There is rarely one clear moment to outsource — it’s usually a build-up of smaller signs. Tasks are getting delayed, admin work is eating into time that should go to clients or strategy, or the same repetitive process is being redone manually every week.
A useful test: if a task is well-defined, repeatable and doesn’t require your personal judgment every time, it is very likely a candidate for outsourcing.
Starting small — with one function like inbox management or bookkeeping — is often the easiest way to test the model before expanding it further.