Hiring a great administrative assistant requires two things: first, knowing what skills, experience and personality traits are necessary to succeed in the role. And second, spotting those qualities in candidates through the right administrative assistant interview questions. Simple enough in theory. In practice, it takes thoughtful preparation.
So, what should you ask? You'll want questions that explore organizational culture, hands-on experience, workplace relationships, work style and genuine interest in the role. The 25 interview questions for administrative assistants interspersed in the article below can help you get a fuller picture of each candidate and make a confident hiring decision.
Administrative assistant interview questions to ask in 2026
Interview questions about workplace culture
Hiring people who will be comfortable in your corporate culture takes skill. Be upfront about what it's like to work at your organization, then ask questions like these that reveal whether the candidate would actually enjoy that environment.
1. What comes to mind when you think of our company? Why do you want to work here?
2. What appeals to you about this job?
3. How do you thank an administrative assistant contributes to an organization’s success?
4. What type of office environment brings out your best work?
5. Why did you leave your last administrative assistant position? Or: Why are you looking to leave your current administrative assistant position, and what would have convinced you to stay?
See this post for additional tips on how to hire a great administrative assistant.
Examination of specific skills and experience
Today's administrative professionals handle far more than typing and answering phones. When preparing administrative assistant interview questions such as these, think about the technical skills your role requires, such as word processing, spreadsheets and scheduling software, along with any industry-specific experience or communication skills that would be valuable.
6. Why do you think you’re well-suited for a position as an administrative assistant, and for this job in particular?
7. What skills do you have that will help you do well at our company?
8. How comfortable are you with [specific software program]? What's the most recent version you've used?
9. Can you give me examples of how you've used [the software app mentioned] on the job? What advanced features are you familiar with?
10. What would you consider your biggest professional accomplishment and your biggest professional setback, and what did you learn from them?
Questions about work style
You won't fully know someone's work style until they're on the job, but it's worth asking how they take direction, communicate, structure their day and handle multiple responsibilities.
11. Can you walk me through a typical day in your current/most recent position?
12. Have you ever reported to multiple supervisors at once? If so, how did you juggle each person’s priorities?
13. What is your first step when given a large project to manage? How would you organize it?
14. Can you describe a challenging project you were assigned in the past and how you approached it?
15. Are there any tools, equipment or procedures you would replace or change at your most recent/current job? If so, what changes would you make and why?
Administrative assistant interview questions about artificial intelligence
Administrative work is changing fast. Generative AI tools such as ChatGPT and Google Gemini are reshaping daily workflows, from drafting correspondence to summarizing customer queries and managing schedules. According to research from Robert Half, 83% of administrative and customer support leaders now offer higher pay to candidates with specialized skills—and AI-driven data management ranks among the top abilities they're willing to pay more for.
You don't need to hire someone who's already an AI expert. What matters is asking administrative assistant interview questions that identify candidates who are curious about new technology and willing to learn. The best administrative assistants understand when AI can speed up their work and when a task needs human judgment and attention.
16. What software tools have you used to manage calendars, scheduling or travel arrangements? Have you worked with any AI-powered tools like smart scheduling assistants?
17. Tell me about a time you learned a new software program or technology for your job. How did you approach it?
18. Are you familiar with AI tools like ChatGPT, Microsoft Copilot or Google Gemini? If so, how have you used them at work?
19. How do you decide when to use a technology shortcut versus handling something manually? Can you give an example?
20. Have you ever received incorrect or misleading information from an AI tool? How did you catch it, and what did you do?
For more on how technology is reshaping the role, see AI for Administrative Professionals: Tools, Skills and Career Growth Tips.
Questions about relationships and working with others
Assessing how candidates handle workplace relationships is essential, so this section is structured differently than the earlier sections, with commentary after each question.
21. What type of supervisor helps bring out your best performance?
This question helps you understand how a candidate prefers to be managed. Pay attention to whether their answer aligns with your own management style—whether you tend to provide detailed direction or set goals and allow flexibility in how work gets done.
22. Can you share a piece of constructive feedback a manager has given you? What adjustments, if any, did you make because of that feedback?
You could also preface or follow up on this question by asking the candidate to explain the difference between constructive and destructive feedback, or between helpful and unhelpful feedback.
23. Have you ever reported to multiple supervisors at once? If so, how did you juggle each person’s priorities?
This question can give you a better grasp of the candidate’s aptitude for interdepartmental collaboration as it applies to the position you are hiring for.
24. Can you tell me about a workplace conflict you were involved in as an administrative assistant and how you handled it?
This question can be more narrowly tailored to difficult situations an administrative assistant might encounter, such as something along these lines: “Describe a time when you had to mediate a disagreement between two colleagues."
25. Can you describe the most challenging colleague you’ve had to work with? How did you handle that relationship?
This question helps you assess how a candidate handles ongoing interpersonal challenges. Listen for signs of professionalism, adaptability, and the ability to stay focused and constructive when working relationships are difficult.
Finding top job candidates to interview: Of course, having the right interview questions for administrative assistants works best when you have top job seekers to interview. At Robert Half, we can help make finding and hiring an administrative assistant easier.
