I see many Linkedin group discussions in which new oDesk contractors express difficulty in finding consistent work. To address these concerns, I’ll be writing a series of posts aimed at helping the newbie find consistent success.

oDesk worker guide

You might consider it logical to start with a list of “how to” tips for navigating oDesk job postings. In reality, that would be a waste of your time unless you have a firm foundation on what employers are actually looking for. Regardless your specific skillset, there are three key characteristics that any oDesker must possess prior to seeking employment.

1) Be overly available (like Dwight Schrute)

2) Be accountable to your word

3) Be willing to act as a manager – even if you’re not “management material”

Let’s take a closer look at each.

Wisdom from Dwight Schrute

For those of you not familiar with The Office series on NBC, Dwight Schrute (played by Rainn Wilson) was a quirky, extreme character who loved his job as a paper salesman. In fact, he loved it so much that he once said the following:

Here’s my card. It’s got my cell number, my pager number, my home number and my other pager number. I never take vacations, I never get sick and I don’t celebrate any major holidays. ~Dwight Schrute

Now obviously I’m exaggerating here, but the Dwight Schrute example gets at a bigger point. In a virtual work environment, you must be overly available. Every day I get dozens of unannounced chat sessions via Skype, Microsoft Link, and Google Hangout (I have 5 Google accounts), each of which require my immediate attention. In addition, clients have my office and cell number in case they want to talk on the phone. I even have a few clients that text me. By making myself overly available, I’ve instilled a level of trust with my clients. Unlike Dwight, I do take vacations and celebrate holidays; however, I make a point to inform clients when I’ll be gone. Also, I don’t have a pager.  🙂

Now, here are a few more helpful tips from Dwight.

Do As You Say

For some reason, many contractors find this one difficult. I’ve hired countless oDeskers who said they’ll do one thing – and then do the exact opposite. Unfortunately, in a virtual setting, you only get one shot at winning a client’s trust. If you fail, the bond is quickly broken. Plus, the client is likely to give you a negative oDesk feedback, which can have a ripple effect.

Here’s my simple equation for success on any oDesk contract:

  • Step 1: Fully understand the scope of the project. Ask lots of questions and get any unknowns on the table in advance.
  • Step 2: Set clear deadlines for your project. Make sure the client is OK with these deadlines.
  • Step 3: Work diligently to provide a quality project by the stated deadline. Put smaller, internal milestones in place to ensure the client milestone is attainable.
  • Step 4: About halfway through the project, send the client an update on how things are going. Ask any additional questions, share your concerns, and state any new unknowns.
  • Step 5: Offer to schedule a “presentation of findings” meeting with the client to present the final deliverable. Sometimes clients will decline this meeting, but it’s in your best interest to get this “facetime” with the client (think feedback management and upsell opportunities).
  • Step 6: Upon successful completion of the project, request feedback from the client.

Now, this is all contingent upon you picking good clients to work for. Yes – I said you should pick your clients. Just because someone invites you to interview, doesn’t mean that they’re worth your time. During the interview process, you have a chance to ensure your clients are legitimate…and that they’ll do as they say.

Management Material?

Finally, if you can hold others accountable, there’s always going to be work for you. Many oDeskers take the word “freelance” to the extreme and mistakenly think that they are only responsible for themselves. Having worked for many clients in a variety of virtual roles, I can attest that one of the biggest opportunities for online workers is the ability to manage others. Given the logistics of working from home (or virtual office), it’s rather complex to keep everyone on the same page. Virtual workers who are able to provide project and task management services are always in high demand.

When managing others virtually, here’s a process I follow:

  • Delegate via Google Docs (or task management system such as Basecamp), clearly stating the desired outcome and due date.
  • Follow up directly with the team member on the due date (or before if appropriate). I prefer to do this via a real-time conversation on Skype.
  • Review the work completed. If additional changes are needed, provide more feedback in Google Docs. Send another email and/or instant message to the team member.
  • Do a final review of the work. Again, make suggestions if necessary.
  • Finally, send the finished work to the client.

Remember, even though team members aren’t your employees (or in many cases, even affiliated with your company), it’s technically your responsibility to ensure quality.

If you’d like to receive my additional tips for staying busy on oDesk, please subscribe to our blog email group. I’ll be sharing more tips in the coming weeks.


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.

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