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.
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 add another project to my task manager, this little image pops into my head and I add it to my “Someday/Maybe” folder rather than my “Current Projects” folder…

This is an illustration of two different ways to attack three projects.
In the first approach a project is worked on for three days until completion and then you move onto the next three day project, complete it, etc. This illustration is probably more helpful:

The other approach is to work on one project for a day, switch to another the next day, the next, back to the first, etc. This isn’t meant to be representative of typical behavior, only to show the impact of switching between projects.

Focused approach:
Average completion time = 6 days
Best completion time = day 3
Worst completion time = day 9
Unfocused approach:
Average completion time = 8 days
Best completion time = day 7
Worst completion time = day 9
This is the point: The more you try to take on, the longer it takes to get any one thing done.
- Even though you worked on each project for three days – your average completion time is two days less by seeing one project through till completion and then moving on to the next.
- Your best completion time is 3 days with the focused approach and 7 days with the unfocused approach.
- Your worst completion time is no different.
If you have the discipline to see projects through without having to switch to something else to break the monotony, you’ll get projects done faster than you could by switching constantly between projects. You are spending the same amount of time, expending the same amount of energy, but you are getting things done faster than your “unfocused” competitors. Your clients will like it and you’ll know you are using your time in the most efficient way possible.
Of course, in the real world, you can’t work on only one project at at time because you’ll hit a dead end, be waiting on someone else, another project has something urgent come up. However, I do think it is still important to limit the number of projects in motion at any given time and to switch back to that original project as soon as forward movement on it is possible.
As a business owner, I feel it is my responsibility to constantly generate ideas that will move the company forward. If more than a few days pass without some new way to market or improve our company, I don’t feel quite right. I’m sure most small business owners feel the same way.
But, as your list of unexploited opportunities and un-executed idea grows, the gnawing feeling you should be doing more intensifies. “Look at the opportunities I am neglecting!” you think to yourself.
The temptation is to start working on as much as you possibly can so that none of your ideas feel left out and you feel oh-so-productive. “I made progress on 10 initiatives today!” you proudly say to yourself as you close the screen on your laptop at the end of the day. I call this the shotgun approach to getting things done. It’s deceptive because you are getting a lot done. The problem is nothing gets done as fast as it could. (a.k.a. the illusion of productivity).
Digital Bushidō: “Master your tools”
July 20, 2010
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:
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.
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.
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. 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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