17 Questions to Ask When Interviewing a Potential Virtual Assistant Virtual assistants can be a boon to startups but there are potential problems with long-distance relationships.

At some point every entrepreneur asks the question "How do I clone myself?" Since cloning isn't actually possible yet, the next best thing is to hire an assistant. If you can offload half the work you're doing to others, it's just as good as having a carbon copy of yourself. Today, many entrepreneurs are hiring virtual assistants from the Philippines and other offshore destinations, where one can hire a full time assistant with great English and internet skills for between $500 to $1,000 per month.

I was first inspired to search for a virtual assistant when I read Tim Ferriss' best selling The 4 Hour Work Week when it was first released. I made a few attempts, but I struggled to make it work out the way I needed it to. I felt like I was making mistakes, but I weren't sure what they were or where I could learn how to work with virtual assistants the right way.

Then I read Virtual Freedom by Chris Ducker, which goes in depth into the details of exactly how to find, interview, hire, and manage virtual assistants. Ferriss had given me the inspiration, the "why," but it wasn't until reading Ducker's book that I got the "how" part of the equation.

I've since begun to build a team of virtual assistants in a very different manner than my previous attempts, and with much better results. Part of the success I've experienced has come from asking the right questions during the interview stage. Another book that has been a great resource in this process is Who by Geoff Smart and Randy Street, which takes a scientific approach to the hiring process that has completely changed my business.

While I ask other basic questions during the process of hiring my virtual assistants, here are some of the key ones I get the most value from, and why I ask them.

1. How did you end up where you are today?

This isn't idle chit-chat, I want to see whether the VA is comfortable talking about himself, whether he's comfortable with such an open-ended question, and what he chooses to share and emphasize, and what he doesn't share. It's also a great way to start the conversation in a relaxed, casual way.

Related: 10 Things to Outsource to a Virtual Assistant

2. What do you enjoy doing outside of work?

This allows me to learn more about the VA on a personal level and reveals things I might not find out with other questions. One VA I interviewed recently chose to tell me that he runs his own small business on the side, which was valuable information to me because I like hiring entrepreneurs. Note: "I like to party, get wildly drunk, and disappear for three days at a time," is not a good answer to this question, and yes, I had a VA who did that once. He didn't last long.

3. What type of work are you best at? What are you most interested in learning more about? What are you not good at? What work do you prefer not to do?

The last thing I want to do is plug someone into a role that isn't the right fit, and if I only talk about what I need done, and the VA is desperate for a job, he's going to tell me what I want to hear, rather than what I need to hear. I ask these questions as early in the process as possible to make sure the VA has only minimal information about what I'm looking for.

Related: Do These 3 Things Before Hiring a Virtual Assistant

4. What is your favorite way to communicate?

I'm an email guy. My business partner is a phone guy. I'm open to working with a VA either way, but would probably lean towards hiring a VA whose preferred method of communication is email. Choose what works for you.

5. Have you hired and fired other employees? Tell me about your worst experience firing someone.

I've found that hiring employees who have experience hiring and firing have a different perspective that is beneficial to my business. They are harder working, more proactive, less entitled, and willing to do whatever it takes to get things done. It also tells me they have management experience and the potential to help me manage a team.

6. How have you handled a situation where someone you managed wasn't performing well, but not so poorly that you needed to fire them?

It's easy to keep someone who is doing a great job, and easy to fire someone who is doing a terrible job, but it's hard to know what to do with people in the middle. I like to see how a VA with management experience has handled this type of situation. I want to see how they've communicated with the struggling employee, what steps they've taken to help him, and if they have a structured process.

7. If I asked you to perform a task, and after accepting it you realized you couldn't do it on your own, what would you do?

I'm not just looking for an answer, I'm also looking to see if they are thinking about the answer for the first time. If they say, "Well, I guess I would…" then that tells me they aren't as experience as I would like. If they say "I've been in this situation before, and even though it was kind of embarrassing, I went back to my boss and asked for clarification," that's much better.

Related: 3 Ways a Virtual Assistant is the Fastest Ticket to Growth in 2017

8. What would you do if I gave you an assignment, and you thought you understood it, but then later you realized you didn't understand?

This situation is potentially much more embarrassing for a VA than the last, because once a VA has said he understands an assignment, he has to "come clean" in order to get clarification. What I'm looking for is a VA who has no problem telling me "Sorry, I thought I understood this, but I'm running into some challenges with it, can you clarify things for me?"

9. If I gave you a bunch of assignments, and you realized you couldn't get them all done fast enough to meet deadlines, what would you do?

Nobody wants to tell the boss that they won't have an assignment done on time, and yet that's exactly what I want. If a VA tells me he doesn't think he'll get the job done on time, but then he does, I'm going to be happy. If he tells me he will get it done on time, but then he doesn't, I'll be unhappy. The VA who understands this is the kind of VA I want to work with.

10. Can you tell me a story of when you spoke up and contradicted a boss or supervisor?

I love an employee who will challenge me and ask "Have you considered this other way to do such and such?"

Related: Hiring a Virtual Assistant Grew My Business, and Changed My Life

11. What communication problems have you noticed in previous work situations?

Lack of communication or poor communication is the cause of so many workplace issues, especially with remote workers. I want to know that the VA has experienced these issues and knows how to work around them.

12. You're working on an urgent deadline and your computer crashes, or your internet goes down. What's the first thing you do?

Most VAs will answer that they have backups, or that they will find a cafe, but the correct answer is that the first thing they will do is notify you of the problem, and that it might impact their work temporarily. One of the most frequent complaints I've heard from employers of VAs is "My VA disappeared for three days, I had no idea what was going on, and then it turned out her internet had gone down. I was pulling my hair out! Why didn't she find a way to tell me?!"

13. What's an example of a time you proactively addressed a client's need?

It's not enough for a VA to to do everything you ask, you need a VA who will anticipate what you need, and do it before you ask.

Related: How to Hire a Virtual Assistant for Startup Success

14. What tools do you use in your work? What are some of your favorites?

Whatever the tools are that you use, it's a plus if your VA already uses those tools, whether it's Google docs, Basecamp, Asana, Freshbooks, or any others. But rather than listing all your favorite tools and asking "Do you know how to use these?" make it an open-ended question, and see if you get some matches.

15. How quickly do you typically respond to emails?

The right answer is not "Immediately," because nobody can always answer emails immediately, but "Usually immediately during working hours, unless I'm focused on a project for my employer, but always within 24 hours, Monday through Friday," is a great answer.

Related: The Virtual Assistant: A Startup's Secret Weapon

16. What are your schedule restrictions? What is your preferred schedule?

Some VAs are single parents taking care of children, some like to work at night, some like to work starting early in the morning. Whatever the case is, it's important to discuss to make sure it works for you.

17. Who were your three most recent employers? What tasks did you regularly do for them? How will they rate your work on each of those tasks when I ask them?

I can't overemphasize the importance of getting references and contacting them. It's the quickest way to avoid making a big, expensive and time consuming mistake.