When trying to get hired, the answer is more math than preference

If you're going to send a letter, send it directly to the hiring manager and not to HR -- but get the conversation started with a call too

Dear Bob ...

I'm female (semi-relevant) and currently "between engagements" and trying to find a suitable position. Adding to the challenge, oddly enough, is that I'm quite good at what I do -- good enough that I can handle more responsibilities than are usually listed in the job postings I'm interested in.

[ See also: Is it fair that new graduates don't get hired? | Get sage IT career advice from Bob Lewis' Advice Line newsletter. ]

A lot of my friends (mostly the male ones) are advising me to bypass HR, pick up the telephone, and cold-call likely hiring managers in companies around town.

When I explain that I'm very uncomfortable cold-calling and prefer to work the old-fashioned way of applying for a job in writing with the people who are paid to handle such things (HR), especially because I'm a much better writer than schmoozer, they come on pretty strong about how I'm shooting myself in the foot.

My female friends are more understanding. Their advice is to work the way I'm most comfortable and skilled -- to play to my strengths.

What do you think?

- Looking for work (in all the wrong places?)

Dear Looking ...

What I think is that you and your friends of both genders are taking subjects that should be graded on the A, B, C, D, E, scale and instead are grading them pass/fail.

You say you're a much better writer than schmoozer. Sadly, this isn't about you. It isn't about what's right or even what's courteous either.

Sending a letter and resume to HR is a low-probability play. Especially during times of job scarcity and plentiful applicants, the typical HR recruiter's goal is to find reasons to reject applicants. It's understandable, even if it isn't to your benefit. They have a flood of applicants and are paid to send through only a handful of high-likelihood candidates to the hiring manager. Coping with the flood means finding shortcuts. So they aren't looking for reasons to toss yet another resume onto the "good fit" pile. They're looking for ways to keep that pile small enough.

So if you are going to send a letter, send it directly to the hiring manager and not to HR. The hiring manager looks at the world differently. He or she has a problem, and it isn't the flood of resumes. It's work that isn't getting done. You're the solution to the hiring manager's problems -- he or she just doesn't know it yet, and you need to maximize the odds that you'll have a chance to explain it.

Look at the world through the hiring manager's eyes, though, and you'll see that a letter and resume, no matter how well-written, is likely to be classified as spam (if it's electronic) or junk mail (if it's on paper) if he/she doesn't know you. (If you don't know the person's name, just their title, it's even worse. A to-whom-it-may-concern letter has no chance at all.)

So all things being equal, call. If you lack confidence, use your writing skills to create three scripts: one for reaching the hiring manager live, one for reaching an administrative assistant, and one for leaving a voice mail. Except for the last one, the script is just enough to get a conversation started -- and to help you not flounder around wondering what you ought to say.

When you call, keep your goal firmly in mind: You aren't trying to have your conversation in the call. You're trying to interest your prospect just enough to accept an appointment; you want the actual conversation to be face-to-face.

I'd also advise against knowing whether the hiring manager has an open position, because if you know, you'll have to explain why you're a great fit for it.

But if you don't know, you're free to explain all the things you could do to help the hiring manager, whether or not they're listed in the job description. That's a much better conversation to have, because you get to set its agenda.

- Bob