The 10 Step Guide To Hiring, Training & Managing Virtual Assistants For Your Print On Demand Business

Marcel Behrens - The POD Partner

When your print on demand business starts to grow it’s inevitable that you will have to outsource some or all of your daily operations work or you risk getting a burn-out.

Hiring a virtual assistant (VA) is the most logical first step to take.

As simple as it may sound, there is actually a lot of work involved to find, hire and manage a loyal and experienced virtual assistant.

This guide describes 10 steps you need to find a valuable assistant that fits this description. It’s based on 10+ years of experience hiring assistants online for my own businesses, including The POD Partner.

It’s a long read, but I’m sure it will be helpful to get you started.

Table of contents

If you read this for the first time I advise you to read all ten steps in the order I wrote them. However, if you have been here before this table of contents will help you find the information you need faster. Simply click on the step you want to view again.

  1. 1. Document the tasks to be oursourced
  2. 2. Create a job post
  3. 3. Post the job to job boards
  4. 4. Review the applications
  5. 5. Schedule interviews
  6. 6. Have top candidates perform a test
  7. 7. Set up the contract
  8. 8. Train your virtual assistant
  9. 9. Manage expectations
  10. 10. Ending the contract

Document the tasks to be outsourced

The first thing that needs to be done is to make a clear overview of the tasks you want the virtual assistant to perform.

Even though this sounds simple, it’s important to take the time and think this through. Nothing is more annoying than to find out halfway through the hiring process that you actually need your VA to perform other tasks as well, and need to adjust your job post and reselect the candidates.

A good way to find out what exactly needs to be done is to grab your workflows and Standard Operating Procedures (SOPs) and list all the requirements for a VA to be able to do the work.

Next, it’s important to consider whether these tasks need to be performed by someone with a specific skill set, or if the skill set of a general virtual assistant is enough.

You may even find out that you need to hire multiple assistants to make sure the work is done properly.

My best advice: Never rush this part. It’s a mistake that is made by a lot of print on demand business owners.

Create a job post

Now that you have a list of tasks to be done it’s time to create a job post. Let’s have a look at a few important sections of the job post.

The headline needs to stand out

As with all copy that is written, the headline for a job post needs to trigger the reader’s attention immediately. If your headline is pretty much the same as all the others the response rate will be lower.

The difference between “Looking for a T-shirt designer” and “Love to create designs people wear with pride?” is huge. The first one is pretty common, the second one will trigger an emotion with the reader. If they relate to it, they will click immediately.

Focus on the candidate

I dare to say that in 90% of the job posts the writing is focused on the job and what the business wants and needs.

To get loyal assistants you want to write like the other 10%. You want to focus on the candidate in your job post.

You see, not every virtual assistant just works for money. Some prefer to work for an employer who treats them as human beings and understand their values.

They are already used to business owners who demand more and pay less. When you make a difference in your job post, chances are the loyal assistants will react to it. They will be the ones who write a response that will include the parts that highlight the human side.

Screw the cover letter

The logic behind a cover letter is that you will get a first impression of the virtual assistant, both who they are and what they can do.

To me, cover letters are a waste of my valuable time.

The average cover letter is just a load of written keyword-rich, copy/paste, ego-bloating ‘Look what i can do’ nonsense.

I demand that applicants do not send one. If they do I will decline them instantly.

Here’s a better way:

Hide an easter egg

The fastest way to select serious applicants is to hide an easter egg in your job post.

An easter egg is a hidden message or request inside the job post which people need to take into account when they apply. .Usually I hide it somewhere at about 2/3 in the job post.

The goal is to find out if people actually read the job post, or just read the headline and decide to apply, hoping they are one of the first to reply and get the job.

Remember that most general virtual assistants have to fight for the general tasks that are offered every day. The more experienced and specialized they are, the easier it is for them to get work, either by previous employers or by referral.

Be specific and list requirements

To find the right person, you need to be specific in what you are looking for. Make a list of the tasks you need done, and what you are looking for in the virtual assistant.

I found that making a list of what I’m not looking for actually increased the quality of the responses, and thus lowered my time investment in selecting candidates.

Taking the time to write down what you do and do not want will save you valuable time during the rest of the hiring process.

Post the job to job boards

There are many job boards online where you can drop your job post. There are also a lot of businesses offering virtual assistant services by their employees. Here are five to consider, and I’ll start with the most well known at this moment.

Formerly known as Odesk and Elance, Upwork is a huge platform for businesses and freelancers to connect and collaborate remotely. You can hire people pretty fast and the quality of work in most cases is good.

It’s still the preferred platform for print on demand business owners to find virtual assistants.The question is how long this will last.

Over the years Upwork has adjusted their pricing strategy. Currently they charge a 3% administration fee to both freelancers and agencies. Plus they take a cut from what you pay your virtual assistant, starting at 20% for the first $500 per client. After that it goes down to 10% and eventually 5% for billings that exceed $10.000.

To me, that is plain theft.

It’s also the reason businesses and freelancers start to find ways to work outside of Upwork. Of course Upwork doesn’t allow this in their terms of service, but I understand why they do it.

Another good job board that isn’t known by many people but is popular in the Philippines. They consider themselves the job board for virtual workers in the Philippines.

I’ve hired people there before and am pretty satisfied with the results. However, they have a different approach when it comes to hiring, and it generally takes more time before the virtual assistant can start.

The first thing you will notice is that you can view job applications, but you cannot contact the workers unless you pay a monthly fee of $69 (and you can cancel when you’re done recruiting). This will allow you to contact 75 workers

Now that may sound like a steep investment, but it’s not. Two reasons:

  • Applicants are screened after the apply, including ID proof. Everyone has an ID trust score, the higher the score the better.
  • You directly pay them a monthly salary, full-time or part-time. This will be significantly cheaper than upwork.

If you look for assistants for a long period of time and have time to go through the hiring process you may find good assistants here.

Virtual Staff

With a focus on small business owners, online entrepreneurs and internet marketers this website claims to be the number one provider of dedicated, experienced Filipino virtual assistants.

They operate in a different way than Upwork and OnlineJobs. They are a middle man.

They will help you create your job description and then they will select the candidates, test them and set up 3 interviews with the top contenders for the role. Then you hire one. After that it’s up to you.

This process will take 7-14 days on average. The costs? $495 one-off service fee, to be paid upfront.

Is it worth it for you? Hard to say as it would depend on the business case and the quality of the worker. However, it will save you time and that is worth something as well.

The advantage of Zirtual virtual assistants (try to say that 10 times in a row fast…) is that they are US based and each one has at least a college education. They claim only 2% of their applicants are hired so that you only get the best.

Although they are not trained for print on demand business activities specifically, they are perfect to support you as a personal assistant, especially for administrative tasks. They can make your life more manageable once you need to work on the business instead of in the business.

And the price? Definitely not cheap compared to the previous ones, but you should get value for money. Monthly plans start at $449 for 12 hours of task work per month up to $1499 for 50 hours of task work per month.


Shameless plug, but we should be on the list as this post is for print on demand business owners, which happens to be our target audience.

When you work with The POD Partner you have the option to let us find, hire, train and support your virtual assistants. And if you don’t want to have your own team, you can hire ours. It’s that simple.

First question I get most times: “Are you cheap?”

Here’s my answer: “No, we’re affordable. We save you valuable time and as we are specialized in helping print on demand businesses we know how to get the job done while keeping your customers happy.“

Simply hit me up and let’s have a chat to see how we can help you.

Review the applications

If all went well you should see the job applications roll in. Depending on the platform you posted on this can be within a few hours up to a few days.

For this post I will assume you posted your job post on Upwork.

Now before you start to read all of them top to bottom, start to make a selection first.

Remember the easter egg you planted? Look for that first. No easter egg? Decline the application.

Remember the cover letter part? Check that second. Sent a cover letter? Decline the application.

You will notice the number of applications left goes down fast. Which is great as it saves you time going through them..

When you read an application, first read their reply to you. It will give you a good impression about how serious they are, and how well they read your application.

Remember, some assistants find it really hard to apply for jobs (especially if they are more introvert). This doesn’t mean they aren’t good at their jobs.

Next, read their profile. Not to see what they can do, but to see if you can find ‘soft skills’ like communication skills, adaptability, attitude, responsibility, empathy, motivation, flexibility, problem-solving, conflict resolution and critical thinking.

To me, the more soft skills a virtual assistant has, the bigger the chance I will hire them.

Last, check any reviews they have on their profile. When you do, don’t just look at the stars, but read between the lines, and also read the feedback the VA gave the person that hired them. It can give you valuable insights.

Schedule interviews

You went through the serious applications and now it’s time to make a selection and schedule the interviews.

My advice: Select the top three for interviews. Follow your gut feeling if you’re not sure which three to pick.

Here are the things to consider when you invite virtual assistants to an interview and during the interview itself.

Use specific instructions when you invite them

You have to take the lead when you invite them. This means you need to be specific and in control.

Don’t ask when they are able to do the interview. Give them 2 dates with a time that suits you best. You’re a busy business owner, you call the shots.

Ask them to prepare something

Keep it simple but make sure they will need to take time to prepare it.

The reason you want them to prepare something is to pre-qualify them. If they did it, great. If they didn’t prepare it, well, that is what you can probably expect when you hire them. Politely let them know that the interview is over as you have already talked to other qualified assistants.

Ask a weird question during the interview

Really, do it.

Most assistants use canned responses for the interview. They have had them many times before, and for most questions they have prepared an answer already.

By asking a weird question in between you will break their pattern and actually force them to think, which most likely will give you an honest response. Simply because they have no clue what your preferred answer is.

Look for soft skills during the interview

As mentioned before, look for the soft skills during the interview. Yes you can ask about the skills necessary to do the task, but the soft skills will make the difference when it comes to selecting the right candidate.

Have top candidates perform a test

Once you have a good feeling during or after an interview you should have the potential new assistants perform some kind of test to see if they actually are able to do the job.

Here are a few ideas for tests you can perform:

Test if they have an eye for detail

When you have a print on demand business, an eye for detail is a key element for designers, order fulfillers and customer service representatives.

As an example, I had some designers perform a simple task in Photoshop.I sent an image of a dog and told them I wanted to use only the head in a personalized design. I asked the designers to cut out the head part and put a stroke on it. Then they had to send the result plus the time it took them to do it.

Simple to do this fast and precise? Yes, it’s a 5 minute job for anyone who knows a little Photoshop. And the combination of the result and the time spent told me if they preferred to do things fast or precise just by looking at the details of their work.

I was able to pick the good designers pretty fast.

Test their software skills

This speaks for itself. If they need to operate specific software you need to test if they know how to operate it.

The previous example also covered this one.

You can even test the skills verbally in the (second) interview if you want, but this will not apply to every job you post.

Test how they would communicate with a customer

When your virtual assistant will be in touch with customers or colleagues you need to make sure they know how to communicate properly. This is especially true for customer support representatives.

Make sure you test both their written and verbal skills. Important parts to look for are correct grammar and punctuations, empathic responses, problem solving skills, choice of words and attitude.

Use some real life customer support situations you encountered and ask them how they would respond to it, and why they chose that response. Make sure they understand the balance between a good customer experience and making the business money.

Set up the contract

Once you have found the right virtual assistant for your business it’s time to set up the contract.

Time for a disclaimer before we move on:
I’m not a lawyer nor do I pretend to have legal knowledge that is applicable in your state or country. To be sure your contracts cover every liability consult a lawyer in your jurisdiction.

Here is some general information to consider putting inside your virtual assistant’s contract.

Start with a trial period

It’s pretty common to start the contract with a trial period. Be sure to clear about the applicable terms, like the period required to give notice and the length of the trial period.

Work for hire clause

This is an important part of the contract if you work with people creating content or designs for you. Basically it’s a clause that states that whatever they create based on the contract gives you the full copyright.

Confidentiality clause and Non Disclosure Agreement (NDA)

Unfortunately, not every virtual assistant works in an ethical way. You want to make sure that everything your virtual assistant learns about your business is protected by an NDA so it won’t end up with a competitor in case the VA decides to work somewhere else. As always, it’s better to be safe than sorry.

Sick leave & holiday leave

Be very clear upfront how your business handles sick leave and holiday leave. Those issues are a nightmare to discuss after the fact, especially if the virtual assistant is expecting this to be handled as they are used to in their country.

Payment terms

Your virtual assistant will ask for this if it’s not in the contract, for obvious reasons.

Make sure you mention their salary and bonus payments if any. Also mention when the salary will be paid, if it’s paid before or after the work has been done (or both), and the payment method you will use.

By being transparent with your terms your virtual assistant knows what to expect. It will remove any friction during the contract period.

Train your virtual assistant

Now that the contract has been signed it’s time to get your virtual assistant up and running. Here’s what you will need to do to train them properly:

Arrange a smooth onboarding experience

Make sure everything is set for your assistant to start the work. Do they need a company email account? Do they need access to cloud storage folders or company software? Do they need to access your store or your customer support desk? Do they have a list of who to contact and how to contact them?

Having an onboarding template ready is a must to make sure you get everything ready before they start

Also, a welcome email telling them what is happening in the business right now, and giving them links to resources works very well.

Meet the team

If they will work together with other teams and team members introduce them to each other. Encourage them to work together to get everything done, and in case they get stuck they can get in touch with you.

Make sure to mention something positive about the team member you introduce them to, and if possible hint on something they have in common.

Something like ‘This is Jason, he’s the guy who can spot if there’s a misplaced pixel from 25 feet away, and we love him for that!” is a fun way to say somebody is very detail oriented. And “Oh, and just like you he is also crazy about his dog” can build a connection (assuming they both have dogs they love!)

Making your new assistant part of the existing team as quickly as possible will improve their performance within the team.

Hand them the necessary documentation

The most important things your new assistant needs to get used to are your Standard Operating Procedures (SOPs) and your workflows. Usually these can be found in the Employee Handbook.

You should hand them over as soon as they start, and preferably the day before they start so they can walk through the information as soon as they can.

Any other documentation should be ready either the moment they start their workday, or right before they need it the first time.

Manage expectations

So that is it! You posted a job, went through the hiring process and hired a virtual assistant. If you think your work is done well…. It’s not.

Your work actually begins now. Let me split up some vital things you need to keep in mind:

You both have expectations

Yes, you’re not the only one with expectations, your assistant will have a few as well. It’s important - especially during the first weeks - to periodically check in with your assistant to see if everything is still going as expected.

Time management

New assistants need time to get used to their new job. Most times they will get the big picture, but need more time to learn all the specific details applicable to your business and workflows.

Eventually you will want them to do a certain amount of work in the hours they work for you.

It’s important to keep an eye on how they spend their time. Fortunately, there are some good time tracking softwares available to track their work, like TimeDoctor. For $10 per user per month you get a suite of tools to help you get valuable insights.

Create mandates and check them

Eventually you will want to give your virtual assistant a mandate to act on your behalf up to a certain level. A well known one is giving them access to your PayPal account to be able to handle refunds and upload tracking information.

Another one is to give them the responsibility to upload orders at the supplier and send them to fulfillment, meaning you’ll be charged for the order.

Although some mandates can have more impact than others, you still need to keep an eye on things to make sure they don’t overstep the boundaries you set, or accidentally (or not) make a mistake.

Not doing this may hurt your business big time as most times you will find out long after a mistake was made.

Performance evaluation

Another recurring activity - but one that is often overlooked - is the performance evaluation meeting. Here you and the virtual assistant will hop on a call and talk about how the assistant is performing.

A common structure is for the assistant to fill out a questionnaire beforehand and send it to you, and you fill out a performance evaluation form as well. This will be the basis for the meeting.

The goal is to make sure the virtual assistant is still performing as planned, and if they do or did even better than expected make sure to praise them for what they have done. In case they are not where they should be at it will give you an opportunity to set new goals, make clear they need to improve or - worst case - to say goodbye.

Most times performance evaluations are also used to discuss a raise in salary. If the assistant is performing well you should reward them, either by promoting them, raising their salary, their bonus, or both.

Ending the contract

Eventually, everything comes to an end. Whether your virtual assistant decides to leave you, or you are forced to say goodbye, it’s important that you handle the situation professionally.

Based on personal experience, the most important thing to keep in mind when ending a contract is to be honest, especially if you are ending the contract.

This will help the virtual assistant understand the reason why, so they can take what they learned from it with them and prevent it from happening again in the future.

Have an exit meeting

It still happens a lot: People send an email telling their assistant they are no longer welcome. Or worse, they click the ‘End Contract’ button on Upwork and move on.

Besides that this is pretty rude, it will also hurt your (business’) reputation over time.

Simply invite the assistant to an exit meeting and explain why you ended the contract. Give them feedback they can work with, and ask them if they would like you to write them an honest review and/or be available as a reference for their future employers.

If they ended the contract themselves, ask them what it is that made them decide to go and work for somebody else. It may give you valuable insights in where you can improve your business. Be humble here, show gratitude for what they did for your business and wish them all the best on their new adventure.

Remember that in case things don’t work out for them as expected, you’ll be the first person they will contact to see if they can come back to work for you!

Phew, that was a long post. Congrats, you made it!

I hope this will help you to find, hire, train and manage your virtual assistant. If you have questions or like to add something just let me know. I’m always happy to help people!

Don’t want to do this yourself? The POD Partner can help you out!

We make running your print on demand business easier. We can help you set up your backend operations, or fully manage it on your behalf with the goal of improving the customer experience and giving you more time to focus on the stuff you’re good at!

If hiring, training & managing your virtual assistants gives you headaches, we love to have a chat to see if we can help you out!

Marcel Behrens

Marcel Behrens

Founder of The POD Partner