If multiple non-technical people have to contribute, choose tools like Confluence or Google Docs. If multiple technical people are involved, consider a docs-as-code workflow.

Some tools are simple to set up, but lack advanced features. Tools that do have these features vary in their ease of use.

For large volumes of documentation, build times matter.

Offline documentation is mandatory in some industries, so if you choose a cloud-based tool, make sure it has a way to export the documentation for offline consumption.

If you want to set up a delivery pipeline for the documentation, choose a tool that supports this (e.g., command-line-only tools or those with batch versions).

You may need to adapt the look and feel to your company brand. Some tools offer visual customization, while others require web development knowledge.

The choice of editor (WYSIWYG vs plain text) depends on who is contributing to the documentation.

If the documentation needs to be password-protected, choose a tool that supports it or budget time and resources to implement it.

Do you need to generate a website or a standalone document? Not all documentation tools generate PDFs natively, and Word support is ever rarer. The support for customizing PDF output varies from tool to tool.

If you already have documentation in a different tool, consider the migration cost.

If you need to publish to platforms like Salesforce or Zendesk, choose a tool that offers native export.

Analyze the support offerings before choosing a tool—this could range from official vendor support to StackOverflow and GitHub issues.