Questions to Ask in an Executive Assistant Interview
Strategic questions to evaluate executive assistant roles, understand executive support expectations, and assess company culture fit.
1What does a typical day look like for the executive I'd be supporting?
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What does a typical day look like for the executive I'd be supporting?
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Why this works
Reveals workload patterns, meeting intensity, and what your daily responsibilities will actually entail.
2What are the executive's working style and communication preferences?
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What are the executive's working style and communication preferences?
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Why this works
Shows personality fit, whether they're detail-oriented or big-picture, and how they like to interact.
3What are the top three priorities for this role in the first 90 days?
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What are the top three priorities for this role in the first 90 days?
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Why this works
Indicates immediate expectations, urgent needs, and where you should focus initial energy.
4How does the executive prefer to handle their calendar and scheduling?
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How does the executive prefer to handle their calendar and scheduling?
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Why this works
Reveals calendar management philosophy, autonomy level, and scheduling complexity.
5What happened to the last person in this position?
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What happened to the last person in this position?
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Why this works
Shows turnover patterns, role challenges, and whether position setup for success or frustration.
6What tools and systems does the executive rely on daily?
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What tools and systems does the executive rely on daily?
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Why this works
Indicates tech stack, software proficiency needs, and whether you'll need training.
7How much travel is required, and what's involved in travel coordination?
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How much travel is required, and what's involved in travel coordination?
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Why this works
Shows travel frequency, complexity of logistics, and whether you'll travel with executive.
8What level of confidentiality and discretion does this role require?
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What level of confidentiality and discretion does this role require?
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Why this works
Reveals sensitivity of information you'll handle and trust placed in position.
9How does the executive handle stress and tight deadlines?
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How does the executive handle stress and tight deadlines?
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Why this works
Indicates working environment during pressure, emotional management, and what to expect in crises.
10What opportunities exist for professional development and career growth?
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What opportunities exist for professional development and career growth?
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Why this works
Shows whether role is dead-end or stepping stone, and investment in your advancement.
11How is success measured for this position?
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How is success measured for this position?
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Why this works
Reveals performance metrics, evaluation criteria, and whether expectations are clear.
12What's the relationship like between the executive and their team?
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What's the relationship like between the executive and their team?
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Why this works
Indicates management style, team dynamics, and organizational culture you'll navigate.
13How much authority will I have to make decisions independently?
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How much authority will I have to make decisions independently?
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Why this works
Shows autonomy level, trust boundaries, and whether you'll truly assist or just execute orders.
14What are the biggest challenges facing the executive right now?
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What are the biggest challenges facing the executive right now?
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Why this works
Reveals context you'll work within, pressures affecting your day, and business realities.
15How does the executive prefer to receive information and updates?
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How does the executive prefer to receive information and updates?
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Why this works
Shows communication style, reporting preferences, and how to keep them informed effectively.
16What's the work-life balance like in this role?
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What's the work-life balance like in this role?
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Why this works
Indicates after-hours expectations, weekend work, and whether boundaries are respected.
17How does this role interact with other assistants or administrative staff?
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How does this role interact with other assistants or administrative staff?
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Why this works
Reveals team structure, collaboration opportunities, and support system availability.
18What projects or initiatives would I be involved in beyond day-to-day tasks?
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What projects or initiatives would I be involved in beyond day-to-day tasks?
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Why this works
Shows whether role includes strategic work or is purely administrative.
19How does the executive handle feedback and constructive input?
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How does the executive handle feedback and constructive input?
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Why this works
Indicates whether your opinions matter, openness to suggestions, and psychological safety.
20What do you think makes someone successful in supporting this particular executive?
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What do you think makes someone successful in supporting this particular executive?
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Why this works
Reveals insider perspective on personality fit, required traits, and success factors.
How to Use These Questions
Expert tips and techniques for getting the most out of these questions.
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