How we completed orientation for our new virtual assistant in just 1 week

How we completed orientation for our new virtual assistant in just one week-53.jpg

A couple weeks ago we found the perfect replacement for my VA role, but we were under a bit of a time crunch to get our new hire, Dean, all oriented to my business and ready to work!

The week after hiring on my new assistant I was heading to a conference for the full week. I knew before I left that I’d have next to no time to send over instructions or logins or answers while at the conference, so I wanted to have her fully oriented in my business and ready to work solo within a week.

And the great news? We did it! I headed off to the conference knowing my business was totally taken care of and didn’t stress for a moment about customers being served or content going out correctly.

So how did we get her completely ready to work, including handling those unusual, out of left field issues that sometimes come flying our way in just a week?

Here’s how we did it!

1. Prepare orientation materials in advance

During the weeks we were scouting candidates and hiring on a new assistant, we were also handling 2 other major projects, launching my podcast and getting onboarded with our new FB ads team to start running ads. It was a month of juggling a lot of important projects all at once.

This meant we really did not have time to suddenly document how we handle everything in my business to help someone new learn how the business functions.

Thankfully, we were well prepared to bring on someone new at any point. My old assistant, Mary, very kindly gave me a solid heads up months in advance of when she would be heading out, meaning we knew that everything and anything she normally did we had to turn into SOPs.

In the months between when Mary let me know she’d be leaving and hiring on her replacement Dean, we made a conscious effort to create orientation video tutorials, to write out our policies and make ALL of the canned email responses.

Writing policies:

I never thought my business would have ‘policies,’ they sound super corporate and serious, but as it turns out, they’re a necessary evil and now we have them.

Previously Mary and I basically just made judgement calls when sticky situations arose and then remembered what we did last time if it ever happened again.

We had to write policies for things like how we count the 7 day refund period (does the day they buy count? What if they bought at 11:59 PM?), what happens when someone defaults on their payment plan, what happens when a student accidentally missed all the Q+A calls that goes with their course, what happens when someone requests a longer, more affordable payment plan for a course, etc.

But of course, having all that info in our brains wouldn’t be much help to someone new, so instead we wrote our answer for each of these situations into a policies document. Legit, right?

Creating orientation videos:

Hands down my new favorite software is Loom!

(Is it lame that I have a favorite software? Whateves 😂.)

How our softwares all work together can get pretty confusing, and how to use the softwares correctly in certain situations can be tough, so we’ve recorded a video on how we pretty much do all the things in my business!

We have them all housed in Asana in an ‘orientation materials’ project. We’ve organized them into columns based on what aspect of the business they’re related to. Inside each card there’s a link to a Loom video with the explainer.

We didn’t ask my new assistant to go through all of these orientation materials, just made her aware of where they were and to check there first in case she got stuck with an issue which worked out perfectly.

In order for us to create these, anytime we’d do a task that didn’t already have a video, we’d click ‘record’ on Loom and walk through whatever we were doing both by explaining the instructions and showing where to click in the video.

Using Loom made creating these SOPs as simple as absolutely possible and not some massive undertaking like writing out the steps for each and taking screenshots and then arranging them into a document like is normally done with SOPs.

(I also use Loom to explain more complicated tasks to my assistant. Often my tasks to her look like ‘Fix XYZ issue - see video’.)


2. Give logins

My new assistant would be a bit helpless without access to all of our softwares, so our first step after hiring her and signing the contract was to get her all the logins she would need.

We use 1Password to store our logins, so we added her on to that… but the login fun doesn’t end there. A lot of softwares, eg. GSuite and our payment processor, take a lot of effort to get someone into, so we worked on that during our live call.


3. Held an orientation call + finished logins

We don’t by any means have some massive corporate rah-rah brain washing orientation (lookin’ at you Starbs and Lulu), but we do have a little powerpoint presentation that walks through important aspect of the business which anyone who works for us should know.

This live video call is where we go through the history of the business, our mission and values, our offerings, how to get paid, a look at the calendar of the year to come, and upcoming goals.

After we’ve wrapped that bit up, we have to finish getting the new hire into any hard-to-access softwares. We do this while live on the call because often security login confirmation codes expire within a certain period of time, so we’ve found doing this on the live call very helpful. We make sure they can access every single software before getting off the call.

We then go through their tasks for the day, clarify anything confusing and let them get to work!

We strategically give them a lot of tasks in the first week, one of everything they’re likely to do in the future. We do this because we want them to do every task once before training week is over, because I’ve purposefully set aside time in my week to answer their questions and help solve issues. I’d prefer to spend a lot of time helping them in the first week than having to take time out of my day for weeks or months in the future helping with these issues.

We did however leave course launching training until the next launch instead of doing it in training week, and I just know that during that first launch with a new hire, I’ll need to be super available again. We determined that with a launch so far off, it’d be too abstract and the new hire wouldn’t know what questions to ask until they were in it, so that’s why we left that training until later.

We also pick a time for calls for the rest of the week.


4. Daily check in calls

We held a 20-30 min call every day for the rest of the week as well. Often if you need to set up a call or send a message asking for help on a small issue, you might be less likely to do it and just guess because it feels like too much to ask. Instead, when there’s a time set and in the calendar for a new hire to ask questions, they’re more likely to ask everything and anything on their mind.

So I encouraged Dean to write down all the questions she had from any tasks she was doing the day before or about any tasks set for that day and we went through them on the call.

We made sure that we didn’t have her doing anything time-sensitive, so that if she got stuck in a task, she didn’t feel pressure to finish it without first being able to get on a call and get answers.


5. Give permission

I make a conscious point to give my assistants permission and let them know I trust their judgement.

In the 4 Hour Workweek by Tim Ferriss he mentioned that he was doing 40 hours a week of customer service, fighting fires and answering questions. He’d get interrupted with special product requests or customs forms from the assistants he had hired to deal with customers and it was taking up a ton of his time.

So he tried out giving power and permission to his customer service agents instead. “If it involves less than $100, please make the decision yourself,” he told his team.

He found that suddenly when people had permission and the power to make decisions themselves, they became “significantly more intelligent” and were able to solve almost all of the problems themselves.

I know that it puts people in a real pickle when they’re presented with an issue but don’t know if they’re allowed to make a decision on it or if they need to get permission first. This is especially a problem if the person they need to get permission from isn’t around or easily accessible.

So I give my assistants permission to make decisions for me, permission to use their best judgement, permission to do things in whatever way works best for them, and permission to suggest better options or ideas.

I hire people who have brains and who actually use them, and then I let go and have all the confidence in them to do what’s right in any situation.

I really don’t want to put my assistants in the situation where they’re stuck not knowing if they can make a decision, so that’s why I give them permission in advance.

I give it during our orientation call and then again anytime I know I’ll be less available than normal (eg. conferences and vacations).

I make a point to tell them to use their best judgement with any issues and to feel free to decide on whatever is necessary. I tell them do whatever they would do if my business was their own, and it’d probably be the same decision I would have made.

My new assistant was quite surprised at how hands off I was when I headed to a conference for a week recently and mentioned that it gave her a lot of confidence in her ability to do her job, which is exactly what I would have hoped for!


I’m happy to report that after going through this process, my new assistant was totally self-sufficient to run my business while I was gone when it was just her 2nd week on the job!

So if you’re also looking to actually get yourself out of the weeds of your business and get to working on some major projects that only you can (or taking a vacation business-care-free!), then feel free to go through the same process too!