Every once in a while, I think — if only newspapers had done things differently way back when.

The race isn’t over yet, but there are mistakes newspapers have made that I think will have lasting consequences. We need to think through the impact of these mistakes and what we’ll do about them. There are plentiful opportunities, but we’ll pay for these mistakes for a long time.

My list of mistakes are things, I think, that are beyond hindsight. These are things we knew, or should have known. Obvious things that were obvious years ago.

• Newspapers were slow to embrace blogging. Newsrooms dismissed blogging as a fad, and unprofessional and ladened with rumor and misinformation. Meanwhile, audience flocked to blogs. Isn’t it logical that what is arguably the first web-native publishing model would provide the template for how its done? I fear now that too many newsrooms are looking at online video through the same big-media view finder instead of seeing online video the way web natives see video. (Solution: Embrace blogging. Encourage large swaths of newsroom bloggers and hire (meaning, pay) experts in the community to blog for you. Make blogging a central feature of your content strategy.)
• The failure to develop a web-centric classified model before the advent of Craigslist. Newspapers were slow to put classifieds online, and when they did, they were hard to search, didn’t include e-mail addresses, didn’t have web enhancements and you couldn’t easily place an ad online (or even online only). Today’s classified struggles have less to do with Craig’s free model, and more to do with the fact that newspapers didn’t act aggressively to establish market dominance online before the disruptors came along. (Solution: Fix your classifieds. Make online free, with pay-for-print up sells and enhanced classifieds; make classifieds a social networking opportunity; promote the hell out of the fact that your classifieds still reach more people than any other local alternative.)
• Failure to protect vertical categories, especially auto and real estate, by building robust, content-centric, user-centric vertical sites. A lot of newspaper sites really struggle with one or both vertical, and few newspaper sites have established a strong enough position to guarantee the retention of auto and real estate advertisers, who find it easy to go their own way online. (Solution: Invest in your verticals. Use the best-of-breed solutions and create original content and utility.)
• The failure to invest in search. Right from the beginning, when Yahoo! was still an HTML 1.0 site, it was clear that people needed help finding stuff. Newspapers have been slow to build robust search engines on their own sites, but more importantly, the best thing to come out of the New Century Network was NCN’s Topix-like (only better) newspaper content search engine. If NCN could have done nothing else but keep that search engine going, we would all be better off. (Solution: Put a great universal search engine on your site, and crawl all content (not just your own site) related to your coverage area.)
• It was a mistake to view content as something we do and audiences read, take it or leave it. Fear kept newsrooms from allowing comments on stories for years — fear of the “graffiti on the bathroom wall” effect. Newspapers tried forums, found they quickly devolved into ghettos of banality, spam and hate, so they shut them down. But forum failure wasn’t the fault of the community or the software. It was the fault of management for its lack of management. Before there was a web 2.0, we called participation “virtual communities.” That’s a term that pre-dates the web and it was clear more than a decade ago that audience engagement was tied to participation. (Solution: Create a robust UGC community for your newspaper.com. Engage local bloggers as part of the local civics discussion. Be the platform, not the media package.)
• The newspaper web operations that did discover how to get five percent or more of newspaper revenue from up sells and forced buys should have been reinvesting that money in online operations, instead of trying to juice the bottom line. That money could have been used to pay community bloggers, create community and develop software that would be helping us today. (Solution: Invest more of your online revenue in content operations and application development.)
• Newspapers did not want to believe that the web was pull rather than push, so simply dumping each days edition of the newspaper online seemed like a good idea. But with pull publishing, you need to give a reason for people to remember to visit frequently, and the same old content isn’t going to do that. You need frequent updates and you need to barter in links. You need to be as engaged in your community as it is in you. (Solution: Be the platform. Update frequently, encourage participation, add more and broader levels of content, converse with your site visitors.)
• Newspaper sites have long suffered from a lack of utility. Community calendars, if they exist at all, are too often incomplete and hard to navigate. There is also a lack of broad and rich community data. We don’t do a good enough job, even today, of turning our web sites into an information resource for our communities. About 8 years ago, newspaper companies got hot on the portal idea, but that fizzled out when it turned out it cost money. Newspaper sites should be the community information hub. (Solution: Add robust calendars, get into community database publishing, and gather all the community content you can and publish it (or link to it). Make all kinds of community content easy to find through your site.)

The good news is that in none of these eight points is the game completely lost yet. There is still time and opportunity, and newspapers still have tremendous advantages in content resources and community brand and good will. But these are eight things that need fixed in a hurry.

The flip side of this last bit of tempered optimism is that technology is moving fast. The release of the iPhone is a big leap forward for mobile content and most newspapers haven’t really even contemplated mobile-native content strategies.