Questions to Ask an Executive Assistant
Build a productive working relationship with your executive assistant using these strategic questions that help you understand their capabilities, establish workflows, and maximize their support.
1What's your preferred method and frequency of communication?
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What's your preferred method and frequency of communication?
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Why this works
Establishes communication expectations and ensures you're aligned on how and when to stay in touch.
2How do you typically prioritize competing demands and urgent requests?
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How do you typically prioritize competing demands and urgent requests?
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Why this works
Reveals their organizational approach and helps you understand how they manage multiple priorities.
3What information do you need from me to manage my calendar effectively?
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What information do you need from me to manage my calendar effectively?
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Why this works
Clarifies what context they need to schedule appropriately and protect your time.
4What tasks can you handle independently versus what requires my approval?
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What tasks can you handle independently versus what requires my approval?
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Why this works
Establishes clear boundaries for decision-making authority and empowers them to work efficiently.
5How do you prefer to handle scheduling conflicts or last-minute changes?
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How do you prefer to handle scheduling conflicts or last-minute changes?
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Why this works
Sets expectations for how to manage the inevitable scheduling challenges that arise.
6What's your experience with [specific tools/systems we use]?
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What's your experience with [specific tools/systems we use]?
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Why this works
Assesses their technical proficiency and identifies any training needs upfront.
7What do you see as your primary responsibilities in supporting me?
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What do you see as your primary responsibilities in supporting me?
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Why this works
Aligns expectations on their role and ensures you're both clear on priorities.
8How do you handle confidential or sensitive information?
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How do you handle confidential or sensitive information?
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Why this works
Ensures they understand the importance of discretion and have appropriate protocols.
9What time management strategies have worked well for you in past roles?
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What time management strategies have worked well for you in past roles?
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Why this works
Reveals their organizational skills and approaches that might benefit your partnership.
10How can I best support you in your role?
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How can I best support you in your role?
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Why this works
Shows you value their success and opens dialogue about what they need to be effective.
11What information should I share with you about my priorities and projects?
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What information should I share with you about my priorities and projects?
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Why this works
Helps them understand context so they can better anticipate your needs and make decisions.
12How do you prefer to receive feedback?
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How do you prefer to receive feedback?
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Why this works
Establishes how to provide constructive input in a way that works for them.
13What are your professional development goals?
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What are your professional development goals?
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Why this works
Shows investment in their growth and helps you identify opportunities to support their career.
14How do you handle situations where you need to push back or advocate for my time?
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How do you handle situations where you need to push back or advocate for my time?
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Why this works
Reveals their comfort with gatekeeping and protecting your schedule when needed.
15What works best for you when I need something quickly?
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What works best for you when I need something quickly?
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Why this works
Establishes protocols for urgent requests and ensures they're equipped to respond effectively.
16How do you stay organized and keep track of multiple ongoing projects?
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How do you stay organized and keep track of multiple ongoing projects?
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Why this works
Shows their project management approach and how they maintain oversight of complex tasks.
17What challenges have you encountered in previous EA roles?
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What challenges have you encountered in previous EA roles?
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Why this works
Reveals potential issues to avoid and shows what working conditions help them thrive.
18How do you prefer to handle travel arrangements and expense reporting?
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How do you prefer to handle travel arrangements and expense reporting?
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Why this works
Clarifies processes for routine tasks and ensures you're aligned on procedures.
19What do you need to know about my work style and preferences?
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What do you need to know about my work style and preferences?
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Why this works
Invites them to ask questions and ensures they understand how to work effectively with you.
20How should we structure our regular check-ins?
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How should we structure our regular check-ins?
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Why this works
Establishes a rhythm for staying aligned and ensures ongoing communication about priorities.
Best Practices for Working with an Executive Assistant
Expert tips and techniques for getting the most out of these questions.
Best Practices
Invest Time Upfront
Spend quality time early in the relationship to understand each other's working styles. This investment pays off in long-term efficiency.
Provide Context, Not Just Tasks
Share the 'why' behind requests so your EA can make better decisions and anticipate needs. Context enables them to be more proactive.
Trust and Empower
Give your EA authority to make decisions within agreed boundaries. Micromanaging defeats the purpose of having executive support.
Question Sequences
The Communication and Workflow Sequence
The Partnership Building Sequence
Common Pitfalls
Don't Skip the Relationship Building
Treating your EA as just a task-executor rather than a strategic partner limits their effectiveness. Invest in the relationship.
Don't Assume They Know What You Need
Be explicit about your preferences and priorities. What seems obvious to you may not be clear to them.
Don't Bypass Your EA
If people can go around your EA to reach you, it undermines their authority and makes their job much harder.