7 Questions to Ask Your New Boss

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The most important relationship to get right when starting a new job is the one with your boss. How do you build trust right from the beginning? And how do you get the feedback you need to succeed? The author offers seven questions to try. You will accelerate your career success if you can manage your boss better, which requires you to understand them better, which requires a deliberate strategy. 

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 question marks is your new boss. How can you set your relationship up for success?

One of the biggest things I learned in my coaching career is that helping people manage their bosses is arguably as important as helping them to manage themselves. This often means relearning what it means to adapt to an organization, as everything that may have made you effective with your previous manager may not necessarily help you with your new one. For example, I once went from working for a very sociable, hedonistic, and assertive boss, to working for a very quiet, cautious, and serious boss — my personality stayed the same, but I was forced to learn new habits, adjust my behaviors, and relearn how to adapt. 

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 seven to consider:

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

Although we have come a long way to make organizations more talent-centric and merit-based, the old premise is still true: what you know is often less important than who you know. This is why office politics are so importantyour 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. How do you prefer to communicate?

With many people uncertain about their short-term work environment — working from home, returning to the office, some type of hybrid work, etc. — it is important to be flexible about how you can best communicate with your manager, particularly if you have never met them in person. 

3. 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. 

4. What can I do to support the team and add value to the organization?

This question will enable you to clarify your role, align with your boss on expectations, and strategically prioritize tasks and efforts. Managers often fail to clearly and explicitly articulate what their top priority is, how they see team members fitting in, and what they mostly need from them. Understanding this quickly will help you deliver where it matters most.

5. 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.

6. How can I further develop my potential?

As the brilliant Hermina Ibarra noted, 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).

7. 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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