How to hire the best VA ever

And the failures it took to learn this process...

Here’s how I hired the best VA - Virtual Assistant (or EA - Executive Assistant) ever, including the services I used to find and evaluate them, how I work with them today, and the failures and lessons I had to learn along the way (so you don’t have to).

The epic fails will be sprinkled in to each section, as they happened.

1. Who I used to find the best VAs available

2. What services, assessments, & questions I used to test them

3. A note about SOPs

4. What will help to know before working with VAs

5. What are the non-negotiables

6. UPDATE: SOP and weekly agenda examples

Let's go...

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1. Who I used to find the best VAs available

This one is simple. I have only one recommendation.

Talk with Stefan from QuickHireVA.com.

(If you use the code NATERITTER you’ll also get $49.50 off, too, but the affiliate commission is not why I recommend them.)

QuickHireVA asked me about what tasks I wanted taken care of and what was most important to me in an assistant.

Then, they provided 3 candidates for me to interview as I saw fit.

By the end of the process, I honestly was choosing from amazing, great, and fantastic.

The “Don’t do what I did” section

Previously, I hired virtual and executive assistants from the biggest VA companies out there. I also hired from people who were just starting out.

There might be some great VAs in both those channels. I just didn’t find my fit there.

What I didn’t do was go looking outside a native-English speaking country. I thought it would waste my time because I figured there was a high likelihood of having communication and/or cultural issues.

That was partly wrong.

It’s key to have cultural and language alignment, sure. But, just because my native language is not their native doesn’t mean it can’t work. Don’t throw the baby out with the bathwater, as they say.

It should be a factor, but not a filter.

2. What services, assessments, & questions I used to test them

After email introductions were done, I sent each of them two assessment links which I created with the following services:. 

A. TestGorilla.com (free plan)

The history on the Enneagram is a little woo-woo, and I'm more of the logical scientific type, but it's strangely accurate for both myself and everyone I've given it to (including my wife, business partners, employees, bosses, colleagues, etc).

I use it to understand a person's basic motivations, fears, desires, and world views. 

It's obviously generalizing people, so this one should not be a hard pass/fail. But, to get a starting point to ask more questions on later regarding cultural fit, it’s more than helpful.

I call it the “not-personality-test”, because the results also seem to stick throughout a person’s life, and are not as contextually volatile as other assessments.

Here's some sample preview questions I used.

TestGorilla screenshot:

B. Testlify.com (using their free trial period). 

I chose the "Virtual Assistant" assessment and added 5 additional questions they had to complete with video or open ended text (see screenshots for additional questions I asked). 

The goal here was to evaluate whether they are organized, good at time management and problem-solving, have good customer service skills, and can be discreet with confidential information. 

I also use this one to weed out anyone who simply didn't complete the task at all since showing up is a prerequisite.

Testlify screenshots:

Once the applicants completed the assessments, I interviewed them individually for personality and cultural fit.

I chose the one I thought fit the best and had a call about expectations. This is a key step in the process. Do not skip over this.

I explained:

1. My expectations (time zones, timelines for different examples of work, regularly scheduled meetings, communication methods, documentation, etc)

2. What success looks like to me

3. The process of leveling up - we'd start with small tasks and, if all things went well, move into more complicated ones (i.e., email and calendar were last since they're such a huge part of my daily life).

The “Don’t do what I did” section

With all my previous assistants, I didn’t use assessments, nor communicate my expectations.

Really, I didn’t have a process at all. I simply interviewed them and went with it if I liked them.

Don’t do that.

Think through what your needs and expectations are. Don’t rush the process because you need help.

And if they don’t fit, don’t waste your time and money hiring them. Find another couple candidates.

3. A note about SOPs

The one thing I did do right with previous VAs is ask for SOPs to be written and followed at all times.

If it wasn’t written down somewhere, write it down. Then link it to the appropriate parent doc, and make it searchable.

I expected previous assistants to write the docs, and use them.

Every. Single. Time.

So, I had a bunch of SOPs already written.

Granted, nobody’s perfect, so they weren’t in perfect order, but at least we had a starting point.

We had decision trees and preferences dialed in.

Do this. It’ll help you later when/if we have to part ways for any reason whatsoever, as tragic as that could be, you’ll have a starting point for the next person.

They’ll thank you for making their life (and yours, by extension) that much easier.

The “Don’t do what I did” section

Actually, I did this one right. So, don’t.. ahem… not.. do what I… um.. did.

Whatever, just write (or record on Loom) SOPs and preferences you have. The VA will ask you anyway. Might as well just jump the gun and give them what they need to be great.

4. What will help to know before working with VAs

I highly recommend reading Buy Back Your Time by Dan Martell.

There are a few areas in the book which are most relevant to this article, so I highly suggest reading these sections:

• Calculation as to what you should be delegating in dollar terms.

  • For example, don’t give assistants tasks an expert should do, like writing content for your company, specific types of research, or design.

  • Do give them tasks that are the lowest dollar value that you are still stuck doing for some reason or another, don’t want to do, and/or are not great at doing. Those are perfect tasks to give a VA.

• How to decide what to delegate with time audits

  • I do time audits quarterly, now.

  • They help to understand even more of what I mentioned above; things that make you money vs don’t, gives you energy vs saps your energy, and what you’re good at vs not good at.

  • These things change over time.

• How to work with a VA

  • This whole section includes things I didn’t realize I was doing wrong with earlier VAs, as mostly explained in this article.

  • It also gives tactical meeting agendas, SOPs, documents, and more, to help you do it well.

  • In particular, I use the weekly agenda and a modified version of the email labels from the book.

• Explaining adding "context to everything", a principle that's helped me immensely

  • The gist of it is best explained using a calendar event or task. If there’s a task I’m to do, or an event I’m to be present at, everything I need to do the thing or need to know about the person is in the calendar event itself.

  • For travel events this includes booking codes, access instructions, check-in/out times, emergency or host contact phone numbers, email addresses, and best method of contact, addresses linked to Google Maps, links to documents or emails that are helpful to get context on our last communication, etc.

  • The goal is to not have to search in another system for whatever it is I need when I’m doing the thing. Reduce switching costs as much as possible. This is a huge time saver.

The “Don’t do what I did” section

I missed on all of the above.

I didn’t do a time audit. That was dumb, because it took way too long for me to figure out what I should be delegating vs not.

I delegated specialist tasks. I thought it was smarter to have them help me get sales in the door. Don’t do that. They’re not sales people. Don’t expect them to be. They’re not designers or writers either. They’re generalists. Let them be great at that.

I didn’t calculate the cost of the things I was doing myself. If you can outsource something and make 4x your money on that time, do that. Don’t be dumb. Like I was.

5. What are the non-negotiables

Finally, I expect the following with everyone I have the pleasure of working with. I’ve had these expectations for ages, ever since working with my first contractor on my first website.

These are non-negotiable:

A. Proactivity

• Making reversible mistakes is ok.

• Not acting, when the mistake can be reversed, is not ok.

• Try never to make irreversible decisions, or at least push them out as far out into the future as possible.

B. Over-communication

• Tell me why you are doing what you're doing

• Tell me how's it going before I have to ask

• Tell me when we're complete with a task and what the results were

Being proactive and over-communicative can cover a multitude of sins. The more the person is proactive and communicating what they’re doing, the less you have to worry about trust issues, timing, looking over their shoulder, and micromanagement.

These two things give me my sanity back.

Have your own non-negotiables and communicate them early on in the process.

6. SOP and weekly agenda examples

UPDATE: Some people had asked, after publishing this article, for some specific examples.

Weekly agenda example

I started with every other day meetings with my VA, and as mentioned we started small. There was a lot of knowledge transfer about procedures, preferences, and other things to document, so we had a lot to go through at the beginning.

Now, we meet weekly, and our agenda looks like this:

The first two sections are mine to run through. The last 4 are hers. This should be done in 30-40 minutes, but I talk too much, so it takes me 1.5 hours. I strive for 1 hour.

• Nate’s Off-load - Anything on the top of my mind I haven’t already communicated (tasks, high-level objective changes, etc)

• Past Meetings - Every meeting I’ve had, from my calendar. I talk about why I met with them, give context to who they are, and if there’s any to-do’s that should have come from that meeting that didn’t yet. She also has a chance to give thoughts or ideas about what we could do with that person, given she knows me and my business inside out.

• Nate’s Action Items - Tasks she is giving to me. This includes all context necessary to complete the task, listed in the description. We discuss it briefly. If it’s something I could delegate back to her or someone else, I do so then and there. If not, I move the task over to my personal list to do on the appropriate day.

• Feedback Loop on Projects - I usually have some longer-term projects for her to do - research, outreach, communicate with service providers, etc. This is her chance to update me on progress made that week on those items so I don’t have to ask.

• VA’s Items / Emails / Questions - This is where she might have questions related to how to process or handle a particular thing, because it’s not in the SOP. She updates the SOP with my answer and/or handles it accordingly.

• Questions for Nate - This is a time where we can get personal. Am I sleeping well, eating healthy, exercising, spending quality time with the family, etc. Asking these questions (1) keeps me accountable to them and (2) gives her an understanding of my mental state. If I’m floundering somewhere, she’ll be able to adjust to my needs. The goal for her is to to ensure I have time to spend in these places, so whatever she can do to get me back to these priorities, she’ll work towards. If I’m not doing those things, she should know why, and be able to consider ways to help me get back to them.

SOP examples

Dan Martell’s SOPs are a better example than my own because he’s been doing this for years longer and is much more “type A” than I am. So, I recommend you check out his own examples of one of his SOPs.

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That it’s it. Easy peasy.

Go forth and conquer (with an assistant having your back)!

Feel the relief as things get done without you.

Find something better to do with your time. You’re an entrepreneur for goodness sake. I know your to-do list is forever long.

And hey, if you want to dive deeper into strategies like this for growing your agency with recurring revenue, or getting your SaaS business unstuck, grab some time and let’s chat.