For a small business, software licensing is a job that only gets attention when something breaks, such as an audit question, a new hire without a licensed copy or a rebuilt PC that will not activate. A little organisation up front avoids all of it.
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Software Licensing for Small Businesses: Single PCs, Multi-PC Packs and Volume Licenses
How to count what you need, choose between single keys and a pack, and keep your licensing in order as the team grows.
Direct Answer
Count every PC and user that needs the software, choose single keys for one or two machines and a multi-PC pack from around ten, and keep a simple record of what is licensed where. Check each product's terms for commercial use.
List every PC, server and user that needs each product. Separate them by what they run: Windows and Office on desktops, Windows Server and SQL Server on servers. Remember remote workers and spare machines that are in use.
Pro Tip
Buy a pack slightly larger than today's headcount if you are hiring. Adding one more key later is easy; finding out mid-project that you are short is not.
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