Interview
Questions

Chief of Staff Interview Questions

Behavioral questions for Chief of Staff and Executive Assistant interviews 2025. Covers prioritization, stakeholder management, discretion, and executive support.

23 questions·@speaking.app·Updated 10d ago·
Question 1Problem Solving

Describe a time you had to pay attention to small details in high-stakes situation.

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Question 2Problem Solving

Describe a situation where you had to analyze a complex issue from multiple perspectives.

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Question 3Problem Solving

How would you decide between showing a user an ad versus suggested content?

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Question 4Problem Solving

Describe your approach to onboarding a new enterprise customer.

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Question 5Conflict Resolution

Tell me about a time you disagreed with a decision but committed to it anyway.

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Question 6Adaptability

Tell me about a project that did not go as planned. How did you adjust?

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Question 7Adaptability

Describe a time when you had to quickly adapt to a major change at work.

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Question 8Conflict Resolution

You notice a colleague making repeated small errors. What do you do?

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Question 9Conflict Resolution

Describe a situation where you admitted a mistake and what you learned from it.

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Question 10Conflict Resolution

Tell me about a time you had to deliver difficult feedback to someone.

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Question 11Leadership

Tell me about a time you took the lead on a difficult project. What approach did you take?

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Question 12Leadership

Tell me about a time you had to make an unpopular decision. How did you handle it?

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Question 13Problem Solving

Describe a time when your first solution did not work. How did you pivot?

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Question 14Problem Solving

Describe a complex problem you solved at work. What was your process?

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Question 15Adaptability

Describe how you handled a situation where priorities shifted unexpectedly.

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Question 16Conflict Resolution

Describe a time when you received criticism you disagreed with. How did you handle it?

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Question 17Conflict Resolution

Tell me about a disagreement you had with a coworker. How did you resolve it?

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Question 18Adaptability

Give an example of a time you had to learn something new quickly to complete a task.

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Question 19Leadership

Give an example of how you have developed or mentored someone on your team.

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Question 20Leadership

Describe a situation where you had to motivate others who were resistant to change.

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Question 21Conflict Resolution

Give an example of how you handled a situation where team members had conflicting priorities.

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Question 22Problem Solving

Give an example of a creative solution you developed to solve a recurring issue.

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Question 23Problem Solving

Tell me about a time when you had to make a decision with incomplete information.

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