How to Hire Virtual Assistants Who Stay and Get the Details Right

In January 2019, Lead Cookie and Content Allies had a team of over 20 virtual assistants working with us. They ran most of our day-to-day work. Our success rate when hiring a new assistant was 95%+, and only two team members had ever left.

It wasn't always like that. In the early days of Lead Cookie we were at about 50%: most hires didn't work out. Assistants disappeared, made mistakes or didn't show up. On the content side, I hired four freelance assistants from Upwork to publish my content before I figured this out, and each of them flaked out.

What fixed it was a structured hiring process and a culture people wanted to stay in. I wrote this playbook in January 2019, while running Lead Cookie, the LinkedIn prospecting company I built and later sold. The process below explains what to delegate, how to screen applicants and how to keep them, with current guidance on pay and hiring platforms.

Why virtual assistant hires fail

Most people like the idea of a virtual assistant. They post a job on a freelance marketplace and expect it to solve their problems. Then the work comes back poor, the assistant disappears for days, and the details get missed. Many give up and go back to doing everything themselves.

In my experience, four things lead to that failure.

1. Sending the wrong kind of work

Assistants, especially offshore team members, are not at their best with random requests. Taking whatever you hate doing and sending it to an assistant usually doesn't work.

They do best with a repeatable process you run every day or every week. Our team at Lead Cookie handled work like this:

• Updating the CRM, including from email notifications
• Publishing my blog posts, my podcast and my daily blog to my website
• Sharing my content on social media
• Sending me a daily summary of upcoming calls, with relevant links for each prospect
• Handling steps in customer onboarding
• Cleaning up lists of data

Every one of these is repetitive and runs on a schedule. We trained the assistant once, documented it, and they handled it from then on. For my podcast, I got to the point where I recorded the episode, emailed the audio file and the headline, and the team handled everything else.

2. Poor training and delegation

One of my mentors told me something that changed how I managed people:

Whenever you are having a problem with a team member, 90% of the time you are the problem in how you are delegating and managing them.

When someone doesn't produce the result you wanted, it is easy to blame the person and decide you "can't find a decent VA." More often the expectations or timelines were never clear, or the training at the start was never done. There are unreliable assistants out there. Too often, though, the problem is how the work was handed over.

3. Hiring without a filter

When I wrote this, a site like Upwork listed thousands of virtual assistants at extremely low prices, and they were not all equal. You need a systematic, predictable way to find strong candidates and screen out the weak ones. The application below is that filter.

4. Treating assistants as disposable

Even a good assistant will leave if the working relationship is poor: inconsistent work, two months of silence followed by a demand for 20 hours this week, no recognition when they do something well.

They may be on the other side of the world, but they are people with families and lives. Treat them as you would a neighbor or a close friend.

What to pay a virtual assistant

Rates depend on the skills you need. My 2019 figures were for an admin-level assistant: no design or development skills, but good communication, attention to detail and the ability to handle standard tasks.

For someone full-time in the Philippines, Colombia or Southeast Asia, they started at $400 a month at the absolute low end. At that level I expected people who could run a process we taught them and deliver a consistent result. From $500 to $750 a month we found people with excellent communication who learned quickly and could make more of their own decisions. Lead Cookie had a mix of both levels.

Those are 2019 numbers. OnlineJobs.ph, the Philippine job board, publishes a salary guide, last updated in April 2026 (opens in a new tab), drawn from its own database. For a full-time virtual assistant, its monthly table runs from $480 to $900 for a beginner, $800 to $1,100 for an intermediate and $1,200 to $2,000 for an expert. My $400 floor is below its beginner range, and the $500 to $750 I described for strong communicators sits inside it. The guide recommends a monthly salary for someone joining your team, and around $4 to $7 an hour if you are unsure where to start.

Two parts of my old advice still hold. When you find someone with strong communication and problem solving, plan to give them a raise over time to keep them. And don't underpay: the same guide says underpaying often leads to higher turnover. It also recommends paying new hires weekly for the first couple of months, which helps build trust.

Where to find virtual assistants

Four current options, from a freelance marketplace to a managed service. Prices and terms are the sites' own.

A marketplace or job board puts the hiring, training and culture in your hands, which is where this playbook applies. A managed service such as The Virtual Hub takes on recruiting and training for a monthly fee; its homepage carries a testimonial from Verne Harnish, the founder of Scaling Up.

The application that finds the right assistant

I assembled this application from authors including Mike Michalowicz, Russ Perry and Chet Holmes, and from others I can't remember. It has five parts, and it gets you to the right candidate quickly.

Sell the job

Most job posts are a dull list of duties and required skills. That attracts anyone. Instead, sell the applicant on why they should apply: talk about your culture, how you are growing and what you value. Show some personality.

A post like that brings more candidates and better ones. Several of our team members told me that when they saw the Lead Cookie job post, they wondered whether it was even real because it sounded too good to be true. They applied anyway, and they joined us.

Hide instructions that test attention to detail

Every job post I put up included what I called Easter eggs: small instructions hidden in the text that catch whether someone actually read the post or sent the same cover letter they send everyone. These are the ones I used:

1. In a random paragraph of the post: "For the first word of your cover letter, write the word 'Moist'." In 2019 I wrote that this alone would disqualify 80% of applications before I opened them.
2. Include a funny YouTube video with your application, no longer than 30 seconds. One of our values was "Have fun", so this screened for culture fit and for who caught the 30-second limit.
3. In the voice memo, say "Moist" as the first word and "Toodaloo" as the last.
4. Upload the voice memo or video to Dropbox and make that link the last item in the application. We listed the Dropbox upload as step 3 but told applicants to put the link last.

Before reading an application, I checked two things. Is "Moist" the first word of the cover letter? Is the Dropbox link the last thing in the application? Plenty of applicants used Google Drive instead, or put the link somewhere else, and that ended it. Dropbox Basic (opens in a new tab) still offers a free account. Some applicants even wrote to complain about the word "Moist", which told us they were not a fit for our culture.

Image

Zoom

Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

Ask questions that show your values

I was still adding this part when I wrote the playbook. Until then, the hires that failed tended to fail on a mismatch of values.

At Russ Perry's business summit, he shared Design Pickle's hiring process at the time. Its applications and interviews included questions that reflect its values, such as "What is one thing you are obsessed with?" Their best team members all had some interest they were passionate about, and the question found people like that.

Jon Tucker of HelpFlow, a friend, asked applicants, "What are the last three books you have read about personal or professional development?" Personal growth was one of their values, and the question found people who were actively reading to improve.

Set a small test project

At Content Allies we used a simple test: the applicant set up a free blog on Tumblr and created a post with specific information, following instructions we gave them. Every applicant did the same task, so we had a benchmark to compare them against. This was another idea from Russ Perry's summit.

At Lead Cookie we also asked a scenario question: "You are working in one of our client's accounts and you make a mistake and accidentally send the wrong message. What are your next steps?" Many of them would face exactly that, so it showed how they would think it through.

If you hire through Upwork, its help center lists free work among the jobs it does not allow (opens in a new tab), so the test project has to be a paid contract at or above its minimum rate.

Ask for a recorded message

The last part asked for a voice memo or video on why the applicant would be a good fit, with hidden instructions in it too: "Moist" as the first word, "Toodaloo" as the last, and Mozart's 5th Symphony playing in the background. That takes real effort, and it screens out many people.

It is also one of the most telling parts of an application. For an assistant, communication matters enormously, and a recording shows it directly, along with commitment and interest. Some applicants said little more than that they were recording the video to meet the requirements. Others told us about their background, their credentials and their life stories. You can guess which ones we hired.

How to keep virtual assistants

A fellow founder once asked me how I kept my assistants, because nobody stayed with him for more than a month or two. My answer was culture. On my podcast in February 2019 I added the condition that matters: if you are paying a market wage and still can't keep anyone past two months, the problem is probably the culture.

Of the more than 20 assistants we had in January 2019, two had ever left. One was approved to immigrate to Australia, and the economics of working with us no longer made sense. The other was offered a job at triple the pay. Everyone else had stayed.

We treated them as part of the team, because they were:

• Every assistant was invited to our weekly stand-up meeting.
• They shared weekend updates like the rest of the team, and they could raise ideas or problems.
• They could take time off, just like the team in North America.
• We gave holiday bonuses.
• A "VA of the Month" award, voted on by our North American team, came with a small cash bonus.
• We started a personal development fund of $50 a quarter for every team member, and extended it to the team abroad.

In 2019 I wrote that most offshore team members were not used to this. People on my team told me about earlier jobs: one had been required to work 60 hours a week to keep his job; some freelanced for clients who went quiet for weeks and then sent a burst of work and were upset when it wasn't perfect; others had spent two to four hours a day commuting to call center offices. Most could not imagine time off without a pay cut, and almost none had ever received a development fund from an employer.

Image

Zoom

Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

Building a workplace that respects people doesn't cost much. It takes consistent work, fair pay and real care, and that is how you keep a team. By May 2025 I had finally made the trip to visit my team in the Philippines (opens in a new tab) for a three-day team get-together; one of the people I met there was one of our top podcast producers, and still with us at the time.

What still holds, and what has changed

Most of this playbook holds. Give assistants repeatable work, document it once, filter applicants for attention to detail and communication, and treat them as members of the team. These are the parts that changed since 2019:

• Pay. My 2019 rates sit at or below the beginner range in OnlineJobs.ph's April 2026 guide ($480 to $900 a month for a full-time virtual assistant). Budget from a current guide.
• Paid tests. Upwork does not allow free work, so any test project run there is a paid contract at or above its minimum rate.
• LinkedIn work. Our assistants also sent LinkedIn connection requests and drip messages, and scraped email lists for cold email. Where that work runs inside someone's LinkedIn account, LinkedIn's User Agreement, effective November 3, 2025 (opens in a new tab), asks members to keep their password secret and not share their account, and bars bots and unauthorized automated methods for sending messages, and tools that scrape the site. Its help page on prohibited software (opens in a new tab) warns that accounts using them risk being restricted or shut down. Don't give an assistant your LinkedIn login or a scraping tool.
• Where to hire. The table above compares four current hiring routes, with their fees and terms.
• Content Allies. I launched it in January 2019 as a virtual-assistant service for content marketers and shut that version down a few weeks later. The name came back for my B2B podcast production agency, which is how its site (opens in a new tab) described it in October 2026.

The constant is the one I started with: when an assistant fails, look first at the work you gave them, how you trained them and how you treated them. Get that right and a good team takes the repetitive work off your plate, and the job you offer can change things for them too.