CTO: "This is an important and disruptive decision. I feel that we need X more time to gather information and make sure we don't kill the company doing it incorrectly. What do you suggest?"
It's the CEO's job to be able to weigh different kinds of risks and make a decision. So bubbling up your concerns is the correct answer.
Spot on. This is surgery and requires precision, not axe work, and definitely not something that you're going to solve by coming up with some clever algorithm.
Intra-team relationships are super important, as are the degrees to which the team members have arrived at the company, how long they have known each other, whether they knew each other prior to their arrival and so on. Before you know it you have a mass walk-out on your hands with those that have options leaving first.
The best way to deal with this is to do it very gradually and taking great care to not inadvertently wreck the core structure of the tech department.
It's the CEO's job to be able to weigh different kinds of risks and make a decision. So bubbling up your concerns is the correct answer.