Important Lessons from a Gig Outsourcer

Estimated reading time: 12 mins

When I started my own business, I did almost everything because I had the capacity – and also because I had little cash to spend on using other resources. This is how most small businesses start off, if they don’t have a big pot of working capital to draw down on. Now, running several concurrent businesses and projects, I have to outsource some of the work. Although it’s a nice problem to have (too much work), outsourcing can be a big undertaking, and not without its perils.

I wrote this post because I have had some bad experiences in the past – and I am resolute in not repeating them. I’ve learned from them, and I share them here. If I can help you avoid the mistakes I have made, then I am glad to do so.

But first…

Reasons I Choose to Outsource Tasks

  1. It gives me greater capacity: outsourcing expands my capacity. Simply put: I can get more done. Many hands make light work, as the saying goes. If only it was that simple!
  2. It makes my services more affordable and commercially viable: some tasks are commoditized to a certain extent, and therefore expensive to my customers if I do them myself. My time costs too much to spend it on the simpler tasks that I can outsource out to freelancers who can do it faster, better and cheaper.
  3. It means that I can focus on my strengths: some activities are not in my sweet-spot, so doing them myself means that they’re not done professionally and competently. It makes them double-expensive against my profit margin, or my customers’ bills, if I have to re-work badly done tasks.
  4. I get to do the tasks that interest me: and get other people to do the tasks that don’t. Who wants to do boring work? Not me – so I outsource it.

The last decade (or so) has introduced a number of online platforms that have enabled me to find, engage and manage freelancers for outsourced tasks. They’re marketplaces that bring togethers buyers of services with those who can provide them.

Some of the platforms I have used include:

  • Upwork – I use Upwork mostly for coding tasks and development of plugins, scripts, apps, etc. These are the larger gigs.
  • Fiverr – I’ve used (but no longer use – see below) Fiverr for the micro-gigs, such as small pieces of writing, creatives (logos, infographics, etc) and proof-reading
  • eLance and oDesk – now Upwork!

The Strengths of Gig Outsourcing Platforms

  1. They’re International, Open Markets: Freelancers from across the world are made available for work, with the economical advantages of competition and labor arbitrage (cheaper labor in developing economies)
  2. Quality Assurance through Ratings and Reviews: You get to see the feedback from other customers and identify the freelancers who have reportedly done a great job on tasks similar to yours
  3. Project Tracking: These platforms show the status of your outsourced gigs and all project information is shared between customer and supplier
  4. Billing and Payments: Platforms make it easy to track invoices, pay bills and dispute charges
  5. Low costs: The charges levied by these platforms are either paid entirely by the seller, or are low. Put it this way, it would cost me far more to recruit freelancers off-platform.


Makes them sound great, right? Well in my experience, you have to have your wits about you in order to gain the benefits, and avoid being ripped off. And ripped-off you will be, if you don’t buy with care, because there are so-called freelancers who lurk on platforms that will:

  • Try to give you less than what you paid for (even if it is a small amount)
  • Try to fob you off with low quality work
  • Try to delay and delay until you give up
  • Try to pass off the work of others as their own (plagiarism)
  • Try to bully you or troll you
  • Try to make you feel guilty with sob-stories and claims of destitution

Yes, I have seen them all! Too many times. And I know for sure that I am not the only one – I haven’t been singled out as a soft touch (I am 6’4″ for pete’s sake). The sad thing is, the more time goes by, the more disappointed I have become in what I have experienced. BUT these experiences have hardened my approach and meant that I don’t lose out.

Related: How to be an Awesome Gig Freelancer

Lessons Learned

  1. Provide specific, unambiguous briefs: I can’t stress this enough. Even if the gig is only worth a fiver, you must make sure that the brief of your gig is water-tight. Despite what I wrote earlier, I still believe that more freelancers than not intend to do a good job – but if your brief is ambiguous, you may end up with a result that you didn’t intend. Be specific about everything. A good framework to employ is S.M.A.R.T. – I have used this before when describing personal objectives.
  2. Keep all communication within the platform: No matter what pressure you’re put under, do not take communication off platform. Recently I was in negotiation to acquire services and the seller asked me to communicate over a Skype call. Then he pestered me to use Skype. My refusals were ignored. Because I am transparent, my Skype id is publicly available so I received countless Skype calls that went unanswered. I guess because he wanted to negotiate on terms that breach the conditions of the platform, or possibly to avoid a written record. I walked away from the deal, and made a complaint. He got banned! You must keep all communications on-platform, because if there is a dispute, the platform admins can step in and see what transpired.
  3. Protect your Intellectual Property: It’s easy to get carried away about how cool and innovative your project is. You need a logo for your ground-breaking service? Do you really need to share how it will work in detail before market launch? In your briefs, and other communications, share only what you need to share to assure that the work can start and be delivered on time. Setting context of your tasks can be necessary, but I advise not to give away knowledge that is not required.
  4. Be timely in reviewing work, providing feedback and requesting revisions: These platforms rely on high turnover and a quick response. Fiverr, for example, will assume that a gig is closed three days after it has been delivered. Asking for a revision in day four won’t be possible, if it’s your first. When your freelancer delivers, review and feedback immediately. A delay could cost you in cash, and time. Not just that, as a buyer, YOUR reputation is on the line. Unnecessary delays because ‘I just couldn’t be bothered’ impact the seller realizing their revenue. This is bad for business and you will soon gain a reputation for being a lackadaisical client.
  5. Don’t tolerate lateness: This might seem harsh, but I believe it to be fair. If you contractually agree a timeline, make your freelancer stick to it. If on the due date your gig isn’t complete, give them 24hours. After that, cancel the gig and give it to another freelancer. Sure, this is being a hard-ass. And you probably won’t do this the first time, or the second. But come the third, you will have had enough! You wouldn’t tolerate a burger being served 24hours after you ordered it. Or a haircut. So cut to the chase and don’t accept lateness on the first instance.
  6. Get what you pay for, when you expect it, or demand a refund: Recently, I requested some supporting materials (10 documents) to be written by freelancers on #Fiverr. I created the gig, and received a number of proposals – one of which I accepted. Received on time, I received the work and reviewed it – the quality of the writing was excellent, but there were a few ‘character encoding’ issues (I assumed because the freelancer was not a native English keyboard user). Whilst these were being rectified, I ran a plagiarism checker against what I received and was aghast at what I discovered. All ten documents had been plagiarised almost to the letter. Dang it. I had been specific in the brief that all content must be unique. The freelancer also stated in their proposal that all work will be unique. But that ain’t what I received. So without argument or hostility, I demanded a refund, and explained the violation of our contract – this was immediately provided (well, they were bang to rights!)
  7. Check for consistency: One clue that led me to check for plagiarism (as above) was that the writing quality of the product was very good, but the quality of the English writing in the communication from the seller was poor. To me, this was obviously inconsistent. Hang on a minute, I thought. And sure enough, the above unfolded. Not all inconsistencies will be as a result of skulduggery; it is conceivable that a freelancer may indeed sub-contract out some tasks, but you’ve gotta ask how they will turn a profit. More than one freelancer in the supply chain means more mouths to feed. A lack of consistency is a good indicator that your tasks have been distributed amongst several workers – or – and in my case, created from plagiarised sources.
  8. Use a Plagiarism Checker: Just like I did, check that all work is genuinely unique and free from plagiarism. For written work, you can use a free online plagiarism checker or if you have a Grammarly account, they have one. For creative image work, you can still check for plagiarism – use a ‘reverse image search tool’ like this one, which uses the power of Google image search. If you detect plagiarism, discard the work and get a full refund.
  9. Provide honest feedback: Honest feedback – good and bad – is critical in making these platforms work. Providing positive feedback is part of the reward mechanism for a job well done. Negative feedback helps other outsourcers make a judgment on whether a freelancer is right for them. I have given negative feedback many times, with justification. A freelancer (once again, through #Fiverr) who delivered to me a very shoddy piece of work was given the opportunity (by requesting a revision) to fix their delivery, but instead they demanded more money. ‘No Fu**king Way’ was my thought. ‘No thank you, just deliver what was requested and paid for’ was my actual response. In the end, after several reminders of what I had requested, I actually received what I had requested, but the behavior of the freelancer left me with a bad taste in my mouth. So of course I gave them negative feedback warning other outsourcers about my experience.
  10. Report Trolling, and don’t Engage in it:  that wasn’t the end of my experience as described above. Because of the negative feedback, the freelancer’s reputation had been tarnished. So I received a number of messages telling me what impact I have had, pleas for a retraction of my feedback, and then it escalated to name calling, foul language and unprofessional words. I didn’t reply to any of it. To me, the transaction was over – in fact I considered myself generous for paying for what was delivered (just imagine if this experience was replicated in a restaurant!?) Any further communication was futile. Instead, I reported the seller to #Fiverr. So far, I haven’t had a response or even an acknowledgement from Fiverr!
  11. You’re entering into Business Relationships, not Friendships: Your freelancer is contracted to perform a task, not become a new buddy. Total trust is not an option. Poor delivery or late delivery with an associated excuse is not an option. Unprofessional behavior is not an option. Leeway is not generally advised. Be a hard-ass. That doesn’t mean to say that a ‘virtuous cycle’ is not possible. I maintain relationships with several freelancers who I employ and consult with – but they’re not friends – just more trusted.
  12. If you’re not sure that you will get what you will pay for, or the risk of failure is high, then don’t do it: Proceeding with hope and a prayer is a big gamble – one which you will likely lose. It’s better to walk away and do the task yourself than risk a calamity. These platforms allow you to proceed to the point where you retract the gig, with no penalty.
  13. My advice – start small: Outsource gigs, at first, that you can afford to write off (both the time and the cash). It’s a learning process and you can’t expect of yourself that you’ll be a solid negotiator and expert manager of other people’s activities.
  14. Be prepared for sunk costs to find the right freelancer: To find the freelancers who deliver great work that you can build a long term partnership with, play the long game and cast your net wide. A strategy that I use to great success – rather than risking backing the wrong horse, I back all the horses. I give the same gig to several freelancers and select the best to use. I still pay for all the work (providing that it meets the requirements) – I am prepared to throw away all but the best. And on more than one occasion, the long term benefit is that I find a shining star freelancer who I give repeat business to.

I’ve Stopped Using #Fiverr

Fiverr causes me too much hassle. It was great when it first launched. But I’ve had more reason to complain than I have to rejoice, sadly. There are way too many players and fraudsters operating on this platform, in my personal opinion. You might have a different experience, but then again you might not. Perhaps if you heed the words from my lessons learned, you could be successful. I’ve just found alternative ways to get the tasks done.

So far, Upwork has been a positive experience (and to be clear, I am in no way affiliated with Upwork, other than being a customer). I’ve found the quality of the freelancers on Upwork to be high. It’s not been plain-sailing though: for one gig, I didn’t get what I asked for entirely, because my brief had too many holes in it. My bad.

What is YOUR Experience?

Do you regularly outsource gigs on platforms like #Upwork and #Fiverr? Or are you considering doing so for the first time? What are you concerned about… or what have you discovered that works for you? Share you story (or nightmare) by leaving a comment below.

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