Questions to ask a VA before the first handover

You've hired someone to manage your diary and inbox, and the first handover call is this afternoon. You've done your vetting, they've got references, but now you need to confirm they'll actually work the way you need them to. The questions you ask in the next hour will either set the tone for a smooth handoff or expose gaps that'll cost you time later.

The technical and access questions

Start by asking how they'll access your systems. Will they log in through a separate account you create for them, or use shared credentials? A good VA should insist on their own login—it's cleaner for security and creates an audit trail. If they say "just share your password," that's a red flag. They should also walk you through which apps they'll need access to: email, calendar, any booking or CRM software you use, document storage. Ask them to name these specifically rather than giving vague assurances. You want to hear "I'll need read and write access to your Gmail and Google Calendar, and read-only access to your Asana board so I can see task deadlines."

Then ask how they'll handle sensitive information. Your inbox will contain client details, financial correspondence, personal matters. Do they have a privacy policy? Do they work from a secure location, use a VPN, keep client information encrypted? Don't accept a hesitant answer here. A professional VA should have clear, honest practices they can articulate.

Ask about their backup and contingency plan. What happens if they're ill or their internet fails during a critical week? Do they have cover, or will your calendar go unmanaged? You're not being paranoid—you're checking they've thought through reliability.

How they'll actually work with your calendar and inbox

Now get specific about their process. Ask: "Walk me through what you'll do the first time you see my inbox." A vague answer like "I'll organise it" is unhelpful. You want to hear something like "I'll scan through unread emails, flag any that need your immediate response, sort the rest into folders based on sender or topic, then give you a daily summary." This shows they think in systems.

Ask how they'll handle urgent emails. Will they alert you immediately, or batch alerts? What counts as urgent in your world—client requests, invoices, feedback from your boss? You need to define this together, not hope they guess right. A good VA will ask clarifying questions back.

For your diary, ask how they'll decide what gets scheduled where. Will they create a buffer between meetings, or pack them tight? Do they know about your team's standups or any patterns you want protected? Will they confirm meeting times with attendees before putting them on your calendar? A VA who says "I'll check your preferences" rather than "I'll just fill the gaps" understands that diary management is about protecting your working day, not just filling slots.

Ask how they'll keep you in the loop. Will they send a daily summary, weekly, or only flag decisions they're unsure about? You want something manageable—daily email can become noise; monthly is too infrequent. Many VAs use a shared document or brief Slack message; find what suits you.

Then ask about their own working hours and response time. If you're in South Africa and they're elsewhere, when will they actually be working? If you fire off an 8 a.m. email, when will they see it? If something urgent lands at 4 p.m. your time, are they still online? This prevents frustration later.

Finally, ask them what they'll need from you on day one. The best VAs will request a walk-through of your filing system, a list of your key contacts and how they prefer to be reached, and your calendar preferences written out. If they don't ask, offer it anyway—it sets them up to work intelligently from the start.

A good handover doesn't mean they agree with everything you say; it means they ask the right questions back and explain their thinking. When you find someone on Strove who listens more than they talk, that's often your sign.