10 Questions To Ask Your New Boss

Pointy hair bossWhether you are starting a new job or whether a new boss has just been named for your group you will need to get a sense of who she/he is and what her/his expectations are. More than that you will also want to begin to build a strong relationship with her/him. If this is a new job then you may have covered some of these during the interview but you can reconfirm the answers just to see if anything has changed. Some people feel that speaking privately with the boss is something to be avoided. It may be stressful initially but going forward if you are out of synch with her/him the going will be more stressful. If there is too much stress you will not be happy at work. Here are 10 useful questions to ask:

  1. What is the most important goal for me to accomplish in the next 30, 60 or 90 days? If you don’t know what is important to the boss you may not deliver the work she/he wants. The time frame of the goal is up to you. Some jobs lend themselves to a particular time frame. It is better for you to have a 30 day goal though so that you can accomplish something quickly. It also gives you a reason to meet with your boss again. Keep building the relationship.
  2. How do you see my position here impacting your goals and the company goals? To really be engaged in the company’s success you want to know how you fit in to the business. You want to feel good about what you do there and get a sense of the need for your work-one key to being happy at work.
  3. What do you see as your biggest challenge and how can I help you to resolve it? You want to support your boss in any way you can. It may involve some extra work and perhaps a challenge for you but if you can help your boss you will build the relationship. One key to being happy at work is to have a good working relationship with your boss.
  4. Who are the most important internal and external customers for my role? You may have your own ideas on this one but if you and your boss are not in synch you must take time to discuss and resolve it immediately. Listen to your boss’ reasons for her/his choices and iron out your differences.
  5. Is my role a new one? If not what happened to the person who had it last? This would be a question for a person recently hired or promoted. If the boss is instead new to the group she/he may have created a new position then it is important to learn the reasons for the new position and how she/he sees it fitting into the group.
  6. How will I be measured? What are the milestones that are important? This is something everyone needs to know but frequently people do not ask and many bosses do not volunteer the information. You need to know so that you can perform to expectations. When you feel a sense of accomplishment by performing to expectations it does a lot to keep you happy at work.
  7. What is the best way to communicate with you? Do you prefer email, phone or in person? How can I be sure to get an important message to you? Listen to what the boss tells you but also observe whether she/he responds as she/he predicts. Some people do not know what their preference is and what gets their attention in a crisis. While you are at it observe yourself too. You may need to answer it for your direct reports so it is easy for them to engage with you and they can be happy at work..
  8. Is there anything I should be aware of that has not been spelled out before? In every job or group there are usually things you need to be aware of. Maybe the boss knows them and can guide you. You’ll also need support from the team to alert you to hidden rules or agendas. If you are getting a new manager she/he may ask this question of you too. When you ask the question of the new boss she/he may share some of their own quirks or hot buttons.
  9. How frequently do you like to meet with your direct reports? If you feel you need more frequent feedback initially, negotiate this with her/him. More frequent meetings can help you to build a good relationship. Some people avoid meeting with the boss because the meetings are contentious. You need to find ways to keep your boss in your corner.
  10. As I think over this information I may have follow up questions. Can we set up an appointment in a few days to make sure I understand everything fully? If you don’t have questions then you can cancel the meeting letting the boss know you are comfortable with the answers. Every meeting though is a chance to build your relationship so if you do have more questions get them answered.

What kind of relationship do you have with your boss?

The biggest reason people are not happy at work is because they don’t get along with their boss. This may signal that it is time to look for another job or it may mean making adjustments in the way you work and interact with the boss. I can help you to sort this out so that you can find the right solution for you. Call me at 781-598-0388 or email me at asparker@asparker.com.


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