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About a year ago, Jordan Draper, President of our sister company, Greenway Insurance, hired an Executive Assistant through Cover Desk. Over the past year, I’ve been impressed by how quickly she became an integral part of his team. She operates with a high degree of independence, understands his priorities, and has become someone he can confidently rely on.
Watching their working relationship made me reflect on my own experience.
I had previously tried working with an Executive Assistant, but with limited success. I struggled with questions about the skills I really needed. Did I need an EA or more of an analyst? How proficient did this person need to be in Excel? Would an EA truly be helpful unless they had access to my meetings, conversations, and other sensitive information? If so, trust and discretion would be essential.
Eventually, those questions became roadblocks, and I never fully established the role, which is admittedly ironic for the CFO of a company that helps businesses successfully integrate Virtual Assistants every day.
The Person Matters, But So Does the Onboarding
Recently, Jordan and I were in Austin with Andy Priesman, Founder and CEO of Cover Desk, when I mentioned how impressed I was with his EA. I wondered aloud whether there had been something unique about her background or the way we recruited her.
Jordan’s response was immediate: “No! It’s because of me!”
He was joking, but he also had a point.
I had watched the investment Jordan made in their working relationship from day one. He dedicated time to teaching, communicating, providing context, and giving her the tools she needed to succeed. I realized I had not made that same investment in my previous experience.
That distinction is important for any leader bringing a Virtual Assistant, or any new employee, onto their team.
Set Your New Team Member Up for Success
There are several lessons agency leaders can take from Jordan’s approach:
Invest heavily in the beginning
Bringing on a VA creates capacity, but that capacity isn’t necessarily immediate. The time you invest during the first several weeks explaining processes, answering questions, reviewing work, and providing feedback can lead to significantly greater independence later.
Teach the “why,” not just the task
A checklist can show someone how to complete a process, but context helps them make better decisions. Explain why the task matters, who it impacts, what a successful outcome looks like, and when something should be escalated.
Use outside resources to fill knowledge gaps
You don’t have to personally teach every skill. Jordan has used resources such as Coursera courses to help develop skills when formal training already exists. Identify the gap, find the right resource, and give your VA dedicated time to learn.
Give them access to the right information
A team member cannot anticipate your needs if they only see a small piece of your world. Determine what meetings, systems, communications, and workflows they need visibility into to understand the bigger picture while maintaining the appropriate security and confidentiality controls.
Create a feedback loop
Don’t wait for a formal review to address questions or make adjustments, especially in the beginning. Regular check-ins give your VA an opportunity to ask questions, learn your preferences, and improve. As confidence and competency grow, the level of oversight can gradually decrease.
Build toward ownership, not just task completion
The ultimate goal shouldn’t be to create a team member who waits for the next assignment. With training, context, and trust, a VA can begin anticipating recurring needs, managing workflows, and taking greater ownership of their responsibilities.
You Can’t Expect Someone to Simply “Plug and Play”
This experience reminded me of one of our most important responsibilities as leaders: making sure our people have what they need to be successful.
Even a talented, well-trained Virtual Assistant cannot walk into a new organization and immediately understand how you operate. Every agency has its own clients, systems, workflows, communication preferences, priorities, and culture. Training provides a foundation, but leaders have to provide the context.
It’s easy to conclude that a new hire “isn’t working out” when what may actually be missing is the investment required to help that person succeed.
The time Jordan invested upfront didn’t create more work indefinitely. It created a team member who could eventually operate with greater confidence and independence.
That’s the lesson I’m taking into my own leadership: Don’t judge the value of a new team member solely by what they can take off your plate on day one. Invest in what they could take off your plate six months from now.
