For assistants to be successful in their career they must must must have a good working relationship with their boss. The role is ultimately making the boss a success so the assistant has to ensure that the relationship is strong from the outset. The first meeting an assistant has with their new boss is so important and must be used wisely. During this meeting an assistant can lay the foundations for the relationship going forward, gain an insight into how their boss operates and understand what is expected if them. Get the first meeting right and the relationship should develop nicely. Here are 20 questions to ask a new boss in that first meeting:

  1. What did you do before you were my boss?
  2. What are your objectives?
  3. What do you value most in your staff?
  4. What is your life like outside of work?
  5. How do you prefer to receive information (email, as and when communication is required, during pre-determined meetings etc)?
  6. Have you worked with a personal assistant before?
  7. If so, what did you value in your assistant?
  8. If you have not worked with a personal assistant before what are your expectations?
  9. What are your priorities for the week, month and year ahead?
  10. What are my priorities for the week, month and year ahead?
  11. What frustrations do you have and how can I help to relieve them?
  12. How do you organise your calendar and how do you like to have your meetings set out?
  13. How do you organise your emails? Are you happy for me to answer emails on your behalf?
  14. What details bother you? What doesn’t?
  15. What decisions can I make without seeking your approval first?
  16. Do you think the job description accurately reflects my role?
  17. Apart from the specific tasks outlined on my job description are there any ‘informal’ tasks you would like me to take on (such as organising team socials etc)?
  18. Do you see my role as a gatekeeper?
  19. If so, how vigorously do you want me to protect your time?
  20. Why did you hire me?

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