17 Questions to Ask When Interviewing a Potential Virtual Assistant

At some point every entrepreneur asks the question “How do I clone myself?” Since cloning isnt actually possible yet, the next best thing is to hire an assistant. If you can offload half the work youre doing to others, its 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.

General virtual assistant interview questions
  • Tell me about yourself.
  • How might your coworkers describe you?
  • How might your current manager describe you?
  • What’s your greatest strength as a virtual assistant?
  • What’s your greatest weakness as a virtual assistant?
  • Where do you see yourself in five of 10 years?

Virtual Assistant Interview Questions | Virtual Interview Tips 2020

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?”

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.

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.

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