Posted in: Uncategorized

Hiring (and Firing) on Upwork

Upwork for Your Business

Upwork is an online workplace that can connect you to a pool of contractors from all over the world. If you use it properly, you can find reliable contractors who you can build long-term partnership with. If you are able to do this, you can run your future projects more efficiently and with greater ease since you already have a go-to team that you can tap instantly.

Let me give you a quick overview on how to do the hiring process right with Upwork (or of course, any other platform like Freelancer, Guru, etc).

Job Posting in General

The success of hiring the right person on Upwork depends greatly on the job posting.

In the past, I experienced a lot of frustration when hiring people from a job site called Seek ( The number of generic cover letters I received was shocking and usually it was from Easterners, particularly Indians. I haven’t lived in India however having visited there, and having run a company in China as well as living in Indonesia, I can somewhat understand the cultural reasons for the many generic cover letters.

The problem is, this has wasted my time, and I can predict that the exact same thing will happen on Upwork or other similar job sites.

To avoid this from happening, I created an initial FILTER for applicants.

In ALL my Seek job postings as I do in ALL my Upwork job postings, I put a spelling mistake in the job description and mention: “those who are good at finding spelling mistakes in job postings will most likely be the ones to receive an interview”.

So, it was a subtle hint that only those “on the ball” would take the instruction and follow it. Any job application without reference to the spelling mistake went directly to the bin. Simple. I can’t work with people who do not have attention to detail or are simply too lazy to take notice of such things.

I not only highly recommend doing the same on Upwork – it’s the only way I hire now. Within my job posting I’ll slip in, “… and you must tell me your favourite colour…” or, “… and tell me capital of Vanuatu”. Every single person that answers that question, is considered for the job. Every person that doesn’t… I don’t even look at their application or profile. If you read no further, then simply implement that tactic and you’ll end up with quality contractors on your team.


The Structure of a Good Job Posting

Since the job posting is the secret ingredient for a successful hire on Upwork, let me show you how to structure it correctly.

1. Decide if you want an individual contractor or a contractor working as part of an agency. An agency is someone who has 5 or 10 or 50 Upwork contractors “under” them. You deal with the agency manager and they deal with the contractor. I never liked doing that. It meant that I didn’t have direct communication with the contractor. Often the agency manager would say it’s because the contractor doesn’t speak English. This means not only do I have to communicate through an agency manager, but then they have to translate messages to the contractor. If you’ve been in business long enough (or just lived long enough) you know that passing the message is the main cause of misunderstanding. There is no time for poor communication and misunderstanding if you want your business to succeed.

At the very start of your job posting, put:


2. Briefly outline who you are and what your business needs. Many employers on Upwork are just as bad as some contractors. They post jobs and never hire. Make your applicants feel confident that you’re a legitimate company, you’ve hired on Upwork (or on other online work platforms) before, and you’re serious about employing people.

3. Write the description of the actual job that you need to get done. Be VERY specific about what it is that you want, when it should be completed, and other essential information that the applicant needs to know about.

When I write the job description, I make sure that the details are written as clearly as possible. I mention what my requirements are, particularly the skills that the contractor must possess and what should be accomplished for the application process and for the actual job. I also put a specific schedule whenever possible.

Pro Tip: If you don’t want to draw attention to what you are doing, keep your job description vague and discuss details only with parties you are interested in working with. You can also make your job visible only to registered Upwork users rather than having it come up on search engines.

4. In the past, Upwork only required the contractor to write a cover letter in order to submit an application. This just caused more applicants to send generic cover letters, or worse, other applicants used automation (auto-send, robotic app) to submit applications even without reading (and understanding) the job posting.

You can now choose from the pre-formulated questions on Upwork or add your own custom questions that applicants must answer. I don’t use this feature. I’m guessing Upwork implemented the ability to ask question because of the huge amount of generic cover letters. The problem is, if I have to prompt someone to answer questions to compensate for a generic cover letter, then I don’t want to employ them!

My preference is still to ask the questions within the job description itself. If people don’t answer the questions, then they don’t get hires.

5. Specify other criteria for application such as having 5 out of 5 English, at least 100 hours under their belt, 5 star feedback rating, etc. You can always lower the criteria as deemed necessary. You can also specify the hourly rate or the fixed price you’re willing to pay for, but I tend not to request this because I’m actually happy for someone experienced and in the US to apply at $30 per hour if they can convince me that they’re awesome. Sometimes, I end up paying the higher rate because they are actually awesome. And it’s always good to build a list of potential contractors you might use on another job in the future.

If you want a fixed price job, then make sure you put enough information about the scope of the job in the posting so people can accurately quote a fixed price. For me, if the job is really simple and clear, I insist they offer a fixed price. I decline anyone who doesn’t give a price and just want to discuss it on Skype. One problem with fixed price jobs is you have to set your budget. I did an experiment on Upwork. I posted the same simple job twice, once for $5 and once for $50,000, both fixed price. I got the same number and quality of applicants, each group quoting me $5 and $50,000, respectively. The lesson: no matter what budget I put, they’ll just say they can do it for that budget. So now I post all jobs that have a really clear scope as hourly and in the text of the job I insist on a fixed price to be quoted.

If you do create a fixed price job and want to attract the better developers, set your fixed price to $500 or more. Quality contractors will be actively seeking for jobs of $500 or more.

Believe it or not, even after putting much effort in constructing your job posting, you’ll still get generic cover letters from people who clearly haven’t read it. I decline them as “spam application – recycled cover letter” and move on.

6. Time your job posting. Since Upwork is a global work platform, you should understand that people from all over the world can see and potentially apply to your job posting. It is best to post it during the time of day when your target contractors are awake or active on Upwork.

Think about the time zone where you’d like applicants from. If you post on a Monday morning, Australian time, but you’re looking for US applicants, then they’re not going to see your ad for another 12 hours. 12 hours is a long time for an Upwork job posting and in that time you may have many applicants already from other regions, and your ad is no longer a “new” ad.

Another important note is that generally speaking, Asian culture really respect weekends as a non-working time, more so than Westerners. Posting a job on a Friday night or a weekend is unlikely to get many quality applicants from the Asian region. By Monday, applicants will see that 10 people have already applied and it’s been 2 or 3 days since it was posted – they’re likely not to apply by then.

If the general process of creating a job posting will not work for you then you can just invite workers who have matching experience. For instance, if you are looking for Joomla help, search for workers with Joomla experience and good ratings. Sort them by the by the last active date and then invite them to your project. If you really get fed up with hundreds of generic applications, then post your job but make it hidden, and then just invite contractors directly.

Pro Tip: If you are worried about protecting your intellectual property or idea, create an NDA and make sure you are exchanging it with a real entity. Make your terms and conditions reasonable (most of these sites have a standard NDA you can modify).


Trimming the Pack

Once you’ve published your job posting on Upwork, the meticulous process of finding the right applicant begins. With tons of application, here’s what I usually do to trim down the applicants until the search leads me to the right contractor.

  1. Anyone that didn’t answer the “hidden” question, I decline
  2. Any that are definitely over my required hourly rate / budget I decline with “rate / bid too high”
  3. If I have a lot of applications, any with 0 feedback or 0 work history, I decline as “preferred other applicants”
  4. I then sort the applications (you can open each application up in a new tab in your browser and then move the tabs around, ordered from “worst” to “best”). You can sort them by hourly rate (that’s what I do), or by how many criteria they filled (English skills, hours under their belt, star rating, etc).
  5. It’s only then I actually read their full cover letter, work history, etc…

These rules of thumb have helped me avoid wasting time on applicants with no potential to make the project successful. These also made the hiring process more manageable since I only have a handful of applicants to deal with afterwards.


The Hiring Process

The hiring process is tricky, but having a set of rules can make it easier to handle. After publishing the job posting and trimming your pool of potential contractors, here’s what you need to keep in mind next.

  1. Don’t interview too early. For me, as a contractor, if I see a job I like but 10 people have applied and 3 are being interviewed, I normally won’t apply. More so, if my rate is $70 per hour and they’re interviewing people with an average rate of $4 per hour, then I definitely won’t apply. I prefer to give it 8 – 12 hours at least before interviewing so contractors from all walks of life are encouraged to apply.
  2. Any with negative feedback in the last few jobs, I decline
  3. If there are not many feedback, and the only ones are for small ($5 or $20) jobs, it’s possible that they’ve simply paid their friends to hire them so they can get positive feedback. I only consider feedback to matter if they are from $100+ jobs.
  4. Look at the type of jobs they’ve completed in the last few months. Many contractors will apply to a web DESIGN job, even though all their work experience is in web CODING. Many contractors just apply to ANY job.
  5. Look at their hourly rates on previous jobs. Often they’ve only ever worked for $12 per hour jobs but are asking for $20 per hour in their job application. They likely want to slowly increase their rate on Upwork, but chances are they’re still going to accept $12 per hour jobs since their other jobs were at that rate.
  6. For me, the first interview step is just asking some questions on Upwork. By doing this, you won’t waste your time interviewing 5 people on Skype for 30 minutes each. In one or two simple Upwork conversations, you can gauge their English proficiency, ability to answer questions, and other criteria that matter to the job at hand.


Which Countries Should You Hire From?

To get the best of the best when hiring on Upwork, there are specific locations where you should hire from depending on the nature of your job posting. Here are a few.

  • Former Soviet Union (Russia, Belarus, Ukraine, etc) – These are good places to find low cost but technically superb coders. When I need a serious coding job done, I hire from the Ukraine. Even those with zero Upwork history are good with coding as they usually write good applications and read the job posting.
  • Philippines – Contractors here are incredibly diligent workers in all areas. It’s possible to find good writers, marketers, researchers, and programmers. This is one of the cheaper places to hire great staff.
  • USA / Canada / UK – These locations are excellent if you are looking for skills in a particular area, but it’s still important to look at work history. In general hiring someone in these places is more likely to get you a better result but is also more likely to be 2 – 10 times more expensive.
  • Asian countries, and particularly in China, “losing face” is a big cultural concern. They don’t like asking questions, they don’t like suggesting a better idea, and they won’t tell you if they don’t understand something. To them, it’s embarrassing and they don’t want to “anger” their employer. Of course these are social/cultural generalisations but I found this to be the case when I lived in China, Indonesia, etc.

In each country, you should be aware of natural disasters. For example, typhoons can wipe out power on entire cities for a number of days in the Philippines. Political turmoil or severe heat waves can also create problems in some countries.

For specific jobs, like Graphic or Web Design, don’t hire designers from South East Asia if you expect a Western-looking result. The Philippines is an exception. South America seems to have good illustrators and Flash programmers.

You can hire expats to acquire great talent with lower rates. Hiring someone from the US or UK living in Thailand, for example, can be a great way to get very talented people at a lower hourly rate. Their living costs are lower and they might not find it easy to get a high paying job in their place of residence, so freelancing might be an extremely appealing option. Advertise on expat forums.

In general, most of my experiences with workers from India, Bangladesh, and Pakistan have been negative. In my experience, it’s common for these freelancers to ask for bonuses before work is completed, complain that the work is taking longer than expected, ask for money, and will often create really poor excuses for not reaching milestones: rare diseases, non-existent floods, house fires, and everything in between have been used as an excuse to under-performance.

To be honest, my experience on Upwork has been positive but has continually being marred by contractors from these countries. The problem is they’re so cheap so it’s tempting to hire them!

In the end, it really depends on the person you’re hiring. There are extremely talented people in India, but finding them amongst the masses can take time. My suggestion is to really test their ability to read job postings and respond. Ask questions and other necessary filtering before hiring then at $4 per hour.


The Interview – Getting to Know the Potential Contractor

When I was just starting the business, I would interview each and every potential contractor when employing local talent, and later on, Upwork contractors.

A thorough interview process can really identify the best candidate for the position. However, I learned that I never really had the time to do it thoroughly, and because I didn’t have a Ph.D. in Psychology or Human Resources, there were many people (locally and on Upwork) that I would employ with great confidence, only to find they were a horrible fit in the end.

For local people, I usually just interview 3 to 5 of those that found the spelling mistake and place one (sometimes even two) on a 1 week trial. I was surprised how many people were willing to do this but it makes sense. They didn’t have a job. They need to know if they like the company just as much as I need to know if they can do the job. So a 1-week trial worked brilliantly. If I hired two people, I would hire each for a different position (eg: 1 for admin, 1 for customer service) as I didn’t want them feeling like they were competing for the one job. And actually, often I’d employ both anyway because they were too good to let go. Sometimes one would not want to stay on after the first week which meant the other would, by default, get the job.

Same on Upwork but it’s even easier. If I had a graphic design job I needed done and I was willing to pay $30 for it, I would just employ three people on Upwork, each at $30 each, and then I’d pick the best contractor. This was great as I was building an Upwork team because I had a range of people in various skill areas that I could choose from. But it also meant that instead of interviewing a bunch of people, for $90, I didn’t need to interview AND I got three design options.

Moreover, like a local employee might just spend a week in our office and then decide they don’t like it, it often happens on Upwork where a contractor will work for 3 days and then simply disappear. It is good to have another contractor as a backup or even already working on the same job because that meant I didn’t need to go through the entire hiring and interviewing process again.

Alternatively, you can always give them a “test” project. Get them to spend 2 hours doing a simple task. For me, often their skill level wasn’t important as I also wanted people who were good in communication and are available.

Over time, you’ll collect a group of contractors that show attention to detail, are very available, and who check their own work before telling you it’s complete.

If you already have a good team, or you’re not willing to spend on employing multiple people for the one job, then a quick interview is a good option.

When I have 3 to 5 potential contractors, I would send them a message saying that I’m interested, asked a couple more questions, and then asked them if they had any questions. You’d think that all of them would reply then you’d read their replies and pick the best one but what usually happens is this:

–       2 won’t reply at all

–       1 will reply with an excellent answer

–       1 will reply with horrible English

–       1 will reply, 3 weeks later, citing the death of their mother as the cause for the delay!

So, you can see that hiring people on Upwork is a numbers game. Often, you’re dealing with people that seem great to begin with but have no interest (or ability?) to reply to your email. I would have hired over 100 people in my time and by the time I sold my business there were less than 5 that were still active and available for work. Be prepared to employ a lot of people and make NO compromises for lack of communication, poor English, or random excuses.



Even when you think you’ve found a great contractor, and you’ve given them a test job and they did well, there’s still one thing to consider – modularizing your project.

Again, particularly if they’re not from a Western country, giving an entire project (web design, coding, SEO, etc) to the one person usually doesn’t work. They’re not able to organize themselves, they miss deadlines, and it’s a finger-pointing game as to who didn’t communicate clearly.

The problem is, sometimes you have no idea what the steps are within a project. If you know nothing about web development or SEO then you’re not going to be able to guide a contractor through each module of work.

There are a few solutions:

–       learn the basics of web design, SEO, or whatever skill or technology is relevant to guide a contractor

–       find a project manager in the USA or similar location to put together a modularized plan in consultation with you, and even to be the one to keep an eye on the project and contractor(s)

–       take the risk and give the entire project to the one person, but set very strict milestones and only pay once they reach those milestones

Finally, if you are able to modularize your project then often hiring multiple contractors is a good way to ensure you’re not left with a single non-responsive contractor. So for building a new website, have one contractor to design the site, another to code the basics, another to code the interface, and another to do testing.

I had a large project which was the development of an “image uploader” and I had one coding the upload function, another coding the integration with PayPal, another coding the interface, and so on and so forth. For a time-sensitive project it’s okay if one developer “falls off the face of the planet” – the other developers can pick up the slack and they already have an understanding of the whole project.

Once you’ve hired your first employee, you need to get them onto Basecamp and Skype.


Firing from Upwork

Firing someone on Upwork is quick and easy as clicking one button – End Contract. However, firing someone online should just be similar as firing someone in real life, it should be reasonable and done ethically.

It is important to keep in mind not to wait too long to fire some. If a contractor is misbehaving, proper disciplinary should be taken. If the contractor keeps on missing deadlines, not following instructions, always committing “silly” mistakes, then fire that contractor.

As an added protection against your funds on Upwork, there is a client money-back guarantee program. Take time to be familiar with it.


Have your say

Recurring Date Settings

day week month year on
date of month day of week