What Type Of Executive Assistant Should You Hire? (FAQ + Questions To Ask Agencies)

If you’re looking to hire an executive assistant but you’re not sure what you need to know and where to go looking for the best assistant for your unique needs, this article is for you.

I’ve been working with virtual assistants for over 25 years. They’ve helped me to build and launch courses, onboard and support my coaching clients and sell my products and services.

In the last ten years my main job has been co-founder and CMO of InboxDone.com/50hrs.com, an agency that places executive assistants with busy founders and leaders. In this role I have conducted the majority of sales calls, which means I have hundreds of hours listening to people explain what they want from an assistant.

These experiences place me in a unique position to know both what it’s like to work with and succeed with a virtual assistant (and fail many times too!) and also know what hundreds of other people want from executive assistants.

Hiring an executive assistant isn’t one decision. There are many variables, including location, structure, budget, skill level, trust and security — and what you value most is based very much on your unique situation.

Below I have outlined a series of questions you should ask yourself, along with a list of sources (the most appropriate agencies) to hire an assistant if that question is important to you.

I also include a question you should ask when speaking to the agency or during the hiring process. These questions focus on elements you might not think to ask about before working with an agency, but can surface criteria that makes your decision making process much easier.

1. Should you hire onshore or overseas?

This is the fork everything else branches from. Overseas assistants (Philippines, India, Latin America, South Africa) cost a fraction of onshore rates and can be excellent for structured, repeatable admin work. Onshore assistants (US/Canada) cost more but bring closer cultural fluency, easier real-time overlap, and are typically trusted with more judgment-heavy, client-facing, or financial work sooner.

Neither is “better,” it’s a tradeoff between cost and how much independent judgment you need the role to carry.

Best sources depending on your answer:

Ask this: What percentage of your current assistants are still with the company after 12 months?

2. Is American onshore important to you?

If you want US-based, English-first, high-context support, there are several good options. An American assistant shares your business culture, your idioms, your sense of urgency, and your working hours without translation or time-zone gymnastics. They can write client-facing emails that sound like they came from you, and pick up on the unspoken context, tone, and priorities that offshore assistants often need far more explicit instruction to catch. For anything client-facing, judgment-heavy, or reputation-sensitive, that context saves you the ongoing correction and re-explaining that eats into the savings of a cheaper option.

The tradeoff is cost, American assistants run several times the hourly rate of offshore talent, and the market is crowded enough that quality and support vary widely between providers. Offshore and Latin American options can absolutely handle structured, repeatable work at a fraction of the price, but you generally give up some of that instant cultural and contextual fit, and you take on more of the training and oversight yourself to get the same result.

Best sources:

Ask this: Are your assistants W-2 employees or 1099 contractors? (This affects consistency, training investment, and how much oversight they get.)

3. Is a Canadian executive assistant a priority?

If you specifically want a Canadian assistant, either for time zone overlap, cultural fit, or just a preference to support Canadian workers, your options narrow fast. Most of the well-known premium agencies are US-based even when they serve Canadian clients.

Best sources for Canadian talent:

1. InboxDone — Vancouver-founded, North American team including Canadians
2. 50hrs — same company/team as InboxDone, broader scope
3. Virtual Gurus — originally a Calgary-founded company built around Canadian talent, though worth noting they were acquired by Zirtual (a US company) in late 2025, so confirm how much of their current team and management is still Canadian-based before assuming that’s still their model

Ask this: Is the company Canadian registered with Canadian assistants, or American owned, but with some Canadian workers?

4. Which overseas region should you choose?

Philippines is the most mature offshore VA market, strong English proficiency, large talent pool, good overlap with US evening working hours.

Latin America has better real-time overlap with US business hours, growing talent pool, generally a bit pricier than Philippines/India.

South Africa is similar cost range to Latin America, strong English fluency and Western cultural alignment, with a smaller but growing VA talent pool.

India/Pakistan has strong technical and data skills, larger time zone gap with North America, and like Eastern Europe, tends to skew more toward engineers and technical talent than general admin/EA work.

Eastern Europe, like India, leans more toward technical and engineering talent rather than general executive assistant work, at a higher price point than the other regions above.

Best sources:

1. Athena — sources talent primarily from the Philippines, full-time model
2. Wishup — sources primarily from the Philippines and India, flexible plans, fast placement
3. Stealth Agents — sources from the Philippines, lower cost, full-time dedicated model
4. Virtual Latinos — sources from Mexico, Colombia, Argentina, and other Latin American countries, bilingual, US time-zone overlap
5. RecruitMyMom — sources from South Africa, strong English fluency and Western cultural alignment

Ask this: What time zone will my specific assistant actually be working in, not just where the company is headquartered?

5. What’s your budget?

Roughly speaking:

• $5 – $15/hour for offshore contractors
• $500 – $3,000/month for managed offshore services
• $2,000 – $5,000+/month for premium onshore agencies
• $1,600 – $2,500/month if you go the direct full-time hire route in the Philippines or similar.
• Direct in-house hiring onshore runs $47,000 – $90,000+/year in salary before benefits.

The cheaper the assistant, the more structure and management you need to bring yourself. Premium pricing buys you less oversight on your end and an assistant you can delegate more to, giving them full responsibility to take on complete workflows.

Best sources by budget tier:

1. Under $1,000/month: Wishup, Time Etc, Stealth Agents
2. $1,500 – $3,000/month: InboxDone, 50hrs, Prialto
3. $3,000+/month: Athena, Boldly, Belay (higher tiers)

Ask this: What’s included in this price, and what counts as an “overage” I’ll be billed extra for?

6. Do you need basic admin, or advanced judgment-based support?

Basic tasks: data entry, labeling emails, simple scheduling, booking flights, light research. These require accuracy and reliability, not judgment.

Advanced tasks: replying to emails in your voice, filtering meeting requests based on context, managing CRM and invoicing workflows, client-facing communication, and understanding what to escalate versus handle independently. This is the difference between someone who completes tasks and someone who owns outcomes.

Best sources:

1. Basic admin: Wishup, Fancy Hands, Stealth Agents
2. Advanced/judgment-based: 50hrs, Prialto, Boldly

Ask this: Can you walk me through an example of a judgment call your assistant made for a client without asking first?

7. Is email management specifically your biggest problem?

If your core pain is an overflowing inbox and all the tasks and responsibilities that are triggered by email, you want a specialist who can move beyond just triage and labeling emails. You need assistants who bring a system to take responsibility for replying to your emails for you and the workflows that emails trigger like scheduling, client success, onboarding, lead nurturing, invoicing and more.

Best source: InboxDone. This is literally what the company was built to do since it was founded in 2017, specialized email and calendar management, not a side feature of a broader admin role.

Ask this: Do I have to teach the assistants how to handle email or do you have an established system you bring to me to take over my inbox and reply to my emails for me?

8. What are your time zone and phone/call needs?

If you need live phone support or heavy real-time overlap, overseas time zone gaps become a real constraint, especially with Philippines or India-based teams. If your work is mostly asynchronous (email, calendar, data tasks), time zone matters far less.

Best sources:

1. North American timezone: InboxDone, 50hrs, Belay
2. Overseas timezone: Wishup, Stealth Agents, Magic
3. Phone call specific support: ReceptionHQ

Ask this: What timezone are the assistants working in and when can I expect replies from them?

9. How important is security and privacy?

If your assistant will touch financial data, student data, client information, or sensitive systems, security training and protocols aren’t optional. It matters even more if you’re in a regulated field, healthcare, legal, financial services, sciences, education, where an assistant might be exposed to private records or other protected information.

If relevant to your business, ask specifically whether the agency and its assistants are trained on HIPAA compliance, not just general confidentiality, since the requirements and penalties around health information are far stricter than standard business data.

Understanding how passwords are managed, device security and data is transmitted, are all important questions to ask. Whether there is a documented cybersecurity policy along with cybersecurity insurance and professional liability (errors and omissions) insurance should be clarified. NDAs are typically in place when you sign up with an agency, but you should ask to see them, especially if hiring a contractor directly, or if necessary bring your own tailored NDA and have the assistant review it and sign before work begins.

Best sources:

1. Established agencies like 50hrs, Prialto, Boldly and Belay should have the appropriate protections in place, but always ask before signing up.
2. If you are hiring through a platform like Upwork, Indeed, or LinkedIn, take the lead when it comes to security and privacy, don’t assume your assistant will come prepared.

Ask this: Do you have a signed NDA, a documented cybersecurity policy, and insurance coverage?

10. How do you protect against assistants quitting/disappearing?

You hire, train, and invest months into an assistant, then they leave, and you’re back to square one. Sadly it is a very common situation, especially with low cost offshore assistants.

At one stage I completely stopped hiring from the Philippines because I was tired of them not completing tasks, claiming reasons like trees falling on the roof, family members dying, or simply ghosting me completely. I understand sometimes these things happen, but for me it happens far more often with Fillippino workers (they do have big weather events there!).

Generally speaking, the more premium the service, the better the assistants are paid, the more qualified they are, the longer they stay working for a company — and working for you!

Some agencies have specific policies in place to help mitigate the impact of assistants leaving, even if it’s just expected short term leave for holidays, health reasons or family emergencies. For example, 50hrs.com places two assistants who learn how to support you so if one is off, the other is there. You are never left alone to do the work yourself.

Best sources:

1. InboxDone and 50hrs — both include two assistants from day one specifically for this reason
2. Prialto — team-based model with shared account knowledge
3. Any agency with a documented backup/replacement process

Ask this: What’s your average client tenure, and what happens to my account the day an assistant leaves?

11. Direct hire, agency, placement service, or Upwork?

Direct hire means you own the entire recruiting, training, and management process. Choose this if you have the time to run interviews, test candidates, and build your own onboarding, and you want full control over who joins your team and how they’re paid, in exchange for the lowest ongoing per hour cost and the most effort. Be prepared to experience more problems, mistakes to fix, and more monitoring of your assistant.

A placement service finds and places someone, then steps away, you’re on your own after that. This makes sense if you want help sourcing a candidate but you’re comfortable managing, training, and replacing them yourself afterward. It typically costs less month to month than a managed agency, but you carry all the risk if that person underperforms or leaves.

A managed agency stays involved for the life of the relationship, handling replacements, backups, and ongoing quality. This is the right choice if you’d rather pay a premium to have someone else own the hiring, vetting, training, and turnover risk entirely, so you can start delegating on day one instead of spending weeks recruiting and managing HR issues yourself.

Upwork and similar platforms put you in the recruiting and vetting seat yourself, with lower cost but higher risk and time investment. This suits business owners who are comfortable screening contractors, don’t mind higher turnover, and want the cheapest possible hourly rate without committing to a full time person.

Best sources depending on your answer:

Ask this: If my assistant leaves for a family emergency, what happens next? 

12. Full-time, part-time, or fractional?

Full-time typically gets you the lowest effective hourly rate, but only pays off if you consistently have 30-40+ hours of real work to hand over each week. The risk is paying for a full-time person and then scrambling to find enough for them to do, which is expensive busywork disguised as delegation.

Part-time works the same way as full-time, just at roughly half the hours, a fixed weekly commitment, but it may be a higher hourly rate than full-time, but still a set block you’re paying for whether you fully use it or not.

Fractional is the most flexible: you pay a higher hourly rate in exchange for the ability to expand or contract your hours as your workload changes, month to month, without renegotiating a contract or re-hiring. This suits businesses with workloads that genuinely fluctuate, or anyone not yet sure how many hours they’ll actually need.

There’s also a structural question underneath all of this: is the assistant an employee of the agency (with payroll, benefits, and taxes handled by that agency and baked into your rate), or a 1099 contractor you or the agency engages more loosely? Employee-based models tend to mean better retention and more consistent quality, since the agency has skin in the game to keep that person happy and trained, but that overhead is part of why the rate is higher.

Some services, including 50hrs, are built to move with you across this whole spectrum, starting fractional with just a few hours a month, then scaling up to full-time, and beyond that to covering multiple people on your team, providing as many executive assistants as you need, all within the same relationship. In these models the effective hourly rate typically drops as your total hours increase, so growing your usage over time can end up cheaper per hour than staying small and fractional indefinitely.

Best sources:

1. Fractional/flexible: 50hrs, Time Etc, InboxDone
2. Full-time dedicated: Athena, MyOutDesk, Stealth Agents

Ask this: Can I change or cancel my plan month to month, or am I locked into a fixed commitment?

13. Are you hiring for yourself, your leadership team, or your whole company?

One assistant for one executive is the simplest case. Shared support across a leadership team requires a service built for pooled hours across multiple people. Company-wide admin support (multiple departments, various task types) needs multiple assistants with a management team behind the scenes.

Best sources:

All agencies like 50hrs, Belay, and Zirtual, can scale up with you offering support for one person all the way up to your entire company.

Ask this: How do you handle prioritization when multiple people on my team are asking my assistant for help at once?