First, let’s talk about Upwork.

Upwork is a global freelancing platform that lets you post jobs and hire people for hourly or fixed-price work. It’s not perfect, but it is transparent.

Personally, I don’t make use of screen recording. I prefer to start from a place of trust. I let my VA log her own hours. Most of my work is task-based, so as long as the task gets done to a high standard and within a deadline, I don’t mind when she does it. This flexibility works well for both of us.

I start with a fairly thorough job description. This doesn’t mean that completely inappropriate Upworkers won’t apply but it reduces the likelihood. You can find the job description I used to recruit the amazing Aira >>here. 

The process of posting a job is really simple and can be done in under 5 minutes. With Upwork’s new AI job description creator it can take even less. 

For a quick tutorial on how to post a job ad in Upwork see my 3 minute video walkthrough below.

When selecting candidate preferences, I filter based on:

Location

Most of my hires have been based in Australia (yes, there’s local talent on Upwork too) or the Philippines, due to language fluency, cultural fit, and overlapping working hours.

I’ve found it hard to manage VAs in vastly different timezones unless it’s for very specific tasks. Some of my eCommerce clients solve this by hiring two VAs (one for local daytime hours and another for U.S. coverage on customer service shifts).

As a side note: VAs from the Philippines often handle creative tasks well, especially if you give them detailed brand guidelines and a clear brief. Don’t expect them to guess what good looks like.

Screening Questions

I always ask a screening question. Just a simple one like “How many hours do you estimate it will take you to complete this job?” for a project based job or “List your relevant work experience” will suffice. This helps sort the genuine candidates who read the job description from those who spam job postings with AI generated responses. 

Agencies vs Independent

I don’t tend to hire from agencies for 1:1 work with a single freelancer. They just add fat and another point of contact. Additionally, agencies will often lure you in with the profile of one freelancer with excellent reviews and then switch you to another who may or may not be any good.

Private Jobs

Sometimes, if the job is very specialised, I’ll post a private job on Upwork so that only people I invite can apply. This gives me better control over who I’m considering and saves me from wading through dozens of irrelevant applications.

When the applications start rolling in, don’t panic, just filter with purpose. I start by sorting for the basics: solid star ratings, relevant job history, and hourly rates within budget. Then I look for signs of actual thought in the cover letter. I shortlist the ones who’ve clearly read the brief, reference the task, and ask a smart question or two. The really good applicants have started to add a quick 1-2 minute Loom video to their application. Bonus points if they reference the specific job in the Loom video. It means that the video isn’t a generic one. 

You can shortlist by clicking the ‘Thumbs Up’ icon. I give it 24 hours for the applications to roll in, then choose 3 and send them a message. You have to be ruthless. You’ll get 30+ applications. Don’t get emotional. Keep your objective and what you need top of mind.

Once I’ve shortlisted a few promising candidates, I send a short message with 5 or 6 questions to get a clearer read on how they think and work. Here’s what I ask:

1. What types of clients have you worked with before?

2. What are your favourite kinds of tasks?

3. How stable is your internet connection?

4. If I gave you a task with a rough brief and no SOP, how would you approach it?

5. Do you have any questions or feedback about the job post?

6. What’s your general availability week to week and what hours do you prefer to work day to day?

If you are serious about working with this VA for the long term, I’d also suggest that you schedule a video call. You can do that within the platform. Yes, it makes it harder to say no to the unsuccessful candidates when the time comes but you’ll get a better candidate. It’s short term discomfort for a long term payoff.

NOTE: If you give them your email address or try to contact them outside Upwork before you offer them the job, you’ll be banned from the platform, initially for 24 hours. Keep comms within the platform. Honestly, the dispute resolution process, easy billing and separate comms channel is worth keeping it within the platform. There is literally no downside for the client.

I don’t love wasting money on VA trials that don’t work out. I also hate rejecting people. But I’ve been burned too many times by jumping in too fast.

So now, I pay to test 2–3 VAs, each on a short, specific task:

This gives me a sense of their communication style, initiative, quality of work, and how they follow instructions.

Each candidate gets the same task. They’re paid hourly, but I cap the hours at 8 per person to avoid bill shock. I also budget the recruitment process as a project in itself: 3 people x 8 hours = 24 hours. That’s manageable.

Because I hate disappointing people, I prepare a short rejection message before I even post the job. And I make sure the job post clearly states that the role involves a trial:

This sets expectations early and saves awkward conversations later. I’ve even ended up recommending second-best candidates to friends or clients who needed help. So their effort doesn’t go to waste.

Once the job is complete and it is clear who I wish to work with ongoing, I always thank the unsuccessful candidates for their time, tell them they were great and that I found someone with a more relevant skill set. They too know it’s a numbers game and you’ve paid them for their time so it’s a win/win.

To brief the candidates, I’ll record a Loom video. If I’m being really professional, I’ll also knock together a SOP in Clickup. Even better, I’ll get them to write their own SOP as they complete the task. 

To give them access to my software, I use Lastpass. NEVER give your passwords out to an Upworker. 

When the tests are done, I choose the VA who’s not only skilled, but also:

The red flags?

I want someone who’ll improve my processes. So I actively ask for their feedback. What’s unclear, what could be better, what would help them work faster or smarter? A good VA will speak up.

All up, this entire process from beginning to end, including job briefing and 3 x 30 minute interviews takes about 8 hours of my time. So you’ll need to factor that into your week. If you cut corners, you’ll brief candidates poorly, waste everyone’s time and end up in the same position you were 2 weeks ago but 24 hours of salary and 4 hours in the hole with no upside.

Hiring well on Upwork takes a little bit of effort in the short term. But once you find the right person, it frees up your headspace, your calendar, and your capacity to focus on the work only you can do.

It’s a small investment for a huge long term benefit. 

Not sure which task to handover first? See my list of >>100 Things Your VA Can Do for You Before You’ve Eaten Breakfast.

Got 99 problems but your diary isn’t one? Book into a >>free 20 minute strategy session with me to get unstuck and chat about what you need.