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Virtual Assistants: Hype or Help?
As chamber CEOs juggle busy schedules and increasing demands for their attention, virtual assistants (VAs) can help reclaim time and restore work-life balance.
But how well do they work in practice, and are they the right fit for chamber leaders?
Two chamber CEOs shared their experiences with VAs and provided insight into the challenges and benefits of delegating tasks virtually.
What is a Virtual Assistant?
With the rise of remote and hybrid work, VAs offer a cost-effective way for busy executives to manage daily tasks. They come in two forms:
• Human: Remote professionals who handle email, scheduling and project support from home offices worldwide.
• AI-powered: Tools like Siri, Alexa and ChatGPT that automate tasks, answer questions and streamline communication.
Taking the First Step Into Virtual Support
When Matt Morrow, president and CEO of the Springfield Area Chamber of Commerce (Mo.), lost his longtime executive assistant to retirement two years ago, he considered his options. One idea that caught his attention was hiring a virtual assistant.
With his board’s support, Morrow researched several firms and chose one that assigned him two English-speaking VAs: one lives in Costa Rica and the other in Austria. He finds that having two VAs is extremely helpful because the work is never interrupted, even when someone’s on vacation.
He admitted, however, that after working alongside his previous assistant for years, trusting someone new to manage his inbox and respond on his behalf, especially someone he would never meet in person, felt like a big leap.
“I liken it to rappelling,” said Morrow. “You're okay once you get going, but it's a little hard to lean back and let go on that first step.”
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In Texas, Becki Womble, CCE, IOM, president and CEO of the Bastrop Chamber of Commerce, was overwhelmed by emails and scheduling demands. Without an executive assistant, she knew she needed support.
“A former board member, who was using a virtual assistant himself, shared how it had transformed his workflow and overall productivity. I figured if it worked that well for him, it was worth giving it a try,” she said.
She used the company he recommended and was paired with an English-speaking VA based in the Philippines.
Like Morrow, Womble was apprehensive, but she had high hopes for how a VA could help, especially after reading “Buy Back Your Time” by Dan Martell.
“The idea of giving someone access to my inbox and allowing them to communicate on my behalf was intimidating,” remarked Womble. “However, I recognized that for the sake of my sanity and maintaining a healthy work-life balance, I needed to take that step.”
Intensive Onboarding
For both Morrow and Womble, working with a VA began with intensive training.
“You spend a lot of time on the front end really engaging, coaching, instructing and helping to understand things,” explained Morrow.
For about a month, he communicated with his VAs multiple times a day as they studied his inbox, reviewed past correspondence, asked how he preferred certain situations handled and drafted responses for his approval. Once they built a strong knowledge base, the workflow became smooth.
In Womble’s case, training was ongoing. “In the chamber industry, no two days are the same, and priorities shift constantly,” she said. To stay aligned, she and her VA set specific working hours—8 to 10 a.m. CST, about 10 hours a week—to manage her inbox and schedule. This ensured there was overlap with the chamber’s business day.
“We used Microsoft Teams for daily communication and collaboration so that other staff could stay in the workflow as well,” she explained. “We also included her in staff meetings via Teams or Zoom to keep everyone connected and aligned.”
Womble made it a point to set expectations early, provide context for each task and check in regularly. “It’s also important to extend grace and patience as both sides learn how to work together effectively,” Womble added.
Two Experiences
Though Morrow and Womble embraced virtual support, each had very different experiences. Where Morrow found success, Womble encountered challenges.
“My goal was for the VA’s role to expand into additional tasks over time, but unfortunately, the arrangement only lasted about three months,” said Womble.
At first, the VA was very responsive and helped to lighten her load. Over time, though, she began working beyond the agreed-upon hours and requested additional compensation for those extra hours. Ultimately, some situations crossed professional boundaries, which led Womble to end the arrangement.
Despite the disappointing outcome, she still sees the benefits of a VA, so leaders can then focus on higher-level priorities. “For leaders with dynamic schedules, a VA can provide flexible, focused support in a way that is both efficient and economical,” she said.
In Missouri, Morrow continues to work with the same two VAs he started with nearly two years ago.
While the VAs have taken on a few additional tasks to save Morrow time, like helping with his expense reports, their primary responsibilities remain managing his inbox and calendar, handling appointment setting and juggling scheduling tasks.
“They organize and sort my messages, tagging them in the inbox by category, such as what requires my action, what’s a scheduling item or what’s an FYI. They check in with me several times a day with updates and send written summaries via group text.”
When it comes to confidentiality, Morrow noted that everybody is under a non-disclosure agreement (NDA). “They have a standard NDA that they sign for anything they would come across, and they're also willing to sign any specific NDAs that we have.”
Morrow stands by his decision to go with a VA. “By and large, it's working out as I had hoped, and in some ways, it's working out better than I expected. In other ways, there are things we're just doing differently,” said Morrow.
The Final Verdict
Even though the arrangement didn’t work out for Womble, she still believes in the value of VAs and encourages others to give it a try. “You’ve got nothing to lose and potentially a lot of time to gain.” Morrow agrees, “It may not be for everyone, but sometimes you don't know until you try.”
Advice to Keep in Mind
- Set realistic expectations. According to Morrow, “You're not exactly doing an apples-for-apples replacement.” VAs can manage many tasks efficiently, but they won’t have the same day-to-day familiarity, so leaders must determine which duties fit the role and which require other solutions.
- Onboarding is crucial. Devoting time and actively participating in this step lays the groundwork for success, establishing clear expectations, communication routines and the context a VA needs to work independently and effectively.
- Weigh cost and time benefits. Both agree that hiring a VA can be significantly more cost-effective than an in-house employee. “You typically pay only for the hours worked, without added expenses of benefits, office space and equipment,” explained Womble. Morrow added a time perspective. “If you have enough for a part-time employee, try this. You’ll likely find that you're working with people who do this kind of work all the time, and you don’t have to train them to be an administrative or executive assistant.”
- Trust the process. In Womble’s opinion, the biggest adjustment for leaders delegating is learning to let go of control and trusting the process. “When you can’t see someone working right down the hall, you have to shift your mindset from managing activity to managing outcomes. That requires confidence in your systems, your communication and ultimately, your team.”
- Anticipate challenges. Time zones, communication and accountability can be challenges when working virtually. Set clear expectations and norms upfront so everyone knows how tasks, responses and accountability will be handled. Address issues early.
- Safeguard IT security. Keep your IT team in the loop. It was a bit alarming for Morrow’s IT firm when they saw a login as him from Costa Rica. Once the IP address was confirmed as safe, the issue was resolved.
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