Who in church world hasn't sat through a boring message preached at church? I'm sure I may have even preached a few myself. But I try not to. One of the transformational books in my life was "Communicating for a change" by Andy Stanley. The concept asked this simple question: Are you communicating when you preach for information transfer (much like a school teacher) or for life change? The bottom line, Sunday morning, though not on its own, is much less for information transfer and much more about the love and Word of Christ transforming hearts towards His.
When evaluating the teaching and preaching of the message of a church, there are some important keys that can help both those seeking a church family and those doing the preaching.
1) Scripture is central. A healthy church is based completely on the Word of God in all they do - it is in the hearts of it's leaders because they are devoted to growing towards Jesus, not out of duty of office, but of relationship with Christ. I don't know how to say this, but often a message seems forced - like a person is saying things that they should say, not that they MUST because it just has to come out of what they are learning. If a leader is truly in the Word on a personal level, it will be in and through all their life, especially their preaching.
2) People are accounted for. People were the focus of Jesus' time. He healed thousands, spending time knowing their problems and needs. The message of a church should take into account it's community, knowing it's needs. This is something that I have not done a great job at in the past, frankly because it requires a reorganization of your time and getting your hands dirty. But when you do it will shape what you talk about. I'm not saying that messages should be need or topic or activist driven, but it should show an awareness of the people listening and who they are. One other thing here - we are done and far past the days when the pastor is the Holy Man. Accounting for people means being transparent and honest about your struggles. If people think you are un-relatable - that you are better than them - then they simply won't listen.
3) The Preacher should like preaching. This is one of those things that those outside of the church world just don't get - why would you have someone who is bad at public speaking... speaking publicly? The hard pill to swallow is that perhaps the head pastor is not the best preacher and this requires humility to lead where your strengths are as a pastor and let others who are gifted rise to the place where it fits. If God has called the head pastor to lead the church, why do they need to preach also if they are not gifted there? Too many pastors have been too prideful to admit that others may fill that roll better than them and that doesn't mean that they are not the lead pastor. On the other hand, it's not to say that one cannot improve their skills in this area. But again this requires humility in admitting that they are not good at something and need help and training. We are not called to perfection, but excellence for Christ. This is an important are that is seen most often and evaluated least, especially from the church leadership side of things.
One last thought: if you are a preaching church leader, do you have people that will give you honest evaluation? These people are those you are in deep relationship with, not usually the "back door poll" as people walk out the door. For me, it's a very small group, starting with my wife. Honest evaluation may hurt sometimes, but is necessary for life change.