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7 Common Mistakes to Avoid When Outsourcing Your Work

odesk_lobbyI’ve had a lot of experience with outsourcing in the last few years. It’s really been a Godsend that I can give some of my work to other quality people who can do a job well-done at a price I can afford. I’ve had good experiences and bad experiences, and I’ve learned a lot along the way, so I’d like to share with you some tips, 7 mistakes to avoid when outsourcing, and what to do instead (and how to do it, of course).

1. Looking for Contractors in the Wrong Place

There are different places to hire contractors for different types of tasks. Some sites aren’t established or trustworthy. Some sites are geared more toward protecting the buyer or employer. Some sites are more reliable than others at helping you determine whether someone is right for the job. You may just want to find someone to do one quick thing for you, or you may want to hire someone for the long term, and I suggest different sites for that.

My two favorite sites to find people to help me out with various tasks are odesk and fiverr. For small one time things, I typically look on fiverr. It’s easy to sort through all the contenders and hire someone quickly and get the job done fast. People on fiverr are expecting (and hoping for) sales. I’ve never had a problem contacting someone and asking a question about their service (just in case I’m unsure about something before I click that order button). Sellers on fiverr tend to respond quickly (within 24-48 hours). And they typically get their work done in the allotted time frame (that they have chosen and you’re aware of).

When I’m looking for someone to hire for the long term and do certain tasks for me on an on-going basis, I turn to odesk. There I can offer my job and then search for qualified candidates and ask them to take a look and apply for the job. Then I can go through a thorough interview process (or even a trial run with a few top contenders). Which brings me to my next point…

2. Hiring the Wrong Contractors

It’s very important that you find qualified contractors. There are a number of ways you can do this. On oDesk, you can see their qualifications. Candidates have typically taken tests to show what they’re actually good at. For instance, English proficiency tests, which for me is very important. If we can’t even understand each other, how are they going to know what to do? How are they going to do a good job? How are other people going to understand them?

The other way you find out if they’re qualified is through the interview/hiring process. I always ask my candidates one simple question: What would you do with a million dollars. The answer to this question tells me so much about this person. For one, how thorough are they in their response? If they are extremely thorough and detailed in their response, they will be thorough and detailed with their work. If I want quality work, I typically need someone who’s detail oriented.

The other thing is you see how well-balanced they are. My favorite candidates usually say something like “I would help my family, pay off my school loans, save some of the money, and maybe go on a nice vacation.” Answers can’t really get more well-rounded than that. The more well-rounded someone is, the more balanced they are as a person, and a balanced person is typically available enough, responsible enough, and caring enough. They also have boundaries, so hopefully they’ll be honest when they can’t do something I ask them to. I don’t want them to waste their time and fail at something they’re really not capable of, and I don’t want them to tell me they have time if they don’t and then they end up not being able to meet the deadline. So I do like someone who will be honest and not let their “boss” walk all over them.

The other thing you discover with in the answer to this question is how smart someone is. The people who say they’re going to invest some of the money into business ventures I really like because they’re already business-minded and they already understand the fact that businesses take investments. I like to work with people who understand business because they will better understand why I make any decisions I make, and how important a role they play in my business. These people are also typically real go-getters who aspire for success. People who aspire for success typically do better work than people who are fine with living a so-so life.

I almost always have the most success with someone who gives me a detailed, well-rounded, smart answer (and written well in English).

Ask your candidates other questions as well, but include “What Would You Do With One Million Dollars?”

3. Outsourcing the Wrong Tasks

This is pretty self-explanatory, but I think I’ll go into just a bit of detail. For one thing, you obviously don’t want to outsource something to someone who is not qualified for it. Someone might be really good at software programming, but horrible with their English skills. You don’t want to give this person the task of handling your emails, writing articles, or answering for you on social media.

The other thing to consider always is when to delegate and when to not delegate. If it’s a one time thing, and it will take more time to explain it than to do it, then just do it yourself. This is the type of thing that’s best not to delegate. However, if it’s something that will be repeated in the future, but takes longer to explain than going through the task once, I say delegate. In this instance, the time it takes to explain the task will be an investment of time for your future. After your contractor has done the task 2 or 3 times, you will make made back your time investment, and you’ll be glad you did, especially if it was an extremely tedious task that you hate doing yourself.

4. Not Training Your Contractors Properly

I create video tutorials with screen-capture software, I create pdf instructions, and I also create screenshots, etc for almost every job I want someone to do. I also give them an excel spreadsheet with any info they need to get the job done efficiently.

This one is really important: after I give them my training materials, I always tell them to let me know if they have any questions, and don’t hesitate to ask, anytime.

The other thing I do is I always do a test run of a task. I give my contractor all the training materials I created and allow them to do the task once through (or if it’s something very small, a few times through, to get a good idea of how well they’re doing). After they’re done, I check on their work and I let them know how they can (or need to) improve their work. After that (for long time contract work of the same type of task) it is usually pretty streamlined and I just periodically check on their work and give them my feedback (positive and negative, with tips on what needs to be improved if anything).

5. Not Staying Organized

If you are delegating a lot of tasks, you need to keep track of everything, who’s doing what and when, how much you’re paying them and when and for what, etc. I have tons of folders on my computer, and I have tons of subfolders in those folders. And I even have subfolders in my subfolders. I like to stay organized. I don’t care how many folders I need to create to stay organized.

I have excel spreadsheets, notepad documents, word documents, pdfs, images, screenshots, videos, etc. Some of these things are training tools and instructions. Some of these things are just for my own records. Some of these things are just to remind me what the heck is going on, lol! I also keep a special folder in my email for emails from my contractors so I can easily find something when I need it.

6. Not Rewarding Your Contractors

If you have a quality contractor who you really enjoy, who does really great work for you, and who you’d like to have on for the job for the long term, then it is imperative that you reward your contractors. I do this two ways. One way is constantly giving them positive feedback. I don’t just tell them what they’re doing wrong, I tell what everything I notice that they’re doing right. I tell them how much I appreciate them. I tell them they’re awesome. I boost their self-esteem.

The other thing I do is I financially reward them. I ask my regular long-term contractors when their birthday is and I send them $20 for their birthday. I send them a Christmas bonus. This is just really good for morale. Sometimes the things we hand over to our contractors is very mundane/tedious work we don’t want to do ourselves. They deserve a bonus for making my life better (even if it means that I just don’t have to do that crap). I’m extremely blessed to have them, so I want to reward them.

Rewarding your contractors will keep them around longer, and they will appreciate you more and do their best for you because they don’t want to lose you since they’ve never had a better client/”boss”.

7. Not Outsourcing At All

If you run an online business and you want it to grow to be something substantial, you need to outsource some of your work. You only have two hands, and you only have so many hours each day, many of which are taken up just by sleeping, eating, and running errands. To me, it’s extremely important that I have balance in my life. If I’m spending too much time working and not enough time living, then what’s the point? So I need to delegate.

Too much time sitting at the computer can also lead to health risks. Check out this info from


So if you’re making any money at all, consider setting aside a percentage of it to hire others to do some work for you. You’ll not only see that your business will start to grow, but you’ll also have more time to enjoy life and maybe get out there and get some exercise!

What are your tips for outsourcing? Got any horror stories from bad experiences with outsourcing? What have you learned? Leave a comment so we can all learn from each other.

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2 Responses to '7 Common Mistakes to Avoid When Outsourcing Your Work'

  1. Diana says:

    What a nice post! Glad i found your blog (thanks for following me on Twitter – that’s how i found you 😉

    I have been playing A LOT lately with the idea of hiring a VA to help me our with some tasks but can’t seem to get it done. I am a bit of control freak LOL – i know, i know – and i totally agree we have only so much time so, i hope soon i will make a run for it.

    By the way, oDesk is one of my fav. sites, too but you should also check out Elance – they are close second in my book (and maybe will be #1 soon!)

    Will send you some social media love, too!

    • Lisha says:

      Hi Diana, I’m exactly the same way. I always feel like if I hire someone else to do something they won’t do it right (my exact way) and I’m very particular about details. But it’s amazing how freeing it is to hand over work to someone else and know that the work is getting done while you go on a bike ride, or do other more important work.

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