14 Best Practices for Managing your Virtual Assistants

Cody McLain
9 min readMay 25, 2018

Ever since I finished reading the 4-hour-work-week, it opened up my eyes to the possibilities that exist with outsourcing.

As somebody who had already been an entrepreneur for many years, I used outsourcing for one aspect of my business (customer support) but had never thought to reason that I was always so stressed out because I had set my business up in a way that would entrap me to it.

Now I’ve written previously about how I went through the process of unwrapping myself from the business using SOPs and Kaizen methodology, but there is still a huge component I left out: Virtual Assistants.

I immediately searched on google and found a few different avenues for outsourcing but very few resources on how to actually outsource, how to manage your virtual assistant once you find them.

Herein lies some tidbits of wisdom I’ve picked up over the years from the many mistakes I made in hiring and managing a virtual assistant from the Philippines.

1. They’re human beings who have feelings

At times it’s easy to forget that we’re talking to another living, breathing human who experiences the full range of emotions that we do. It’s all too easy to get upset when something isn’t done right, or a mistake was made. Most Filipinos are sensitive and will not express their fear or resentment at all, you’ll just wake-up one day and they’ll be gone.

It’s important to remain emotionally bonded with your VA and for me, that means having at least 1 call a week to review current objectives and even to show genuine interest as to what’s going on in their life.

Another way to help prevent your frustration or anger from presenting itself to your VA is to actually fly out and visit them. After working with my VA for over a year, I finally went and hung out with him for a few days and it greatly expanded and grew our understanding of each other by leaps and bounds. After that experience, I found myself to be more compassionate and caring.

2. They’re not entrepreneurs

One of the biggest mistakes I made when I first started hiring was having an expectation that I’d be able to hire a web developer, designer, copywriter, SEO person and then just throw them at my business to figure out what needs to be done.

In retrospect, this was a horrible strategy, but I’ve seen many other entrepreneurs continue to make the same mistake.

You can’t hire somebody who has skills in a certain area and just expect them to know what to do. Even if you lay out the objectives for them, each hire requires a hands-on training process.

3. This won’t be a piece of cake

If you’ve never managed a team before, let alone a remote one, then you might not yet have a clear understanding as to the kind of work that it requires. Even having a single virtual assistant is not always easy. Even if you find the right person, that person will require ongoing training and management of their responsibilities.

4. Don’t hire a Project Manager

This is a mistake I made at first. After hiring my whole team, ones to handle Web Development, Design, SEO, Content I hired somebody specifically to act as a project manager. The problem is I didn’t have a clear vision as to what I wanted each person to do. I just knew the objective I wanted and figured they would use their knowledge and skills to work together to create something.

It can be very difficult to find somebody to come in from the outside who is able to manage your team from the onset. It often takes somebody who is already intimately familiar with your processes before they can take on management responsibilities.

Therefore, it’s best not to hire for a PM but instead hire and train a VA to learn various aspects about how your business operates overtime. Eventually, they will naturally start to learn the ropes and can then teach and manage others to take over.

5. Hire only 1 VA at a time

When you first discover the world of outsourcing, it can be easy to imagine the possibilities and get excited. This is how I found myself paying for a handful of assistants in the Philippines to help me launch a business. I ended up having to let all but 1 go as I later realized my excitement blinded me from the difficulties of managing and building a team.

As they say, Rome wasn’t built in a day — and neither can your team.

6. Document your Processes and create SOPs

In order to make things efficient in life and especially business, you must get used to the idea of creating documentation for your corresponding tasks. Otherwise, you might end up in a situation where you’re employees are able to blackmail you because you let them build up operational knowledge about how your business functions.

The quickest way to teach somebody is to use a screen recording tool or create a series of screenshots you can put in a document that outlines instructions on how to do any particular task.

7. Don’t prepay for work

The biggest fear that most Filipinos have is that the person that hires them doesn’t pay them for work they’ve already completed. In some cases they may ask for money upfront, however, I’ve heard too many stories of somebody taking their money and disappearing.

While the vast majority of Filipinos are honest, hard-working people, many fear that they won’t paid as many have at one point or another experienced an employer who stopped paying them all of a sudden or never paid them after a whole month of work.

Instead, it’s better to extend an olive branch by offering to pay them on a weekly basis to start and move it to bi-weekly or monthly after you’ve worked with them for a while.

8. Learning never stops

Did you stop learning new skills when you graduated school? Probably not, and when it comes to managing employees, instilling a Kaizen philosophy of continuous improvement among your workers will seek to add further value to your business while simultaneously motivating them to keep learning.

Filipinos in particular, Love to learn and will take a job that pays less if they enjoy it more (go figure?). A key to whether or not they like the job is in making sure they are working in the Goldilocks zone.

This means that you must ensure that what they are working on is neither too easy nor too difficult. Maybe this means you have to work with them at first to do some initial training and help them establish a process of their own.

For example, if you hire a content writer, you can’t just expect her to be able to produce something right off the bat. It often takes collaborative effort to eventually produce something of your own standards. In order to often accomplish this successfully, you should be able to produce the same level of work you expect your assistant to handle for you. Only be having a foundational understanding of your own process can you teach it to somebody else.

9. Generalist vs Specialist

I often come across those who claim themselves as being familiar with SEO, marketing or a development language. The problem with many of these candidates is that they end up only having a surface understanding of the subject.

Many virtual helpers will claim to have experience in any area when in fact they’re only experience was carrying out a specific strategy trained to them by a previous employer. In one case, a person I interviewed claimed to have vast SEO experience but couldn’t seem to give me good answers to what were relatively basic SEO questions.

I asked him what he did know and he did know how to submit a site link to various online directories and leave comment spam. This theory of SEO was many years outdated as Google’s algorithm has effectively banned the practice.

It was in this case, I realized that many virtual workers will claim to have their hand in many different pots, but in retrospect, this means they will lack the foundational knowledge that will allow them to ask the right questions and form the appropriate conclusions on their own.

Now, this isn’t necessarily a bad thing, but make sure you know who you’re hiring.

10. Train them on all aspects of your Business

Many entrepreneurs have a dreaded fear if they teach somebody how to run their business that they might end up stealing or duplicating the idea for themselves. Now at least when it comes to Filipinos, they have no interest in trying to build or run a company of their own; what they value are knowledge and learning. Most don’t wish to be the leader but would rather follow direction from somebody they can respect and admire.

By being willing to teach your methods and strategies you’re able to offload the large burden that often comes along with creating and growing a self-sustaining enterprise.

One way I do this is by using software like droplr.com to quickly annotate screenshots and create video walkthroughs of a task or software. I can then upload this to something like Slimwiki to maintain a central repository of How-Tos and other relevant information to reduce future time spent training.

11. First perfect the process on your own, then delegate it

I’ve seen this all the time, in fact, I fell prey to this when I first started out too. Once I discovered the power of outsourcing I thought I could outsource all the parts of my business that I wasn’t familiar with. However, as your own boss, you also become the manager for those that you hire.

Until they can become intimately familiar with their role and the expectations you have for them, every hire will require a hands-on approach. Hiring for a position in which you aren’t sure yourself what all the parts are that makes it work means you’re not ready for that hire.

It’s not always easy, but sometimes you have to be your own employee so you’ll understand what you’ll be outsourcing.

12. Have them sign a Pledge

When it comes to remote hires, there is often a lot of anxiety on both ends. The VA will quite often wonder if they’ll get stiffed for payment, verbally abused or simply find they don’t enjoy the job. On the employer’s end, you might worry if they don’t show up, lie or steal something.

It’s best to start slow and even offer an olive branch to start. This is why I recommend you offer to pay them weekly at first before transitioning it to a once a month payment if possible. It’s also a good idea to lay down your expectations as an employer and to let them know what they should expect from you.

That’s why I created what I call a Filipino Manifesto that I have any of my remote VA’s sign before they start working for me.

13. Make and Keep an updated Job Description

For most companies, they’ll create a job description to search for a candidate to fill the position. Often though they fail to update that job description as the requirements of the role change. Now it’s easy to hire a VA and then expect them to be able to quickly pick up new tasks that seem simple to you but can often be hard for them to grasp outright.

For most Filipinos, if you ask them if they’re willing to do something, they will say yes because they don’t want to disappoint you. This often backfires though when they don’t fully comprehend the task and be afraid to ask you for help. Make sure by talking with them about their work-load and comfort level of trying and learning new things; all the while adding any new jobs to the original job description.

14. Use Time-tracking but be wary of Screenshot monitoring

When you’re hiring a worker for the first time, you can certainly justify your desire to want to use software like staff.com or hubstaff.com to track the time, log activity, websites and take screenshots in regular intervals to make sure they’re doing actual work and nothing else.

The downside to this is that it immediately creates a relationship that is founded on mistrust. I use this software with some staff but not with others. It’s often best though to start using it at the beginning of the relationship as soon it will just become routine and can even automate the pay schedules. Just know if you start to feel like a worker isn’t being honest, or is slacking off on the job then it’s best to have a conversation with them first and look for an improvement before jumping off the cliff so to speak with the implementation of such a software.



Cody McLain

Founder of $12m SupportNinja, Author of From Foster Care to Millionaire book, Host of MindHack.com Podcast