Jessica Kay

Whether you’re a workforce newbie or a seasoned manager yourself, having a trusting relationship with your own manager is critical. Your manager, more so than anyone else in your place of employment, has the power to make or break your future. While this is more or less common sense, the lesser known fact is this: how you ask your manager for help is key in shaping your relationship for the better.

Let’s face it, at some point in all of our careers, there will come a question that can only be answered by someone with more experience, authority, or both. More often than not, that person is your boss. If asking raising a question is inevitable, how do you make sure that it adds to your reputation as a great employee and not detract from it? To start, here are a few simple things to avoid:

5 Things to NEVER Do When Asking Your Boss For Help:

  1. Ask your boss to solve your problem
  2. Give your boss insufficient time to respond
  3. Commit a crime of his or her pet peeve
  4. Vent while asking for help
  5. Speak ill of a co-worker

Now you know all the things to avoid, let’s take your ask-for-help-skillsets to the next level. Here is a convenient check-list for you to go through every time you want to raise your hand, schedule a meeting, or casually walk on by to your boss’s office to ask a question.

1. Simplify your issues/questions so they can be easily comprehended and answered

If it takes more than a minute or two to explain the scope of your issue/what you need help for, you haven’t simplified it enough. The most annoying way to ask a question is, on top of asking the question, ask your manager to decipher for you what your question is. It shows that you lack organizational skills and are not courteous of people’s time.

2. Demonstrate that you’ve done your research and you aren’t asking for a handout with your question.

If your manager spends all his or her time answering everyone’s impulsive questions right as they pop up, he or she wouldn’t have time to do anything else. Take the time to try to find an answer yourself before you reach out to the boss for an answer. Do your research and put in your time. Efforts like this will change the way you phrase your question. You and your questions will come across as more thoughtful and well-thought-out.

3. Use complete honesty and ownership

If your question is related to a screwup or mistake on your part, don’t try to sugarcoat it. Be smart about the way you position it but be honest and own it like you mean it. And apply rule II mentioned above while you formulate your question or request for help.

4. Be patient; wait till your 1:1 if the questions aren’t urgent.

Don’t be “that person” that emails someone and immediately walks over to talk about what you just sent them an email for. The world doesn’t revolve around you and your priorities. Exercise patience when you are asking questions, especially to your superior. And if you could wait, always leave the questions for your regular one-on-one meetings.

5. Be conscious of the mode of communication you pick; better yet, know what he or she prefers.

This is one of the best questions to ask your boss when you first start out. Ask them if they prefer emails, texts, office visits when it comes to getting their attention. Additionally, ask if the urgency of the matter changes their preference. This will prevent you from worrying whether texting them is too intrusive or if they are even seeing your email in their filled inbox.


Jessica is a writer, a digital marketer, social media aficionado and a lifestyle blogger at Cubicle Chic. Through her writing, Jessica aims to connect with fellow corporate 9-5ers who may be bound by an office physically but crave for much more in life. She writes blog posts about inter-office politics, how to climb the corporate ladder, resolve interpersonal conflicts, and how to do it all in the best outfits possible. Jessica lives in sunny San Diego with her husband and two cats, Lulu and Miles.