Exclusive or not
The first choice is whether the license is exclusive. An exclusive license generally has to be in a signed writing, because the law treats it as a transfer of an ownership interest, and an exclusive licensee may be able to sue infringers within its scope. A nonexclusive license can arise from a short email or even from conduct, which is why informal arrangements so often produce disputes about what was actually permitted. Scope is defined by terms such as media and territory, and rights not granted generally stay with the owner. Sublicensing and transfer to a buyer of the licensee's business deserve explicit treatment.
Money and control
Payment can be a flat fee, a royalty, or a mix, and royalty deals need clear definitions of the revenue base, along with reporting and audit rights. Owners often want approval over how the work is used or altered, while licensees want certainty that they can ship on schedule. Warranties that the licensor actually owns the rights, and an indemnity if that proves wrong, matter most to licensees. Credit and attribution terms, if they matter to you, should be written in, because US copyright law gives most authors no general right to be credited. Gather the works at issue, any earlier licenses covering them, and the business plan for their use.
Endings and long tails
A license should say what happens on termination, including whether existing copies can still be sold and whether derivative works can continue to be used. Authors also hold a statutory right to terminate many transfers and licenses they granted, exercisable long after the deal was signed, though it does not apply to works made for hire. Licensees building a business on licensed content should know whether that right could reach them. On a proposed license, we check the grant language against what you intend to do with the work and flag the gaps that tend to cause disputes later.