how to apply for multiple jobs at one company

A reader writes:

There is a community development organization I really want to work for because it seems to fit my personality very well; they share an appreciation for community outreach, planning policy, and youth. However, I am interested in two job openings. The first position is within the field of my professional degree, but I might be underqualified with my years of experience. The second position is working with youth, which I have volunteer experience in but might have grueling competition in this economy. Is there a way to apply for both? Or do I have to choose? If I must choose, which one would you suggest?

You can apply for both, but you need to be careful about how you do it.

The danger in applying for multiple jobs at the same organization is that you can come across as unfocused or naive about what you’re well-suited for. Here’s an example of this: I’m currently hiring for a wide range of positions — and I mean wide range, everything from an executive assistant to the director of an entire state organization, with lots of variety in between, like a job working with celebrities, a job working with college kids, and so forth. I’ve had applicants say they’re applying for the director job and the executive assistant job (hedging their bets, I guess), as well as applicants who just say, “consider me for all your openings.”

These jobs have very different responsibilities and very different qualifications. On the off chance that one of these applicants is really the renaissance man/woman who could do it all, they need to make the case for it, meaning that their cover letter needs to acknowledge that these are very different jobs, explain why they’re qualified for any of them despite that, and — and this is crucial — offer a convincing explanation of why they’re being so scatter-shot in their approach. Maybe that explanation is that they really want to work for us, in particular. Maybe it’s that their dreams have always competed among these areas. Who knows. But minus this explanation, it’s going to look like they’re either wildly naive or just applying for every job they see and hoping something will stick. (That’s not attractive in job-seekers; it’s the job-hunting equivalent of the guy in the bar who hits on every woman there, figuring eventually the odds will pay off and someone will go home with him.)

So back to you. If you’re interested in both, apply for both — but use your cover letter to provide context that will make sense to the hiring manager.