Eric Evenstad

Maximize Your Virtual Assistant's Productivity: The Ultimate Onboarding Checklist

Maximize Your Virtual Assistant's Productivity: The Ultimate Onboarding Checklist

Eric Evenstad • Jan 15, 2023

Read Time: 6 Minutes

Last week, I showed you how to find and hire a full-time virtual assistant for as little as $500 per month.

Today I’m going to teach you something even more important. I’m going to show you how to train, onboard, and manage your new virtual assistant.

It may not be as exciting as hiring, but a great onboarding process and management system is the key to maximizing your virtual assistant’s productivity and freeing up your time.

And just like last week, I’m going to throw in a few of my favorite onboarding templates and outsourcing tools so that you can get your VA up and running ASAP.

Here's What We're Going to Learn


  • How to prepare for your VA’s first day
  • How to set clear expectations
  • How to train your VA like a pro
  • Cultural considerations when working with someone from the Philippines
  • Management tips to get the most out of your VA
  • Tools to help you communicate, assign tasks & send payments

How to Prepare for Your Virtual Assistant’s First Day


Your virtual assistant’s first day will be here before you know it and it’s crucial that you are prepared so that they can hit the ground running.

Here is what I do ahead of time to ensure that the first day is a big success:

1) Set up a company email address for them. I always recommend using 
Google Workspaces for this because it comes with email addresses, Google Chat, Google Meet (for video calls), Google Calendar, and Google Drive (for sharing files and collaborating on Docs).

2) Set up login access to other important software like your project management and CRM tools. In some cases, you’ll need to set up a separate user account for your VA. Other times, you’ll be able to provide them with login credentials to access your accounts.


ProTip: 
Set up a free LastPass account for you and have your VA do the same. This will allow you to give them login access to software tools without sharing your username or password. Here is a video I recorded a few years ago that walks you through all of this.

3) Prepare any necessary contracts or non-disclosure agreements that they will need to sign.

4) Record video tutorials or find 3rd party video tutorials on Youtube that explain how to access and use your primary software programs. Then add those videos to your project management tool and assign them to your virtual assistant.


ProTip: 
If you don’t already have a project management tool, I would recommend using Notion or ClickUp. Both are easy to use and they will make it significantly easier to train & manage your VA.

5) Send your VA an email the day before they start with instructions for their first day. 
This is the email that I generally use.

How to Set Clear Expectations


Setting clear expectations, discussing communication preferences, and outlining your VA’s role and responsibilities are all things that you want to do on the first day.

I will typically record a video ahead of time where I cover these things, but you can also schedule a live video call on the first day to do it in person. If you opt for the live video call, I’d highly recommend recording the call so that your VA can refer back to it later.

Here are a few important rules & expectations to cover:

Working Hours
For most of my VAs, I tell them that I want them to overlap with my work hours for at least 3 hours per day. This makes it easier to communicate and offer feedback. Then, I let them choose the other 5 hours of work time. You can do whatever works best for you, just make sure you communicate your preferences to your VA.

Communication Preferences
I prefer to communicate via Google chat and my company’s project management tool so that is what I ask my VAs to do too. Figure out what works best for you and explain your expectations to your VA.

Daily Check-ins
At the end of every day, I have my VAs send me a message explaining what they accomplished that day, what they struggled with, what they need help with, and any ideas they have to improve a system or process.

Performance Expectations
Clearly explain what success looks like. Discuss any quotas, goals, or metrics that you will use to assess their performance. It is also a good idea to schedule a performance review after 2 weeks, and then quarterly after that. Here is a Performance Evaluation template that you can use.

Quality Expectations
Some tasks require precision and careful attention to detail. Other tasks require speed. For each task that they are responsible for, I carefully explain what success looks like.

Policy on Asking for Help
From my experience, many virtual assistants from the Philippines are hesitant to ask for help or to ask clarifying questions. I think it’s just cultural differences, but it is something that you should address early and often. You must make it known that you want and expect them to ask questions. When they do ask a question, praise them. This will eliminate many problems down the road.

How to Train Your VA Like a Pro


Start by creating a list of tasks that your VA will be responsible for. If there is a task that you do at least once per week, you should outsource it.

The easiest way to delegate a new task to your VA is to record your screen the next time you do that task. My favorite screen recording tool is 
screencast-o-matic.com.

All you have to do is plug in a microphone, hit record, and explain what you’re doing as you complete the task on your own. Now you have a step-by-step training video that you can share with your VA.


Pro Tip: 
When I share a new training video with my VAs, I will ask them to watch it and then either send me a written message that summarizes what I want them to do or I will ask them to take the video and turn it into a written, step-by-step process that can accompany the video tutorial. The point of this is to ensure that they fully understand the task and it also forces them to ask questions about anything they don’t understand.


Here is an example of a written process in ClickUp.

Cultural Considerations When Working with Someone From the Philippines


Filipino culture is very different from Western culture. Everybody is different, but for the most part, I’ve noticed these things about Filipinos.


  1. Family is extremely important to them. I always ask for my VA's birthday and the birthdays of their spouse and kids. Then I tell them to take those days off (fully paid) for as long as they are working with me. Doing this builds trust and makes my VAs feel like valued members of the team.
  2. They value strong relationships. Take the time to get to know your VA on a personal level. Ask about their hobbies, their family, and their traditions. And don’t forget to tell them about yourself!
  3. Filipinos are very respectful of authority figures, which includes you since you’re their boss. As a result, they may avoid asking clarifying questions or they may avoid offering suggestions when they see opportunities for improvement. The best thing you can do is encourage open communication and make yourself readily available and easily approachable.
  4. Scheduling & time management: For some reason, I’ve found it difficult to get my VAs to show up on time every day. I think part of the reason is the time difference. If I want my VA to work during US business hours, that means they will be working in the middle of the night. But the other part is that I just haven’t done a good enough job of setting those expectations. At the end of the day, I usually don’t care when they do their work as long as they do a good job. But if you want your VA to keep a regular schedule, you’ll need to be diligent about setting those expectations.


Management Tips to Get the Most Out of Your VA


Offer Regular Feedback
The whole point of outsourcing is to free up your time, but if you’re not careful, managing your VA or team of VAs can turn into a job of its own. To combat this, I recommend reviewing their work daily for the first 1-2 weeks after you give them a new task. By offering regular feedback you’ll be able to set expectations and trust that they’ll do the job the right way for as long they’re working for you.

Focus on Recurring Tasks
Unless it’s a super time-consuming task, it usually doesn’t make sense to outsource one-time tasks to your Filipino VA - the training time just isn’t worth it. Instead, focus on handing off recurring tasks so that you can create a single set of instructions that they can follow over and over again.

Use Time Blocking
To increase efficiency, I’d recommend setting up a daily schedule of prioritized tasks for your VA. I use ClickUp to create a list of recurring tasks for each day of the week.

Use Time Tracking
Every so often I will ask my VA to track the time it takes to complete each task for an entire week. This tells me where they might be struggling and allows me to follow up with questions.

Record Their Screen
If I think my VA is struggling with a task, I will create a Loom account for them and ask them to record their screen the next time they do that task. This allows me to review what they’re doing and identify opportunities for improvement.

Express Gratitude & Use Positive Reinforcement
Your VA desperately wants to do a good job for you. If you are constantly telling them all the reasons they are failing, they will retreat into their shell. A much more effective strategy is to reinforce all of the things they are doing correctly. When you see them do something well, take time to acknowledge it and explain why doing it that way is so important.

Pay on Time
Don’t make your VA ask you over and over again for their paycheck. Be respectful and pay it on time. I send paychecks on the 15th of the month and the last day of the month. You can set a recurring calendar reminder or you can instruct your VA to email you an invoice on their payday.

Pro Tip: You can send money to your VA using PayPal, but your VA will get hit with some pretty hefty fees. As a result, I’ve started using wise.com to send money. It’s free for you, easy to use, and your VA will greatly appreciate the lower fees.

Ready. Set. Go!


I just hit you with a lot of information, but don’t let it overwhelm you. With the help of the templates, tools & tips that I’ve shared here, you should be able to create all of your onboarding docs and training materials within a week or two.

That’s when the fun stuff starts. That’s when you start to see your schedule open up as your virtual assistant relentlessly tackles your to-do list.

Outsourcing will change your life. Invest a little bit of time and effort right now and you’ll be rewarded with a passive income business in the future.

With that, I want to wish you good luck.

If you have any questions about outsourcing, please feel free to message me on Twitter. My handle is 
@ericevenstad and I am more than willing to help. 

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