Hiring on Upwork
Hiring on Upwork

Freelancers wanted

Would you like to always hit the freelancer jackpot?


Not going too much into historic details, Upwork was born out of the merger of Elance with Odesk and if not the best, it is one of the best freelancing marketplaces out there.


Upwork banner



Well, if a given platform is the one with both the larger services offering (freelancers) and procurement (clients) then, free market’s “competition leads to natural selection” law applies; meaning that one should be the best available platform.

One main concern when hiring a 3rd party either a company or a freelancer is, reliability; meaning will that provider live up to his word and deliver as promised? If not what is the impact for me?

Hiring via a web-based platform may represent (figuratively speaking) jumping into the unknown, nevertheless Upwork has some processes and features in place that “bring light to the subject”, so let’s go through the process, shall we.

So, you have a need and decided to Outsource via Upwork. Start by defining the payment terms, Upwork enables escrow which means money is both safe kept for you as the client as well as the freelancer, only to be released upon your acceptance, but being already safe kept by Upwork it gives the freelancer the confidence that he will get paid.


Requirements Specification


The importance of a clear message

Take the time to describe what you require being done in a crystal clear assertive manner, so that even a 6-year-old would “get the picture”. Your job posting needs to clearly convey: WHAT is it about; WHY do you need it; WHICH are the relevant details; WHEN is the deadline; HOW do you expect to receive the end product.

The more detail you can publish along with your posting the lesser volume of unfit bids you will get, so the effort you incur into at the beginning is compensated for having less effort while choosing amongst the bidders as well as having fewer problems or misalignment between needs and deliverables once you get the service done.

A bit of advice, include one or two specific questions that can show you the good and the very best along with a keyword/ expression to be included in the bid text like “Darth Vader” or other completely displaced from context. The reason is simple, it will demonstrate that the bidder has taken the time to carefully read your message and therefore the chance of knowing what you want is higher than someone who uses prefab bid text and “shoots every single duck” (answering as many postings as possible).

Choose the work method, meaning fixed price or work hours based. If you got for fixed price, then it helps to define milestones and I will give you easy an example; you want a simple website to build in one week but comprehending specific web design elements (logo and artwork), maybe you should define something like: Milestone 1 (two days after work start) Web Design mockup; Milestone 2 (again two days afterward) Web Site functional version 1.0 and Milestone 3 (day 7) final working version of the Web Site.

If the budget is $150, you can settle $50 per Milestone or other values or even the full amount at the end.

In the case of work hours based contracts, it is advisable to require the use of the Time Tracker tool (although you can allow manual inputs), at the end of the day this helps everybody in case of dispute. The tool collects snapshots of the freelancer’s desktop during the time he is working and therefore serves as proof of work.



Finding the “golden needle” in the haystack


The flood

Now “it’s raining bids”, you become overwhelmed with proposals literally from the 7 continents, Upwork helps with the first impact by allowing you to list them by: Best Match; Newest or Oldest applicants; Feedback (meaning freelancer’s rating); Upwork worked hours or rate/ price.

Use the above-mentioned criteria to reduce the list; all that haven’t written the “strange word” or didn’t bother to write a cover letter because they have answered the posed questions or just do not meet your expectations should be promptly forgotten.

Now, and concerning the remaining ones you need to start by looking at what they have attached as work samples; then you need to visit their profile starting by checking the Job Title and declared skills set. Avoid “one fits all” profiles, go for people who have narrowed their portfolio for it shows focus and expertise.

Now carefully read the Overview text; Who is that person, what’s the background and knowledge backlog, why are they freelancing (just getting an extra buck or a full-time occupation?). If the overview is not properly written or the description doesn’t fit your posting requirements, skip it.

Depending on the relevancy and the potential pain severity that will strike you if choosing poorly, cross check the Upwork profile with Linkedin or another source if available (google it).

If we are pragmatic about it, an Upwork profile of a freelancer that has participated in several projects is more reliable than most Linkedin profiles, because that freelancer has been reviewed by several clients while the Linkedin profile usually has not more than 5 written feedback messages and some may be from “non-independent” sources.


Tight fit

Now read the answers to your questions along with the Cover letter in detail to assess if the freelancer has understood which role he/ she will play in your business. A freelancer who writes “I do understand that missing your posted deadline may represent your inability to please your clients” is a different applicant from one that merely states “don’t be worried, I will do it by Tuesday”.


The best talent may prove not to be the best fit after all


So that no doubt remains in your mind, it is a great idea to perform a proper personal interview (if not video, at least audio) to the best match freelancer/s, by the way, Upwork also enables the tools for that.

The relevancy of speaking “face-to-face” is that you will have the chance to “feel” the other person’s attitude and personality, effective interest, time zone potential impact, workload potential impact, awareness about your request and the level of communication (ability to speak and be spoken to in English as well as to articulate a point of view).

Once you have made up your mind, you will submit an offer to the selected freelancer and if he/she accepts it then you are on (contract has started).


Ok, now you got him/ her, what’s next?

Communication! A good communication plan is vital for almost any human interaction and guess what, it is even more vital when you and the hired freelancer are literally “one ocean apart”.

Start by recapping your expectations, the agreed timeframe, communication channels, response times and deliverables.

Bear in mind that distinct cultures have different values, like someone once said while working with freelancers from the Philippines he had to force them to provide their opinion, because culturally it is not acceptable to do any type of criticism towards a client. So be aware of cultural differences.

Make sure you keep the dialog alive so any eventual misunderstanding or misalignment can be promptly tackled and fine-tuned.


The freelancer has proven to be a top performer, now what?

keep him/ her! Good talents are hard to come by.


The good and the bad

Upwork has some issues and some unique selling propositions as well, so let’s have a look.


  • Slow platform with technical problems, mainly due poor responsiveness capacity concerning heavy traffic
  • Rising costs


Unique Selling Propositions:

  • Protective escrow feature
  • Huge number of available freelancers (mainly driven from the former platforms merger)
  • Transparent reviews
  • Time tracking
  • Great dashboard for Team management


Most good freelancers won’t bid if

payment is not labeled as verified.



Previous Article The Trump Factor
Next Article Why you really need a VA