Hiring & Working w/ a Virtual Assistant: Onboarding and Long-Term

by | Aug 3, 2021 | Productivity Tips

Onboarding your Remote Worker for Success

In a different post, I covered knowing when to find a remote worker such as a Virtual Assistant (VA) and or a freelancer. Be sure to check out that post here.

This post will cover how to successful onboard and set realistic expectations for yourself and your remote worker.

Start with the Project ‘Why’

Freelancers can provide more support if they understand the end in mind and why of the project.

This might seem like an unnecessary step, but in fact it is quite underrated. This can determine your project success because it allows your remote worker to really understand your intentions and the project’s goals.

What to Share

The size of the project should determine how much information you give. If it’s a logo creation, copy writing, video editing or a translation project, you want to give highlighted pertinent details for your specific brand and the project.

For example, if your project is writing email newsletters (by the way, be sure to sign up for my newsletter community to get exclusive tips and resources for free!), some details you can share with your freelancer are:

  • Sharing information and updates

  • Providing free content

  • Creating a feeling of a community/tribe

  • Should be written and sent out every week

If you’re hiring a project manager, VA or some other type of remote worker who is going to represent you to the public while being immersed in your business, sharing what makes your business tick specifically will only benefit your business.

Sharing your mission vision or values can give important guidance and guardrails for the freelancer to provide more value.

But, now you might be asking: “Who is this person that is so valuable and beneficial to my business?”

Hiring & Onboarding Questions

Like I describe in part 1 of this series, who you hire is very important. You cannot hire any old remote worker. Even if you have 2 candidates who do the same thing, they are still different.


Because no business, no person, is the same! We are all unique.

As a review, here are some questions you can ask yourself to help you discover your ideal worker.

Who You Hire

  • Who is your ideal client?

  • Who is your target market?

  • Who will this person work with?

  • Who will the VA/remote worker communicate with?

  • What is your expectation of the communication style, follow-up and reporting status updates to you?

What will They Do

  • What do you do?

  • What will they do?

  • What are the specific tasks?

  • What is your desired outcome working with this person?

  • What is the importance of what they are doing?

  • What does this person need to be able to access:

    • Drives, Dropbox, email, calendar, Quickbooks, PM Tools?

  • What accounts do you need to set up for this person:

    • Drives, O365, Asana, Monday.com, email address?

  • What training resources would you recommend?

When will They Work

  • When do you expect this person to be online?

  • Do you have specific needs at a specific time (email reviewed at 1:00 daily)?

  • Do you care when they complete the task? Is the preference get it done and let me know?

  • When is each task due?

  • When do you want to review the progress?

How will They Work

  • How are you going to train this person:

    • Screen share, record and transcribe notes for future use, recordings?

  • Will you have how-to documents:

    • Compile documents into a project / company where you or your worker can go when you need help thinking?

  • Time to shadow and watch you online?

How are you going to stay in contact with progress

  • Schedule regular meetings

  • Be available for screen sharing when needed

  • Create and use an ongoing meeting document that can be updated.

    • Example: I have an update Google Doc to use internally between myself and the SPP Coordinator. We are able to track updates, add questions, and be on the same page in 1 place.

  • Be intentional with communication tools to determine where to communicate:

    • Update Slack, Google Hangout, Telegram, etc.

  • When to respond to email

How are you going to provide access to this person

  • Lastpass or password sharing program

  • Set-up a time to use the screen sharing function when the person is onboarding to show specific details and or programs

Providing Feedback & Working Together Long-Term

Let’s be honest, while working on a remote team with someone you have never met in person who may live on the other side of the world, building a relationship can be a challenge.

Its is also an opportunity for an adventure with true growth opportunities.

No matter the situation, building a relationship and providing feedback is critical for the success of your project.

How are you going to do this?

  • Be intentional to set-up and follow-up with realistic expectations

  • Be available to connect so you get to know one another

  • Know yourself and your communications habits

    • Share these habits and be honest.

      • Are there any communication preferences or personality tests you can both take to understand each other?

  • Ask how things are going, then shut up and listen!

  • Be involved and invested in this process knowing it will lead to amazing results!

How Much [Insert word]

  • Be honest and realistic to communicate how much time and effort you would like spent on each task

  • Be clear about how much resources and effort is needed

  • How many hours do you expect this person to work daily / weekly?

  • How much are you going to pay? Are there any bonuses or increases available?

Ongoing Improvement

Now, you have the perfect fit for your communication style, for your project, for your business, etc.! Let’s start looking at long-term working relationship.

  • Review your expectations and criteria for the worker and the project on a monthly basis during the first 6 months, then on a quarterly basis.

  • Ask yourself monthly do you like how things are going?

  • Ask these questions of yourself, then ask with your freelancer and identify next steps for continuous improvement.

  • Be honest and identify what you like, being sure to provide feedback

  • Identify what did not go well and what you did not like, being sure to provide CONSTRUCTIVE feedback

  • Identify what has changed and or what needs updating or improving, with CONSTRUCTIVE feedback again

  • Ask yourself and your freelancer if you/they need any additional resources or assets to improve

  • Identify what you want to improve and come up with an action plan alongside your freelancer

  • Ask what’s the next step. Work through this with your VA so you are both on the same page

Working with someone is a great way to keep pushing your productivity further! As much as we want to be Superman/Wonder Woman, we are only human. We cannot do everything at the same time, perfectly.

Hiring a complimentary worker to help with all your tasks is a fantastic start. I have hired a handful of remote workers and I am happy to chat more about my specific experiences and to pass on any names if need be! Feel free to email me or schedule a call!


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