"When is the right time to update your messaging?"
The question often crops up as to whether it is necessary to change anything when your company is doing well and has been marketing and selling the same way over a number of years. I would never suggest changing anything if your profitability is where you want it to be. In this case, your business is working.
However, that doesn't mean you shouldn't be prepared to change. It's important to understand that techniques which have been working for your business may disappear, as practices and technologies change. Therefore, there needs to be a structure and culture in place where you as the leader have your ears and eyes open and are capable of changing when it is necessary.
Basically, enjoy profitable sales while they last, because selling techniques are bound to change. Remember, if you are not disrupting your own sales techniques and processes, somebody else will.