7 Questions to Ask Your New Boss

  1. Who should I meet with outside of our team? 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. How do you prefer to communicate? 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? 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. 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.
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