I look at a lot of job applications submitted via the Web and I am consistently surprised by the number of applications that I see that don’t include cover letters. The thing is, I also know a lot of people who never read cover letters when they’re processing job applications. When you skip the cover letter, you take your chances.

Here are some of the things I wonder about when I see an application that doesn’t include a personalized cover letter:

Are you applying to so many jobs that you can’t be bothered to write cover letters? We want people who want to work with us specifically. Giving me the idea that you want “a job” rather than this job does not put you on good footing.

If your résumé seems oddly suited to the role, I usually assume that you didn’t actually read the job description. You can clear that sort of thing up in the cover letter.

If your résumé is not really well written, I assume that you didn’t include a cover letter because you’re not good at communicating in writing. I put a high value on the ability to communicate in writing.

The final thing I may assume is that you just didn’t care enough to bother with the cover letter. You were provided with the opportunity to do a little extra work on the application and you skipped it. In my mind, this reflects poorly on an applicant.

When I look at an application, I look for the cover letter first. What I’m looking for is an explanation of why you’re interested in the job and how your skills map to the requirements in the job description. A paragraph or two will do. This is also your opportunity to convey your passion about the company, the work, or both.

Leaving out the cover letter requires me to use my imagination when it comes to mapping your experience to the job requirements. If that’s a no brainer, you may be able to get by with skipping it, although I don’t recommend it. If I’m looking for someone to do PHP development on a high traffic Web site and your previous job was at Yahoo doing PHP development on a high traffic Web site, you may not need a cover letter. I can figure that out. If your previous job was doing Ruby on Rails development on an academic project, more imagination is required on my part. Why leave it up to my imagination?

The cover letter is one of the only opportunities you’ll get to provide information to help make the hiring decision. Unless you customize your résumé for each job, it’s the only shot you get to tell me exactly what you want about yourself. I don’t particularly like to phone screen people. Before I schedule a phone screen, I’m going to go on the Web and look at your LinkedIn Profile if I can find it, your GitHub account if you have one, and anything else that comes up in the first few pages of a Google search.

One other benefit of writing a cover letter is that it gives you the opportunity to do some sales, by way of explaining where you are in your job search. Let’s say that your résumé is an obvious perfect fit for the job requirements. If you’re already interviewing for jobs, including that fact will likely get your résumé handled with more urgency. Indicating that you’re happy with your job but you are really interested in this job in particular can be flattering as well. This is not an opportunity the job seeker should pass on. I write this as someone who’s reviewing résumés because I appreciate it when people are thoughtful about what they’re doing.

The other day al3x on Twitter linked to a Seth Godin blog post about structural unemployment. Godin talks about the effects of the changing economy in blunt terms:

The networked revolution is creating huge profits, significant opportunities and a lot of change. What it’s not doing is providing millions of brain-dead, corner office, follow-the-manual middle class jobs. And it’s not going to.

And here’s his prescription:

The sad irony is that everything we do to prop up the last economy (more obedience, more compliance, cheaper yet average) gets in the way of profiting from this one.

What’s clear to me from his post is that he doesn’t have much sympathy for the people whose jobs are being restructured out of existence. He displays a level of callousness that I find to be common among people who work in the technology industry, one often displayed by people who, as Ann Richards said of George Bush, Sr. were born on third base and think they hit a triple.

People need work, regardless of whether their specific skills are as marketable as they once were. The fact that some of us are in professions that continue to be viable or even lucrative and others are in professions that are no longer in demand is attributable mostly to luck. I often tell people that I’m one of the luckiest people in the world. I’m a white man, born in America, whose family placed a high value on education. Lucky. When I was a kid, I was obsessed with computers and the first thing I wanted was a modem so I could get online. Lucky. Did I know when I was a kid that being a computer geek would eventually lead to gainful and happy employment? No. But it has, and I’m very fortunate for that.

The other career I considered was newspaper journalism. Had I taken that path, I’d probably already have been laid off with no prospects for a new job in the same field. Or, even if my job was fine, I’d still be in an industry shedding workers at an alarming rate. It wasn’t strategic thinking that led me to choose software development, it was the realization that I didn’t really like interviewing people.

At this point, if the economy changed and the need for software developers evaporated, I would have no prospect of finding any other job near my current level of compensation. I’ve spent my entire career getting better at building applications to the neglect of nearly every other skill I could have possibly honed. The labor market encourages people to specialize, but the same specialization that yields large rewards in the right markets can put you out of the job market entirely as the economy changes.

The question we face as a society right now is what to do to help out people who’ve lost their jobs and don’t have the opportunity to find a new job that matches their skills. Maybe we need to make people who are over age 55 and have more than 100 weeks of unemployment eligible for Social Security early. Maybe we need to make it easy to get grants to start new businesses for people who are among the long-term unemployed. Maybe we just need to extend unemployment indefinitely. I’m not sure.

As Seth points out, the structural changes in the economy created an awful lot of wealth. If you believe that this is created entirely through foresight and cleverness on the part of those who have reaped the benefits, then your response to structural unemployment is likely to be, “Suck it up,” or more often, just to ignore the actual people who lose their jobs entirely.

There’s no doubt that individual merit plays a part in individual success, but luck plays a part as well. It makes sense to tax the lucky so that we can help the unlucky stay on their feet as the economy transitions. Few people can accurately predict decades in advance which career choices will serve them well for their entire adult life and which will leave them in a lurch before retirement age. Besides, it’s good for society and for the economy when everyone is making the contribution that they can.

Acknowledging the fact that a good portion of the current level of unemployment is a result of structural factors isn’t the end of a conversation, it’s the beginning. And yet, the conversation about what we need to do to help out the victims of economic restructuring is not one I see occurring in the political discourse right now.