I like the OP. It largely reflects my feelings on the matter.
There are 5 aspects of this I see off the top of my head.
1. Is our intent restoration, edification, correction, and the benefit of the recipient of our message? Or is our intent primarily to spout off, prove we are correct, and to stick our nose in where it is not helpful?
2. Have we prayerfully discerned if indeed that what we want to say is God's highest priority for that person or group at that time? Or is there some other issue that is really the core problem we should address first? Are we chasing symptoms or fixing real problems?
3. Have we discerned the most effective means of communicating?
4. Is the issue we plan on addressing really as clear cut as we think it is? There are some things about which there are legitimate differences of opinion among Christians.
5. Are we the person God wants to say it?
Here's the rough order of thinking I apply before jumping into anything.
1. I first look at my attitude and determine if it is about showing off my personal "greatness" or to help someone.
2. I then try to spiritually discern what the real issue is. I've observed that very often the most obvious stuff that most people focus on are often merely symptoms that are masking the real issue. I try to figure out what is really going on and needs to be addressed.
3. I then decide if I have something helpful to say or not that will help people grow spiritually. And most importantly, I seriously consider if I am the person to be saying it, or if this is for someone else to deal with.
4. I then try to figure out what is the best way of saying something in a way that is most likely to communicate clearly and with the most gentleness and patience possible. This is challenging because it is about determining how the recipient will best understand and consider my words; not about how I would prefer to hear them.
Some people are blunt communicators who want to deal with the immediate issue at hand and resolve it and can't stand it when people "beat around the bush". Other people are more indirect communicators for whom people's feelings are of great importance and feel personally attacked and dismissed when people are blunt. This is rooted partially in personality differences as well as cultural differences. As an example, imagine I am in a meeting and have some yogurt in my beard. A direct communicator sees the yogurt itself as a distraction and problem and goes after the yogurt, so in front of everyone says, "Dude, you've got yogurt on your face. Get rid of it." An indirect communicator is most concerned about my potential embarrassment and will catch my eye and discretely rub their face trying to indicate I should check mine. Now, if I'm a direct communicator, I'd prefer to be told and would probably look at the person rubbing their face and ask, "is something the matter?" in front of everyone. If I'm an indirect communicator, being called out for bad hygiene and unnecessarily embarrassed in front of everyone would hurt to some degree. Of course, "bluntness" and "indirectness" are somewhat ambiguous and on a continuum. But many people do tend to lean one direction or the other and a few quite strongly one way or the other.
May what we perceive as our factually accurate words never harden a heart through discouragement, condemnation, and error because of our own arrogance, clumsiness, ignorance, and impatience in speaking them. May our words spoken to the best of our ability and love bring life, encouragement, enlightenment, and a zeal to move forward.