1. What is your specialty?

You now know what your potential virtual assistant can do. What about what they like to do? These questions are important for opening up the conversation and getting to know your interviewee. They’ll also help you to determine whether you can call on this person in the future to do tasks that may need to be done months down the line. A great virtual assistant truly enjoys their work and shares nuances about the Internet with you as you continue to build a relationship with them. Do you see this person as someone you’ll want to call upon again and again?

2. Can you accomplish my tasks?

Share your list of projects with your virtual assistant candidate. Can they do them all? Are they are willing to share some examples of their past work. Listen to how confident your potential virtual assistant sounds when answering your questions. If they sound unsure or give you a flat-out “no”, do you really want to hire them? Is it acceptable to you if they are willing to learn how to do tasks that they haven’t done before? (This may mean that they’ll take more hours working on your project than a more experienced virtual assistant would need).

3. What is your experience?

For each task that your potential virtual assistant can do, ask them about their experiences doing it. In what field of business did they do this work? If your interviewee has absolutely no experience in your business field, is that important to you? How long did it take them to complete past projects? This may make a difference for you if you are on a deadline to get some items on your list completed quickly. Which leads us to the next question…

4. How quickly can you get to my tasks and complete them?

Are they overloaded with work and cannot get to your jobs for three weeks? Or maybe they can complete some quickly and others will take more time to finish. Your potential virtual assistant may give you different answers for each task that you’ve discussed. That’s okay, because it will give you a good idea of how much time they’ll need to devote to your projects.

5. What is your communication style?

When can they be reached? How quickly can you expect a response from them? Do they exclusively communicate via email, or will they be available to meet with you by phone, in person, or via web conference? How often will they update you on the progress of your projects? Are they willing to answer technical questions for you, or are they only available to accomplish specific tasks? The answer to this final question is very telling, because a virtual assistant who wants to build an ongoing relationship with you is a keeper.

6. What kind of software and office equipment do you use?

On the surface, this question may seem mundane and of little importance. However, if for example, you use Macs and run Apple-compatible software, but your potential virtual assistant only sees things from a Windows point of view, there may be issues. The kind of answer you’ll want to hear is something like, “I can run things on all browsers and can interpret what you send me from screen shots, if there are any issues.” You’ll want your virtual assistant to be willing to get around potential obstacles.

7. What security measures do you have in place?

Let your virtual assistant candidate speak openly about this. A great virtual assistant will talk about password protection, data backups, and a confidentiality policy for your intellectual property. Are they a member of associations like the International Virtual Assistants Association (IVAA) and the Better Business Bureau? Do they subscribe to a Code of Ethics? If you are particularly concerned, you can ask if they are willing to sign a non-disclosure agreement of your creation, a contract to protect your property and trade secrets? It is especially important to vet out your interviewees when a friend or colleague has not referred them to you. Note: Security issues are the most important reason not to entrust virtual assistant tasks to college interns.

8. Do you have a back up?

I don’t mean a security back-up here—This is about making sure you are covered when the virtual assistant goes on vacation or has other things coming up in their life. Who do you call upon if you hire them and they are not available? Just like any webmaster, a virtual assistant should not leave you in the lurch when they have a personal commitment and are unavailable to respond to you.

9. How much do you charge?

Your potential virtual assistant may charge per job and will itemize each task on the list you provided. Or they may quote for the entire list of jobs you have presented. Regardless, they will probably want to get back to you with quotes, because they may need time to research the number of hours each task will take to complete. Ask about which form of payment they accept, when you will be billed, and how often you will be billed. Some companies expect a deposit before work is started, others will bill you in full upon completion, and still others have billing cycles and bill as different tasks are completed according to their own internal billing schedule. If you need some “creative” financing, for instance spreading out payments over a period of time, it never hurts to ask.

And the most important question to ask, and this is a question to ask of yourself:

10. Do I like you?

Sounds a bit odd, but this is the best way to test the “chemistry” between you and the virtual assistant candidate in question. If you feel in your gut that you have found the perfect virtual assistant, you may have found a winner. But if you hear a certain catch in their voice, a less-than enthusiastic tone, or something off, honor your intuition.

Ask yourself this question when interviewing all potential contractors, not just virtual assistants. The answer may foretell how much they’ll contribute to the success of your products and services.