Tips for Headline Writing from the Omaha World Herald's Steve Buttry. I bolded some of the best stuff but am including it all. My headline focuses may not be yours.
Schlander offers this advice on perhaps the most common headline-writing technique: "Think of key words and do some free association to develop angles. This is how most wordplay, good and bad, seems to develop. Good wordplay makes good use of contrast, or delightfully twists a phrase or is somehow pleasing to the ear. It's not a groaner pun, and it doesn't rely purely on alliteration. A great wordplay example from sports (and a monthly contest winner): So close, so Favre (when Brett Favre and the Packers stole a game from the Bucs). Think also of rhyming words, or words that sound like they look: gritty kitty, for example, or beep and boom. The reader can almost hear the headline."
Make fun of your headline.
Does it state the obvious? Is it full of headlinese? Could it have a double meaning? Does a nearby photograph or another headline present an embarrassing juxtaposition? If you make fun of the headline yourself, chances are Jay Leno won't.
Spellcheck after you write the head.
Typos happen as easily in headlines as in stories, but they're more embarrassing in large type. The reporter has the city desk, you and the slot backstopping him. You have the slot, and you know how busy she is.
Consider the tone of the story.
A light, clever head on a serious story can be silly or even offensive. Yet a light, clever story demands a light, clever head.
Hold gimmicks to high standards.
Effective alliteration, rhyming and puns make a memorable headline and draw readers to a story. When such techniques don't work, though, the headline becomes an embarrassment. Be demanding of such headlines. If you're not sure whether it works, it probably doesn't. If your alliteration uses four words and only three of them actually fit the story, it doesn't work. Be especially demanding of headlines using titles or lines from movies, songs or books. Be assured that you will not be the first copy editor to pen (OK, keyboard) a head on an Iowa story asking if this is heaven or on a sports salaries story demanding that someone show you the money.
Be careful with, but not afraid of, puns.
Pisetzner offers this advice: "The pun must scan both ways: as a joke and literally. My favorite spot is in photo overlines. In June 1997, over a photo of an 87-year-old woman in cap and gown at a Harvard graduation - the university's oldest grad ever - I wrote 'No longer a senior.' Many kudos followed. What made this so effective, I think, was that the humor was sweet-natured as well as counter-stereotypical."
The headline should tell the reader the important news. Vague headlines, even catchy vague headlines, are not informative. Decks can help here. The main head can be catchy but a bit vague if the deck is informative.
Consider photos and graphics.
The headline, photo, graphic and story are a package to the reader and should be composed as such. Look at the photo and graphic to see whether they complement or contradict the head.
Punch with your verbs.
Consider whether you can use a stronger, fresher or more specific verb. With your limited space, you need to make every word count, and often the verb is the most important word in the headline. Give it the attention and time it deserves. Schlander offers this advice: "A fresh verb can really make a headline. Great example: Summer muscles its way into spring. Deputies inch toward unionization. This also creates a strong mental picture. Strong, well-chosen verbs often do that."
Remember the reader.
The story may be about a government body taking action, but the reader cares most about how it affects him. Instead of "Council approves new trash contract," perhaps the headline should be "Council allows later trash pickup."
Don't plagiarize the writer's phrases.
If the reporter used a clever turn of phrase in the lede or the kicker or nut graf, don't scoop the writer by putting it in the headline.
Get an early start.
A headline should not be an afterthought. When you can, read the story as the reporter is writing it, so you can gain some time to work on it or think about it.
Identify your weaknesses.
Know where you need to improve. Focus on one weakness each day. Tonight perhaps you will try not to be so serious on the lighter stories. Tomorrow maybe you'll work on using stronger, more active verbs. The next day you'll try to be more conversational in your headlines. You can improve your headlines better by addressing one skill at a time, rather than making a general resolution to do better.
Pisetzner offers this tip, dated but still helpful: "I'm not sure why, but possessives (his, their, Pope's) tend to give headlines more zing and make them sound less like 'headlinese' and more like conversation. I'll choose 'Clinton breaks his leg' over 'President breaks leg' every time."
Buddenberg suggests, "For wire stories in particular, focus on why the assigning editor chose that story from among the hundreds available. That will lead you to the aspect to focus on in the head, or to the right angle (1st day, 2nd day, something in between)."
Tell someone about the story.
Again from Pisetzner: "If you were to meet a friend on the street and wanted to tell him/her about the latest news you've just heard, what would you say? The two or three things you would tell your friend in your first sentence are the two or three things that should be in your headline. Is one of those details something from deep down in the story? Define that paragraph and move it higher." And, by all means, consult the writer about such a move.
Read the headline aloud.
This will help you spot and avoid clunky "headlinese" writing and move toward more conversational heads.
Buddenberg cautions: "Don't go for the hack stuff -- alliteration and obvious puns and the like: On a good story it's like putting an ugly paint job on beautiful wood; on a bad story it's like an admission."
Watch for traps.
Read the headline one line at a time. Does the first line, read alone, take on a funny meaning that detracts from the headline and the story? Does a nearby but perhaps unrelated photo create a juxtaposition that could make the headline offensive or funny?
Recognize headline writing as an art.
Again from Buddenberg: "Heads are like poetry. Hell, they are poetry. You're a poet: You choose words that tell and find a way to fit them into given limitations."
Take a walk, or whatever.
Sometimes it's helpful to step away from the screen a minute or two when you're stuck. Stretch your legs or scan the bulletin board perhaps. Pisetzner put it best: "Friends from other lives will attest to how often I, having just copyread a difficult story, will go to the men's room (after delaying nature's call the requisite hour or two) and will come out with a great headline idea. I can't explain it. But I recommend that copy editors drink plenty of liquids."