Editor’s note: This article was last updated on September 22, 2017. Originally published January 13, 2013.

Hiring decisions are difficult enough Hiring on oDeskwhen made in a “traditional” work environment. Hiring online workers to freelancing gigs is even more complex. You can’t shake their hands. You miss out on nonverbal cues. There’s just something missing. So, how can you make an informed hiring decision in the virtual workforce?

Unfortunately, there’s not a secret recipe to hiring virtual workers. However, in my experience, there are five personalities you want to avoid when building your outsourced team. In a previous article, we discussed how oDesk contractors can avoid bad clients. In this article, I’ll offer up my tips to clients for how to hire on Upwork (formerly oDesk) while avoiding bad contractors.

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Persona #1 – The Flake

Warning sign you’ve hired a “flake”:  Seems normal, but then suddenly stops returning emails.

Ah yes…perhaps one of the most common personas on the “do not hire” list. Unfortunately, this might be the one most difficult to spot before it’s too late. Everything seems to be going swimmingly. You’ve trained the contractor, he or she is doing work and billing time, and then randomly…nothing. No email, no phone call, no hours billed. Just a lot of silence.

Unfortunately, there are many contractors who view Upwork on the same equivalency as a fantasy football league. It’s interesting and kind of exciting, but other things tend to take priority. When unexpected life events occur, such contractors “flake out” and vanish into the abyss. As a client, you’re stuck looking for a replacement.

Persona #2 – The Faker

Warning sign you’ve hired a “faker”:  Upwork screenshots seem mysteriously bogus.

Picture this:  you decide to hire freelance writers to help you oDesk Work Diarybuild SEO for your website. For one of the writers, you set a billing limit of 10 hours per week and get things started with a few delegations. The next day, you log in to your Upwork account and learn he’s maxed out the 10 hour billing limit. Strange, but perhaps he’s taken some initiative and identified some additional issues that needed to be addressed. Upon reviewing his Upwork Work Diary, you start to become more cynical. For five of the ten hours, you see the exact same screenshot. When you ask the contractor if there was a billing mistake, the contractor is adamant that the billing is correct. He claims that he was working on a different computer that didn’t have the time tracking software installed.

Moral of the story?  You’ve got yourself a faker. Time to cut bait and find someone else.

Persona #3 – The In-Your-Face Pounder

Warning sign you’ve hired an “in-your-face pounder”:  Overwhelms the system with emails and questions.

Questions are OK. In fact, I ask a lot of questions. However, I typically know where to draw the line. The in-your-face pounder gets into your system and, like a virus, infects every corner of your business with confusion and chaos.

In my years of dealing with Upwork contractors, I have to admit that this persona is quite rare. However, those who fit this persona can do a lot of damage in a short amount of time. Contractors who fit into this category tend to be extremely passive-aggressive. They’ll constantly load up your inbox and chat window but refuse to jump on a phone call to resolve issues. Pounders are dangerous because they can overwhelm your systems, frustrate existing employees, and cause your company to lose focus.

Persona #4 – The Desperate Dude

Warning sign you’ve hired a “desperate dude”:  Keeps saying things like, “I just need money.”

It’s sad there are so many desperate people out there.Avoiding Desperate Contractors Unfortunately for Upwork clients, virtual marketplaces tend to attract desperate people. Upwork does a pretty good job of providing recruitment filtering tools. However, desperate people still slip through the cracks of any recruiting system.

Some employers might think that hiring desperate workers could be to their advantage. I’m sure there have been situations where this is true. However, in general, desperate people tend to be teetering on the verge of persona #1 (i.e. the “flake”). Unless you’re feeling really confident, avoid hiring people who are only interested in the next paycheck you can give them.

Persona #5 – The Total Fraud

Warning sign you’ve hired a “total fraud”:  You get a call from the FBI.

OK, maybe not the FBI. But, I have seen situations where Upwork or other virtual marketplaces have shut down contractors’ profiles because they had been involved in illegal activities. In doing so, companies such as Upwork will notify the contractor’s client(s) of the cause.

Harsh?  Maybe, But…

I know it seems like I’m categorizing people, which may not sit well with some readers. However, as one of my clients routinely says, “I didn’t make this world, I’m just living in it.” The truth is the truth. If you’re going to be a player in the virtual economy, you have to be aware of possible problems. To build an amazing virtual team, it’s important you avoid the personas outlined in this article.

All that being said, there are a ton of highly qualified, hard working people on Upwork and other virtual workspaces. In fact, Upwork has invested significant effort and resources to make their marketplace the most trustworthy in the industry (in my humble opinion).

Stay tuned for future articles on how to identify and hire winners.

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Matt Keener is the original "Executive in Sweatpants," having built a successful online consulting business (from home). His best-selling book offers tips for capitalizing on outsourcing and freelancing. Matt holds an MBA and has been featured by many recognizable brands, including Upwork (formerly oDesk), Elance, Insightly, the Dave Ramsey Show, and Entrepreneur.com.


  1. Very thoughtful article Matt.. You hit the nail on the head here.. Keep them coming. I have seen many of these types and yes screening out them is a very difficult job.

  2. Brilliant.

    Now do one exactly like this for the five types of employers one shouldn’t work for. ODesk chases off good contractors due in part to really bad employers, as well.

  3. I agree with Barbara, there are A LOT of scam Employers which do want perfect profiles with such a very low payment and yet they want you to lower the cheap price that they offer to make it even LOWER, I see this as a contractor in an unfair way. Matt Keener maybe you should work on another article this one reflecting those employers who like to offer $5 for 2500 words and yet they add who ever bids lower then will get the job…

  4. Thanks for the post Matt. I am going to try ODesk for the first time. I think I won’t get as many negative impressions as you had.

  5. Nice post Matt – I have hired a couple of flakes in my time using upwork. I can usually tell from their rating and hours worked, but one sneaks through every once in a while.

  6. sumit kumar Reply

    Nice article can u write a article on how to get your first job on upwork.

  7. Anthony DeStefano Reply

    Your post is very interesting but does not tell the whole story. I’m a CPA and CPAs charge a lot for their time. I saw one guy at $175 an hour. I work for much less and people get suspicious but they should learn to ask. I charge less to do “bookkeeping” not accounting so I say to myself, “What would a bookkeeper charge?” In addition, I am semi-retired and I can only earn a certain amount of money, so I charge less to reach that amount in total. You should publish an article on what makes a good contractor.

  8. Anthony DeStefano Reply

    One more comment if you please. It’s about fraudulent clients. I had a client who hired me and wanted me to sign an NDA (Non-disclosure Agreement). I agreed if the NDA was reasonable. What he sent me in addition was a “Consulting Agreement.” This was very bad. It included provisions that would have caused me to violate my laws for CPAs. In addition, the agreement negated the terms and conditions required by Upwork and removed them from the transaction completely. He told me that all of his contractors signed the NDA and I responded by telling him that he is confusing the issue. The issue was not the NDA, it was the Consulting Agreement. So I told him I couldn’t sign this and had to let the client go. I am lucky to know the rules and regulations I have to follow, but some contractors might not. So be careful of clients like this. They’re out there lurking. And make sure you read the terms and conditions from Upwork. There are many client protections already in place.

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