A Practical Guide for Hiring a Virtual Assistant

A practical guide for hiring a virtual assistant
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It took me over a year to get used to it. For months after starting my own business, I struggled to break out of the routine of corporate work hours and doing everything myself. Hiring a virtual assistant changed everything for me and my business. This practical guide will give you the exact steps I followed for hiring my virtual assistants. As a result, this is what my remote team looks like now.

Remote work is the new normal. According to a 2019 study from the Bureau of Labor Statistics, only 7% of workers in the United States, or roughly 9.8 million people, have access to a “flexible workplace” benefit.
This is clearly going to change in the wake of COVID-19, with non-essential companies being required to send entire workforces to work from home.

With this shift in how work gets done will come a shift in who does the work. If your executive assistant is going to work remotely, why can’t they be based anywhere in the world? Customer support, call center and data capture work is already outsourced offshore in a big way by big corporates, but as traditional companies get used to remote teams, why can’t more work be completed in the same way? Work can be parceled into tasks to be completed by specialists paid by the hour.

Of course, business owners like myself have been doing this for years now. With large traditional corporates joining the fray, the trend over the last 19 years as seen below is sure to continue.

The global market for outsourced work has been growing for the past 19 years
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Table of contents

  1. Why should you hire a virtual assistant?
  2. Why the Philippines?
  3. When should you hire a virtual assistant?
  4. My exact steps for hiring virtual assistants in the Philippines.
  5. Tips for successfully working with a virtual assistant.
  6. Ideas for what to outsource to your new virtual assistant.

There are a number of benefits to hiring a virtual assistant. Let’s look at these before diving into how to go about it.

Why should you hire a virtual assistant?

Get things done

Learning to delegate is a core skill for any manager or business owner. We all know intuitively that if we can successfully delegate the tasks on our plate we can increase our output by orders of magnitude. What holds many people back, and perhaps this is true for you, is they don’t know where to start. Freelance marketplaces abound, but the quality of work varies widely. This practical guide for hiring a virtual assistant will give you the exact steps to follow to find the right person for your business.

Get access to global talent and specialization

There is no limit on where someone can be based. Not only is this a perk for digital nomads with unique skills, but it opens up the global market of talent. You can now find people who specialize in everything from writing blog posts, to designing images for them, to promoting posts on social media. These can be three different people, all paid by the hour, all working towards the single goal you set for them.

And what’s more, you’re no longer confined to the working/waking hours of your timezone. The globally remote team I have assembled allows me to produce content for clients around the clock. I can set required tasks at the end of my day, and wake up the next to a completed set of work to share with clients.

Place a premium on the value of your own time

Your time has never been more valuable than it is now. You likely have to juggle family life and work-life if you’re working from home. Even if you’re not, you could be covering for colleagues or serving clients while short-staffed. Your ability to execute on the most important projects in your life right now is paramount. Spend some time thinking about the routine tasks you can outsource (see the end of this article for ideas) to free yourself up for these projects as soon as you can.

Give yourself space for ideas

One of the first things to go out the window when we are overwhelmed with tasks is the space to think. You need that right now. In his book, Deep Work, the author Cal Newport distinguishes between deep work and shallow work.

Deep Work: Professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.
Shallow Work: Non-cognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend not to create much new value in the world and are easy to replicate.

Get enough off your plate to be able to block out chunks of time, or entire days if possible, to do your best deep work.

Give yourself space for life!

Most importantly, give yourself time for life. Time for family. Time for nature. Time to connect with friends. Time for hobbies. Time for learning. Time to binge your favorite show. We all need this right now.

Why the Philippines?

You can get a virtual assistant anywhere in the world, including in your own country. But I have found that the Philippines is ideal for the needs of my business, for 3 main reasons.

  1. The English (spoken and written) is world-class.
    English is taught in schools as one of the two official languages of the country, making almost all educated Filipinos fluent.
  2. The culture is hard-working and online savvy.
    Working online for companies in the West is commonplace. And purely anecdotally, from conversations with my friend’s Filipino wife and experience working with Filipinos, I have found a culture of hard work similar to the culture we have where I am from, in South Africa. We are the underdog and feel we need to prove ourselves. We also need to provide for our families. These traits we share with Filipinos too.
  3. The exchange rate makes for favorable labor rates for US/European companies.
    As a developing country, the cost of living is relatively low compared to the US and Europe. 2018 data shows the Philippines as being 56% cheaper to live in that the United States. A USD or GBP or EUR salary goes a long way.

When should you hire a virtual assistant?

It may not seem obvious at first when to hire a virtual assistant. It might feel like you have things under control, or you couldn’t possibly explain to someone else how to do the thing you need to do. But as we’ve seen, the benefits to doing it are immense. Here are signs to look out for to know when is a good time to hire a virtual assistant:

  1. When you feel overwhelmed by your current workload.
  2. When you’re doing the same thing over and over again, and you know the process inside-out.
  3. When your need is more one-off project-based and a full-time employee doesn’t make sense.
  4. When you know you need to challenge yourself.

Paying someone can be a daunting thought, but it acts as a forcing function, pushing you to maximize your new-found free time and make the investment in your virtual assistant worth it.
Now that we’ve looked at the benefits of hiring a virtual assistant and how to identify the right time for it, let’s look at how to go about it.

My exact steps for hiring virtual assistants in the Philippines.

Document your processes

Begin by taking notes of the process you’d like to outsource. Write down each step, include screenshots when applicable, and add nuanced insight into how you prefer these tasks completed. This will help you identify which skills and experience are absolutely necessary to include in the next part of the process

Finding your virtual assistant

The two most popular freelancer websites are the gorilla-in-the-room Upwork (formerly eLance) and Fiverr. I’ve had great success and regularly use both. But the site I used to a virtual assistant from the Philippines is OnlineJobs. You have to pay to use it, but trust me, the amount of time you’ll save thanks to their identification and vetting process is definitely worth it.

The hiring process

Job description
First up, craft a detailed job description outlining what the applicant can expect from the position. Make sure you cover things like:

  • who you are
  • who you are looking for (including specific attributes so people know what they will be measured on)
  • what the job entails
  • what the interview process will look like
  • work arrangements including location, hours and timezones
  • salary range
  • how to apply

Here is the post we used on OnlineJobs.

Detailed job description
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Note that you can filter by ID Proof score. This measures the relative level of proof of identification. I set this to the highest minimum of 70 to ensure we only received legitimate applications.

In retrospect, I might have added more details about what the job entails, but we didn’t really have specifics at the time. Turns out this wasn’t too important as we still received excellent applications.

Screening test
Note at the bottom of the job description that we asked for applications by email. Some applicants submitted through the platform but we didn’t look at any of these. We were looking for people with attention to detail, and this was the first test.

Every applicant that emailed us received an automated response thanking them for their application which included a link to a communication skills test.

Screening test
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It contained multiple-choice questions like these requiring applicants to identify sentiment in messages.
Multiple choice questions testing ability to recognize sentiment
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This allowed us to quickly filter out candidates that were not able to do this accurately. We also included data entry tests which were also easy to filter out incorrect responses and a few long-form answer questions to gauge writing ability.

Easter Eggs
Finally, we included an easter egg – a line at the bottom of the job description asking applicants to “Include their favorite Steve Jobs quote” or something like that in their reply. This ensures you weed out assistants who haven’t actually read your email or are not detail-oriented. Can you spot ours?

Use easter eggs to test attention to detail
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We received 69 applications in 2 days! What the email submission, screening test, and easter egg allowed us to do was export a spreadsheet of 69 submissions, and filter out those that incorrectly answered right-or-wrong answers like the sentiment category question and the pink Cadillac question you saw above. We saved all the responses in Airtable and the result can be seen below.

Applicant responses
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Using this approach we were able to filter the 69 applications down to 7! We then only had to read 7 sets of long-form responses to get a better idea of communication skills.

Finally, we settled on 3 candidates to interview.

We used a 2-stage interview process, where a senior team member conducted the initial interview and made recommendations on who I should interview. I ended up interviewing all 3 anyway as they were so strong.

But I could have done better here. I didn’t prepare as well for the interviews as I did for the other steps and as a result ended up forming a gut impression of the candidates rather than an objective comparison of responses. This turned out to be fine for me, but your results may vary.

The key is to look for intangible qualities like how they manage shifting priorities, how they structure their work day and how they respond to stressful situations. If you’re looking to polish your interview skills, this is a good resource.

I called references for all 3 candidates. This is an important step, so don’t skip this.

In my interviews, I asked each candidate to rate themselves on a scale of 1-10 and give me what they saw as their strengths and, more importantly, improvement areas. Acknowledging that no one is perfect helped to ease their natural fears here.

I then told them that I would be asking their references the same question, and asked, would their references agree? This resulted in a slightly more nuanced version of the earlier response in all cases, which was helpful in itself.

But the real value came in the calls with references. These can be tricky as in most cases a candidate will pick a reference they’re friendly with who will give them a favorable review. But now, armed with improvement areas that the candidates themselves had identified, I was able to focus the discussion on these improvement areas to identify potential reasons to not hire them.

In my experience, a reference can happily list reasons why you should hire someone, most of which are subjective, but the real value comes in discussing reasons not to hire and how those have been addressed or can be mitigated.

Other good tips for reference checking:

  • tell the reference giver it’s a cross-check and ask them how you can make sure the candidate is successful when they join.
  • when someone gives you a reference and you’re unsure if they’re telling the whole truth, ask “if this were a negative reference, would you be comfortable giving one?”
  • message the reference saying, “I want to know if this person is one of the top ten people you’ve ever worked with. If so, would love to hear why. If not, no need to reply.”
  • ask if you were to hire this person in a pair, what would their pair look like? References will usually say something like “probably someone who is more detail-oriented or better at X”, which will tell you what your candidate’s weaknesses might be.
  • hypotheticals can be helpful,
    • e.g., “If you were to design the perfect job for , what would it be?”
    • another good question could be, “assuming I want this person to be at their best, what is the one way I could most help them?”
    • or “suppose we hire this candidate, they’re fired one year later, why?”

In the end, I had three extremely strong candidates. After the rigorous process I started to find one new hire, I was ready to hire all three! I ended up hiring two and I’m delighted to have them both on my team.

The training process

“Training is the highest leverage activity a manager can do to increase the output of an organization.” – Andy Grove

Arguably the most important step, you have to give your new hires time to learn your business.
One way I did this was to ask them to spend the first week researching my website, blog articles, competitor websites and industry publications.

For example, in researching my blog posts I asked them to come up with questions people may ask that the blog post would answer. This meta-cognitive process forces you to think critically about what you’re reading to uncover the purpose behind it. It showed me quickly whether or not they understood the piece, and had some nice little SEO side-benefits too. ? Here is what a typical report looked like:

Blog research report
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The other thing my team did was supervise tasks for the first few times to give live feedback. Scheduling regular one-on-one’s meant we had a regular time to go through tasks in detail to answer questions in the moment and iron out any misunderstandings. These supervision sessions were hugely valuable, with the extra time needed early on paying off big time once our new hires were up and running.

Do not skip this step. Do not even hire a virtual assistant if you are not prepared to spend the necessary time in this step. Trust me, the success or failure of your new hire is probably 90% down to the effort you apply here.

Have realistic expectations

Finally, it’s important to have realistic expectations. I learned this the hard way a few years ago when I first dipped my toe into hiring virtual assistants. I had this preconceived notion that I was hiring someone proficient in a certain set of skills, so surely they should be able to hit the ground running and do what they’re good at doing, right?

Remember, until recently this person knew as much about your company as you know about growing up in the Philippines or Bangladesh.

It can be overwhelming starting any new job – now imagine working for someone in another country that you only rarely see over video.

Give your new hire time to get to know your business, how you work, and most importantly, you. Your expectations and standards are going to be vastly different from anyone else they’ve worked with, so invest the time to get to know each other.

Another thing. You’re hiring a virtual assistant, not a full-time employee. Don’t expect them to care as much about your business as you do yourself. No one will. If you find someone who does, consider yourself extremely lucky!

And finally, don’t be afraid to cuts ties and move on quickly. Another lesson I learned is that persevering in the face of obvious signs of it not working only makes it worse. You’ll know if it feels right and you’re seeing the green shoots of a relationship of trust and respect develop. If not, move on. It’s in the best interests of you and the assistant you hired.


Make sure to have a contract in place if you are hiring directly. In other words, if you are hiring through a service like Upwork or Fiverr, they handle contracting, but if you use OnlineJobs as I did, then you’re going to want to put a contract in place.

You can find pretty good templates online. The main agreements you want to have in there are:

  • compensation and incentives
  • work hours and timekeeping
  • clarification that the business relationship is as an independent contractor
  • termination process
  • confidentiality
  • ownership of work and intellectual property
  • outline of services to be performed

Paying your virtual assistant

My assistants use TimeDoctor to track time. My biggest takeaway for time tracking is to set up your project and task hierarchy carefully. You want to be specific enough to not have time tracked as ‘general’, but not be too specific to the point of having 157 tasks to track. The Goldilocks point is where the tasks provide meaningful comparisons over time. Think more in terms of activities.

  1. What areas of your business is your new hire going to have a responsibility in? Set these as projects.
  2. What ongoing activities are they going to be performing in these areas? Set these as tasks.

For example, in the area ‘Grow Curious Lion Audience’, the activities (called tasks in TimeDoctor) are as follows:

Setting appropriate activities and related tasks makes tracking time easy
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For payment, there are many options. I use PayPal and Transferwise. Set a payment schedule and a mechanism for payment, such as having your new hire send you an invoice with hours worked. Keep it simple.

Tips for successfully working with a virtual assistant.

Communicate, communicate, communicate

Few things are as important when you first starting working with your virtual assistant as communication. No one can read minds so default to over-communicating things like deadlines, expectations, and how you want a task performed. There are two primary types of communication to keep in mind.

Video face-time
Regular one-on-ones are the best way to build rapport and trust with your virtual assistant. Seeing each other face-to-face raises the intimacy even higher. Use these video one-on-ones to discuss indicators that signal trouble, clarify goals and expectations and share praise for what they’ve done well.

“People who feel good about themselves produce good results” – Ken Blanchard, in the One Minute Manager.

Use these times to be open, honest and vulnerable with your assistant. If you want their best work, you need to create psychological safety for them.

Asynchronous messaging
As Basecamp put it so well in their Guide to Internal Communication, “Meetings are the last resort, not the first option.”.

I used to fill my day with team meetings (probably a carryover from my days at professional services firm KPMG), and they are, by far, the biggest drain on productivity. Balance regular one-on-ones with an intentional communication plan that emphasizes writing over chatting. The benefits are far-reaching from forcing people to reflect and articulate ideas better, to defaulting to having everything documented for future reference.

But I’m getting ahead of myself. This is not an article about communication, so refer to the Basecamp guide or this one from GitLab to learn more about asynchronous communication and how to practice it effectively.

Monitor performance

I found this an easy one to forget: check time records early on and assess the productivity you’re getting from your assistant. In the beginning, set aside a portion of your regular one-on-ones to discuss performance. Legendary Intel CEO Andy Grove advises us to “focus on vital, measurable indicators of output. Avoid measures of activity, subjective measures and unquantifiable measures.”

Some signs to look out for as you build trust:

  • your assistant adopts an attitude of proactively looking for ways to make your life easier.
  • your assistant is careful with company resources, for example not recording time when they feel like they’re not being productive.
  • your assistant asks insightful questions about your business that shows they’ve been thinking about how and why your business operates.
  • your assistant has suggestions for how to make internal processes more streamlined and effective.
  • your assistant has an opinion of their own on matters that are in line with your goals for them and your company.

Prioritize rapport

Perhaps the single best thing I did when I first hired my two assistants was set aside 30 mins each week to all get on a Zoom call and talk about anything other than work.

On a recent call, we discussed where each of us lives while looking at Google Maps. We talked about our home countries, exploring customs and cultures in a relaxed way, joking, learning, asking questions.

I really enjoy these calls and firmly believe they are critical in establishing a culture that defines how you work together. The more integrated your virtual assistant feels in your company, the more they’ll be invested in producing work that aligns with your values and goals.

Ideas for what to outsource to your new virtual assistant.

Hopefully, this post has inspired you to take the leap and hire your first virtual assistant. As you’ve seen, the benefits are immense, and if you follow the process I used at Curious Lion you will set yourself up for success with the right assistant for your business.

If you’re looking for inspiration on what you can outsource to a virtual assistant, here are some ideas:

  • Market Research
  • Data Entry
  • Email Management
  • Online Marketing
  • Scheduling
  • Call Answering
  • Search Engine Optimization
  • Web Development
  • Content Writing
  • Transcription
  • Graphic design
  • Photo, video or podcast editing
  • Accounting/payroll
  • Social media marketing
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