How do pastors know what hills are worth dying on?

From Gospel Translations

No doubt questions like this must be answered on a case by case basis, but here are seven general areas in which pastors may be called upon to stake their job:

1. The gospel. The closer an issue is to the gospel, the more willing a pastor should be to take a stand. Clearly, this includes taking stands against someone teaching a false gospel, or other doctrines that could lead to a false gospel. But this could also include taking a stand against philosophies of ministry that compromise the gospel, such as a decision to stop or downplay evangelism and focus instead on social action.
2. Unity. A pastor should firmly take a stand against anyone or anything which would wrongly divide the church.
3. Doctrine of Scripture. A pastor should take a stand against anything that would undermine the authority of Scripture (like attacks on inerrancy), since the Scriptures are the source of the church’s life and health.
4. Personal Integrity. A pastor should refuse to do anything that would compromise his personal integrity or wrongly bind his conscience against God’s Word.
5. Holiness of the church. A pastor should take a stand against anything that would violate the holiness of the church or its members.
6. The good of the sheep. If a pastor is not willing to stake his job on the good of the sheep, he is no pastor.
7. Preaching. The most important thing a pastor does is preach God’s Word. Therefore, he should be willing to leave a church that does not allow him to preach the Bible openly and clearly. This does not mean he shouldn’t exercise judgment about when or how to preach certain doctrines from the Scripture.

In any given situation, it will not always be clear whether one of these principles is at risk. Yet they point to the kinds of questions a pastor should ask when deciding whether or not to take a strong stand: “If I don’t act in this situation, will the sheep be harmed?”