BlogTrainingTraining Your Virtual Assistant – The First 90-Days Guide

Training Your Virtual Assistant – The First 90-Days Guide

Unlock the full potential of your business with MyOutDesk's top-tier virtual assistants. Say goodbye to time-wasting and hello to efficiency as our virtual assistants are handpicked, ensuring not just a skill match but a cultural fit, making onboarding swift and seamless. With our exclusive MyTimeIn application, monitor your assistant's progress in real-time, ensuring transparency and trust, and dive into the transformative first 90 days where we guide you step-by-step, setting both you and your virtual assistant on the path to success. Don't just work—thrive with MyOutDesk.


Key Takeaway

Elevate your business efficiency and growth with MyOutDesk’s virtual assistants; trained and primed to save you time and increase revenue, while our proprietary MyTimeIn tool ensures transparency and accountability. Take the leap and discover the potential of a seamless onboarding process, complete with the tools and training to ensure your success.

Every time a prospective client connects with us at MyOutDesk to learn more about virtual assistants, we always ask them several questions about their own business. This helps us not only get to know the people we may be doing business with, but it also helps determine how viable our service even is for them. One of the most important questions we ask is what their primary pain point currently is. What is the aspect of their business that they believe is the biggest obstacle to growth? A vast majority of them respond with the same answer; tired of wasting time and looking to save time instead. Additionally, the second most common responses say they want to grow revenue more efficiently. It makes sense that time and money are the top two pain points, because as the old saying goes; time is money. And that’s where we step in to save you both.

“We gave it a shot, and not long after doing so we were like well crap, that was easy!” – David Perry, Director of Finance at ‘A Better Contractor, LLC’

Time Travels

The time you invest in something now typically pays for itself in the long run. Provided you’re investing in the right things, of course. Like training someone to do a job. Psychologists have proved that it takes about 90 days to solidify a habit. And once that habit is formed, it’s easier to stick with it than it was to establish it. That’s why we at MyOutDesk take the onboarding and training process very seriously. Because when a business comes to us for help, they often needed that help yesterday. We’re experts at talent matching our available virtual assistants to the needs of every individual business. And that goes beyond their experience, skills, training, etc. It includes who they are as a person and a professional. Are they the right culture fit? The better a glove fits the first time, the faster you’ll break it in and become comfortable using it. And the faster those gloves become your favorite pair. That’s why we provide all the necessary tools and support to ensure the entire onboarding process for our clients is fast and easy, regardless of the role.

‘MyTimeIn’ – Exclusive to MyOutDesk

Before we dive into the first 90-days with your shiny new virtual assistant, we want to tell you how you’ll be keeping track of them. We have a proprietary application that all of our clients have access to, called MyTimeIn(see what we did there?). It’s kind of like a fitness tracker, except you’re tracking your virtual assistant. You can monitor their productivity via real-time updates, so you’re never in the dark about what your remote working employee is up to. You can also use it to access your assistant’s work history, manage email preferences and billing, and get support. Have you ever felt frustrated because you couldn’t get ahold of an employee who was working remotely? You never have problems like that with our virtual assistants. And no other service like ours provides any kind of MyTimeIn alternative. 

The First 90 Days

Training a new hire is an investment in them, as well as your business. You get out what you put in. That’s why at MyOutDesk we don’t mislead by making unrealistic promises of having someone up and running in just one week. No one worth your time and effort is completely autonomous in that short of time. Proper onboarding of a new employee will always require an adjustment period, whether they’re in the next room or across an ocean. The key is making sure that time is as effective and efficient as possible so that it’s not eventually wasted. Because then you’re back at square one, and probably in an even worse position by then. So, let’s go over the first 90 days with your virtual assistant. This won’t be a completely extensive deep dive, as we have training manuals that cover every single detail you need. Consider this a helpful overview, to give you an idea of how worthwhile this business model can be for you, especially if you follow our recommended onboarding guide.

“Once she learns the task you know that it’s done. You don’t have to think about it twice.”Stephanie Masterson, president and chief sales consultant for The Raines Group / HER Realtors in Ohio

Days 1-30

The first 30 days with your new virtual assistant(s) should be basic training. Things like your market overview, the company vision as well as mission(those are two different things!), core values, and of course individual team introductions. It’s a good idea to schedule some shadowing sessions for your VA, with existing team members. This is immensely valuable when trying to instill a thorough understanding of what you all do, and what will be expected of your VA. Having clearly defined expectations from the start will go a long way towards getting your VA confident about the role ahead of them. Providing training materials that they can review at their leisure is also very helpful, so have training videos and/or documents ready for them.

The first month with your VA is a lot of introducing and learning. Here is a basic checklist of actions that should be taken during these crucial first 30 days.

  • Add your VA to relevant team meetings. Including them in higher-level meetings as a “fly on the wall” can be great for educational purposes initially.
  • Set them up with the software, applications, and tools your team uses. Anything relevant to their role should be ready for them to use so as to avoid speedbumps.
  • Create to-do lists for them, so as to track their training progress. Things like setting up their profile in your systems, adding calendars, and reading materials.
  • Set goals. These are different from to-do items because they aren’t simply something marked off a list. The first goals should be things like tasking with auditing an inbox and resolving a set number of inquiries.

Day 31-60

The second month is where things should tighten up, so to speak. Your VA should have a clear understanding of what their job will require, and a strong familiarity with the product/service they support. You’ll want to keep up to date with them, via regular meetings to touch base. They should have full access to everything they need by now, so they should be tackling tasks on their own confidently. They will have questions occasionally, so those 1-on-1 chats will be helpful for you both. It may still be a good idea to have them do roleplay scenarios with other members of their team if they are in a customer service role. This is also a crucial time to get to know your VA. You likely will have already had some friendly conversations before, but you need to maintain that connection as if they were any other usual hire locally. Here is a simplified checklist of what to remember and focus on during this second month.

  • Test your VA’s familiarity and confidence with your business, their role, and why it’s important to the bigger picture. This is where you solidify their basic training and plug any gaps.
  • Implement procedures and productivity tracking sheets. Your VA should be able to confidently handle the duties of their role, and overcome most basic objections on their own. Speedbumps do happen, so having procedure materials and a tracking sheet is imperative.
  • Get serious about time-blocking, and checking in regularly. Your VA should have a solid schedule for their day-to-do now, and that should include set times for checking in with each other. 
  • Get to know them on a personal level, just like any other employee. Who are they, outside of work? What are their career goals and life dreams? When you put your own heart into the people you lead, they’ll put their heart into the job they do for you.

Day 61-90

This is the home stretch, the final month of an employee’s crucial first 90-days. By now your VA should have an above-average understanding of the business you provide and the market you’re targeting. They are now well trained and tested, capable of diving into their role confidently and independently when necessary. Comfortable reaching out to their teammates and leaders when necessary, as well. Less supervision is required at this point. They are adept enough in their trained responsibilities that they can now expand beyond them and help with other tasks when needed. Meaning you can now experiment with your VA! Give them more challenging tasks, assign them a more difficult goal, and measure their success accordingly. Set editorial calendars, if they are helping with any marketing-related tasks. Here are some quick tips.

  • We recommend having at least bi-monthly meetings with the team your VA is a part of, as well as regular 1-on-1 sessions. Communication and understanding is key.
  • As training subsides, continue to invest in implanting your VA into your office culture. The more a part of your “work family” they feel, the greater the mutual success and growth.
  • Communication is the gateway to success with your VA. Be open and set clear expectations; your VA cannot help you win if they don’t know how to score.
  • Every MyOutDesk client is assigned a success coach, who can answer questions, address concerns, and provide any necessary support. Don’t forget about them!
  • You will have more free time than you’re used to! Take advantage of the extra breathing room to focus on high-value prospects and new projects.

Good Luck, Have Fun

And that is the first 90 days with your virtual assistant, in a nutshell. Again, we have free PDF training manuals that go much more in-depth, available for every client. And in future blogs we’ll be going over the first 90-day breakdowns just like this, but for more specific roles. Like marketing, inside sales, and service/support roles. By going along with at least most of our recommendations, you set up yourself and your virtual assistant for the greatest chance of success. We’ve been doing this for 15+ years, and have humbly learned a lot as we provided our service to thousands of clients. We know what you want and what you need, regardless if you have 10 employees or 1000. To summarize the above in an even easier-to-digest cheat sheet, here are the absolute essentials to your first 90 days:

  • Invest the time, and don’t get impatient. Rome wasn’t built in a day. Remember: you get out what you put in.
  • Communication is key. Don’t leave them working in a silo; encourage and foster an open-door policy with your VA.
  • Set them up for success. They should have their log-ins and access to every system/tool/software necessary to do their job, as soon as possible. 
  • Use MyTimeIn! It’s the perfect tool for transparency and accountability.
  • Experiment! Once they’re up and running with their trained responsibilities, don’t be afraid to challenge them. Especially once you have perspective on their strengths and weaknesses.

Everyone Wins

So, what are you actually waiting for? If you are like a majority of our clients and seek to get more time back as well as increase revenue, then you’re in the right place. You just need to take one more baby step and talk to us about your individual needs and concerns. That’s why we have an open door for all curious business owners, to answer any questions you have via phone call with one of our experts. You can request a session with the link below. No obligations, no pressure, just knowledge. You have nothing to lose and everything to gain.

Related Posts