Empowering Initiative: Strategies to Cultivate Proactive Virtual Assistants
Encourage Initiative in your Team: Tips, Strategies & Real Examples
Author: Carmen Williams
How to get your Virtual Assistant to show initiative
If you’re a business owner, you’ve probably wished for a team member who just gets it—someone who doesn’t wait to be told what to do, but jumps in with ideas, solves problems, and keeps things moving.
That magic quality? It’s called initiative,
a team member who just gets it—someone who doesn’t wait to be told what to do, but jumps in with ideas, solves problems, and keeps things moving.
That magic quality? It’s called initiative,
In fact, one of the most common things I hear from business owners is:
“I just want a Virtual Assistant who shows initiative!”
It’s one of the most valuable things a Virtual Assistant can bring to your business.
During a team training recently, we were unpacking what initiative really means, What it is, why business owners value it so deeply, and how to show more of it. why it matters so much, and how Virtual Assistants can show more of it. To explain it, I shared a story that’s stuck with me for years.
When I was a teenager, I remember being frustrated with my mum (as most teens are), and she’d calmly say:
“Carmen, I am trying my best; I have never been a Mum to a 12-year-old. I am learning.”
And when I turned 16, she said it again.
“I may have parented a 12-year-old before, but 16 comes with a whole new set of challenges.”
That line has stayed with me, because now, as a business owner, I find myself in the same position.
Even after years in business, I’m still learning. New stages bring new challenges. I don’t have it all figured out—and that’s true for so many business owners.
Which is exactly why initiative stands out.
We love team members who think for themselves. Who don’t wait for perfect instructions. Who are willing to grow alongside us.
In this post, I’m sharing the exact resources, examples, and downloadable tools we used in our training to help Virtual Assistants develop that mindset. Whether you’re leading a VA or you are a VA, you’ll find practical ways to build more confidence, take ownership, and make a bigger impact.
Let’s get into it.
First, let’s understand….what’s holding your VA back…?
Before we jump into how to encourage initiative, it’s essential to understand what might be holding it back in the first place.
It’s easy to say, “Just speak up!”
But there are real reasons why some Virtual Assistants stay quiet, even when they have great ideas. In this quick 1-minute video, Sheila shares some of the most common reasons VAs might hesitate to show initiative. Understanding the invisible barriers that can stop even the most capable VA from contributing ideas is the first step in creating a more supportive, proactive working relationship.
This short video is a great place to start!
3 Strategies to help your VA show more initiative
Let’s start with some practical, easy-to-implement ways to encourage initiative in your Virtual Assistant.
In just 4 minutes, I walk through three specific strategies I use with my own team, strategies that have helped them feel more confident, proactive, and empowered to take ownership of their work.
See Initiative in Action: 100 things our VAs did while we were in Fiji
Want proof that proactive Virtual Assistants can keep things running…even when the business owners are on a beach in Fiji?
Maureen and I signed up for a retreat in Fiji a few years back, but that didn’t stop the business from still operating. Instead, our team of VAs kept everything moving. In fact, they did 100 meaningful things without needing to be supervised or hounded.
We’ve turned that list into a downloadable PDF to inspire you and your team. It’s a real-world example of what it can look like when your team feels empowered to do their jobs and are not afraid of making some minor decisions because they feel trusted and confident in their roles.
Download the full list: 100 Things Our VAs Did While We Were Away
“She Bugs Me for My Videos—And I Love It”
The title of this podcast episode perfectly sums up what it’s like to have a Virtual Assistant who truly takes initiative.
In this conversation that I had with Victoria Berry, businesswoman extraordinaire, she talked to me about what it’s like working with her Marketing VA, Samm, and how Samm helps keep her three businesses running smoothly and her marketing on point. Samm doesn’t just wait around for a daily to-do list — she takes action and will even nudge Victoria when she needs content, ensuring that Victoria’s grand ideas are brought to life.
It’s a fun, honest look at what can happen when you’ve got the right VA by your side
Listen now: She bugs me for my videos and I LOVE it!
Initiative is one of the most powerful qualities a Virtual Assistant can bring to your business, and as you’ve seen throughout this page, it’s absolutely something that can be encouraged, supported, and strengthened.
Now that you’ve got some practical strategies and ideas of how to build a team that keeps things moving, reach out to us if you need help finding that incredible VA who’ll help take your business to its next stage.