Not Enough Trust Entrepreneurs are prone to micromanaging. Some business owners, says Jennifer Goldman, founder of My Virtual COO in Baltimore, want to know everything an outsourcer does -- but don't want to pay for the extra time and effort involved in documenting those details.

Too Many Bosses There are benefits when companies bring in consultants or have a team manage outsourcers, says Jason Shindler, CEO of Curvine Web Solutions in Bellevue, Washington. "But if no one is empowered to make a singular decision, we can be sent in conflicting directions," he says.

Unrealistic Expectations Too often, entrepreneurs approach vendors with unrealistic timelines and budgets. "We've had a few clients that thought outsourcing IT would do miracles for them," says Raza Imam, CEO of Adaptive Solutions, a software development firm in Chicago. "The relationship went south when their unreasonable expectations weren't met."

Neglecting the Project Matt Perez, COO of Nearsoft, a software development firm in San Jose, California, says some entrepreneurs think they can "phone projects in," meaning they just hire a firm and don't check in until the project deadline. "When entrepreneurs don't make the time to stay in contact with us, we wind up building something they don't want," he says.