Perhaps the biggest obstacle to outsourcing is the trust factor. I know this because I myself have outsourced to a virtual assistant who gave me numerous reasons to distrust her. In the end I cut ties with that VA and replaced her with someone that didn’t leave me in a cold sweat when I divulged a password or anything else I deem to be confidential information about my business–information that, unfortunately, some contractors will NOT use for good.

Which begs the question: how can a business person avoid outsourcing to a shyster when there is no way to look a candidate in the eye?

When all you have is a cool, emotionless email instead of a warm handshake? Something like 60% of communication happens through body language, so even if you hear a live voice, how much can you really learn about someone over the phone?

Here’s the thing: you put your trust–your life in fact–in the hands of complete strangers every single day. These transactions happen without much thought and cause you relatively little stress if any at all:

• When you get in your car and drive across town, you trust the citizens driving alongside you on the road to obey traffic laws.
• When you turn on the water and step under the hot shower in a 4-star hotel, you trust that the plumber followed protocol for temperature control.
• When you drop your child off at school, you trust the teachers to protect and nurture your little one despite threats abound to her physical and emotional safety.
• When you give your credit card number to the 15-year-old who answers the phone at your local pizza joint, you trust him to use that information responsibly.

None of these choices we make every day is foolproof. Not even close. Yet you continue to make these choices over and over again. You make them because you’ve already assessed the risk and decided the risk is worth the potential reward. You get to where you’re going. You wash a days’ worth of dirt off your body. Your child gets an education. You get pizza when you’re hungry and too lazy to cook on a Saturday night.

Do I have your attention yet?

Yet when it comes time to virtually outsource your business admin or web design or copywriting tasks, there is an inevitable gnashing of teeth through the entire exercise. This is for a number of reasons. Fortunately for web entrepreneurs everywhere, various risk-mitigating measures are available to you:

1) The Internet is a relatively young and lawless place, at least when you compare it to driving or the pizza-by-phone method of satiating hunger. If someone screws you over digitally, who are you gonna call? Internet Busters? If you call the police, what are they going to do? As in what are they going to do about it right NOW? Send a SWAT team to ambush the cyber criminal? Will the police even understand the offense that’s been committed? My own lawyer still has almost no clue what I do or how I do it.

Trust measure: If the contractor or virtual assistant doesn’t ask you to sign a contract, ask for one. Better yet, ask why he or she doesn’t offer one for both parties to sign. Remember, it’s not so much that contracts are easily enforceable (because often they are not), but that a contract creates an opportunity for mutual understanding and clarity. Why would you forgo this in any business deal?

2) Where is your money really going when you click the “Buy Now” button? Most of my business cohorts here in my hometown still don’t understand how it is that ALL of my clients actually pay me in real currency instead of Monopoly money. Though a few of my virtual clients have been intimidated by the big bad PayPal button.

Trust measure: Larger contracts (e.g. $1,000+) can be divided into payments, with a deposit due upfront and the rest payable upon completion of the project. For projects extending beyond a few months and for considerably large sums of cash, negotiate paying in 3 or 4 installments instead.

3) We like to see who we’re doing business with. Much like we prefer to see a person–anyone with a heartbeat really–deliver our pizza right to our door. (This is instead of placing the box on the step, ringing once, and running away knock-knock-ginger style.) Of course, the way a person presents him- or herself can say a lot about the care and diligence he or she puts into business dealings with clients. Looks aren’t everything, however, so keep some perspective. For example, do you really care if your web developer wears a purple Mohawk if he’s the best web developer in town?

Trust measure: Look for a photo of the person you’re doing business with on his or her website. Then look for a photo or bio of that same person elsewhere on the web. All you’re wanting here is to know that this is a real human being running a real business with real products and services. Suspicious web entities usually don’t post much of anything about the owner, let alone a photo or bio.

4) We are tribal by nature and therefore want the approval of our peers before bringing someone new into the fold. That includes the VA or contractor you’re considering. When we allow someone into our professional “space” it’s not just intensely personal but inherently social. As such, there are all kinds of sociological implications to outsourcing, and cyberspace is no exception. Nearly every business owner intuits that he or she runs the risk of “guilt by association” should something go wrong in the relationship.

Trust measure: Talk is cheap, unless we’re talking referrals. What others say about a independent contractor counts. And, perhaps unfortunately so, there is usually a grain of truth to the gossip you hear. That doesn’t mean you should decide not to outsource to someone on account of a nasty rumor. Indeed, the onus remains on YOU the business owner to use your own good judgment and intuition.

5) Letting go of something we love is hard. Letting go of something we loathe is harder. Why? Because we’re afraid that, in the hands of another, the something we loathe will morph into something even worse. As if our inability to manage the loathsome task is evidence of everyone else’s inability as well. It’s the folly of entrepreneurs everywhere: “If I can’t do it then NO ONE can!”

Trust measure: Get over yourself. Let go of the dreaded tasks that are chaining you down. Exercise judgment according to the principles I’ve outlined here, and then accept that risk is an inherently desirable part of being in business for yourself. You take risks with much, much more important things each and every day. Taking informed risks with your business will be at least as, if not more, rewarding.

It will be okay. Really.