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Do Ask. Don't Tell.

Updated: May 26, 2019

Dissecting the equation to successfully working with your Virtual Assistant.

Do Ask. Don't Tell. The key to working with your Virtual Assistant.

Relationships take time. And the great ones are worth it. Call me crazy or cliche, but the same goes with working with your Virtual Assistant. VAs are not robots, or computer screens, they’re humans. And not just any ordinary humans, humans that have a passion for serving and for marking tasks off your list of things to do. We are the kids in class that are obsessed with stationery, mechanical pencils, and making sure everything is organized beyond your wildest dreams. We love lists and always turned our homework in on time (or early). VAs want to help add value to your life, to help give you the time you need to be successful in all areas of your life -- work, family, personal, hobbies, whatever is important to YOU. The kicker is, they like to be respected, too. In fact, VAs love going the extra mile for you when they are treated like humans (as opposed to robots). It’s easy to fall into the routine of just sending tasks and having them done, but you may be surprised at just how effective and productive your VA is if the relationship is a two way street. I’m not saying if you’re having a bad day or are in a hurry that you can’t send a short, to the point email with what you need done, I’m just saying, respect is a daily habit, not a holiday gift.

If you ask your VA why they chose this career path, 9 times out of 10 you’ll get answers along the lines of “I wanted to spend more time with my family, but didn’t want to give up my career,” or “I love helping others, but need a flexible schedule.” When you ask clients why they need a VA, you’ll hear things like “I’m too busy to even go to the bathroom,” or “I need help getting organized, to put systems into place so I can be more productive and still make it home in time for dinner.”

Seems like a match made in heaven, right? Wrong. Just because needs and wants can be met by this type of mutualistic relationship doesn’t mean that’s the end of this equation. Working virtually with someone requires a high level of mutual respect and also for both parties to continually participate, be more open, detailed, and proactive. The mutual respect is key. It’s what allows continuous participation and relationship growth.

Here’s an example:

The client, Mr. Jones, emails his VA, Stacy, the following:


I need these done today please:

  • Schedule an appointment with my doctor for Monday at 9:00 AM.

  • Get my auto insurance information to XYZ Car Dealership by 3:00 PM today. Ask for Lisa.

  • Transcribe the attached audio file and upload it to my drive.



Stacy replies to Mr. Jones:

Hi Mr. Jones,

Happy to take care of these things for you today.

I don’t have your automobile insurance information though, can you please take a picture and send it to me? Or, I see you have 15 minutes available today at 10:30 AM, I’ll call you then if I haven’t received the image.

All the best,



Mr. Jones does not send the picture and does not answer at 10:30 AM. Stacy follows up again that afternoon with no response from Mr. Jones. The next morning when the car dealership calls Mr. Jones and asks, again, for the information, Mr. Jones immediately calls Stacy, frustrated, and tells her she dropped the ball on this task. This, in turn (and maybe unintentionally), creates an atmosphere of disrespect and heightened emotions.

If Mr. Jones would have called Stacy and asked what happened with the task he assigned to her, he would have understood Stacy didn’t have the information she needed to complete the task and that she, in fact, did her part to overcome the roadblock she encountered. At that point, Mr. Jones and Stacy could’ve discussed solutions to make sure that didn’t happen again in the future and how he preferred she contact him when he’s unresponsive. Hence, respect = relationship growth. Ever heard the expression “Seek first to understand, then to be understood?”

Failure to participate in a virtual working relationship guarantees a breakdown of that relationship. Like I said before, this is a two way street and BOTH you and your virtual assistant need to continually participate. Finding the right virtual assistant is another part of this equation, which is something we will talk about later in this blog series.

Remember, when in doubt, do ask, don’t tell.

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