WordCount – Freelancing in the Digital Age

You don’t have to look hard to see the publishing business is changing. Newspapers are cutting jobs left and right as advertising dries up and the economy spins closer to recession. At the same time, publishers are finally sinking more effort into their digital properties, though they still haven’t figured out how to make money.

Freelancers need to change too, if only for the fact that hundreds of freshly out of work newspaper reporters are writing letters of introduction and pitching story ideas to the magazine editors that established freelancers have had all to themselves until now. In many cases, those newspaper reporters already have the skills that freelancers need going forward, skills that will keep them in demand as publishers get their digital groove on. What are those skills?

• Knowing enough HTML to put links in a story
• Creating an online story package
• Using content management software to file stories
• Shooting audio and video
• Producing a podcast
• Running a blog

I’m learning this stuff along with everyone else, so for all our sakes, in the coming weeks I’ll be writing about the skills freelancers should have in the age of digital news, and in some cases, interviewing writers who’re already acquired them to find out how they did it.

Today’s lesson: SEO, or search engine optimization. An entire industry has developed around the science of putting frequently searched words and phrases into the text of blog posts or Websites so they’ll appear high in search-engine rankings and get more traffic as a result.

To understand how freelancers can pick up SEO skills, I turned to two writers turned SEO experts, Marty Weil and Gary Pool, who’ve offered to share how they got into the business.

Marty Weil has been a freelance magazine writer, blogger, owner of a PR consulting and ghostwriting firm, and most recently, SEO writer. The Asheville, North Carolina, resident has been in the writing business long enough to have lived through down times before, so when things started to look bad again, he decided he needed to do something to stand out. That something different was SEO. In his own words, here’s what he did:

“Over the course of several months, I dedicated several hours a day to studying SEO. I studied blogs of leading SEO gurus and read top SEO forums. After months of self-study, I took a SEO/SEM class at A-B Tech in Asheville to gauge how much I’d learned. I was pleased to discover that I had not only grasped the main principles, but was able to instruct the instructor on some of the more cutting-edge aspects.

“If I hadn’t launched a blog several years ago — and put into practice what I was learning — it would have been much more difficult to develop an expertise in SEO. Using SEO principles, I’ve been able to take my blog traffic from a few dozen page views per month to more than 14,000 in January, 2008.”

Gary Pool got into SEO writing a different way. Pool was a Website designer who wanted to understand why sites he built appeared high in Google or Yahoo searches. Researching the reasons led him to the world of SEO, and he’s been there ever since. Pool uses his SEO skills for work with small businesses, churches and other clients of his company, White Rose Productions, in Portland, Oregon.

Pool uses SEO software that automates the work of putting commonly used words and phrases into copy on Websites and blogs. Some of his favorites are Niche Bot, a subscription-based software tool, SEO Book, a regularly updated e-book with a variety of SEO tools, Word Tracker, another SEO tool that offers a free trial version.

But there’s only so much you should do with software. The most well-optimized blog post won’t do you any good if you end up with text that’s incomprehensible, Pool says. Other advice: avoid industry jargon and don’t overlook where words are placed. “I’ve got a client who does catering,” Pool says. “If I was searching, I’d search for ‘catering and Portland.’ But people in Portland don’t search like that. They put ‘Portland’ first and then ‘catering.’ That’s a small difference, but if most people put them in that order, you need to have them in that order in your blog.”

Other advice: don’t let SEO keywords sap all of the life out of your Website or blog copy. “If it’s dry and in-your-face marketing, people will get tired of looking at all the ads,” Pool says.

Advice from Weil: The best time to optimize a blog post, ad copy or other article bound for the Web is when you’re writing it. Make sure the keywords you need to use are in the text. Weil recommends using no more than two keywords per post, and a “keyword density” of no more than 4 uses per 100 words, or 4 percent. And don’t forget to include lots of links. “That pretty much sums up the SEO part. The rest is old-fashioned common sense copywriting,” he says. “Write quality, sticky copy that benefits the reader. And the search engines will love you for it.”

There are plenty of online resources for learning SEO writing, including Websites such as SEO Roundtable, a group-written blog about all things related to SEO, and SearchEngineWatch. SEO Consultants maintains a list of blogs about the SEO business.

Some parts of the country have active SEO organizations whose members meet regularly for workshops and conventions. If you live in the Pacific Northwest, you’re just in time to catch SearchFest 2008, sponsored by SEMpdx, the local SEO association. Check out SEO Book’s SEO Conference Calendar for meetings near you.

It happened. Earlier this week, the editor of a magazine I’ve been writing for told me she can’t buy more freelance pieces until summer because of budget cuts. It’s the first time in years that economic cutbacks have directly affected my business. It’s also bad news because I’d just pitched a story I thought was perfect for the publication.

I was bummed. But I’d just finished writing here about smart things freelancers can do to weather bad times. So I had to take my own advice. Later the same day, I needed to send a separate pitch to a different editor I’ve written for a lot lately but at a rate that’s lower that what I usually make. I’d just turned in a bunch of stories that this editor really liked. So thinking about the client I’d just lost, I wrote the pitch letter and at the end asked for a raise. I heard back the next day – the publication agreed to up my rate by 20 percent. It gets better. I called the editor to say thanks, and in the course of conversation, she mentioned another publication that might be interested in using me and offered to pass along my name.

The moral of the story: Don’t get hung up on bad news. Don’t be afraid to ask. Remember to say thank you. And sometimes it pays to pick up the phone.

I recently shared a marketing expert’s advice for freelancer writers and other self-employed creative types to stay happy and solvent during shaky economic times. His suggestions boiled down to a few simple maxims: cultivate existing client relationships, specialize, learn new skills and network.

Reality check time. Do freelancers heed such advice? Or do they use other strategies for beating bad times? To find out, I posted those questions on LinkedIn, the business networking site. What I got back was very concrete and creative directions from writers and other freelance professionals about what they’re doing to cope. Here’s what they said:

Keep regular clients happy – Cultivate a core group of clients and work hard to keep them happy. The best way to do that: deliver above and beyond what’s expected. “Happy clients return no matter what,” says Flip Wiltgren, a freelance writer and game designer in Linkoping, Sweden. Marijke Vroomen-Durning, a Montreal freelancer and author of the HelpMyHurt blog, emails clients every so often with updates on her work and asks outright if they have anything they need done. “Sometimes, your email lands in their inbox at exactly the right time,” she says.

Market yourself as a virtual employee - Down times can be good times for independent contractors because clients can use them without adding to payroll, says AnnaLisa Michalski, a virtual assistant and writing support specialist in Norfolk, Virginia. Susan Emmens, a Richmond, Virginia, freelance marketing strategist, contacts companies looking for full-time employees to offer her services as a contractor. “Some have reasons that make freelancing a bad fit, but many are open to the idea that having a fresh set of eyes who isn’t mired in the company stuff might be just what the doctor ordered,” she says.

Change your thinking about where work comes from - Think outside the box, says Kathee Brewer, a Houston freelance writer. “There are quite a few ‘little’ jobs out there for talented writers who don’t let their egos get in the way,” Brewer says. “It’s hard not to appreciate the benefits provided by small, recurring assignments that, perhaps aren’t career builders, but nonetheless provide a bit of budgetary breathing room while one works on the things that really capture the imagination.”

Vroomen-Durning, the Montreal freelancer, spends time ever day combing freelance job boards, including Craigslist. “I know it has a bad rep, but if you take the time to look, you do find some real gems,” she says. “Two of my best clients have come from there. One in terms of high pay, another in terms of fun and enjoying the work.”

Measure projects by hourly not per word rates – Freelancers sometimes pass up work because the per-word rate is low. But projects should be judged on their merits and not just on per-word rates. Vroomen-Durning takes jobs based on how how well she knows the subject. An $800 project that she can do in 8 hours is a good hourly income. “If I’m offered that same amount for a shorter article but it involves a lot of research and reviewing back and forth, it may take a lot longer than 8 hours so it’s not worth my while,” she says.

Change how you think of yourself - If you want new types of work, create new ways to describe what you do, says Robert Dolezal, a Sacramento, California, publisher, content architect, and content provider. “If you’re usually a copywriter, step up into an editor’s role and re-brand yourself. It’s an excellent way to get new conversations going,” he says.

Call in favors – Use clients or contacts to ask for referrals, advice, and suggestions. “Studies show that more (job) action takes place from casual acquaintances than from those close to you, so getting the word out is important,” Dolezal says. And don’t forget to return the favor.

Go back to old clients – “You’ve already worked for them. That takes away a lot of stress and hard work,” says Terri Maurer, a past president of the American Society of Interior Designers and author of an upcoming book on the interior design business from Wiley & Sons. But don’t call just to ask for work: touch base to see how they’re doing. “The idea is to remind them you’re out there. The odds are you’ll find a few who were just thinking about calling you, or you will have called at just the right time,” she says.

Specialize – If you specialize, dig even deeper into a niche so you become an expert on the subject. Maria Marsala, President of Elevating Your Business, a Seattle consultant that helps small and mid-sized businesses, went from marketing to small business owners to marketing to financial advisers and planners. “It’s working for me,” Marsala says.

Use down time to look for new work – Sue Kristoff, owner of The Kristoff Group LLC, a Boston area engineering and technical writing firm, uses down time to troll online portals for new work. She also publicizes her business by leaving comments on blogs and online forums.

Sell one thing – You might wear a lot of hats, but trying to explain all that to prospective clients is confusing. So sell one thing. For Richard Laurence Baron, who started freelancing after a 30-year career in advertising agencies, that one thing is copyrighting. “Only a portion of my marketing/communications revenue comes from copywriting, but I still SELL that one thing. All the other stuff comes when the relationship and the trust is built,” says the Houston-based freelancer. Read more on his blog, SignalWriter.

Schmooze – Get out of your office and attend a networking breakfast or other real-world function. “Meeting people face to face or (getting) a reference through a contact has yielded me pretty much every major client I’ve got,” says Wiltgren, the Swedish freelancer. Maurer, the interior design author, adds, “Getting to know people before they needed my services allowed us to have some very open conversations about their companies, their needs and how my services might or might not be a fit for them.”

Learn new skills – This is the third big economic downturn that long-time freelancer Marty Weil has weathered. This time, he hopes to differentiate himself from other freelancers by offering search engine optimization (SEO) copywriting in addition to his other writing services. To prepare, he’s taken courses and practiced on his own blogs. Weil is also using his blogs as revenue generators. “My blogs have become successful business units in themselves, and as I’d hoped, have led to some amazing and worthwhile freelance writing opportunities,” he says.

S.W.O.T. – Grant Plowman, owner of Interactive Media Publishing, a Medford, Oregon, e-learning tools company, suggests that freelancers can pinpoint where they are and what they could do better using an assessment technique called SWOT: Strengths, Weaknesses, Opportunities and Threats. The steps: analyze your strengths, honestly evaluate weaknesses, examine opportunities with present or potential clients, look at threats to existing client relationships and whether the services you provide represent a value that exceeds their cost.

You can read the complete text of answers freelancers gave on this topic on LinkedIn’s Answer section here.

The publishing industry is in tumult. Publications are trying to do more with less – less advertising revenue, editorial staff and readers. Throw worries about a recession into the mix, and it means trouble for freelance writers who depend on magazines, newspapers and customer publishers for their livelihoods. Or does it?

Not necessarily. Hard times don’t have to be bad times, at least not for freelancers who have a plan for marketing themselves during a shaky economy. That’s the view of Keven Malkewitz, a marketing expert and assistant business professor at Oregon State University in Corvallis. Malkewitz earned his marketing chops as a brand manager and business unit manager at Adidas, before getting a doctorate and helping consumer and technology companies with their marketing programs.

I asked Malkewitz recently what independent contractors such as freelance writers can do to keep clients and paychecks rolling in during a bad economy. Here’s what he said:

If times are tough, should freelancers hang onto current clients or go after new work?

During bad times, companies hunker down, they put stuff on hold and they don’t do new projects. In that case, you’ve got to work with the hand you have, so work on building stronger relationships with existing clients.

What could freelancers do to make themselves more attractive?

The thing that makes people like writers and designers most attractive is having some type of core competency that most people who do what they do don’t have. New skills are always helpful. For instance, we have an active design community in Portland, so instead of doing general design, a designer could stand out by doing branding or another specialty.

Should freelancers increase their marketing efforts in bad times?

There are fewer marketing efforts in down times, so for the companies that do it, marketing can be more effective. Studies have shown that companies that advertise in down times rebound higher. So invest in yourself. Marketing efforts do make sense.

Any other suggestions?

It’s all about networking, people you talk to and the quality of your work over time. It’s a good time to re-evaluate what you’re doing, to think about new ways of doing things. Really, that’s good to do anytime. We’re creatures of habit. We do things the way we’ve always done then. But bad times provide a positive opportunity to change.

I took to blogging fairly quickly and I finally figured out why.

I wrote a weekly newspaper column for more than five years. After that, I wrote a weekly column for Reuters, the financial wire service, for seven years. After a dozen years, writing something once a week – or more – was so second nature that when I stopped working to take care of my kids, I kept writing weekly columns. It’s just that for a time, my “weekly column” was the weekly email update for my oldest kids’ summer swim team. Then it was the weekly report for my son’s middle-school football team. Then it was a weekly newsletter for a charity group my daughter and I belonged to. It didn’t really matter what I was writing about, I was writing.

When I went back to work, I had to get acquainted with the technical aspects of blogging. But on the writing end of things I was good. Because really, I’d never stopped.

All of this is a round about way of saying, if you’re a writer, you need to write, and one of the best ways to practice is a blog. If you blog, it gets you into the habit of writing often. It’s like playing the piano. The more you practice, the faster you get better. The more you write, the faster you get better.

That’s reason No. 1 freelance writers should have a blog. Having a blog can also help you:

Create a Website – Sign up with a free blog hosting site like WordPress (what I use), TypePad or Blogger, and for nothing more than your email address, you get an online home for your resume, bio and clips as well as a blog.

Establish a beat - Whether it’s the 2008 presidential campaign, animal rescue or vegan cooking, blogging about a particular subject can help you stay on top of interesting trends and developments in a specific field, information that you can use for queries and assignments.

Practice different writing styles – If you normally writing in one style, you can use your blog to practice different styles or voices. If you normally write straight news stories for business or trade magazines, use your blog to practice writing opinion pieces, personal essays or comedy bits. If you’re comfortable writing in different styles and genres for yourself, it’s not much of a stretch to pitch those types of stories to potential clients.

Become an expert – If you blog on a specific topic long enough, you can develop an expertise that’s so attractive editors will come looking for you – or at least that’s the hope. You might also draw conference organizers looking for speakers and like-minded writers who want to network. Which leads to….

Make connections – Your blog can be a calling card to introduce yourself to writers, editors and other people in your field. Since I wrote about blogs for writers, a bunch of writers whose blogs I mentioned have asked to put me in their blogrolls and I’m doing likewise. Bingo, instant community.

Interact with readers – When you write for magazines or newspapers, you don’t always get the chance to interact directly with readers. Some publications still don’t run writers’ email addresses with stories and others run a generic address for all letters to the editors. On a blog there’s no barrier between you and your readers, so you can respond to whatever they have to say, which could lead to more things to write about.

Improve your skills – As publications move from paper to the Web, writers have to follow. You don’t need to know everything there is to know about coding HTML, but you should know a little. That goes for podcasts, social networks and other Web-based software too.

Get instant gratification - Send a story idea to a magazine editor and it might take weeks or months to hear back. Seeing a story in print can take even longer. On a blog, you get an idea, do some research, write it, hit the “Publish” button, and there it is, your thoughts for the world to see.

Make money – Although many writers use blogs purely for marketing and networking purposes, some have turned them into money-making ventures. They sell ad space through Google AdSense or sign up for the Amazon Associates program, or use the space to sell self-published books, e-books, webinars, podcasts and related services. You may find that you like blogging so much you want to look for freelance blogging gigs, which you can find on sites like ProBlogger and BloggerJobs.

Other writer/bloggers have weighed in on this subject. You can read their reasons why writers should have blogs here, here and here.

The Los Angeles Times today named Russ Stanton editor. Depending on how you feel about the present state of the newspaper business, this is either really good or really bad news, and for Stanton, a really good or a really bad job. I’m of the mind that it’s good on both counts, and not just because I once sat in a cubicle across the aisle from Stanton when we were business reporters at the Orange County Register.

For the past year or so, Stanton’s been the paper’s Innovations editor, charged with overseeing the paper’s Web site and more generally, bringing it into the digital age. For Sam Zell, the paper’s new owner, and the David Hiller, the current publisher, to tap a Web guy for the top job over the other finalist, a veteran Times editor whose rise through the ranks was took a more traditional trajectory, says a lot about the direction they want the paper to take. If they use this opportunity to continue beefing up their online news presence – and make money and save newsroom jobs doing it – they could create a template for newsroom innovation other papers would eagerly follow.

But none of this is happening in a vacuum. In the past three years, the Times has seen three editors come and go, all of them quitting to protest budget cuts that lowered newsroom headcount and morale. Revenue from advertising continues to drop at the Times and throughout the newspaper industry. On Feb. 14, the New York Times said it was cutting 100 newsroom jobs due to declining ad revenue. Nice Valentine.

Stanton will have his work cut out for him. For starters, he has to deal with the 100 news job cuts across the entire Los Angeles Times Media Group announced Feb. 13. In addition to the daily paper, the group includes community papers, a Spanish-language paper and an entertainment guide. But he appears up to the challenge. In a newsroom speech after his promotion, Stanton said: “”I have grown tired and am now hopping mad over this seemingly endless ‘Groundhog Day’ nightmare.” He also said The Times would have “to figure out how to break this self-defeating cycle before it does indeed result in our defeat.”

When writers aren’t writing, they’re reading about how to be a better writer, or be a better marketer of their writing, or about who else they could be writing for.

That’s what I found when I asked freelance, newspaper and magazine writers and editors to name some of their favorite blogs for writers. It’s an eclectic list and by no means comprehensive. Just don’t start reading on deadline.

The Mechanics of Writing, Editing and Copyediting
You Don’t Say – Written by John McIntyre, the Baltimore Sun’s assistant managing editor for the copy desk. McIntyre is a human version of the AP Style Guide or one of those other grammar and usage mauals – but funnier. Thanks to Matthew Crowley, business copy editor at the Las Vegas Review-Journal for the tip.

WordWise – Forget for a minute that Dan Santow is a PR guy. His blog on grammar and usage is good – and not just because he’s got fellow flacks discussing things like commas and overused words (for which reporters everywhere thank you). Oh wait, Santow was a reporter before he became a senior v.p. at Edelman, the big PR firm. Now I get it.

WordHappy – Toddie Downs, a freelance copywriter and editor, uses her blog to celebrate good writing of all types – TV, movies, fiction, non-fiction and advertising.

Freelance Writing and Marketing Yourself as a Writer
Erik Sherman’s WriterBiz - Sherman, a long-time freelance writer and photographer, tackles the business end of writing in this very professional if plain-looking entry. Sherman’s written for some of the biggest names in the business including the New York Times Magazine, Newsweek, Fortune, Inc, US News & World Report and knows what he’s talking about.

The Renegade Writer by Linda Formichelli and Diana Burrell, co-authors of The Renegade Writer: A Totally Unconventional Guide to Freelance Writing and The Renegade Writer’s Query Letters That Rock. Lots of practical wisdom on this blog, which fellow freelancer Peggy Noonan recommends for its useful resources and “common sense tips that work.” UPDATE: Thanks Diana, for pointing out that this is a team effort.

Freelance Switch – This group-written blog about freelancers of all stripes – Web designers and illustrators as well as writers – includes classifieds, podcasts, resources and a job board.

FreelanceWritingGigs.com - Started in 2005 by Deborah Ng, this blog posts info on new jobs almost daily. But proceed with caution: the listings include a lot of “work from home” situations, Web content writing assignments and other low-pay gigs.

Men With Pens – Wait, you did want to be a Web content writer? This is the place to learn. This site was formerly known as Web Content Writer Tips.

TheUrbanMuse – Lots of practical advice on writing and the mechanics of freelancing make this well-suited to beginners. Author Susan Johnston Home is away this month and has guest bloggers filling in.

Screw You – Kathy Kehrli calls herself the Irreverent Freelancer and uses her blog for rants against low-paying clients and other mistreatments that go with the freelance territory. Read it as a cautionary tale, or visit when an editor’s got you steamed and you need an acceptable place to vent.

InkThinker - A personal take on the freelance life, written by Virginia copywriter and consultant Kristen King.

About Freelance Writing and The Golden Pencil – Two more personal takes on freelancing written by Anne Wayan, an independent writer, blogger, ghostwriter, editor and writing coach.

Publicity Hound – Although this is written by a public relations specialist for other PR types, freelancers can glean tips on marketing and generating publicity for their own work – and take a peek at how the other half lives.

Jugglezine – Herman Miller’s elegantly designed e-zine is all about balancing work and life, a freelancer’s constant challenge. And if reading it makes you want to spruce up your home office with some new furniture, well hey, you’re in the right place.

The News Business
Romenesko – This daily recap of major happenings inside U.S. newspapers lets ex-staff reporters like me and other news junkies get their fix.

Publishing 2.0 – A blog about how technology is transforming media. Is the Web going to be writers’ salvation, or is it the Dark Side? The publishing industry insiders who write this blog argue for the former.

Copywriting and Corporate Writing
Copyblogger - The well-organized site has multiple authors who cover everything from getting more done to writing better headlines to personal branding. Joel Kelly, interactive media specialist at Cossette Atlantic, calls it “fantastic.”

Bob Bly’s Blog – Bly lifts the veil on the copywriting business and is as good a start as any for magazine writers considering a leap into corporate work. If Bly’s blog – and related Web site – are any indication, there’s a world of difference.

Dianna Huff’s B2B MarCom Writer Blog - Advice from a marketing communications pro.

Copywriter Underground – More solid copy on copy from an industry veteran.

The Bad Pitch Blog – Apparently the P.R. firms whose work gets lambasted on this blog aren’t reading Copyblogger or Copywriter Underground. “Funny and well-written,” says Lewis Harrison, PR and communications manager at Codeworks.

Michael Stelzner’s Writing White Papers – Everything you need to know about writing a corporate white paper.

Computers were going to wipe out paper. That’s what we believed back at the dawn of the PC era. Twenty-six years later, people are still overwhelmed by the stuff.

Face it, getting rid of paper completely won’t happen. It’s too big a part of our lives. The thing is, it doesn’t have to be as big a part. It’s like going on a diet. You don’t cut out food entirely, just decrease the portions. That’s how energy researcher Bruce Nordman, with Lawrence Berkeley National Laboratory, put it when I interviewed him recently for my story on reducing use of office paper for IncTechnology.com.

Since last fall, I’ve been on a mission to reduce my own paper consumption. I have a practical reason and a philosophical one. On the practical side, I have one two-drawer file cabinet in my office for tax records, important papers and work files. The less work-related paper I generate, the more room I have for receipts and tax forms. On the philosophical side, I’m trying to reduce, recycle and reuse all kinds of things, and cutting back on paper fits into that.

Here are my top 5 ways writers and home-based workers can go paperless:

1. Ditch the scratch pad – I’ve always been a major list maker. Now I put daily and other to-do lists in the Tasks section of Outlook. The program’s Notes section is good for keeping track of books I want to read, ideas for birthday presents and my resume. If you don’t like Outlook, there are plenty of Web-based applications like it, such as Google Notebook.

2. Mark up story notes on screen. I’m embarrassed to admit I just started using the highlighter feature on Word. It makes it easy to do the same kind of mark up on notes that I used to do with a paper print out and yellow highlighter pen. When I write, I use the split screen feature of Windows to open my notes file and my story file at the same time.

3. Use a bookmark service for research. Del.icio.us, the social bookmark service, is great for tracking information for stories or other research. It’s easy to use. Sign up, find sites you want to save, tag them with key words, then use the tags to sort through what you’ve saved.

4. Ask collaborators to use Track Changes. This feature of Word is standard operating procedure for most writers and editors, but it’s amazing how many other people don’t use it or even know that it’s there.

5. When you have to use a printer, do it judiciously. Some things you have to print. When you do, print to both sides of a piece of paper. Set printer controls to print out multiple pages per sheet of paper. Set printers so they won’t print out test pages when they’re turned on. If you use company letterhead, create a Word template you can be print out as needed.

You can find more tips for eliminating office paper at a Website energy researcher Bruce Nordman created 10 years ago called Cutting Paper. The information hasn’t been updated for a while, but Nordman promises it’s still valid. And he’s looking for some green-souled individual or group to take over running it. Interested? Drop him a line at the lab.

The same day the New York Times ran this depressing story detailing everything bad about the newspaper business – dropping circulation, constant management changes, drastic staff cuts, etc. – my local paper had a story about how bad sales were at major department store chains in December and January. Coincidence? I think not.

As the Times story points out, departments stores and newspapers grew up together over the past century and good times at one fueled good times at the other. Now both are on a downward spiral. Macy’s reported a 7.1 percent drop in same-store sales during January, leading them to announce a reorganization and layoff.

Department stores are just one category of advertiser that’s doing less print and more online advertising and causing major damage at newspapers as a result. Craig’s List, online real estate listing services, and eBay among others have decimated papers’ classified advertising sections, causing papers to take drastic steps like cutting staff and slicing or dropping sections.

Some papers are managing to crank out the hits despite curtailed budgets and staff. For purely selfish reasons, I’m happy one is my hometown paper, The Oregonian in Portland. The paper’s dynamic duo of Editor Sandy Rowe and Executive Editor Peter Bhatia have been there 15 years – that’s more like 100 in newspaper editor years – and recently were recently named Editors of the Year by Editor & Publisher, the newspaper industry magazine.

During that time, the Oregonian won 5 Pulitzers and was a finalist 14 times. The paper’s owned by Advance Publications, a privately held communications company that also owns Conde Nast, Fairchild, American City Business Journals and 19 other newspapers. Without public financial records to check, it’s difficult to assess exactly what kind of shape Advance’s newspaper business is in. What’s visibly apparent: on certain days of the week the Oregonian’s pretty skinny, and they’ve started folding the business section into the news section, following a trend at other papers.

On the other hand, the Oregonian’s local news and sports coverage is consistently in-depth, informative and entertaining, and the investigative team is as good as any in the country, thus the prizes. The paper has actively pursued new ventures including producing a couple glossy lifestyle magazines like Exploring the Pearl, and has a home and garden magazine in the works. The paper’s Website could be better; the search function is particularly awful. But the Oregonian’s attempts at getting the general public engaged in the news process as bloggers and on online message boards has been successful.

Not long ago, a writer in a freelance group I belong to posted a question on the group message boards. She had an interview scheduled with a subject who had a reputation for being grouchy and wanted to know how to prepare. It’s a great question. Reporters are thought of as thick-skinned hacks who can take just about anything, and dish it out too. While I’ve know some like that, most aren’t and they’d just as soon avoid confrontation as the next person.

So if you’re not Mike Wallace, how do you ask the hard questions? Here’s my top 10 tips for conducting tough interviews:

• Do your homework. The more information you have, the better prepared you’ll be to ask any kind of question, hard or easy. And it’s easier to steer the conversation back to tough topics when you’ve got your facts down cold.
• Write questions down. In an age when everyone seems pressed for time, it’s not uncommon for interview subjects or their PR handlers to ask for questions in advance. That’s fine, especially since it forces you to prepare. But once you’re talking, don’t feel obliged to stick to the script. When you’ve got a subject comfortable, go with the flow and toss out a couple juicy questions that aren’t on the list.
• Don’t ask “yes” or “no” questions. Don’t give an interview subject the opportunity for monosyllabic answers, otherwise you’ll be stuck with no good quotes. Ask open-ended questions that makes them think, such as “What led you to that decision?” or “How did you solve that problem?” or “What else can you tell me about that?”
• Don’t be afraid to look stupid. What if you have the opposite problem and your subject is a know-it-all who talks in circles all the better to intimidate you? If what they’re saying isn’t obvious to you, it won’t be obvious to your readers either. So swallow your pride and ask, “Can you run that by me again?” or “I’m not sure what you mean by that?” or “Can you explain why?”
• Don’t let a subject off the hook. You ask a question, they won’t answer. Ask a different way. Or ask why they won’t answer. I get this a lot because I interview executives at private companies who don’t want to talk about revenue or other money matters – and if they’re privately held, there’s nothing forcing them to divulge it. Coax it out of them by asking “Can you give me a range?” Or “What do companies in your industry generally charge?” or “How much did sales increase over last year?”
  
• Get specifics. Don’t be satisfied with pat answers or industry jargon. This is especially true if you’re writing about a field or subject with a language all its own, like business, medicine or technology. If you don’t understand the terminology an interview subject is using, don’t be afraid to ask “Can you explain that for me?” or “I’m not familiar with that term, what does it mean?”
• If you’re pressed for time, front load. If you’ve only got a celebrity or CEO for a couple minutes, cut to the chase. Ask your three or four most important questions right away so you’re sure to get the information that you absolutely positively have to have or your editor will kill you – or your story.
• Play good cop/bad cop. Interview subject not cooperating? Or do you have to ask someone about something they’ve been blamed for or accused of? Start out polite and only get more assertive or aggressive if you need to. In these cases, save hard ball questions for the very end, so you have time to soften them up and they let their guard down. What’s the worst thing that could happen? They refuse to answer or walk out of the interview – at least you got answers to your other questions.
• Circle back. The subject won’t answer a question the first time around. Let it go, move onto your other questions, then come back to it at the end. Approach it by saying, “Now that you’ve had more time to think about it, what did you really want to say about Topic XXX?” or “I’d like you to reconsider talking about XXX.” All they can say is no. Then again, your solid interview skills may lead them to reconsider.
• Psyche yourself up. Football players get pumped for the big game by listening to a pep talk or their favorite up-beat song, praying, jumping up and down or performing some other ritual. Figure out what psyches you up and use it. Then pick up the phone.