questions to ask new boss Great People Inside blog

Questions To Ask Your New Boss

No matter how many years you’ve worked, starting a new job is often nerve-racking. There are so many unknowns to figure out, and one of the biggest questions are about your new boss. How can you set your relationship up for success?

Understanding Your New Boss’ Expectations

When you get a new boss, things are bound to change. Your new boss will most likely have different expectations for you and your team, a different view of your department’s direction, different ways of communicating, and different priorities than your previous boss. Part of managing your career is taking a proactive part in understanding what is expected of you by your new boss.

Beginning a new job is always a little overwhelming. Not only are you adjusting to a whole new project, office, and set of coworkers, you’re also trying to figure out what your boss wants and how to deliver it. The answer is the same as with getting to know anyone new in your life, whether socially or professionally—you start a conversation, you ask questions.

Of course, it’s not always easy to be the one starting a conversation, but establishing good rapport with your new boss will go a long way toward creating and maintaining a positive work environment. Talking with your boss is the best way to get valuable feedback on your performance, even when it is not annual review time. And, more times than not your relationship with your boss is one of the key factors in advancing your career.

While there’s no universal or simple formula for improving your ability to get along (and work effectively) with your new boss, the good news is that you will make a great deal of progress if you can ask the right questions. Here are a few questions you may want to take into consideration.

1. Who should I meet with outside of our team?

This is why office politics are so important; your ability to figure out how to influence others will improve if you can get to a quick understanding of the unspoken or informal networks that govern the social dynamics of your new team or organization. Your boss is ideally placed to provide you with this intel. 

2. What’s the best way to ask for your input and feedback?

Establishing a cadence where you can get regular feedback on how you are doing, even via 15-minutes weekly chats or regular email check-ins, will help you regulate and calibrate your efforts to improve your performance. 

3. What would you do if you were in my shoes?

This question will not just invite your manager to empathize with you — allowing them to see things from your perspective — it will also show them that you respect them and appreciate their expertise. No matter how logical or insightful their advice may be, it can create a good connection between the two of you and further deepen your understanding of how your manager thinks, feels, and acts.

4. How can I further develop my potential?

Great leaders excel at coaching and mentoring their people. You can nudge your boss to play this role by asking them to assess and develop your potential. This means going beyond your performance to focus also on what you could do. In a world that is increasingly pushing us to reskill and upskill, it is hard to underestimate the importance of expanding our horizons and being open to reimagining or reinventing our talents to future-proof our career. Incidentally, this question will also clarify the existing criteria for promotion and advancement, which will help you be objective and pragmatic about your plans (and will keep your boss honest).

5. What could I be doing better?

After a few weeks on the job, asking this question may encourage your boss to provide you with much-needed guidance for closing the gap between how you are performing and what your boss expects from you. In their attempt to avoid conflict and maintain positive morale, many managers find it hard to provide employees with negative evaluations, so wording your feedback request in this way can help them focus on your improvement areas. It also signals that you are eager to understand how you can get better, even if you are doing well. 

A final point to consider: every person is unique, including you and your new boss. Invariably, this means that some of these questions might not be be applicable given the situation and your growing relationship. But the general rule still stands: you will accelerate your career success if you can manage your boss better. This requires you to understand them better, and a deliberate strategy that starts with smart questions can help. 

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