Not every virtual secretary will make your life easier.
Some will need constant instructions. Some won’t speak up when things go wrong. Others will complete the task—but leave you wondering if it was even worth delegating.
A great virtual secretary doesn’t just take work off your plate—they think ahead, spot gaps, and make your day run smoother without you having to ask.
This article breaks down the key traits that separate average from excellent—so you can hire support that actually supports you.
1. Communicates Clearly Without Needing Hand-Holding
A great virtual secretary doesn’t disappear between tasks. You won’t need to chase them for updates. At the same time, they won’t bug you with every little decision.
They strike the balance: proactive, communicative, and independent.
What this looks like:
- Checking in when something’s delayed
- Confirming task updates without waiting to be asked
- Flagging potential issues early (“Just a heads up—this calendar invite bounced”)
- Updating your task board or weekly summary consistently
You should never be left wondering what’s been done or what’s next.
2. Has Strong Written Communication (Not Just Basic English)
They don’t need to be a copywriter. But your virtual secretary must be able to:
- Draft clean, clear, professional emails
- Write follow-ups that sound like you
- Create task summaries that make sense
- Ask direct questions when instructions are unclear
If you’re spending too much time rewriting their drafts or explaining things twice, the support becomes a time drain.
When reviewing applicants or trial tasks, pay attention to:
- Grammar and tone
- Message structure
- Their ability to summarise long instructions into key points
👉 Red flag: Long, vague messages that don’t get to the point. You’ll waste hours reading and replying.
3. Spots Problems and Solves Them Before You Ask
The best virtual secretaries don’t just follow instructions. They start noticing patterns.
- “I’ve noticed you reschedule this meeting every week—should I block this time going forward?”
- “Client A usually replies late. Do you want me to follow up sooner?”
- “This report is always due Friday. Want me to automate the reminders?”
They’re not just completing tasks—they’re thinking like someone who cares about how your business runs.
👉 Why this matters: Admin isn’t about doing more—it’s about making everything else easier. A secretary who thinks this way adds long-term value.
4. Knows How to Use the Tools You Already Rely On
They don’t need to be an expert in every app—but they should be comfortable with the basics of:
- Google Workspace (Docs, Calendar, Drive, Gmail)
- Project boards (Notion, Trello, ClickUp)
- Scheduling tools (Calendly, Google Meet, Zoom)
- CRM platforms (even if just updating info)
- Slack or WhatsApp for communication
- Password managers (LastPass, 1Password)
They should also be confident learning new tools on their own.
If they’re overwhelmed by tools you already use, that slows everything down. Some virtual assistants come with a generalist background, while others—like those assigned through Outpost—are already trained across popular platforms.
👉 Tip: During onboarding, ask what tools they’ve used before—and how they learn new ones.
5. Makes Smart Decisions Without Constant Supervision
You won’t always have time to explain every nuance of a task. So your virtual secretary needs good instincts.
Can they:
- Make the call to wait vs. follow up?
- Spot when something looks off (like a missing attachment)?
- Choose the right tone in an email without needing a full script?
- Know when it’s okay to make the decision—and when to escalate?
Judgment can’t be taught quickly, but it can be screened. Ask about past situations where they had to make a call without full instructions. Look for signs that they stayed calm, professional, and solution-focused.
👉 Hint: Judgment isn’t about being perfect. It’s about pausing when they should, and moving when it makes sense.
6. Handles Private Information with Care and Common Sense
Your virtual secretary might have access to your inbox, calendar, documents, and even your clients. That’s not something you hand over lightly.
Look for signs of professionalism early:
- Do they respect confidentiality and data access boundaries?
- Are they comfortable using NDAs or password managers?
- Do they ask before accessing or editing things that matter?
- Can they keep client information private—even within your team?
If you’re using a service like Outpost, assistants are usually pre-vetted and supported by confidentiality protocols. But even then, it’s worth discussing access limits, approvals, and how you expect data to be handled.
👉 Bottom line: A great secretary builds trust by how they work—not just by what they say.
7. Reliable, Not Just Once—but Every Week
You don’t need someone who works lightning-fast. You need someone who works predictably, accurately, and shows up the same way every time.
- Replies by a certain time
- Updates the task board daily or weekly
- Follows the same process unless told otherwise
- Doesn’t go silent or disappear during key projects
You want someone you can count on—not someone who’s brilliant once and chaotic the rest of the time.
👉 Final screen: Give a simple test task. Check not just the result—but how they delivered it. Was it structured? On time? Did they explain their choices?
Conclusion
A great virtual secretary isn’t just someone who does what you ask. It’s someone who understands how you work, takes ownership of the tasks you shouldn’t be doing, and quietly keeps things moving behind the scenes.
When you’re hiring, don’t just focus on experience or hourly rates. Look for the traits that actually make a difference day to day. Remember, great support doesn’t need managing. It just needs choosing wisely.
About the Author: Julienne Merza
