Timing is everything, and having an honest company structure
Too early in a project then you can be seen as the doom-&-gloom merchant.
Too late and it will be seen as being reactive.
Too dishonest structure and people will lay the groundwork down to prevent the idea from gaining traction.
Years ago a company a project was going live and I suggested that we find from the supplier what the top 10 data repairs were so that we could code a solution. Suggested it a bit too early and using the suppliers numbers worked out that we would need about 15+ people full time doing the repairs. Well the Project Manager did not take it well, whereas the Business Continuity Manager agreed after the initial shock.
As a result the PM blocked all comments going up, didnt want to be see the costs going up, or that there would be problems with this new project.
When I left that company for pastures new, the system was about 25% capacity and already had 12 people hacking the database doing repairs, all outsourced. Apparently these standard repairs were too adhoc to be coded, or at least this is what the upper management were told.