The award is organized & selected by the Coolest Tool Academy. This group is selected with a variety of criteria ensuring continuity (up to 2 spots from previous years), previous year winners, mix of editors / developers / Wikimedia Foundation staff, mix of geography and languages. This is done to minimize bias. Folks who are interested in organizing the Coolest Tool Award in the next edition are invited to reach out to us. :-)
The nomination process is open between 2-3 weeks, to give time for people to submit nominations for their favorite tools.
You can nominate multiple tools and are encouraged to do so! The more the merrier, the Academy needs your help getting to know all the cool tools in the ecosystem.
A tool is a piece of software in the Wikimedia ecosystem that is useful from your perspective. Some examples of tools are: gadgets, MediaWiki extensions, websites and web services, APIs, mobile applications, desktop applications, bots, PAWS notebooks, user scripts, etc.
The most important thing is to highlight the work of the technical community, no matter what shape or form the tool takes :-)
After the nomination process finishes, the Academy gets together to discuss the entries and selection process, then they individually review the nominated tools, and finally there is a last meeting where the Academy reconvenes and discusses the nominations to finally assign the awards in a variety of categories.
The awarded projects are announced in a dedicated award ceremony. Depending on the situation either co-located with an existing movement event, or if it is not possible, in a virtual event.