This is one of the questions I get most often. My answer is always the same: less often than most teams assume, but more often than most teams act on it.
Changing platforms is not a small decision especially if you run a large team. It means moving data, rebuilding your processes and workflows, retraining the team, and accepting a period where everything will run more slowly as people adjust. That will cost time, money, or focus. Staying on a platform that you know is not working is a cost too.
So when has the time actually come?
When your team is working around the tool instead of using it. People on teams are often reluctant to change and do not immediately adapt to a new platform, even after years of use. That is not necessarily a tool issue. It might be related to the tool being complex to use or it was not set up correctly. Changing a tool as a result of low usage should not be the first move. Try working on it first and finding where the problem lies.
When the tool cannot do things the business now needs. Missing integrations, automation capabilities that have limits costing the team manual hours, reporting that is simply not possible, these are all good reasons to look for a new tool.
Another signal is when the data is unmanageable. You can’t find things easily since it requires extensive searching through items from years ago. Or if the account structure has drifted so far that cleaning it would take longer than starting fresh somewhere else. That is a genuine indicator that a change is warranted.
Curiosity alone could be a reason to explore a migration, but before making any decision, audit what you have. Try to fix the problems within the current system first. When change is not possible, plan the migration properly, with a clear strategy and timelines, and a proper change management approach.