How to evaluate a virtual assistant company: 30 questions to ask

The questions to ask virtual assistant company reps on a discovery call fall into nine areas: employment model, phones, hours, security, management, pricing transparency, replacement, tools and references. Ask all 30 below in one call and you will know within 45 minutes whether the provider runs a managed desk or a marketplace with a logo on it.

Why 30 questions, and why in this order?

Every virtual assistant company sounds the same on its homepage: vetted, dedicated, experienced, affordable. The differences show up in the operating model, and the operating model only shows up when you ask specific questions and listen for specific answers. The order matters too. Employment model comes first because it decides the answers to almost everything else. Phones come second because most providers cannot do them and will say so only if asked directly. References come last because you want them to speak to the exact model you have just been quoted.

Print the list, score each area out of 5 as you go, and compare providers on the total. The scoring template is at the end.

Employment model

1. Are your assistants employees of your company, or independent contractors and freelancers? Listen for a plain answer. “Employed, on our payroll, in our office or on our managed devices” is one product. “Vetted independent professionals” is another, and it means you are the manager.
2. Where do they work from, and who provides and controls the equipment? A managed office or managed devices with monitoring is the standard for anything involving customer data.
3. Does the client have any employer obligations, and how do you avoid co-employment? The right answer is that the client never employs, pays or directs the assistant’s employment terms; the client directs the work.
4. What was your screening process for the assistant you would propose for me, and what share of applicants get through? Belay publishes a 3 percent acceptance rate, for instance; the number matters less than whether they can describe the steps: English assessment, typing and phone tests, background checks, reference checks.

Phones

5. Can the assistant answer inbound calls live, in my business name, during my hours? Many virtual assistant companies are typing-only. If phones are the job, this question ends the call early for half the market.
6. Can they make outbound calls, and how do you handle consent, calling hours and do-not-call lists? The answer must include lawful consent and do-not-call scrubbing, with TCPA in the US, PECR and the TPS in the UK, CASL and the National DNCL in Canada, and the Do Not Call Register in Australia.
7. Which telephony do you use, are calls recorded, and can I hear a sample call now? A phone-capable provider has RingCentral, Dialpad, Aircall or similar, per-client numbers, recording notices per market, and a sample ready.
8. How do warm transfers, messages and voicemails reach me and my team? Look for a transfer path to a cell or Teams, plus messages logged to your CRM or inbox with a timestamp, not a daily email digest.

Hours

9. Which exact hours will my assistant be live, in my time zone, and which shift is that for them? If your 9am is their 2am, ask how the night shift is staffed and rotated.
10. What happens to calls and emails outside those hours, and can you cover after-hours, weekends or a second market? A staffed after-hours desk and a 24/7 option are different from a voicemail.
11. Whose public holidays do you observe? Yours, theirs or both. Get it in writing.

Security

12. What background checks, NDAs and device controls apply to the assistant working on my account? Expect a background check, an NDA per client, MFA, managed devices with no local storage and monitored access.
13. How is access to my systems granted, limited and removed? Least-privilege access set up by you, revoked the day the engagement changes.
14. For healthcare, will you sign a BAA, and are the staff HIPAA-trained? The correct wording is HIPAA-trained staff and a BAA. Be wary of any provider that calls itself HIPAA certified, because there is no such certification.
15. How do you handle card numbers, passwords and recordings? Card data should stay inside your payment portal and never pass through the assistant; passwords in a shared vault; recordings stored with retention rules.

Management

16. Who manages my assistant day to day, and can I speak with that person today? A named team lead with a phone number is the answer. “Your account manager” who turns out to be a salesperson is not.
17. What does the daily report look like? Show me one from a real desk, anonymized. The end-of-day report is the product. It should show what was handled with timestamps, what is waiting on you and tomorrow’s plan.
18. How do you measure quality, and will I see the scores? Look for a monthly QA scorecard on calls and tickets, reviewed with you, not a satisfaction survey once a year.
19. How much of my time will this take in month one and in month three? Honest providers say month one is heavy, an hour a day for the first two weeks, and month three is a 20-minute weekly review.

Pricing transparency

20. What exactly is in the monthly figure, and what costs extra? Ask for an itemized quote: hours, backup, team lead, software seats, phone numbers, AI tools, onboarding. Third-party ranges give you a frame: managed remote assistants at $640 to $2,400 a month full time (Wishup, Cherry Assistant, Zedtreeo, VantaStaff, 2026), Boldly at $2,600 for 40 hours to $3,900 for 60 hours (Boldly pricing, 2026), and Prialto on a team model with a 90-day minimum (Prialto, 2026).
21. How are hours tracked, and what happens to unused or extra hours? Rollover, expiry or true-up, and who can see the log.
22. What are the contract length, notice period and price-change terms? In writing, before the proposal.

Replacement

23. What happens on the day my assistant is sick or on leave? A named, briefed backup who already knows your account is the standard on a managed desk. “We will find someone” is a marketplace answer.
24. If it is not working out, how is a replacement handled, and how long does it take? Ask for the process, not a promise: who decides, how the new person is briefed, whether the SOPs and history come with them.
25. How do you keep my knowledge when the person changes? Written SOPs in a shared workspace, recorded training, the team lead’s oversight. Published estimates put the cost of freelance VA turnover at 2 to 3 months of salary in lost productivity (Zedtreeo, Catalyst and Nacho, 2026), which is what a replacement process is protecting you from.

Tools

26. Which of my tools has the proposed assistant used before, and can I see them work in one? Name your stack: HubSpot, Zendesk, ServiceTitan, Clio, Dentrix, Shopify, Asana, whatever it is. A shared-screen test beats a logo wall.
27. Who pays for software seats, phone numbers and AI tools, and do you train on new ones? Clarity here stops the first invoice surprise.

References

28. Can I speak with two current clients in my industry or on the same desk type? Two is enough. Ask them what happened the last time the assistant was away.
29. How long have your longest clients been with you, and what is your average client tenure? Retention is the one number a provider cannot dress up.
30. What kind of client do you turn away? A confident provider names them: businesses that want a bot, businesses that need a licensed professional, businesses in industries they do not serve. A provider that turns nobody away has no operating model.

Red flags and good answers at a glance

Scoring template

Copy this into a document before the call. Score each area 1 to 5 and note the answer that earned it.

Multiply score by weight and add it up. A provider that scores 4 or 5 on management and replacement at a higher rate will usually cost less over a year than one that scores 2 at a lower rate, because you are paying the difference in your own time. Marketplace hires at around the Upwork median of $13 an hour (Upwork, 2026) score well on price and poorly on nearly every other row; that is the trade you are making, and it is a fair one for one-off tasks.

How AssistBPO answers these

For the record, and so you can hold us to it on the call: assistants are employees of the group, screened with English, typing and phone assessments and background checks, working on managed devices under an NDA per client. Every dedicated engagement is a named assistant, a trained backup and a team lead who reports to you, with a start-of-day check-in, an end-of-day report and a monthly QA scorecard. Phones are the core of the business, not an add-on. Healthcare desks run with HIPAA-trained staff and a BAA. Outbound work runs with lawful consent and do-not-call scrubbing. Plans depend on hours, desks and coverage. Get a staffing plan within 1 business day.