The last four years have been an interesting journey, for myself and my remote executive assistant team. When I started ChatterBoss, the world of virtual assistants was still mysterious. An unknown. We often got asked: 

  • “Are you AI?”
  • “Are you a real person?”
  • “What ARE virtual assistants?”

This makes total sense. The VA role (when done right!) is the virtual counterpart of the personal assistant. And that is a very high-touch position. One that for a long time entrepreneurs wanted to have right by their side. But the COVID-19 pandemic changed that: Working remotely became the norm, and many of those same entrepreneurs started working with their assistants virtually. So now that there’s a general acceptance that pretty much any position can be done virtually, the kinds of questions we are getting asked more often are:

  • “How can I improve my communication with my assistant?”
  • “How do we document processes and put them in place?”
  • “What can I do to get the best result from my remote team?”

This shift is great news for us and our clients. With more and more people willing to give remote assistants a try, the focus of their questions has progressed from “how do we do this?” to “how do we do this right?”, with a particular interest in best practices around communication and positive remote team dynamics.

Communication is not always easy. Right when it seems like we’ve started to master the art of communication in person as a species (with all of its verbal and non-verbal subtleties), we’re thrown into a new reality where the vast majority of our communication is virtual. This is both a blessing and a curse. On the one hand, it’s incredible because of the flexibility it provides, but on the other hand, it’s a challenge because we’ve been stripped of the communication cues that usually supplement our in-person exchanges—the cues that help ensure our message and tone are received as intended. Since these cues (such as body language) are often unavailable in a remote setting, we need to put more thought into the way we communicate, otherwise professional relationships can quickly become dysfunctional (and personal ones too, for that matter!).

Here’s an unfortunate scenario that I’ve witnessed happen all too often, and which I’ve been guilty of as well: You’re in a hurry, doing too many things at once as usual, and you think of something important you don’t want to forget. So without paying too much attention to how your message will come across, you send a note to your assistant that reads “Let’s discuss this ASAP.” Unsurprisingly, though unintentionally, the message comes off as abrupt or even abrasive, and leaves the recipient in an unnecessary state of panic. Of course, sometimes that type of curt message is sent intentionally (ouch!) since you didn’t get the desired result on a task and you’re feeling frustrated about it. You want the assistant to know you’re dissatisfied, so you say something along the lines of “It should never be done this way.”

“It Should Never Be Done This Way.”

Let’s talk about the intentional one first. You’re the boss. You’re upset. You want your assistant to know that you’re upset and maybe want them to feel a little upset too. And if you have a good assistant who cares about the results of their work, then those words will definitely get them to be as upset as you are. You might be wondering, what’s the issue here? If someone did something wrong, they should be aware of it. Well, here lies the crux of the issue we’re confronted with in this virtual space: oftentimes, the “should” in “It should never be done this way” was never properly communicated. The task hand-off is as important as the task itself, and yet it’s often given very little thought. Without proper context and instructions around what “should” be done, the likelihood of a task meeting one’s expectations and being executed in the desired way are understandably quite slim.

The good news is there are many systems you can put in place to avoid this situation, all of which begin by acknowledging that investing some time to provide clear instructions upfront will benefit the task’s timeline overall (and your mental health!). One highly successful system consists of outlining all of the steps of the project and testing them to ensure accuracy. Assistants appreciate this system tremendously since the directives are clear and possible to accomplish, which leads to better results and mutual satisfaction. If the time simply does not allow for a full step-by-step outline, then the alternative is to provide instructions piece-meal as the assistant makes progress on a task. Even if instructions trickle in through a mixture of phone calls, texts, voice notes, and emails, at least the assistant is given sufficient information to know what the task’s end result “should” look like. 

As I mentioned earlier, even though I know what functional communication looks like and I’ve spent many years sitting in the assistant’s chair, I still sometimes give in to the impulse of shooting off an “It should never be done this way” type of message. Thankfully, my assistant (who is better at following my own advice) is great at reminding me of our best practices:

“Hi Valerie, 

Could we perhaps use wording such as "Can we please do x, y, & z" instead of "We should have done x,y & z"? "Should have" implies that we or I should have done something differently, which I wouldn’t have been able to do since the way things “should” have been done wasn’t properly communicated.” 

I’m sharing this because I sit in both seats. I’m both the entrepreneur handing off dozens of things a day to my assistants and also a former assistant who’s been on the receiving end of dreadfully demoralizing messages that take days to shake off. It’s a little embarrassing to share that email, but I hope it’s helpful because the reality is that not all assistants will course-correct a negative exchange the way my assistant did. Most assistants are likely to let it slide in order to avoid conflict. But there’s no doubt they’ll be hurt by the words, and you’ll be labeled unfair. 

“Let’s Discuss This ASAP” 

In the scenario where you’ve written something that sounds abrupt because you were in a rush, should you have anticipated that your assistant would be left feeling unnecessarily stressed out? It depends. I see virtual communication like a set of dominoes: If the dominoes that landed (your communication) were for the most part fair and positive prior to that abrupt message, then there should be no harm done. The assistant should interpret the curt tone as a simple indication of your hurry, rather than a forewarning of an uncomfortable conversation. However, if your prior messages fit into the “It should never be done this way” category, then the abrupt message will further reinforce a stress response from your assistant, and anything you send thereafter will be read with angst. The energy generated by the previous domino directly affects the next one. Careless messages and thoughtless interactions will leave a negative charge that will fuel future exchanges, and so on.

It’s easy to lose sight of the effect our communication has on others when working virtually.  Pair that with the pervasive (and utterly false) idea that virtual assistants are just mindless task doers and you have the perfect combination that leads you to depersonalize and dehumanize your virtual team members. Which leads to another undesirable domino effect: The domino effect whereby an assistant continually second-guesses themself, leading them to make mistakes that could easily have been avoided. 

When an assistant is consistently on the receiving end of inconsiderate communication, they start to expect it. To try to avoid it, they begin questioning every decision they make, second-guessing their instincts. They start to spend more time on a task to try and anticipate what you might find wrong with it. Ironically, at this point, they tend to start making more mistakes while they’re desperately trying to avoid them. Their confidence is so rattled that even though their mental energy is focused on trying to anticipate your needs, they miss some obvious gaps in their work. 

To make matters worse, this is where the entrepreneur starts to believe that the assistant is truly incompetent, furthering the unfortunate domino effect.  Before you know it, you have a superstar assistant who is operating under the premise of “Just tell me what to do” because they’re afraid of making a mistake, which further upsets the entrepreneur... “Can’t my assistant think through anything on their own..?” 

It’s such a vicious cycle. But I’m optimistic about the way the virtual space will evolve as we continue to have more of these conversations. I’m confident that the gap in our communication will decrease over time, and that our professional relationships will not only become more functional, but more enjoyable. 

What are the key takeaways? Hire right and then trust your team. Take the time to communicate your needs clearly and with care. Always assume best intentions. Replace your “shoulds” with “could yous”. And be kind :).

I’m curious to hear your thoughts.  If you’ve experienced any of these scenarios as an assistant, how did you handle them? What did you learn from them? If you’re a business owner using a virtual assistant, have you ever been stuck in this vicious cycle? What did you do to break out of it?

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