a poll. Pose the question in a yes or no manner, and then ask for explanations for the answer. This will help guide you in finding a response.

Also, ask a friend you trust and respect. Someone who has good morality and that you look up to. If they give you an answer that’s against the weird request, then go with that.

4. Form A Planned Response

This is where you want to start crafting your response. Write it down, or even record it. You’ve conceived the advice, you have a gut feeling, now you’re ready to shape your answer on paper.

Write down the pro’s and con’s, and write down possible outcomes. Don’t be afraid to form different ways to responsd. Write things like: “I really enjoy working here, however, I don’t feel like it’s appropriate for me to get involved in this situation.” Try alternatives and go with what feels best and natural.

5. Practice Your Response

This is the most important part, aside from the response. Now it’s time to practice how and what you’ll say. Find a co-worker to practice your response with, and ask for feedback with regards to the difficult request from your boss.

6. Get Proof, Document Your Response

You’ve practiced, you’ve received your feedback, now it’s time to get a tape-recorder or make sure that your phone can record the interaction.

If things go awry, you’ll want proof that you’re being victimized based on something that isn’t moral. You should document and record anything you feel may be illegal.

Now it’s time for your response. It doesn’t matter if it’s a situation such as this one above, or a less extreme one, an answer like this will help you deal with a weird request from your boss. “(Say the bosses first name), with all due respect, this is beyond my qualifications and training. I don’t feel comfortable completing this request, and personally, I think in your circumstance, you need to handle this situation yourself since you got yourself into it.”

All of these six steps, and if needed, tweaking a few steps about the level of your situation, will help you deal with a difficult request from your boss.

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