Copyright 2010 Sean MacEntee/Creative Commons

It’s been 18 months since I started working as a freelance editor of InsideEdge, a startup online finance website created by American Express and Federated Media. So far, I’ve edited close to 120 features and have a couple dozen more in some state of being assigned, reviewed or packaged for publication.

The process has put me on the receiving end of a lot of queries, which has given me a new appreciation for what editors go through when it comes to that part of the story process.

Based on my experience, I believe more than ever that writing the perfect query is difficult. Not impossible, but definitely hard. A query can be great on many levels, fantastic even, and yet be rejected for failing to meet one or two essential criteria.

Here are some of the typical reasons why freelance queries fail, and what a writer can do to get things right.

1. The timing’s off. Pitch a tax story on April 15 or a Christmas story on Dec. 24 and chances are they’ll be rejected. That’s pretty obvious. But because publications have different publishing cycles, it can be hard to know how far in advance to pitch a tax or Christmas story. Women’s magazines are well-known for working on issues six or more months in advance. A regional business magazine I know works on features three to four months out. Some publications that publish every day or week consider story ideas at a story budget meeting that’s held at the same time each day or week. Finding out a publication’s publishing cycle and pitching accordingly can take the guesswork out of knowing when to pitch. Or look for the yearly editorial calendars some publications post on their websites to gauge when to send in pitches for a particular issue or month. If a publication doesn’t have one posted call and ask.

2. The subject isn’t something the publication covers. A pitch could be on a timely, popular subject and you could have sources lined up and ready to talk. But if it’s about a topic that falls outside of a publication’s editorial mission, it’s going to get rejected. That’s the main reason one of the most common pieces of advice editors give is – read the publication. The more you read the better feel you’ll have for what a publication covers. Many publications have posted their mission statement somewhere online – inside their media kit is a common place – spelling out the subjects they cover. Read it.

3. The subject isn’t relevant to the publication’s readers. As with No. 2, some queries are great, just not relevant to the publication’s readers. This happens a lot at magazines that serve specific niches – the editor of a magazine for parents of children up to 2 years old aren’t going to accept a pitch for a story about sending your sweetie off to kindergarten. Likewise, the editor of a website covering Fortune 1000 companies isn’t going to want a pitch for a story on how to get financing for your start-up business. Again, a great place to find out how a publication defines its readership is its media kit. Better yet, look online or call and ask for writer’s guidelines, which editors sometimes put together to take some of the guesswork out of pitching.

4. The publication recently ran  something similar or has something in the works. You could pitch a story that’s a perfect fit – a great angle on a subject the publication covers. But if the publication already has a story in the works or just run or assigned something, chances are they won’t buy it. As a writer, these kinds of rejections are hardest for me because it means I was right on – but another writer beat me to it. When this happens, try querying a publication’s competitors (if those publications haven’t already run something similar) – though that’s tricky because it could mess up whatever relationship you have with the first publication. Or use the opportunity to ask the editor if there are subjects that haven’t been covered as much he or she would like to see pitches for.

5. The query is too short. Some queries have so little detail they’re more of an idea than a pitch. Sometimes that’s OK. If I work with a writer enough to know they understand the publication, I’m OK getting pitched in a line or two. That way if I’m not interested I can say “No thanks” right away and neither the writer nor I have spent much time on the process. If it’s something I’m interested in, I’ll ask them to send me a more fleshed-out pitch. But if you’re querying a publication you’ve never worked with before, the editor will use your pitch, along with your resume and clips, to go on to decide whether you’ve got what it takes to deliver the story. So make it count. On the other hand….

6. The query’s too long. ….don’t write a query that’s as long as the piece. Some editors  like – even encourage – lengthy pitches. I’m not one of them. A writer should be able to state the subject of the query, why now’s a good time to write about it, who they’d interview, what other research or reporting they’d do and why they’re the one to do it and contain all of that information within the space of one computer screen, maybe slightly longer if they’re pitching a lengthy feature. Queries that go on too long are a good indication – at least to me – that a writer can’t be concise, can’t summarize, can’t distinguish between important details and details that could be left out, all important storytelling skills. As the old saying goes, when it doubt leave it out.

What query tactics do you swear by?

The wrap party I hosted at the end of the 2010 WordCount Blogathon went so well, I ran a poll to see if readers would attend Twitter chats on freelance writing-related topics on a regular basis.

The response was an overwhelming “Yes.”

As a result, I’m pleased to introduce WordCount Last Wednesday, a live chat that takes place the last Wednesday of each month on Twitter.

The first WordCount Last Wednesday happens June 30 at 8:30 a.m. Pacific time. To follow along, use the hashtag #wclw.

Each 1-hour chat will focus on subjects you wanted to know more about, including tech tools for writers, writing basics and tips for running a freelance business.

I’ll host each chat along with a guest speaker who’s an expert on that day’s subject (and why does typing that suddenly make me feel like Kelly Ripa).

The theme of the first WordCount Last Wednesday will be WordPress, the popular blogging software.

Joining me to will be freelance writer, blogger and website designer Ron S. Doyle, who understands WordPress better than just about anybody I know.

In coming months, WordCount Last Wednesday will cover topics such as LinkedIn, e-newsletters and e-books, Facebook fan pages, tax planning, online apps for writers, Blogger and more. I’ll post a complete schedule soon.

If you’ve got a suggestion for a subject you’d like to see covered, send it my way.

If you’re an expert in a particular aspect of freelance writing, running a freelance business or tech tools for writers and are interested in participating as a guest speaker, contact me.

See you on the 30th!

So if you specialize, and you regularly work for a handful of publications, do you tell the publications that you work for about each other?

On one hand, it’s kind of like being on a date with a guy one night and telling him about the great time you had with someone else the night before. “Oh Trade Magazine Editor Tim, I just finished the most awesome piece for Newspaper Editor Bob and he loved it.”

On the other hand, it can pay for your editors to know more about the writing you do for other publications.

A couple of events drove this home to me recently:

First, a trade magazine I write for on a regular basis is putting some additional tech coverage in their print issues in 2009. Since the editor there knows I’m a long-time tech writer and cover IT for a national business Website, she asked me to pitch stories for the expanded section – and subsequently bought two of my ideas.

Another example: I keep in touch with an editor of another business magazine on a regular basis – even when she doesn’t have stories to assign – and I always share about projects I’m working on and publications I’m writing for. Her magazine’s publisher is considering launching a new title in 2009. Knowing that the new title’s subject falls into one of my specialties, she contacted me about writing some stories for the premier issue – which they’ll use to sell ads against – maybe even the cover.

Finally, I recently heard about a soon-to-launch news Website. The site’s main focus isn’t what I normally write about, but it overlaps with areas I cover. So I sent a letter to the editor in chief introducing myself and including clips of half a dozen stories I’d done over the last couple years on topics in this overlap area. A week later I heard back – they’re interested and want to see pitches.

Moral of the story: it pays to blab. If you don’t know an editor well, or don’t have a good working relationship with someone, it’s understandable not to want to openly discuss the other work you do. And frankly, some editors could care less. But if you’ve worked with an editor or publication for a while there’s no reason to hold back. And in the case of a new-to-you publication, showing what else you’ve done may be the only way to gain their confidence.

There is a caveat – if you’re going to tell editors about your other work, make sure you show them the love when it comes to the work you do for them. Be reliable, get things in on time, bring your A game. Let them know that although you may work for others, when you’re on their dime, they’re your No. 1.

Make it a practice to send a headline – and a deck too if a publication uses them – with every story you submit. Whether an editor actually uses your headline is beside the point. Writing headlines is good practice. And it shows that:

• You know your story well enough to summarize it quite succinctly.
• You can write short as well as you can write long.
• You care enough about your story to apply all the finishes touches.
• You care enough about your editor to want to make their life easier by doing some of their work for them.

What’s the worst that can happen? The headline ends up on the virtual cutting room floor. What’s the best? Your editor remembers you as that thoughtful freelancer who always includes headlines with their copy – and gives you more work because of it. Or your headline ends up in print. Given the chance, wouldn’t you rather have your story called by the name you gave it than by someone else’s?

Headline writing is an art. The best are like the best kind of diet food: meaty yet lively – and sometimes downright spicy – but without a trace of fat. Cut out articles like “a” and “the.” Use active verbs. Use puns or other word play when suitable. Avoid cliches. Ditto phrases that could be read more than one way – like the headlines that end up on the back page of the Columbia Journalism Review.

Newspaper copy editors are masters of the art of headline writing. Here’s an article about how newspaper copy editors write headlines from Gannett Corp.’s weekly Newswatch column. The story’s really old but the lessons still apply. Magazine and other freelance non-fiction writers can also learn a thing or two from advertising copywriters, who specialize in snappy catchphrases. Here’s a good article called How to Write Headlines That Work in Copyblogger.

Another reason to focus on headlines: your blog. If you’re one of the legion of freelance writers with a blog, it behooves you to write good headlines so your blog posts get maximum exposure. There’s a special art to writing blog headlines. Learn more here and here.