My Guide to Hiring an Assistant


Ever said, “I don’t have time” or “I’m too busy” to doing something you’d really like to do

If you’re like most entrepreneurs, you’ve probably said these phrases hundreds of times. I know I have and still do.

I don’t say those phrases nearly as much as I once did now that I’ve hired a virtual assistant.

She manages my calendar, travel plans, e-mails, researches, and does a few technical tasks.

Here is my guide to hiring an assistant.

Hiring Your Assistant

The key to hiring a VA is finding the right alignment with that person. It’s a lot of work in the beginning. But once you’ve hired and setup a VA, the process can be easily managed.

I’ve spent 2 weeks on Google Hangout interviewing about ~25 top candidates before choosing my VA. I interviewed people from Canada, United States, Philippines, Malaysia, Thailand, China, South Africa, and Mumbai.

Some wasted my time. Some were great. Also, I made sure each interview lasted at most 15 minutes long. Let the candidates know this upfront so we could get to the point quickly.

I asked 3 questions:

  1. What is their passion and values?
  2. When was a time that they were most happiest?
  3. What do you know about me?

You’ll need to tailor your interview questions to your needs, but those were mine.

With me, there were only 2 candidates who knew anything about me. I figured that a good VA would have “googled” me before the interview. I ended up hiring the one that knew the most about me, and aligned with my values.

Once you’ve hired your VA, then comes to hard part: Dedicate at least 2 weeks in the beginning to setting everything up. After that, you only need to spend 1-2 hours daily to iron out details and making sure your VA creates a solid SOP. That way, he/she can reference the SOP when there’s an issue.


You also have to tailor your VA’s training to what you need done. I started my VA’s training by telling her about my core values and what I believed in. That avoids miscommunication in the future.

I told her I wanted someone who was honest, transparent, and could solve problems independently.

I also told her that I wanted someone who if stuck would ask questions and not lie.

Next, I worked online closely with her for the first 2 weeks. We used Hangout at times to go over exactly how I like my calendar organized (I’m picky). Then we went over how I wanted tasks organized.

I even paid her to watch the TV series, Suits, and said, “I’m looking for a Donna.” She watched the show and reported back to me: I’m your Donna. This was a small but profitable investment of time and money.


Managing my VA requires routine. We check in with each other weekly and communicate through Whatsapp or Google Hangout if we need to talk in person.

I dedicate time once a quarter (1-2 hours) to talk about future planning and to tell her how she can grow in the position.

I also plan on spending time understanding what she wants in life and how I can help her achieve it. I believe that if a person can learn and grow in a position, they’ll be happy in it.

Take the time to get to know your VA before hiring him/her, and then spend time creating a solid standard operating procedure (SOP) which will lead to a mutually beneficial working relationship.

If you find yourself saying, “I don’t have enough time” or “I’m too busy” to things you really want to do, you could probably use a VA.

Otherwise, you’ll always be “too busy” to do things you know you should do and you’ll continue to make excuses for not getting things done.

About the author

Jeremy Choi

I’m a husband, father, entrepreneur, mentor, and an irredeemable golf addict. Possibly like you, my big hairy audacious goal (vision) is to make a positive dent in this world. I write about creating better leaders, workers, and people. I also write about my experiences in all aspects of my life. These ideas are my experiences living & learning through my own core values; integrity, authenticity, leadership, inspire, and health.

1 comment

  • Thank you Jeremy! I’m just at that point where I had “too much to do” but was hesitant… should I “hire/ invest” in a VA or not? I’ve started interviewing people and this piece came in perfectly.