Administrative Assistant Tips

Fifty Virtual Assistant Interview Questions

In the modern era, it's easy to hire a virtual assistant online. We cover fifty questions you may want to ask a virtual assistant before you hire them.

When hiring a virtual assistant, there's always a risk that things won't work out.

To improve your chances of getting it right, you should first understand the qualities of an effective administrative assistant. Once you can envision what having a good assistant looks and feels like, you'll be ready to interview virtual assistants and find one that's right for you.

To help you prepare for your virtual assistant interview, you'll want to peruse these virtual assistant interview questions.

We don't necessarily recommend that you ask all of them, as that would be a bit over the top. But let the questions stimulate your thinking on what's most important to you in your relationship with a virtual assistant.

We've also prioritized the questions such that you can bail out early in the interview if you hear something that makes it a certainty that it's not a fit.

Fifty Questions to Ask a Virtual Assistant Before You Hire Them

1. How long have you been a virtual assistant?
2. Tell me more about your background.
3. What aspects of your background prepared you to be a good virtual assistant?
4. What do you like about being a virtual assistant?
5. How does your pricing work? What do you charge? Will that ever change?
6. What are the range of services can you provide? Which of them are your favorites?
7. So what does that exclude? What are some things that you don't do that other virtual assistants might do? Why don't you offer that?
8. Do you have a process for onboarding new client like me? How would that work exactly?
9. Would you be willing to start with a small project that we work on together, instead of me signing up for a longer term contract? I think I'd like to be able to give you a try before I commit to a longer timeframe? Is that an option?
10. What software and technologies are you most comfortable with?
11. With respect to staying organized, what tools, approaches or systems do you use?
12. How many other people are you assisting?
13. How many hours do you work per week and how many hours should I expect you will be able to work for me?
14. If I ever need it, would it be possible for you to work later or to work longer hours in a given week?
15. What's your typical response time? For example, if I text or email you, when should I expect a response?
16. Do you consider yourself to be a fast person in general? For example, how fast do you type? Do you use keyboard shortcuts to do things faster?
17. Do you plan on capping the number of people you work with? My concern is that you might get too busy to support me well.
18. How do you like to work with your clients, in terms of structuring the work and in terms of communication?
19. You told me earlier about what you like in this work. Are there any aspects of it that you don't like?
20. What are your expectations from me in this relationship?
21. What are some potential scenarios where this doesn't work out between us, and how would you suggest we avoid those potential worst-case scenarios?
22. Walk me through the specifics of how you would support me on [insert task here, e.g. growing my social media followers]. What exactly would you do? Or would you want me to provide all the details on how to do it?
23. And do you do all the work yourself or do you outsource some of it? I've heard of some virtual assistants who bring on more clients than they can support and then outsource the work to others? Do you do anything like that?
24. Can you talk to me about some of your other clients? What did you do for them? How did it work out? What went well and what didn't go so great?
25. Let's talk about travel specifically. I often will need you to book me a flight, hotel and/or car? What's your experience with booking trips? Do you have any tricks of the trade that make you especially good at it?
26. How do expenses work? Do you use your credit card and submit expenses for reimbursement? Or do I need to give you my credit card information?
27. Sometimes I just need someone to research a topic for me? Is that something you do? Definitely say no if it's not in your wheelhouse, as it's not critically important because I do have some other research-related resources. But I'm curious if it's something you could help with.
28. If I needed you to learn a new software program in order to support me, would you do that? How would that work? Would I need to pay you extra to learn the new program or would you make that investment on your own time?
29. What publications do you read to stay on top of your profession? Do you belong to any professional trade associations?
30. What's the last new thing you learned that got you excited?
31. What other new skills have you learned in the last six months? Why did you set out to learn them, and how did you go about it?
32. Are you reading any books right now? What are you reading now or what's the last book you finished? Did anything you learned from that book impact how you approach your virtual assistant role?
33. Have you obtained any certifications I should know about?
34. I'm still just getting a feel for who you are and how you work. I know it's an overdone interview question but how do you describe your strengths and weaknesses?
35. What about attitude and personality? How would you describe your personality and your approach to work and life?
36. I feel like feedback loops are important in a relationship like this. How would you want me to give you feedback? Are you a person who doesn't like to get any negative feedback? Do you need praise for good work? I'm just curious generally how you think about feedback, reviews and things like that.
37. Are you a good writer? The last thing I want is to be reading through typos and grammar errors. What's your background with respect to writing and how would you rate yourself?
38. Could you send me some writing samples that were written by you without assistance from anyone else? I'd like to see that.
39. What about timeliness in completing tasks? Do you ever miss deadlines? Why might that happen. Can you give me an example of the last time you missed a deadline?
40. I'm interested in someone who won't drop the ball on tasks we agree on, but I also would like someone who isn't just executing on tasks in a brain-dead mode. I'd rather they come me with ideas to improve the things we are working on together. So, could you talk me through a time when you were working on something and saw that the approach could be improved, or that it didn't make sense, and you spoke up to change things?
41. What about idle time? If I am too busy to get organized and get some work over to you, do I pay you for that time? How would you approach a situation in which I was supposed to get you some work and kept not getting it to you?
42. I'm fairly security conscious. Tell me about your office and tech setup, and what you know about protecting information and confidentiality? I also want to make sure you have a productive work environment, so I'd especially like to know about your computer and your Internet connectivity, as I don't want to work with someone who doesn't have a good tech setup.
43. How do you feel about automating mundane tasks? For example, in Photoshop you can resize images manually one by one, but there is also some automation you could implement to do it in batches. So, if I asked you to manually resize some images for me, I might hope that you'd instead pursue doing it with automation. Can you give me any examples of where you've done that in the past -- taken a manual task and figured out a way to automate it and get the work done faster?
44. Let's talk about scheduling. I assume you take vacations. How will I know when you will be off and how far in advance will you let me know? How much PTO do you take usually?
45. Are there any vacations coming up in the next four months that I should know about and plan for?
46. OK, in terms of timing, if I decide to hire you, when could you start?
47. Is there anything else you want to tell me about yourself and how you work?
48. I've asked you a ton of questions. Thanks so much for all this great information.
49. What would you like to know about me?
50. What other questions do you have?

There you have it. Fifty interview questions for virtual assistants! They will probably reject you if you ask them all. But hopefully it stimulates your thinking as you prepare to hire a virtual assistant. Good luck!

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