Schedule a "right start" meeting. After you've decided on your firm, agency or freelancer, the very first priority should be having a level-set meeting to make sure you're on the same page in terms of how you want to work the engagement. If you're too busy to regularly check your inbox, you don't want someone sending you an email every time they have a question or update. If you're task-oriented, you want emails to be concisely organized in terms of action items. If you're hands on or like brainstorming creative approaches to business, you may want a weekly or bi-weekly call to facilitate open conversation. During your right start meeting, decide how you want to communicate, at what frequency and to what end. Taking half an hour to clearly outline that up front will save you countless headaches and irritations in the long run.

Don't skimp on the onboarding process. As a busy business owner, sometimes the last thing you want to do is carve out half a day or more to onboard a new contractor. After all, you've hired them to save you time. But taking the time to thoughtfully and thoroughly educate the firm about your business will significantly increase your chances of being satisfied with the relationship. Some functions such as marketing will require longer onboarding sessions, where you'll assess your competitive situation, your online presence, your target buyer and your core messaging. But even perfunctory functions like accounting greatly benefit from hearing about your operations, business challenges and short and long-term goals straight from the horse's mouth. Not giving the firm this information is setting them up for failure–and setting you up for disappointment.

Don't pay for ambiguous "strategy consultation." Think about this from your perspective. You wouldn't approach one of your customers and ask for money without telling them exactly what hardware, software, services and support they'll be getting in return. For some reason, we view IT as a more commoditized expertise than something like marketing. But paying a monthly retainer for an ambiguous offering in any job function is just throwing money away. If you're contracting with an expert in a particular field, they should know exactly what the engagement entails, what deliverables they've committed to provide and how long it will take them to deliver. If you bring on a marketing agency to improve your online presence, for example, they should have a process in place that provides you with concrete deliverables such as a detailed SEO audit and PPC recommendations, a messaging strategy or website recommendations. Further, they should be able to tell you exactly how long it will take them to deliver each piece. Don't let any firm or contractor get away with charging you a retainer without giving you something to measure their performance by.