How to Create a Software Sunset Calendar

The calendar components

Each entry in the sunset calendar has five fields. Tool name and monthly cost: the basics, visible at a glance. Contract end date and notice period: when the renewal happens and how much advance notice you must give to cancel or change. Evaluation trigger date: 60-90 days before renewal, when you start gathering data and alternatives. Decision criteria: the specific questions you'll answer before renewing (usage rates, ROI, competitive landscape). Owner: the person responsible for making the renewal decision. This structure ensures no tool renews by default — every renewal is an active decision.

The 90-day evaluation window

For each renewal, schedule a 90-day evaluation window before the decision date. Month one: gather usage data and user feedback. Month two: evaluate alternatives and benchmark pricing. Month three: make the renewal, renegotiation, or cancellation decision. This window prevents the panic renewal — the decision made under time pressure because nobody planned ahead. It also gives you leverage in renegotiation: vendors respond better to early renewal discussions than to last-minute threats to cancel.

Run the free audit to generate a complete inventory of your software with renewal dates — the starting point for your sunset calendar.