After going through Part 1 of this “Beginner’s Guide to Outsourcing,” you should have a value-driven, prioritized list of projects, tasks, and responsibilities ready to be outsourced.

To jump into outsourcing unprepared will leave you frustrated and likely to waste time and money.

But don’t start looking around for a provider just yet. To research and pick an outsourcing partner without carefully defining your needs will leave you frustrated and likely to waste time and money.

There are two important considerations at this point:

Documentation and training:

My feelings on documentation are mixed.

On one hand, I feel that documentation is only important to the extent that it will actually happen. Too many times I speak with a new client who is excited to get started working with us and the conversation ends with, “Alright, well let me work on my documentation and then I’ll get back in touch with you.” Two weeks later I reach out to see what happened and they say that they are still working on their documentation and they’ll be ready soon. After that, I generally never hear from them again.

As with so many other things in life, doing it is sometimes more important than doing it perfectly if you are never going to get it done perfectly. It is better to jump in with weak documentation than to never jump in because all the i’s and t’s aren’t dotted and crossed.

Perfect is the enemy of good. – Voltaire

On the other hand, good documentation is helpful and generally helps things go much more smoothly.

Taking both hands into account, I would give this advice: create as much documentation as you can in one sitting and consider that good enough. Then, knowing that everything might not be perfectly complete, be very available early on to answer, and quite tolerante of, clarification questions.

While video documentation is very easy to make, it is not great for the person responsible for the work. A lot of it is wasted time as someone is walked through things they could have easily figured out on their own and then the brief, important moments that are actually helpful are hard to find and refer back to later. Written documentation is the way to go.

Putting that written documentation in the cloud, for instance on a wiki, and encouraging your outsource partner to edit and add to as necessary is a great way to make sure that you both stay on the same page with how things are supposed to be done.

Pick the appropriate service provider:

Now, this is where I have an unavoidable bias but I will try to be fair and even-handed here (Full disclosure: I own a virtual assistant company that competes with the alternative outsourcing solutions I will discuss).

Referring back to your list, next to each task you are considering outsourcing write down all necessary skills, resources, and training.

If you have a recurring task of posting your blog articles onto various social media networks your qualifications may be:

  • Ability to write well
  • Knowledge of social media
  • 4 hours of free time a week

For this task, you wouldn’t want to outsource to a non-English speaker and you’ll need someone with tech-savvy. Another task may be to create banner ads of various sizes promoting your new book. Your qualifications for this task may be:

  • Knowledge of graphic design tools
  • An eye for design that mirrors your own
  • A quick turnaround time

For this task, you may want to be weary of a busy freelancer because they may be bogged down with other projects. Now, list requirements that may be more general and not task specific. Such as:

  • Stability (will be in business next year)
  • Availability (I can reach them when I need to)
  • Dependable (don’t call out sick or “show up” late)
  • Security (legal protection, bonded, security protocol)
  • Budget criteria (how much do I have to spend on this project per month?)

Consider what type of outsourcing partner is most appropriate:

  • Freelancers (eLance, oDesk, Rentacoder, Behance)
  • U.S. virtual assistants (work from home, alone)
  • Virtual assistant service (work as a team, work at an office)
  • Foreign virtual assistant company (work as a team, work at an office)

To summarize the pros and cons, foreign will be cheap but not well-suited for complex assignments. A U.S. virtual assistant will be most expensive. A U.S. virtual assistant service will have middle of the road pricing and offer a wide breadth of services. A freelancer will be very good at one thing but won’t be able to assist with anything else.

Please see this chart for more information on the pros and cons of different outsourcing options.

In Part 3, the rubber hits the road and we will discuss best practices for beginning the outsourcing process and how to keep the relationship successful over the long-term.

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Imagine a Samurai warrior who “kind of” understands how to use a sword. He is “somewhat familiar” with a bow and arrow. In hand to hand combat he’ll “figure it out” if allowed enough time for trial and error.

It sounds absurd when, for a Samurai, his level of proficiency determines his survival. He has no choice but to pursue mastery so, day in and day out, he trains — eventually attaining a level of intimacy with his tools that borders on unnatural (Samurai would name their swords and considered them to be part of the living world).

Anyone reading this blog post is probably classified as a “digital worker.” Operating systems and software packages are your sword and shield. Yet, in this context, similar statements are not considered absurd, but are commonplace and expected:

“I’m not great with Photoshop, but I can crop a photo if I have to.”
“I think I can do that, just give me a chance to Google it.”
“I can create a Powerpoint presentation but don’t understand all the advanced features.”

We limp along in our digital workplace hindered by our lack of familiarity with the very tools we use to create, perform, and get the job done. We tolerate mediocre capability in ourselves (and each other) seemingly because no one is holding each other to higher standards.

We are constantly struggling to get our tools to do what we want, we waste a lot of time figuring them out. This is due, most immediately, to inadequate training but it boils down to an almost universal acceptance of ignorance.

Software is not complex. In fact, a lot of thought is put into making it as user-friendly as possible. If you struggle with a certain software or performing certain tasks, it’s not because it is challenging, it’s because you haven’t invested the time to train, learn, and master your tools.

If you struggle with a certain software or performing certain tasks, it’s not because it is challenging, it’s because you haven’t invested the time to train, learn, and master your tools.

It is incredible that people spend at least 8 hours a day using software that is that is so intertwined with their livelihood yet they are okay with squeaking through the day with just enough skill and knowledge to do what they need to. They don’t concern themselves with anything more than what is necessary leaving countless, powerful features underutilized. They have constricted their performance by only learning what is necessary.

They awkwardly stumble through the day, ignorant to how they could be working faster and producing better results.

First, master your operating system.

Pick up a guide to your operating system and read it. Then pick up an advanced guide to your operating system and read that. In fact, don’t just read. Do the exercises and take notes. Then reread it six months later. When you are running up against a deadline, you don’t want to get hung up because you don’t know how to install a printer driver.

Then, master your software.

Make a list of the software that is most closely tied to your productivity. Is it the Office suite? Don’t be so arrogant to think you are proficient. You’ll be amazed what you don’t know about Microsoft Word (let alone Excel).

Read through the software’s documentation. If there is a list of keyboard shortcuts, print them out and post them somewhere in plain sight. If the software is common enough, seek out a tips and tricks guide. If it is a more obscure app, subscribe to the developer’s blog or find a user group and monitor the discussions.

Finally, master your workflow.

Define each task you complete and create a process or system for how it should be done. Put a lot of thought into it. This is where the rubber hits the road and, chances are, unless you’ve done this before, you probably aren’t doing things the best way possible.

Unless you’ve done this before, you probably aren’t doing things the best way possible.

Google for other’s tips and tricks for the best ways to handle different situations. There are very efficient ways to do even simple things like checking your inbox and voicemail that you are probably unaware of.

Work without thinking…

When you work, you want to free your mind to concentrate on the task at hand. If you constantly run into knowledge gaps that take you off that focus, you are killing your productivity, creativity, and efficiency.

You should be able to perform tasks without thinking about how to do it.

You should be able to perform tasks without thinking about how to do it. It should become second nature and that only comes through study, practice, and dedication.

It’s not a difficult thing to do, you just need to hold yourself to higher standards, commit, and invest yourself in becoming a better digital worker… one who actually understands his or her tools.

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Outsourcing can be intimidating to start and there are quite a few pitfalls along the way for beginners. Some people try hiring someone on Elance a few times, have a horrible experience, and, unfortunately, go back to doing everything themselves.

Drawing on my knowledge as the owner of an outsourcing company, I am starting a three part series of posts that will help you avoid many of the common mistakes, lay out a strategy that will give you the greatest chance of success, and help you get the most value out of outsourcing.

Part 1: Deciding what to outsource

Deciding what you will outsource is what determines the value you get out of outsourcing. All the leverage resides right here, before anything is even delegated. Many people forget this and don’t put enough thought into this all important planning phase and find that, though they are outsourcing quite a few projects, they aren’t getting any value out of it — they are just as busy and stressed as ever and their business is not moving forward any faster.

Investing a little thought and time into picking the right projects and tasks to outsource ensures that you get the most out of your outsourcing. This is the plan I generally propose:

Step 1: List off ALL tasks and projects within your business

Don’t just list off the projects you think are good candidates for outsourcing. Don’t just list off the ones you don’t feel like doing yourself. Just dump everything your business does into a list. Here are some prompts to help you get everything onto paper:

  • Recurring tasks
  • One off tasks
  • Tasks required for new customers
  • Marketing tasks
  • Administrative tasks
  • Bookkeeping tasks
  • Advertising tasks
  • Neglected tasks
  • Procrastinated tasks
  • Favorite tasks
  • Tasks you hate doing
  • Time-consuming tasks
  • Fun tasks
  • Tasks you’ve planned but haven’t executed
  • Large tasks
  • Small tasks
  • Things you should do but don’t

Step 2: Can it be outsourced?

Go through your list and cross off those tasks that cannot be outsourced. Be careful that you are not crossing off tasks that could actually be outsourced – there are typically very few activities that need to be done by the business owner.

STEP 3: Determine your value criteria

What is valuable to you at this point? What matters most? Do you need more time? More money? Do you need to feel less stress? Do you need to move your business forward?

Pick your top two or three most important value criteria and rate each item on your list of projects on a scale of 1 to 10.

For instance:

Find new advertising opportunities
Time savings: 7
Make money: 9
Average: 8

Taking the average of those ratings should give you a good idea of which items you should begin outsourcing.

In Part 2 of this “Beginner’s Guide to Outsourcing” I will be discussing how to pick the best outsourcing provider and the preparation work necessary to making sure things go smoothly.

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Focus & Get Projects Done Faster

July 10, 2010

It’s easy to find yourself working on several projects at a time but it is horribly inefficient. Like dropping a photo of a triple bypass in progress over the Wendy’s drivethrough menu might motivate me to find a healthy alternative, I’ve found a succinct little illustration that helps keep me focused. When I start to [...]

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The Best Business Books You’ve Never Heard Of

June 30, 2010

There are more great business books than you have time to read and I’m sure you’ve heard of them: The Fifth Discipline by Peter M. Senge, The Goal by Eli Goldratt, and anything by Peter Drucker. But what about the books that don’t become popular because they didn’t have the right publisher, didn’t time things [...]

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Do You Suck at Delegation?

June 29, 2010

One of my favorite statistics is that 85% of drivers think they are better than average drivers. (In case you are mindlessly skimming, that’s mathematically impossible.) We are all prone to overestimate our abilities, especially in certain areas — our love making prowess, our relative intelligence, or how funny we are — just to name [...]

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Justifying the iPad Tablet as a Business Expense

April 1, 2010

A few weeks ago I “had” to justify the purchase of an iPad as a business expense. I’ll admit, rationalizing the purchase of a piece of hardware you haven’t handled, and don’t yet know the apps/capabilities it will have, is not easy. However, I was able to come up with 10 fairly solid reasons I [...]

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18 iPhone Apps for Small Business Owners and Entrepeneurs

March 21, 2010

Notelife – A flexible repository for: the miscellaneous information that we encounter throughout the day but don’t have time to process, great ideas as they strike (notes, audio, and pictures), and even getting work done on the move (draft emails, blog posts, etc.). Omnifocus – After trying, literally, every task management app on the iPhone, [...]

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Benefits of the Pomodoro Time Management Technique

March 14, 2010

I downloaded the free Pomodoro Technique ebook close to a year ago, skimmed it, and decided it wasn’t for me – I tend not to do well with structure when it comes to time management. About a month ago I noticed a few Pomodoro Technique iPhone apps  springing up, purchased one, and decided to give [...]

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Is “Live Chat” for your website effective?

February 20, 2010

Yes, extremely. We get just as many leads through our website’s live chat feature as we do from phone calls. It also seems that the visitors who chat with us are further into the buying process for whatever reason. Live chat offers a number of advantages over the phone for us: It’s really nice being [...]

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