Now that I’ve primed your pump for an outsourcing extravaganza, it’s time to turn our eyes towards the quotidian.  Once you’re ready to hire help, there are two main challenges to face.  Firstly, you have to identify portions of your daily work that can be outsourced, and then you have to find the right person to do that work for you.

Identifying work someone else can do

Finding ways to outsource your work requires a surprising amount of vigilance and creativity.  You have to spend a few days watching yourself work and repeatedly asking: if this task isn't something I can eliminate entirely, could someone else possibly do it?  Don't worry:  after a while, the heuristic becomes a reflex.  But you have to start out by scrutinizing everything you do and seriously thinking about asking for help with all of it.

Unfortunately, you'll find that some of the most tedious and annoying parts of our lives actually do demand our personal presence:  stuff like sitting on the phone with credit card companies (which often refuse to speak to an agent over the phone,) standing in line at the DMV to get some piece of bureaucratic ephemera, and, alas, even going to the gym.  Some other tasks, particularly of the one-off variety, require more time to outsource than to do ourselves, merely because of the overhead of explanation and coordination.

The kind of multi-step projects that comprise most of our working lives often seem as if they would fall into this latter category.  It's easy to tell yourself that it would take too long to figure out how to explain a project to someone else than to do it on your own.  After all, you're the only person who has the grand picture, understands the purpose of the work, and is familiar with the details. But with a bit of pluck and a capacity for seeing projects for what they truly are (collections of discrete actions,) you'll be astonished at how much you can rid yourself of.  I have often found that what at first seemed daunting to explain to someone else actually just required a few moments thinking about how the problem needed to be approached—which is a process I was going to have to go through anyway if I were ever going to complete the task in the first place.

Ethan Schoonover recently wrote a fabulous piece here at 43folders about the value of formulating your GTD next-action lists as if they were written for someone else to do.  If one of your projects isn't moving forward, as the theory goes, you probably haven't sufficiently clarified precisely what physical, visible actions need to be done in order to complete it.  When approached with an eye toward outsourcing, it becomes clear how important and powerful this strategy can be.  Not only have you figured out precisely how the thing needs to be done, you've already packaged it up to outsource to someone else with no (or little) additional work.

Admittedly, some sets of instructions take longer to prepare than others.  Spending ten minutes to write an email can seem like a lot of work to ask a person to do a thirty-minute task, but there are a couple things to bear in mind here.  Firstly, you've tripled the amount of work you can do even if just those numbers are correct.  But also consider that, especially if most of your daily tasks could be classified as "thought work," there are tremendous psychological costs to burying yourself in each additional task in your workday.  For one, if you're banging through your email all at once each morning and assigning outsourcing tasks, you're working only in one context and you can do them all in one batch.  But if you did all those tasks yourself at the appropriate moments throughout the day, you'd have to deal with the overhead of the associated context-switching and the burdens of additional stress that the responsibility for each task incurs.  I have found that the drain on my productivity inflicted by being responsible for lots of "little" tasks far exceeds the actual time it takes to perform them.  I have therefore taken to doubling the amount of time a task will take to complete when estimating whether it's worth my time writing it up for someone else to do.  Ten minutes compared to an hour-long task suddenly sounds more reasonable, and it's probably closer to the true cost of doing a thirty-minute task myself.

It's important to remember that you don't necessarily have to outsource whole projects.  To cite an interesting example, we do occasional podcasts at my company. The editing process is enormously tedious and used to take me many hours to turn a two-hour interview into just 30-40 minutes of talk and music. Sure, I’m slow and a total amateur when it comes to audio editing, but that’s really my point.  There was clearly someone better suited to doing this work than me. 

Since I have embraced outsourcing, I now send the raw audio to my man Ashish at Tech-Synergy, who promptly sends me back a flawless time-indexed transcript in text form. I then mark up that transcript by hand in red ink, which takes about 10 minutes, and scan it rapidly to PDF using my trusty Fujitsu ScanSnap (Amazon: PC|Mac). I send the edits along with the raw audio to a firm in Argentina who edit it all together as a seamless podcast according to my marks. The whole process costs us less than $75 and saves me many painful hours of work.  We're just getting ready to post the first podcast produced under this new arrangement, and I have to say that the process has been so effortless that it has greatly reduced my psychological resistance to going out and recording new interviews.

The reason for breaking the project up in this piecemeal fashion is that I wasn't able to find a firm at an affordable rate that was comfortable making editing decisions for me about what to cut and what to leave in the interview audio.  It still seems a little batty to me to have a single podcast be worked on by various people from Bangalore to Buenos Aires in small little chunks, but the firms are happy to have the work; they cost very little; the whole thing greatly bolsters my ability to generate creative product; and I can be sure I'm only spending time on the one tiny little piece of the whole work-flow that actually requires my personal judgment and intervention.  Hard to argue with all that. 

The combinatorial potential of next-action outsourcing is obvious once we approach it as a sort of grammar for assembling the larger language of projects.  But we must also examine a bit of that language's vocabulary.  What follows is an enumeration of things for which I have found outsourcing to be the most useful.

• A virtual assistant
• Design
• Fulfillment
• Audio/video editing
• Scanning
• Transcription
• Artificial artificial intelligence
• Software development
• Domestic work

A virtual assistant

It took a lot of experimentation to find a good one, but I now rely heavily on my virtual assistant.  She checks and responds to all support emails for my companies, forwarding the ones to me that I must personally handle; she scans and tabulates expense receipts; she helps me draft blog posts; she scours the internet for interesting links to post on our company blog; she handles refunds and complaints; she researches things for me; she even made us a MySpace page.  VAs are also great as "attention gatekeepers," who can screen through things like your voicemail, email, or even RSS feeds to bring important things to your attention, based on criteria you specify, without your having to be distracted by all the chaff.

Design

I enjoy doing web design myself, but sometimes having an outside person come in to add an extra layer of polish or to handle the odd arcane CSS problem can be quite valuable.  The Internet is replete with freelance designers with wildly varying aesthetics and fees.  Most designers can layer a lovely front-end onto your existing website without your ever having to change the back-end implementation.  If you're the sort of person who, like me, can blow an entire day vacillating between various minute changes in page layout, you might find it worth hiring someone who has the experience to be more decisive.

Fulfillment

If your business sells physical goods (like my t-shirt shop) or regularly sends out printed matter, then fulfillment houses like Shipwire and Sprocket Express will save you a tremendous amount of time and hassle.  If the cost of those services seems steep, keep your eyes on Fulfillment by Amazon.  I can't recommend it yet due to the immature state of its API and wonky web interface, but FBA promises to become one of the best (and by far cheapest) options out there as they evolve through their beta and fix their funkyness.

Audio/video editing

Like most tasks that involve a human being going through digital media and performing some operation on it, audio and video editing are perfect for outsourcing.  However, remember my podcasting example.  If you're fussy about style and nuance, you'll want to find a way to give specific instructions on the sorts of edits you want to have done.  Unless you're hiring a very esteemed consultant or firm, leaving subjective decisions about editing up to outsourced help is a bit of a gamble.

Scanning

Document scanning can be one of the most irksome office chores.  Although the aforelinked Fujitsu ScanSnap does a laudable job, sometimes you need a real human to babysit the scanning of each item in a huge pile of irregularly shaped or specialized documents.  For example, I had an old set of bound color catalogs that I wanted in digital form.  Because the pages were bound together (and I didn't want to unbind them because they were somewhat valuable,) digitizing them meant painstakingly placing them page after page on a flatbed scanner.  I bid out this task on Elance and was able to find someone to do it quite professionally and cheaply.  The great thing about this is that I now have searchable PDFs of these old catalogs, which I consult fairly frequently.  I can now sell, give away, or recycle the originals.  By converting paper documents to searchable PDFs in this way over the past few months, I have reduced the size of my physical reference filing system by 75% (!), and significantly boosted the efficiency with which I use those files.

As a part of this outsourcing-enabled move away from paper, I have also used ScanCafe.  You send them your photos and negatives, which they ship on to India to be scanned and hand color-corrected, cropped, etc.  Rather than spending hours organizing and labeling the backlog in my physical photo library, I sent all my negatives to ScanCafe, stored the resulting digital versions on S3 along with all the newer images I've taken with my digital camera, and I threw away the paper originals.  They charge $0.19 an image.

Transcription

As mentioned, transcription is a great way to transmit instructions on how to edit A/V media.  It's also great for quickly digesting TV or radio interviews you don't have time to watch or listen to.  (Humans can read much faster than we can listen to the spoken word.)

Having random phone calls come through at all hours of the day greatly saps and impurifies my concentration.  To get around this, I have found another great use for outsourced transcription:  voicemail.  I hardly answer my phone anymore.  Instead, I purchased a SimulScribe account but never associated it with an actual phone number (just select "other" as your provider when signing up).  I now give that phone number out to most of my contacts (especially sales people,) so when they call, it goes straight through to my recorded message, transcribes the message they leave, and then e-mails me the text.  This set-up forces callers to get the point, and allows me to reply at a time that doesn't disrupt my work-flow. 

Artificial artificial intelligence

Amazon's Mechanical Turk service is pure genius.  It commodifies and automates the outsourcing of very small intellectual tasks.  Here's how they describe it:

For businesses and entrepreneurs who want tasks completed, the Amazon Mechanical Turk web service solves the problem of getting work done in a cost-effective manner by people who have the skill to do the work. The service provides access to a vast network of human intelligence with the efficiencies and cost-effectiveness of computers. Oftentimes, the cost of establishing a network of skilled people to do the work outweighs the value of completing it. By turning the fixed costs into variable costs that scale with business needs, the Amazon Mechanical Turk web service eliminates this barrier and allows work to be completed that before was not economical.

At our online dating site, we use Mechanical Turk to outsource what used to be one of the most maddeningly annoying and boring tasks of my day:  approving photos.  We don't want people to upload inappropriate photos into their profiles, so uploads have to be manually inspected by a human.  (There is no easy way to train a computer to identify an "inappropriate" photo.)  Whereas I used to look over every uploaded photograph personally, our site now automatically uploads a task to Mechanical Turk asking whether each new photo meets our approval criteria.  Each photo gets checked by a live human being, and costs us only a few cents per approval.  I don't have to spend any time thinking about this chore anymore, and as a bonus, our photo approval latency has gone from several hours to only a couple minutes on average.

Other tasks to which Mechanical Turk is well suited:  tagging images, searching images for certain features, transcription, translation, checking for duplicate data (album covers, listings, images, etc.)

Software development

One of the downsides of Mechanical Turk is that it requires a bit of programming if you're going to integrate it seriously into your business.  So you may wish to hire a software developer to help you create a custom application to make use of the service.

I use software consulting heavily in my various businesses because much of my business is itself software.  However, you don't have to run a web company to use the assistance of a good team of developers.  An example might be hiring a developer to create a task to do batch work that you normally do manually on your computer—work like resizing groups of photos and then converting them to black-and-white, or uploading certain files on your hard drive to a back-up service every day.  If, for example, you regularly have to turn a big pile of data into some other format manually, or enter data from one piece of software to another, a custom software script could greatly speed up your daily productivity.  Obviously, you don't want to spend the time to learn a programming language just to speed up one of your daily tasks, but if you could hire a developer cheaply to create a script that would do the repetitive data work for you in a fraction of the time each day, it could certainly be worth it.  Try posting a task on Elance, asking for your dream piece of software.  You might be surprised by how affordable the bids are.  Software development is one of the most competitive areas among offshore outsourcing services, so you can usually get a great deal.  Quality naturally varies greatly.

Domestic work

This is where we stumble into the uncomfortable Jeeves-and-Wooster realm of outsourcing, but I find that domestic work, because it requires skills that almost anyone can acquire, has the highest price-to-payoff ratio for outsourcing.  Geo-arbitrage notwithstanding, it's hard to find a skilled Ruby developer (and thus you must pay for the privilege,) but it's not so hard to find someone who knows how to make dinner or sweep the floor. 

There is something luxurious (and, yes, a little weird) in having your household needs seen to by someone else.  You feel spoiled and silly for hiring someone to do work that you could so easily do yourself.  But outsourcing is about freeing your time and psyche for your most important work, if you can afford to do so. 

In my case, I decided to outsource meal preparation, which I used to spend about 5-8 hours on each week.  My solution came from an idea in Tim Ferriss's blog.  I posted an ad on Craigslist asking for a local cook who would be willing to prepare food in bulk for our household of three on a weekly basis.  I got about 15 impressive responses to my ad and ended up settling on a fellow who was willing to make four or five dishes for us in large quantity (more than enough for the three of us to have great food for each meal of the week.)  He charges us $120-140 per week, which is less than I sometimes used to spend on groceries when I did the cooking myself, and delivery is included!  To be fair, I ask that he prepares vegetarian food, which often costs less to make than meat, but I'm sure the cost of meat dishes would be in the same order of magnitude.  This works out on average to cost us about $2.00-3.50 per meal per person (depending on how many times we eat each day,) or about $45 per person per week.  Under this splendid arrangement, I've freed up several hours each week; we're hardly spending any more money than we used to on food; and we're helping a local cook make some extra money.

It never hurts to post a task just to see how cheaply you can get it done.  Grouping tasks into one bulk job and sharing the service with your neighbors helps.  When you look into it, what may seem like the sole province of the wealthy can prove far more accessible than you'd think.

Identifying someone else to do the work

Take a quick look at the number and variety of providers on Elance, OffshoreExperts, and Guru, or make a post on Craigslist and you'll quickly see that when you're ready to set up an outsourcing relationship, finding people willing to do the work isn't going to be a problem.  What you will also find, however, is that discerning among them is.

The great thing about most forms of outsourcing is that the barrier to entry is usually rather low. To take one typical project I posted on Elance (scanning those catalogs I mentioned,) I got bids ranging from $50 to $695.  If I decided to go with one of the cheaper providers, the money at risk was pretty minimal.  And if I found that I liked their work, I could hire them for bigger tasks in future.  To save on international shipping, I decided to hire a stay-at-home mom in the Chicago area to do the scanning for me at $100, which was on the low end of the US bids.  It took her a bit longer than promised to complete them, but I ultimately decided to use her for further work later on because she was friendly and had no trouble understanding complicated tasks.  I've done this many times.  Sometimes, I've gotten awful work, and I just leave it at the initial task.  Other times I've met providers whom I've loved, and I still work with them today.

Feedback on sites like Elance is sometimes helpful, but I find that only the satisfied customers leave feedback.  People who are unsatisfied tend not to leave unambiguously negative feedback for fear of a retaliatory strike (rather like eBay.)  Sometimes you have to read between the lines.

There are, however, other clues to whether a provider is worth trying out.  Beware providers who over-promise in hyperbolic terms.  If the bid is worded to make it sound like the provider has been waiting his whole life to do this one task for you, I would look elsewhere.  I get these breezy copy-and-paste bids all the time, and close inspection usually reveals that this marketing copy (usually in awkward, broken English) was written by someone who didn't even spend a second looking at the task I posted.  There are a few providers on Elance who will more or less bid on everything, low-balling their fee to win and only then will they spend time to figure out how to do the task.

There remains the touchy issue of nationality.  To be sure, there are plenty of cheap offshore providers available to do "business process outsourcing" of the sort I've been discussing in this article.  Having worked with outsourcing companies across the globe, I have developed a few rules of thumb about when to go offshore and when to find a domestic contractor.

I've long been a fervent proponent of Free Trade and global competition for services.  (If you have any hesitations, politically or otherwise, about the issue, I recommend this illuminating article from Foreign Affairs.)  So my decision-making when it comes to outsourcing is always about value; jingoism doesn't factor into it.  I hope the same will hold true for you.

There is an unfortunate sentiment among many folks in the US that with the cost savings of offshoring comes a decrease in quality.  Sometimes it's true—as I have recently learned in the case of t-shirt manufacture, American-made items are much better quality than their Chinese counterparts—but often it's not true, particularly in the case of knowledge work.  As with firms within the US, there is a wide diversity in quality among companies abroad.  But when Americans encounter bad foreign companies they are too eager to blame it on the company's country rather than on natural variations in quality among all firms in that country, which is what they would likely attribute bad work to if they were dealing with a sub-par American firm.  Don't extrapolate an ill judgment against a whole country based on one or two bad experiences.

I have hired many software consultancies, for example, in the past two years, both domestic and abroad.  Interestingly, all of the American firms I hired were both expensive and inattentive.  I finally decided to give an Indian team of Ruby on Rails consultants a try, and they were so efficient, smart, friendly, and attentive by comparison that I actually ended up going into business with them.  This has been my experience with several foreign outsourcing providers.  They are oftentimes more motivated and available than domestic contractors, and very much worth their (relatively palatable) fees.

I've had some bad offshoring experiences too.  One company of Chinese illustrators on Elance was so inept at English that they couldn't understand the simply-worded instructions for the project they enthusiastically bid on, so we had to switch to something more straightforward.  However, after I simplified the task, I ended up with a sensational end-result for a trivial sum of money.  Other providers have sounded great in their bids but proved to be utterly incapable of communicating or delivering even a shadow of what they promised. 

If you're going to go abroad, it's worth using an offshoring firm with some physical basis in the US if possible.  I used one Asian firm with a local representative here in Boston who was a native English speaker.  This made the whole process go much more smoothly than, for example, those Chinese illustrators who couldn't understand what I was asking them to do.  If you're of a litigious bent, you'll also appreciate having a local legal entity with which to sign a domestic contract.

Another potential down-side to foreign firms concerns cultural sensitivity.  I tried three different assistants at the Indian VA firm GetFriday, but was never able to find one who understood American culture and language well enough for me to feel comfortable letting him represent my company.  They somehow always managed to make their emails read like florid Nigerian spam.  GetFriday charges about $10 an hour now ($15 without a monthly contract).  Since switching from GetFriday, I hired my delightful remote assistant in Texas, whom I found on Elance, at $15 an hour.  Not only is she perfectly versed in English and American culture (so that she can actually do things like help me draft blog articles), but she happens to have a higher level college degree than I do.  I am much happier with a slightly more expensive remote assistant in the US, because there is so much more I can ask her to do.

GetFriday was great for rote tasks that didn't require too much independent thinking or cultural awareness.  Some good examples:  sitting on the phone to Costco to ask if they carry a certain type of rice, removing ads from the PDF of a scanned magazine, calling every Starbucks in Boston to see which one is open latest, and simple research ("when is the best time of the year to go whale-watching off the coast of New England?")  I could never have expected them, however, convincingly to pull off creating a MySpace page for my company, or to draft blog articles. 

If most of your work involves spreadsheets and other brainless enterprisey bullshit (I mean that lovingly,) then go with a cheap offshore VA.  If, on the other hand, you're something like a writer, a creative, or a researcher, you're going to want an assistant in the US (or, to save a little cash, you can usually get a bargain by working with someone in a remote part of Canada or the Antipodes.)

A different aspect of cultural awareness is design.  I would be very reticent about hiring a web designer in India, for example, because their national design aesthetic seems to be stuck in the stock-arty world of 1995.  If you're looking for offshore design, go to countries that have low costs of living but close ties to European culture:  Argentina, Brazil, or the Czech Republic, for example.  If you don't mind paying the big bucks, Brooklyn and Portland are gathering places for our country's best hipster designers.  The best place place to find illustrators in any country is IllustrationMundo.

Above all else, pay attention to the provider's ability to communicate.  Since your instructions must be transmitted largely through an indirect written medium, the ability to understand your contractor and have him understand you is of the utmost importance.  Without good communication, you'll just waste your money and time.  If it takes you twice as long to explain yourself to your provider (or worse, it takes two tries to get anything right) you might as well use one who is charging twice as much.  If you get a weird feeling in the initial e-mail back-and-forth, a sense that the provider doesn't quite get what you're talking about, run the other direction and find somebody else.  If you can't understand each other, no matter what the contractor's fee, I guarantee you're not getting any bargain.