How To Hire People On Upwork

This is how I hire the right people through upwork, it’s a little more work, but the outcome will make your life much, much easier. This is just my take on it through my experience and I hope it helps!

Why I’m writing this?

I held onto an employee for a full year after I knew she sucked because of my emotions. She had a family and needed the work, but this is the worst thing you can do to a person. The position probably just wasn’t good for her and maybe she will excel at something else. By not firing her earlier she continued to be sub par in this position and never grew and learned. Maybe in another company she is leading the pack now, where she wants to go above and beyond because she’s doing things that are more interesting to her! (She actually asks me for work all the time, and sometimes people just suck period as well. haha)

Anyways, this is how I setup my Upwork listing for a Virtual Assistant. I have other tips for my designer position as well, but we will stick to VA for now. I will go through the process in the same order that upwork presents it so you can follow along once you create your job post!


Title: In search of a Superstar virtual assistant to add to my team! Great opportunity for long term work!

Key takeaways: Superstar typically means the best, and if you have a team, you sound allot more reputable, even if you don’t have a team, say that. Long term work is what every remote worker wants, I have been able to cut peoples hourly prices in half by saying this will be a long term position, it’s powerful.


I am looking for a VA to take care of simple to moderately complex tasks in my business. I will go into detail about these tasks in our interview.

Fluent English and faster internet speed is a requirement for this job. Customer Support and social media experience is also very important.

I would only like the hardest working VA, I am looking for a superstar. You will be rewarded for putting in more effort and going beyond expectations, I want to stress this.

You will be trained by my main virtual assistant, so attention to detail and a fast learning curve is a huge perk. Also being up to the times with trending shows, movies and other pop culture things is great!

If all is well and I am happy with your work ethic, your work pace and willingness to learn and implement these skills, this will be a very long secure job for you. My current assistant has been with me for 4 years. Please refer to me as Mr. LAST NAME when replying to this job.

I am looking forward to speaking with you!


Aref Madi

Key takeaways

Explain what exactly the job tasks will be, I don’t go too far into detail as I am typically training them, I am not hiring them based on their current skill level, but their willingness to learn and work ethic.

Fluent English and faster internet speed is very important to me for the job typically, think of what will be a requirement and any other assets you would like the potential VA to have experience in.

I like to literally tell them straight up what I am looking for and they will be rewarded. Being straightforward and honest is important to get the result we are looking for. Actually rewarding your employees is important, I give my main VA seasonal bonuses, and everytime she does something clever to save us time I throw her $20-$100 extra. I only pay her $5.50 an hour, so it definitely encourages her to go above and beyond.

Here I say a few more things I am looking for in the individual, “attention to detail and a fast learning curve is a huge perk. Also being up to the times with trending shows, movies and other pop culture things is great!” Whatever would be beneficial to the position you are looking to fill, add that here and if they will be trained by you or someone else.

Basically I explain they need to put their money where their mouth is and they will be taken care of with a long term secure job, cause that’s what everyone wants in reality. Remember these are people just like me and you, all the benefits we would want, applies to them as well. I add that my current assistant has been with me for 4 years, which further shows the security of the position.

I say “Please refer to me as Mr.Madi when replying to this job.” so as soon as you see “dear sir” “hi aref” ect on the job application/cover letter, I don’t even read it and decline them. These people are most likely throwing applications to every post they see, we don’t want them and shouldn’t consider them if they can’t take the time to even read the entire application.

Details & Screening Questions

To give you an idea, you can change the questions to suit the position you are looking to fill. Also I select the ongoing project option here and I do have them required to add a cover letter.

What kind of experience do you have online and how long have you done this?

What qualities do you have that puts you ahead of all other applicants and why should I choose you?

Are you currently working for anyone else, and how many hours can you put in daily? Is working the weekend a problem?


Select what makes sense for your position here. I selected everything that I think would be important for the specific VA position I am hiring for.


I select “any one” option here so anyone can find the listing and one freelancer unless you want more, but I like doing one by one as you will get more applications each time from each new submission.

Talent Preferences

This is an optional setting that I always use, I will go through what and why. 

Talent type

I always go with independant, I don’t want to work with an agency as you will have much less freedom in almost every aspect.


Typically I leave this blank, there are people who are amazing from all places in the world. I’d say I really enjoy working with Philipenos, just generally really nice hard working appreciative people. I have hired people from India as well and have one working for me right now, so don’t make this a deciding factor. 

Job Success Score

90% & up. We only want to work with the best.

Amount earned

I leave this to any amount earned, you can change it to 1k earned, but I like to check out the people who just got on the platform, sometimes they are real gems that people don’t hire because of the lack of history on upwork. But in reality they worked at a call center for the last 15 years and want out of the corporate world.

English Level

Fluent or Better. Communication is key, you don’t want any complications here.


How would you like to pay your freelancer or agency

I select pay by the hour for VAs and fixed price for designers as I pay by the design.

What level of experience should your freelancer have

This has nothing to do with experience, they word it this way so you think you have to pay more to get someone with more experience which isn’t the case. I always select the entry level.

Do you have a time requirement for this project?

Put whatever amount of time you think they will be working.

Go through the options that they generate for you and see if you can find any potential matches. Do not send any invitations to anyone you are not 100% sure about, because upwork doesn’t let you send unlimited anymore, they charge you for additional invites. You will get people applying to the job as well, so maybe throw out half your invites and wait to see what kind of people apply to the job.

And that’s it on the upwork side, now for the interview!


Once you start getting applications, make sure they refer to you as your last name. Once you find a candidate and you like what you see, accept the chat on upwork. I typically try and get them off upwork to voice chat on skype. If they can’t voice chat that means they probably aren’t fluent English speakers and you should move on.

So as an example “Hey there Ana, thank you so much for your application! You look like a great fit for this position, but I would like to discuss some of the details over skype in a voice chat, would you be available sometime in the near future to get this interview in?”

Note: Upwork will tell you not to leave the platform and use their voice chat as soon as you say skype, don’t worry about it. Just make sure not to mention anything about Paypal.

Once you get the skype interview scheduled I ask these kinds of questions:

Interview business side kind of questions examples

What makes you the most qualified person for this job? (ask questions about whatever they say) 

What’s your primary source of income right now? How long have you been doing that?

What skills do you have that will be an asset to this position?

Interview personal side kind of questions examples

Would you consider yourself an optimist/positive person typically?

Where do you see yourself in a year from now? Are you working on new skills or teaching yourself something?

How important is your health to you? Do you workout/stay active?

What are your 1 year, 5 year and 10 year goals?

Sometimes I do more or less, but I think you get the idea. Ask the questions strategically to get the info you want to know. I am pretty sure I don’t want to work with a negative nancy or someone who has health problems cause they sit around all day and eat bad food. Sure they can lie about this, but you will be able to tell. Try and ask if they have a family indirectly, typically when they talk about their goals they should mention something about their family. A father/mother of 3 is much more reliable than a single younger individual.

Think about the long term and how important this individual will be in your operation. Do the work early so you are not faced with replacing all your staff in the future.


Typically I cut down their rate by allot because upwork makes the minimum $7 an hour, and that isn’t what I want to pay. Most people would rather have the work at $3-4 an hour than no work at all, especially overseas where the USD goes much further. When I ask this question I say, “during your training phase I would like to pay you $x an hour, once you become more experienced we can look into increasing your hourly rate, does that work for you?”

I have literally done this with every VA I have worked with and they all agree. Remember, this is a long term position, and that’s all that matters to them, especially if they have a family to support. The rate you offer is up to you, my main va started at $3 an hour and over the years is now at $5.50, she literally takes care of all fulfilment and support on her own.

I always like to add this in the interview at the end, something along the lines of “I always like to give my employees the option to get paid through Paypal, I know you will make more money this way, but you will also have no record of working for me on upwork. So please let me know your opinion on this. One of my current employees gets paid through Paypal and one through upwork, so it’s really up to you!”

Things to consider

Like I mentioned before, I like to give out bonuses. You have to think about what this person does and the amount of time that person saves you. My assistant is so valuable to me, saving me hundreds of hours, so I treat her that way. If they mess up you should take responsibility and camly show them the proper way or what they did wrong, at the end of the day it’s your fault. My long term assistant made a few bad mistakes and offered to take the pay cut, but it’s all good and our relationship is stronger than ever. Give them a reason to stay if someone else offers them another position.

I think I covered everything, I really hope you guys find this valuable, let me know if you have any questions or anything! Now go hire some superstars!

Leave a Reply

Your email address will not be published. Required fields are marked *