I have heard that statement numerous times from staff or board leaders about a decision that was made that they knew was not a good idea but did not speak up. It only takes one individual who is willing to show up to stop a train that looks like it is gathering steam - toward a train wreck.
Especially is ministry there is a tendency toward optimistic thinking. That things will work out or we just need to have faith. But faith and optimism in foolish or reckless decisions is not faith but folly.
Whenever we have a "check in our spirit" we ought to pay attention to it. That "check" or "doubt" may well be the Holy Spirit, or plain wisdom, saying, "Don't go there." "Speak up even if you lose the day." Never ignore the whisper of doubt when making an important decision.
We have a lot of group think on staffs and church and ministry boards. It is an unfortunate thing. The very reason that God designed church leadership as a "plurality of leaders" is that no one individual has the wisdom or gifts to lead alone. But group think circumvents that design by the group simply acting as one individual. Plurality in leadership only works well when each individual is willing, able and courageous enough to speak their minds and even to go against the flow when necessary.
This is not about being the "gadfly." It is about being an independent thinker who is able to speak honestly, candidly and truthfully even when that means raising uncomfortable questions that others don't want to raise. Often, if one individual has doubts, others do as well and the one who is courageous enough to speak gives others permission to speak as well.
One of the marks of good emotional intelligence (EQ) is the ability to be self defining. That is, to be able to state one own's opinion with conviction and clarity even if it is a lone voice.
There are ministry leaders who exert a great deal of pressure for their boards or staff to go along with them. Healthy leaders and staff are respectful but independent thinkers who hopefully won't wish after the fact that they should have said something.