Holy week preaching is tough. There are two main difficulties: high expectations and well-mined, familiar texts. There is, depending on how you count, a single answer: Jesus.
High Expectations and Unholy Pressure
The people piously desire stirring preaching. This is the week that commemorates the most central and critical events of Our Lord's life. The pastor has been wallowing in Lent for six weeks. He has been pointing and pointing and pointing to Good Friday and Easter. The Church gets decorated. There is a special breakfast and candy and music. This is the beating heart, to borrow Franzmann's phrase, of all our hope. This is what the preacher is all about.
Those expectations, pious though they might be, rarely help the fallen sinner who is called to preach. They seem to us like a set up for disappointment. How can we stand and deliver on such a great occasion? How will the people not felt let down by a dry, boring sermon?
God is There Every Sunday
There are two immediate answers to this. The first, I think comes from Nagel, and I believe it, because I have never known anyone to preach the Law more precisely or painfully than Nagel, with the possible peers being Korby, and Marquart. Nagel says, "God is there every Sunday. You should be worried about disappointing Him and stop trying to impress the people who show up on Easter." That is exactly right. When we worry about disappointing our hearers, we really are worried about what they think of us. Nagel's condemnation is spot on. We need to get over it and remember that it is God who has called us. We preach for Him.
The People Expect to be Bored
But, that is hardly the end of Nagel, or the full answer. And here is the Petersen Law: the people's high expectations and hopes for Easter aren't about your sermon. In fact, they expect, as usual, to be bored. I know this is harsh, but I don't mean it quite as badly as it sounds. Yes, the people expect to be bored. But they are okay with that. They still want you to preach. No, they don't want to be bored, but neither do they really mind it. You see, they like you and they're on your side. You don't have to provide a spiritual mountaintop for them or change the way they look at the world or even teach them anything. You just have to tell them again what they already know and love: that Jesus died for them and Jesus lives. That is it. So calm down. Let the organist have the glory. He can blow their socks off. You just preach the simplest message you can manage.
Familiar Texts and Nothing New to Say
Still, that is only half the problem. The other problem is that the texts not only are the texts well-known so that it seems as though there is simply nothing new to say, but by Palm Sunday you have already said it and said it and said it again anyway. These are the go to texts and events. It is one thing to step up and preach about the miracle in Cana or the healing of the blind man on the road out of Jericho and tie it to the cross, it is another to tie the cross to the cross. I can't imagine the preacher who arrives at Palm Sunday without hating the sound of his own voice. It is a long road.
The Love of the People
We underestimate and devalue the love of the people. We are sick of ourselves but they love us. Synodical types like to preach the harsh, impossible law of "love your people" to us. I think they really don't know that "love" is a command and accuses. They think, somehow, that "love" is Gospel, I suppose, because it is good. Bu the Law of God is always good and upholds only what is holy. Of course, "love" is Gospel if it is switched around to the passive. "Love your people" is law. It does not create love. It creates sin in fallen men. But "your people love you even though you are a dirt bag and don't deserve it," is pure Gospel. We need that Gospel. We need it, desperately, and maybe, we need it even more during Holy Week than we do the rest of the year.
So here it is: Your people do love you. Maybe a few mistreat you. Maybe some have even slandered you. But they aren't the majority. The people that come to the Services on Good Friday and Easter, including the people you haven't seen since Christmas, they like you. They think you're nice. They think you're pious and good. They think you're smart and know a lot about the Bible. They hardly come to Church at all, but they don't realize it. They think they do. And even if you barely know them, they know you. You are their pastor and they love you. They really do. So, again, calm down. They like what you say even before you say it.
The Comfort of Familiar
It might be a hard on your ego and your secret desire to teach at the seminary, but consider what you expect from those you love. What do you want your mom to make for Christmas dinner? A new, experimental dish, or a turkey just like you remember it from your childhood? Do you expect your Grandpa to have new jokes? Or do you find comfort in everything being the same? The members aren't your students looking to be instructed into the deepest mysteries of the faith. They are sheep coming to be fed and they like to be fed with their favorite foods. So, calm down, and keep it simple. Don't try to be profound. Don't try to save the world. Just preach the death and resurrection of Jesus. And they will love you for it.
Charting a Course
I hope that will take some pressure off. Still, the preacher does well to do some planning. Because even if the people love you and the task is simple, some art will be appreciated. I suggest that you chart the theme, at least, the titles of each of your Holy Week sermons. That will enable you to play them off one another and help so that you don't feel that you have to get everything into each of them or that you've accidently gone and said everything in the first and have nothing left for the rest of the week. If you understand the how the sermons connect and progress, the chances of your hearers doing so also will increase.
Here, to that end, are my working titles/themes for Holy Week.
Palm Sunday – The Martyrs greet King Messiah, the Suffering Servant, with Palms
Maundy Thursday – The Supper is Bestowed on the Night of Failure and Betrayal
Good Friday – Good Friday, not Karfreitag, but better yet: Holy Friday
Easter Vigil – Kairpos: The History of the World and the War for Man Culminates in This
Easter – The Snow has Melted, the Day now Dawns: the World is a Garden.
A Freebie
One thing that has worked well for me when I have felt overwhelmed by Holy Week or Christmas or a big wedding, is to look to the Synodical Questions for an outline. Look at the questions "Why was it necessary for Jesus to be true Man?" or "Why was it necessary for Jesus to rise from the dead?" etc. Treating Easter Sunday and Christmas Even, in particular, as Catechism lessons makes quite a bit of sense and I've never had anyone complain, but then, why would they, they love me. :) 
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