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Six Steps To Master The Virtual Assistant Onboarding Process [Free Checklist]

The image shows the back view of a woman sitting at a desk in a home office environment. She is wearing a gray sweater and has her hair pulled back. On the desk, there are various office supplies and equipment, including a computer monitor, a desk lamp, and a potted plant. The walls are decorated with framed artwork, and there is a clock visible on the wall.

Onboarding a new employee is easy in theory, but how do you do it if the employee is hundreds of miles away?

Bringing a new remote virtual assistant into your team is no small task. Onboarding done right is the key to fast productivity, building trust, and long-term success.

An onboarding new employees checklist that works for all employees—including virtual and in-house—makes sense and ensures a consistent experience for your whole team.

One of the biggest advantages of outsourcing your admin (vs. hiring in-house) is that you can look for a company that offers managed, dedicated assistants. This means that company takes on all the tasks of managing, training, and overseeing the assistant (instead of you).

Here at Boldly, this includes a thorough and structured onboarding process — both for hiring and for integrated our remote executive assistants with your team.

After onboarding hundreds of virtual assistants over the past decade, we’ve put together the ideal virtual assistant onboarding training process using just six steps. While geared for virtual assistants, it’s an approach you can use across your entire organization.

The image shows a checklist for onboarding a new virtual assistant. The checklist includes items such as understanding the company culture, accessing technology systems, reviewing key documents and expectations, tracking progress with a task list, communicating frequently, and defining and tracking key performance indicators (KPIs). The checklist can be used for remote assistants or in-house administrative support.

Onboarding New Employees Checklist: 6 Steps To Onboarding For Every Organization

How well you bring your virtual assistant into your team affects your client experience, not to mention your assistant’s experience as well as your own. A good assistant onboarding can become a template your whole team can use as a process for onboarding clients or other employees.

We’ve prioritized this idea as our value of “everybody wins.”

When Boldly team members are engaged and invested in the work they’re doing, they care about doing their best for clients. When clients work with invested, caring team members, they continue to come back and refer their colleagues. It’s a win-win, but it all starts with onboarding.

The key to onboarding is consistency, with each step building to the next in a structured onboarding program.

You can’t cover every possible list of tasks or work scenarios that might come up. But that’s not the point. The goal is to build a foundation with simple steps, where your VA has the information necessary to think on their feet and get to work right away.

Here’s the process at a glance:

  1. Start with your company culture
  2. Give appropriate access to technology systems
  3. Collect key documents and write down your expectations
  4. Create a checklist to track task progress
  5. Communicate early and often
  6. Define and track key performance indicators

1. A Good Onboarding Starts With Good Culture

A company’s culture is only as good as its people, which is why it’s important to explain your expectations, values, and other cultural norms to new team members.

This can start with company handbooks or manuals, but should also include any “unwritten” office or company rules. This is especially important if you’re onboarding a remote assistant, who may not see the day-to-day office interactions.

For example:

  • What is the attitude towards working late?
  • What is considered an emergency that might require your virtual assistant to work outside normal hours?
  • What is the expectation for using Slack or other chat tools — should these be strictly professional or can messages be a bit more informal/fun?
  • Are employees expected to reply right away to certain requests?

2. Give Appropriate Access To Technology Services

The technology stack you’re using is significant, especially when remote employees are involved. If the tech isn’t seamless, it’s going to be much harder than it needs to be.

Before onboarding your virtual assistant, there are technology-related things to prepare in advance:

  • A company email address with a signature that indicates their position in the company
  • A company phone number (or VOIP option) that forwards to their location
  • Calendar, scheduling, and travel software
  • Internal messaging and video conferencing systems
  • Cloud document and file storage
  • Task and project management software
  • Your CRM for managing any contact or prospective client information

Additional software, such as invoicing, social media management, marketing, management of affiliate links, and other software platforms, may be required for the specific list of tasks you expect of your VA.

The level of access and security may vary. This requires trust (which we’ll cover in a bit).

However, restricting access reduces the value of your VA. If you’re crunched for time, making them wait before they can continue their work is inefficient. Plus, it’s challenging to feel like part of the team when your new VA has to request access to files or systems they need to do their job.

If you’re nervous about giving sensitive, personal, or financial information to a virtual assistant, you may actually want a remote executive assistant (who typically handles higher-trust and more sensitive tasks).

Remember, the goal of onboarding is complete integration with your team. Team members and clients shouldn’t feel any lag or confusion due to technology hiccups. There should be little difference between in-house and remote team members.

3. Collect Key Documents And Write Down Expectations As A Virtual Reference Library

When you’re part of a team, it’s easy to forget how much information you instinctively know. Habits and unwritten rules must be documented for those who are new, or you’ll slow down their onboarding process.

That’s where a reference library comes in. Essentially, it’s a collection of critical documents your team needs to do their work. It might include:

  • Basic information about your company, such as its mission or vision statements.
  • Any step-by-step guides you have on how to perform everyday tasks or operations.
  • Employee handbooks that include information about culture and expectations.
  • Contact information for team members.
  • Security and privacy protocols.
  • Style guides and templates for documents, emails, meetings, etc.
  • Audio recordings of sample client or sales calls.

Your VA will also need to know your personal preferences, which other team members may not need to know. These include:

  • Meetings: When do you prefer to have regular meetings? How long should they be? Who should be in them? How much time do you want between meetings?
  • Availability: What hours are you not available? What days are personal days? How do you want to structure your work time? Blocks? Pomodoro?
  • Voice and Tone: How formal (or informal) do you want your office’s emails and communication to sound? How do you like the phone answered? Sample scripts are helpful to learn from.
  • Preferences: What are your travel preferences? Meal preferences or dietary restrictions?
  • Personal: What kinds of personal tasks will they be doing for you? Do they need to know about family birthdays? Your favorite florist? What is your expectation of privacy?

You’ll likely talk about these things, but be sure to write them down. Your VA is initially facing a steep learning curve and needs that reference material to learn. They also can’t rely on in-office cues (e.g., seeing you’re in the office) and will require documentation to define those cues.

Quick documentation on the front end saves confusion or frustration down the road.

4. Create A Thorough Checklist To Track Task Progress

As mentioned, effective onboarding programs are consistent and structured. An onboarding new employees checklist is a must.

Have a task list ready to go on day one for your VA. Over their first few days, this should primarily be onboarding-related tasks:

  • Talk to HR and sign employee forms
  • Confirm or create logins for critical systems and technologies
  • Complete or sign up for training on software
  • Set up email with IT
  • Read through required documentation and reference library

Have your VA check in with you at the end of each day with what they completed, or any questions or issues that arose, through a quick confirmation email. This lets you track their onboarding progress and help your VA see where they need help.

As they begin to work through their onboarding and new employee documentation, you can add VA-related tasks to their plate.

5. Communicate Early And Often

In the early days of a working relationship, it’s good to communicate more than you’re used to.

Gentle correction (and honest praise) will be necessary at the start, simply because you and your VA are learning to work together and need to get a feel for work styles and personalities. Correction and praise are like rudders; it’s how your onboarded virtual assistant finds the right track.

If your onboarding is done right, communication levels should decrease over time; the initial new tasks will require more communication than those already well-established (e.g., the first flight your VA books for you months after starting is a new task even if they’ve been there awhile).

There’s no need to micromanage a virtual assistant who has been onboarded correctly. But that will only happen if you make them clear at the start and establish a pattern of effective communication with your remote team.

The communications piece is where a high-level remote executive assistant begins to outshine most standard VAs and where you see the difference between a virtual assistant vs. a remote executive assistant.

Infographic comparing a low-cost virtual assistant (VA) with a premium executive assistant (EA). Left side shows a conversation with a VA, demonstrating reactive responses. Right side shows an EA proactively managing schedules and anticipating needs. The CEO's requests are more detailed for the VA, while brief for the EA.

Remote EAs typically have more experience (Boldly’s team averages 10-15 years) and proactively start to lead you. They’re experts at communicating what they need and asking specific questions (like where you prefer to sit on an airplane).

Our team of executive assistants has single-handedly created onboarding processes and documentation for many clients!

Documenting expectations is the start. Tracking performance is how you measure if those expectations are met.

Your team wants to know if they’re meeting expectations, and you need to know it. Measuring key performance indicators (KPIs) is the way. There are several ways to measure the performance of your remote workers. And while the KPI reporting format you use might vary in appearance, they all have essential points in common:

  • Clear objectives.
  • Selected KPIs you’ll measure that align with those objectives.
  • Data visualization that’s useful and understandable so you can analyze the results.
  • Consistent time frame with targets and benchmarks.

Gather data from software dedicated to this kind of activity and what you learn during periodic reviews or meetings to track how well those KPIs are being met. While KPI results happen down the road, setting it up and communicating the process during onboarding is how they start.

That First Meeting Matters To Your Team

We have a little secret.

Those six onboarding steps are significant, but you need to start onboarding well before day one. It seems impossible, but consider: the perfect onboarding process with the wrong person will still fail.

Before choosing your remote virtual assistant, it’s important to make sure they’re a good fit for:

  • How you work
  • Company culture
  • Personality
  • Skill and experience required

How you handle your recruiting and hiring affects everything that happens downstream. The wrong person for the job can never be set on course with the proper onboarding.

If you’re sure you have the right person, it’s essential to introduce them to everyone on the team so they know who they are working with. All team members, whether remote or in-person, need to know who they are working with. This includes you.

Because that’s the key: they’re working with you, not just for you.

Building Trust Through High Standards

Building trust with your VA has to go beyond an email or Zoom call.

Bringing a new remote virtual assistant into your team is no small task. Onboarding done right is the key to fast productivity, building trust, and long-term success.

But the trust component is the final pin in the lock.

We know trusting your virtual assistant with important information and work takes time. Trusting someone with your clients and essential business operations is daunting. We get it.

That’s why we created a system to take care of it for you, starting with a highly selective vetting process that means our team meets the strictest professional standards and passes background checks. We also demand extensive work experience. And then, we made the onboarding process easy. We did the work so you don’t have to.

In fact, within a week, you can have a fully functioning, well-matched virtual assistant you can trust, reducing your workload.

About the author Katie Hill is a Content Writer at Boldly, which offers Premium Subscription Staffing for demanding executives and founders. When she isn't writing about remote work or productivity, she can be found adventuring in Colorado's backcountry.

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