Navigating two job postings

Post date: 2023-05-28 18:20:15

How do you handle applying for two jobs at a company when job A closes first, but job B perhaps suits you better?

Over 20+ years, I've acquired a very particular set of skills in a specialized sub-sub technical/professional discipline. I really like my work, in particular the technical aspects. However, my small company is frankly in hard times and I'm not entirely sure it'll be there next year. There are not a lot of job opportunities around in my specialty, and very very few locally.

I've been contacted by local government regarding a job posting for a leadership position; it's low-level leadership, overseeing a team of a dozen or so experienced staff, doing some management work as well as some technical oversight. That posting closes on Monday.

A second posting has also appeared, for a senior technical person in the same group (reporting to the leader) doing a lot of the kinds of technical work I enjoy and am very good at. That posting closes a week later.

I think I could do the leadership aspect, although it wouldn't necessarily be my strongest suit. I don't know if I'd enjoy doing it, though. I honestly think on one hand that a leadership position facing the rest of the organization advocating for the technical work and managing a skilled team could be fulfilling; on the other hand, I think that doing a lot of bureaucracy and working within structures and internal politics plays to my weaknesses, that I might chafe at the organizational structure and that I'd miss the technical work terribly.

I'm fortunate enough that the money difference between roles doesn't need to be a major consideration; the difference in salary between them is much smaller than the difference between them and my current wages. Because of my specific technical history, I think I'm likely to be one of the strongest candidates for either position; this is a technology I've helped create.

How should I approach the two jobs? I assume that the leadership position will be interviewed and probably filled first, because of the deadline (and because I think that they might want at least some input on the new staff member) but I think I'd prefer the senior technical position more.

And more specifically, how do I handle juggling two applications when the first one is my second choice? How should I frame this in an interview or on paper?

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