Good preaching should be challenging, without feeling condemning.
No challenge, no condemnation – this is entertainment preaching. Actually, it could be tedious waffle, but essentially this will tend to be entertainment, ear scratching type of stuff.
Challenging by condemnation – this is burdensome preaching. People feel the challenge of God’s Word on their lives, but the weight of condemnation is a pressure we aren’t intended to carry.
Condemnation by challenging – this is shortcut preaching. The shortcut is the assumption that just pressuring people will lead to conformity in behaviour. It might. But it will be forced. And the fruit will ultimately be minimal.
Challenge without condemnation – this is healthy preaching. The Word of God is making a call on the lives present, it is engaging them and inviting them forward, but the mechanism of change is not pressure, but engagement with the gospel, and ultimately, with a person.
Biblical Preaching 
I’m having difficulty discerning the difference between “challenging by condemnation” and “condemnation by challenging.” Could you give an example of what the two look like in contrast to each other?
Hi Dave – good question. I think that the two are essentially the same thing, but highlighting different features of their application. Burdensome preaching comes across simply as a burden on the listener. Shortcut preaching may be the same thing, but the goal is to get results quicker. I think the article could be clearer, so thanks for the nudge. Warmly, Peter