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The Art of the Outsource: 20 tips for securing successful contract work


The popular press sure likes to paint “outsourcing” as a four letter word.

Well, it actually has 11 letters and it can be a fantastic resource if used effectively. However, if you aren’t careful, it will certainly have you spouting four-letter words… so here are some tips to make the most of your next outsource.

And if you don’t think outsourcing is important, did you know Kevin Rose used an outsourcing site,, to create for $200. I’d say that return on investment should keep you reading….

So what is outsourcing?

In a lot of ways, outsourcing is simply hiring someone else to do a job for you. Great synonyms for outsourcing are freelance or contract work.

It could be anything from making a website to doing your accounting. Most of the jobs you’ll see are things that translate well while working remotely, and include: software programming, graphic & web design, and writing copy.

Here, I’ll largely be focusing on web-business topics, but don’t let that constrain how you use it. Odds are, if you have something you need done, someone will do it for you, and for cheaper than you could do it yourself.

Where to begin

The first thing you do is identify what you need help with.

Ever see a website you like and say, “I wish mine looked like that?”

Do you wish you had a Wordpress blog all set up on your own server but aren’t comfortable with FTP or setting up a MySQL DB?

Want a new logo, but don’t want to pay $500 for new art software or can’t draw to save your life?

Ever wish you had someone to write 150 paragraphs to help fill out a knowledge base?

Things like that are perfect to be outsourced, and in many cases you can get quality work done in a day and for a hundred dollars.

For the first time out, start with a small task that isn’t mission critical and doesn’t have a time-sensitive deadline. Like anything else, there is a learning curve here, and don’t expect things to go smoothly.

Once you’ve done that, the best description I can come up with for the process is something like the fusion of selling (your need) and buying (the vendor’s time) on eBay:
1. First you post a job description and your budget range
2. Then get bids from vendors
3. Converse with vendors
4. Pick a vendor
5. Monitor project process
6. Pay the vendor

Where to freelance?

There are several freelance / outsourcing market places out there. I’ll add to this list if people would like to post their favorite sites. Sites I’ve used with good success are:

Other sites suggested by readers:

The Good, the Bad, and the Ugly about outsourcing

The Good:

  • outsourcing is a great way you can get stuff done you can’t do yourself
  • it’s cheap, rates are often posted $10-20/hr, but in actuality, you can often get it for much less since most projects are priced by the project, not hourly
  • allows you to multi-task and get larger projects done much faster by sending pieces out
  • by polling various vendors it is a good way to build consensus your approach or idea or method is a good one
  • freelancing isn’t just for finding a vendor; you can also hire out your particular skill set as a vendor
  • sites offer you protection for your money and some recourse in the form of a feedback system if you have a bad interaction
  • you have the power to control who you hire, if anyone at all
  • most sites charge nothing or very little for posting a hiring need

The Bad:

  • since a lot of work is sent to other countries, sometimes a language barrier can slow or cripple a project - be ready for broken English emails and potential difficulty explaining complicated concepts
  • again, there’s a good chance you might be dealing with someone half a world away, so make sure you account for dealing with things on a 12-16 hour time difference
  • many vendors simply bid dozens of projects without a lot of thought about your particular project, so the onus is on you to find the right person
  • odds are you aren’t going to find someone that is as passionate about your project as you are, so it is up to you to make sure it is always moving in the right direction
  • at the end of the day, there isn’t much accountability on the vendor’s side other than their feedback rating. Some vendors may run into trouble and simply cut and run. A common outcome is to simply never hear from a vendor again.

The Ugly (things to be wary of:)

  • bidder with little or no feedback - one or two feedback scores can be faked and no feedback should be completely avoided
  • don’t bid too low- outsourcing is great, but don’t expect for someone to write the next iTunes site for you for $30
  • the Re-outsource - many bidders act almost as a project manager (without telling you) and simply re-outsource the project. This means you aren’t really choosing your vendor. Explicitly inquire about and avoid this
  • can be slow- inevitably you will get people that under bid or at the very least, blow their time estimate big time. Expect delays.
  • paying around- just like on eBay, some vendors may ask you to pay them outside the site to save some money. It increases your risk and isn’t fair to the website where you found them.

The Tips

Screen names can protect your identity and escrow can protect your money, but only you can protect against wasting your time. So here are 20 tips to succeed at your next outsource:

  1. Write a good description- vendors aren’t mind readers… the more detailed you can be in description upfront, the quicker you’ll be able to hone in on a vendor. It is much better to have too much detail than not enough
  2. Break your project up into phases- the biggest suggestion I can make is for any meaningful project, is break it up into smaller projects
  3. Make your first project a a trial- don’t try outsourcing for the first time in a time critical situation or for an important project
  4. Define detailed deliverables- be ultra-explicit about what you expect to get…. don’t assume anything. If you are having a website designed, you’ll want to specify you want it uploaded and functioning on your server. If you are getting logo built, specify the size, image type, software package it was created in. If you don’t list it in your description, you can’t expect delivery of it at the end of a project
  5. Define rigid deadlines- similarly, create firm deadlines that are defined in an agreed upon timezone
  6. Do a search for similar projects- this is helpful for several reasons: (1) you can see other people’s task descriptions and find things you might have forgotten in yours (2) in many cases you can find who has bid or successfully completed a similar job and invite them to bid on your project
  7. Make sure to ask for a portfolio- make sure to ask to see what they’ve done. note the variety and quality of their work
  8. Ask for project-relevant example sites- what you really want to see is that they’ve created something just like you need. You’ll get lots of bids for people saying they can do your job, but you really only want to work with someone that has solved your specific problem before
  9. Give examples & URLs when ever possible- one of the best things you can do is say something like, “I want my site to look like site X, with login features like site Y”. It helps the vendors and helps you explicitly define what you want
  10. Ask lots of questions- most sites allow you post private messages to vendors. You can learn quite a lot by asking individual vendors how they intend to solve your problem and what relevant experience they have
  11. Role play- define the description and specs, then pretend you know nothing, or better yet, give it to a friend to look over and ask them questions about what you have described. Have you really given someone enough information?
  12. Use escrow payments- always use an escrow service when ever possible and try to avoid prepaying. Most issues of payment can be avoided if you simply outline what terms you want in your description
  13. Use feedback system- check their feedback, skip any new vendors / people without feedback, and make sure to add to the community by leaving your feedback about your vendor and asking for feedback yourself
  14. Stay connected- once you decide on a vendor, make sure you get their IM / chat / Skype contact info so you can ask and answer questions promptly. Email is often too slow, especially on short projects, and can cause needless delays
  15. Lots of prototypes- this is a classic project management technique that is ultra-effective. As with almost any project, one of the best things you can do is ask for lots of prototypes along the way to make sure things are heading in the right direction. You might have thought you wrote a great description and your vendor might say they understand your vision, but without checkpoints and opportunities to redirect along the way, you might end up with something you didn’t expect. Avoid this common pitfall by building in multiple checkpoints with a tangible delivery to make sure things are progressing as you had hoped
  16. Build a wall- make sure you partition vendor’s work as much as possible, ideally on a test or dev server, or at least in a different directory. Also only give vendors ftp access if possible. Don’t risk losing other data or exposing active parts of your website. You can get a shared server for a few bucks a month… it’s a small price to pay for piece of mind
  17. Change login info- and don’t forget to change their password or freeze their account once they’re finished. If you have to give them broader access to your server, select an temporary password and change it once they’re done
  18. Be creative- there are a ton of things you can out source. Be creative and post it… it never hurts to ask
  19. Know when to cut your losses- eventually, no matter how careful you are, you will run into a bad scenario. Read your site’s terms, but usually if you don’t hear from your vendor in a few days, take the necessary action to reopen the project and find a better fit
  20. Find a good vendor - one of the best things you can hope for is to find a vendor with which you have a good report and they are talented enough to help you on other projects

Good luck, and go outsource ‘em!

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    On October 23rd, 2007 at 8:21 am, Susan Payton said:

    Outsourcing rocks!! I have a VA in India that I share with my husband. It’s incredibly affordable, and takes the mundane tasks that don’t make me money off my plate.

    And my best advice, to reiterate you, Wendy, is be extremely detailed in your assignments. Assume your outsourcing partner knows nothing and needs explicit detail. Then you leave no room for costly misunderstandings!

    On October 23rd, 2007 at 10:37 am, Shiraz Khan at Downline Attraction said:

    Great tips. Here’s another pitfall to be aware of. It was one that was talked about by Eben Pagan of, where he says “No black boxes.”

    What he means is, when you outsource a project, it can be potentially dangerous for you to NOT know how to do it yourself. You don’t have to be an expert as the person you’re outsourcing it to, but at least know enough so you can do it on your own.

    The worse thing that can happen is if you’re website, project, or tool that you outsource is ONLY understood by someone other than you. It essentially becomes a “black box” that you can’t access.

    What if the outsourcing person is no longer available? Or he or she decides to no longer work with you? You’re stuck. And if it’s a major piece of your business, then you can be in deep trouble.

    I hope this makes sense.

    - Shiraz Khan

    On October 23rd, 2007 at 11:56 pm, Debbie said:

    The tip on using an escrow service is a good one. I hadn’t thought of that.

    On October 24th, 2007 at 2:23 pm, James Chartrand - JCM Enterprises said:

    I read this post because I’m a freelance writer – and after reading, I feel like I have to defend freelancers. You’ve painted us all to be quite black and generalized quite a bit in your discourse.

    I’d like to set the record straight on a few points:

    “Don’t expect things to go smoothly.” If you’ve chosen your freelancer or professional well, things *will* go smoothly. It is our job as professionals to ensure the client receives top-quality services and has a good experience. Many freelancers help people new to outsourcing by guiding them through websites, processes, contracts, and we even provide recommendations or suggestions that often are in the client’s best interest.

    “It’s cheap.” Yes, outsourcing is cost effective. It is cheap in that it will cost you less time and money than if you’d attempted the job yourself. But the maxim “you get what you pay for” reigns in outsourcing. If you just want cheap work at a cheap price, take the lowest bidder and toss the rest.
    A better idea is to find the freelancer that fits your needs and has the skills you require and that has reasonable rates – not inflated, and not rock bottom, but somewhere in the middle that is fair to both parties involved. Do you really want to promote sweatshop work?

    “Since a lot of work is sent to other countries…” No one sends the work to other countries but the client. *You* choose the person you want to work with. If you outsource and you select a freelancer located somewhere else in the world, that is your choice. Freelancers who accept contracts and jobs do not further outsource the projects to workers in other countries.

    “There’s a good chance you might be dealing with someone half a world away…” There are many, many freelancers located within minutes, miles, or a couple of hours of your location. There is no need to deal with people half a world away if you choose not to go that route.

    “Many vendors simply bid dozens of projects without a lot of thought about your particular project” I agree that *some* freelancers practice this method. Many, many freelancers care a great deal about your project, you as a client and your ultimate satisfaction. They also care very much about doing a good job.

    Keep in mind, also, that freelancers have to eat – since there is high competition, bidding on multiple jobs to contract one or two is normal and in no way a reflection on the quality of services.

    “Odds are you aren’t going to find someone that is as passionate about your project as you are.” Many freelancers love what they do. They’re pros. They’re experts. They see each project as a challenge to do the best they can do – and surpass client expectations. The odds are more likely to be that you find a freelancer who is just as excited about your project as you are.

    “At the end of the day, there isn’t much accountability on the vendor’s side other than their feedback rating. Some vendors may run into trouble and simply cut and run.” There are two sides to every coin. There are providers who do cut and run, yes. There are also just as many clients who cut and run as well after the work is delivered, leaving the freelancer with no money and empty hands.

    “Many bidders act almost as a project manager (without telling you) and simply re-outsource the project. This means you aren’t really choosing your vendor. Explicitly inquire about and avoid this.” There is no reason to avoid teams of freelancers. Grouping together is common in the freelancing world, because united we stand, divided we fall. The lone entrepreneur and freelancer don’t last long in a virtual world. Consider, rather, that those freelancers who work in teams are possibly the best to choose – there is always someone available for your project, the client is not left hanging should a real life emergency come up, and teams are efficient for large-volume jobs. They also have a pool of skills at your disposal.

    “Expect delays.” There is no need for delays, and experienced freelancers know exactly how much time a project takes. If they can’t pin down an accurate figure due to the project requirements, they can certainly offer a deadline – and they *can* meet it.

    The best bit of advice that you offered in your post is your last statement – that you should find a good freelancer with which you have good rapport and who is talented enough to help you with your project.

    I invite you to visit the “Working with a Writer” section of my blog - there is some valuable advice for those seeking to outsource projects to have a great working relationship with freelancers - and not just writers!

    On October 24th, 2007 at 4:56 pm, Chris said:

    Great reply James! Thanks so much!

    I certainly wasn’t trying to paint all freelancers with a broad brush, but it was my intent to outline lots of the pitfalls someone might come across…. because while you sound great and dedicated (want a job? ;) ) it is easy to get mislead by those people that aren’t.

    Like anything on the internet, all the tools are there to empower anyone that can click a mouse to both achieve great things and to get in over their head. Especially when it comes to something where people may have little or no experience (like hiring someone) erring on the side of caution certainly seems like the prudent approach.

    I don’t think there is any denying that there are potential dangers and speed bumps related to freelancers out there, so I wanted readers new to the game to simply be aware of where they might stumble and to set expectations accordingly.

    Cheers, and good luck.

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