Executive Assistant Questions to Ask New Boss
Essential questions to help executive assistants understand their new boss's preferences, working style, and expectations to build an effective working relationship.
1What's your preferred communication style and how often do you like to check in?
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What's your preferred communication style and how often do you like to check in?
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Why this works
Reveals communication preferences and helps you understand how your boss prefers to communicate and how often they want updates.
2What are your priorities and how do you like to organize your day?
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What are your priorities and how do you like to organize your day?
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Why this works
Shows daily structure and helps you understand what your boss considers most important and how they prefer to organize their time.
3What are your expectations for my role and what success looks like?
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What are your expectations for my role and what success looks like?
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Why this works
Reveals role expectations and helps you understand what your boss expects from you and how they measure success.
4What are your working hours and availability preferences?
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What are your working hours and availability preferences?
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Why this works
Shows schedule preferences and helps you understand when your boss is available and what their working hours are.
5What are your meeting preferences and how do you like to prepare for them?
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What are your meeting preferences and how do you like to prepare for them?
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Why this works
Reveals meeting style and helps you understand how your boss prefers to handle meetings and what preparation they need.
6What are your travel preferences and how do you like to handle travel arrangements?
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What are your travel preferences and how do you like to handle travel arrangements?
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Why this works
Shows travel preferences and helps you understand how your boss prefers to handle travel and what arrangements they need.
7What are your email and document management preferences?
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What are your email and document management preferences?
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Why this works
Reveals organization style and helps you understand how your boss prefers to handle emails and documents.
8What are your delegation preferences and what tasks do you want me to handle independently?
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What are your delegation preferences and what tasks do you want me to handle independently?
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Why this works
Shows delegation style and helps you understand what tasks your boss wants you to handle independently and what they prefer to do themselves.
9What are your feedback preferences and how do you like to provide guidance?
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What are your feedback preferences and how do you like to provide guidance?
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Why this works
Reveals feedback style and helps you understand how your boss prefers to give feedback and guidance.
10What are your technology preferences and what tools do you use most?
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What are your technology preferences and what tools do you use most?
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Why this works
Shows tech preferences and helps you understand what technology and tools your boss prefers to use.
11What are your confidentiality and privacy requirements?
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What are your confidentiality and privacy requirements?
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Why this works
Reveals security needs and helps you understand what confidentiality and privacy requirements your boss has.
12What are your emergency and crisis management preferences?
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What are your emergency and crisis management preferences?
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Why this works
Shows crisis handling and helps you understand how your boss prefers to handle emergencies and crises.
13What are your networking and relationship building preferences?
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What are your networking and relationship building preferences?
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Why this works
Reveals relationship focus and helps you understand how your boss prefers to handle networking and relationship building.
14What are your project management and deadline preferences?
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What are your project management and deadline preferences?
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Why this works
Shows project style and helps you understand how your boss prefers to manage projects and handle deadlines.
15What are your decision-making preferences and when do you want to be consulted?
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What are your decision-making preferences and when do you want to be consulted?
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Why this works
Reveals decision style and helps you understand when your boss wants to be consulted and how they prefer to make decisions.
16What are your personal preferences and what makes you most productive?
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What are your personal preferences and what makes you most productive?
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Why this works
Shows personal style and helps you understand what personal preferences your boss has and what makes them most productive.
17What are your learning and development preferences?
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What are your learning and development preferences?
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Why this works
Reveals growth focus and helps you understand how your boss prefers to learn and develop professionally.
18What are your work-life balance preferences and boundaries?
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What are your work-life balance preferences and boundaries?
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Why this works
Shows balance needs and helps you understand what work-life balance preferences and boundaries your boss has.
19What are your team and collaboration preferences?
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What are your team and collaboration preferences?
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Why this works
Reveals team style and helps you understand how your boss prefers to work with teams and collaborate.
20What are your long-term goals and how can I best support you?
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What are your long-term goals and how can I best support you?
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Why this works
Shows future focus and helps you understand what your boss's long-term goals are and how you can best support them.
Best Practices for Executive Assistant Success
Expert tips and techniques for getting the most out of these questions.
Best Practices
Focus on Understanding Preferences
Ask questions that help you understand your boss's communication style, working preferences, and expectations to build an effective working relationship.
Learn Their Working Style
Ask about their daily routine, priorities, and how they prefer to work to align your support with their needs.
Understand Their Goals
Ask about their long-term goals and how you can best support them to ensure you're contributing to their success.
Question Sequences
The Communication and Expectations Sequence
The Working Style Sequence
Common Pitfalls
Don't Make Assumptions
Don't assume you know their preferences. Ask specific questions to understand their working style and needs.
Don't Ignore the Communication Questions
Ask about communication preferences and frequency. Effective communication is crucial for a successful working relationship.
Don't Skip the Goals Questions
Ask about their long-term goals and how you can support them. Understanding their goals helps you provide better support.