I have worked as a system administrator as well as headed an IT department at several local SMBs over the years. As you can imagine, there were times when management did not see eye-to-eye with some of my proposals or ideas.
Indeed, pushing for new purchases or upgrades can be especially tricky for an SMB. Flatter organizational hierarchy and lower budgets means that it is not uncommon to have to explain your new IT initiatives to a non-technical manager or senior executive.
Let me share with you a three-pronged strategy that I adopt to convince non tech-savvy management to my side.
Return on Investment (ROI) and Total Costs of Ownership (TCO)
Presenting an argument using ROI or TCO (or both) is probably one of the most effective strategies you can use. Exact approaches will probably vary depending on the circumstances. One way you can do that is by adding up the total of all the new purchases you are proposing and dividing it by their expected lifespan to determine the recurring monthly cost. You can then contrast this amount against the lower efficiency or higher operating cost not purchasing the new hardware.
Let's assume that you are trying to sell the idea of implementing virtualization, for example. To start off, you can present the total cost of the new servers as well as the requisite software licenses. Show how it can actually help save money by compare it against the company's historical expenditure to replace ageing servers as well as the typical number of servers that are normally purchased as the company grows.
A relative straight-forward method to bring management to your way of thinking would be to forward them some case studies or news that are pertinent to your situation. It will be easier to convince them once they know what other organizations, or competitors, are up to. In addition, referencing case studies will help convince your management that you are not talking nonsense.
If all else fails, you might want to consider leveraging the expertise of external experts. This might range from independent consultants to equipment vendors. And you don't necessarily have to set up a meeting either -- simply get a confirmation of their professional opinions via e-mail, and forward or copy your management on the correspondence.
And while it is true that vendors will necessarily have vested interest to sell their own products, you can generally eliminate most of their bias simply by talking to two or three different vendors.
I cannot promise that you will be able to convince management all of the time. With some research and application of the methods I outlined, I have found that I am normally able to communicate my point even to non-technical executives and decision makers.