Editor's note: This article was originally published in 2021, but has been updated and revised to include a more comprehensive list of questions. Every day I answer questions from customers and potential customers about working with external IT service providers. Many leaders of small and medium-sized businesses consider outsourcing IT to realize the benefits of a full-time IT staff without incurring the expense. IT providers can provide a wealth of knowledge and experience that many businesses would love to have on staff, but can’t afford. The right partnership can enhance the security, availability, and efficiency of your business. But, choosing the wrong IT provider can yield long-lasting effects. You could be locked into an expensive multi-year contract that doesn’t fit your business needs, or even suffer cyberattacks, data loss, and downtime. I'm writing this article to provide a comprehensive list of common (and not so common) questions you can use when interviewing IT service providers to ensure that you get the right provider for you. Based on my daily interaction with current and potential customers and more than 20 years of IT industry experience, the list I'll provide in this article will be a valuable resource when you are evaluating IT service providers. I’ll provide an easy-to-understand listing of the critical questions to ask to ensure you have all of the information you need to make this important decision. After you read this article, you’ll feel confident that you have done your homework and will be equipped to make the best IT support choice for you.

Most medium-sized businesses don’t have a full complement of IT professionals on staff to provide the total care their technology infrastructure demands. The fact of the matter is that it is an expensive proposition to get all of the experts you need.

When evaluating options for IT support, leaders of small organizations often struggle with choosing between a break/fix provider or a managed IT support partner. There are a lot of factors to consider including cost sharing, efficiency, security, predictability, and strategic alignment.

When working with an external IT support provider, SLAs are an important tool for setting expectations. The SLA doesn’t just matter to the provider, it’s important to the customer as well.

As a business leader, you are accustomed to weighing all of the options when it comes to an important decision for you business. In any business today, technology is the backbone.

As a successful business leader, you know that your organization’s IT infrastructure is important. But, unless you are an IT expert, you may not know the best way to care for it.

Editor’s note: This article was originally published in 2015, but has been updated to include current information.

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