Approaching your Boss with a tough question

Working for somebody else needn’t be stressful if you learn how he or she works, what he or she likes and dislikes, and how to approach him or her at the right time.

It can almost be a game. Knowing when to ask a difficult or awkward question is crucial to getting what you want. Don’t ask them the pressing question when they are stressed or in the middle of something important. Often, a Friday afternoon is a good time when they are winding down after a week of work and have a little more time to give. When you have a request always ensure that before you ask, you have a valid reason why you should be given it. When you approach you boss make sure that you don’t have any ‘I deserve this’ attitude and go in politely and positively.

Here's an excerpt from a Career article in the JobStreet.com vault:

Jenny Lee worked as a personal assistant to the Managing Director of a pharmaceutical company for four years. She enjoyed her job and liked working for her boss even though he could be temperamental at times. She practically ran the office and organised his personal and business commitments. After four years she thought she would be eligible for a pay rise and decided to approach her boss with the request. It was a Monday morning and she decided she would approach him at the beginning of the week.

That morning her boss had a crucial financial meeting with the accounts department. The meeting did not go well and the outcome was that the company would have to make some cutbacks. Although Jenny had been in the meeting taking the minutes, she still decided to approach her boss thinking that her request was still justified. He boss’s response was more than negative and he nearly threw her out of the room for as he put it as being "insensitive to the company's needs."

Jenny was mortified. She felt betrayed that all the hard work over the past four years had been in vain. She knew of others with less commitment in the company who had had a pay rise and she was treated like this! However, once she had calmed down, she realised she had asked at a completely the inappropriate time. She also knew her boss could be reasonable and decided to approach him at a later date.

Two weeks later, Jenny drafted a letter to her boss highlighting how happy she was to have worked for the company and for him and why she still would like to explore the possibility of a pay rise. She approached her boss at a quiet time in the office, when she knew he was relaxed and they discussed her proposal. Eventually they came to an agreement and Jenny was given a 10% pay rise. Even in the company crisis, her boss knew of her value and realised she was a loyal and productive employee.