How to weigh very different career options
February 4, 2014 4:57 PM   Subscribe

I have an unexpected opportunity to apply for an executive director job, but I'm not sure what I want.

I currently work as a communications worker at a statewide civil rights non-profit(c3/c4). My previous boss left a week ago (after just under a year with us). A friend at another non-profit in a totally different field has encouraged me to apply for their open ED position, essentially running a trade group for image production professionals. That job would include running a magazine, as well as all of the day-to-day administration for a nationwide, but modest, 501(c)6.

In the main, I like my current job. We do good work, and I like the people I work with. But it's also really stressful, and there's a lot of turnover. I worked my way up through the ranks, in large part by being able to take on more responsibility when other people left. I'm currently halfway through a pretty big promotion and have the opportunity to negotiate for more, but while I've gotten more money, I haven't gotten a better title, which makes my resume (even) less impressive. But right now, I'm the only full-time employee in a communication department that was already punching above its weight with three people. The second part of the promotion is scheduled to happen in April, but I'll be able to move that up pretty soon. My plan had been to stick around, get my better title and pay bump, then start looking around for a position at another non-profit or with a politician. I never really thought about ED jobs; communications director seemed like it would be the next step.

The executive director's position is something that I'm pretty sure I could do, even if I'm not totally qualified on paper (the only other regular employee at the c6 org. is someone I've worked with before, and she's pressing me hard to apply). But getting together an impressive application package would mean getting references from people who — while they'll be absolutely glowing — would also let my current ED know I was looking at this position before I'd know whether I had a realistic shot at getting it. That's complicated by the fact that if I left, the organization would really be in a lurch — he still hasn't replaced my former boss, or the (underrated) design and web guy who left at the end of October.

The trade group is in the arts and involves publishing; my degree is in journalism and I had gone into it wanting to be a reporter or editor. Along the way, I kind of fell into my current position and have enjoyed and excelled at it (to the point that colleagues assume I have a more impressive resume than I actually do). There's a lot more money in the political arena, and I do genuinely enjoy it. But the idea of being a publisher and editor — along with the other ED duties — is really enticing too.

So, I'm trying to weigh really different career options, both connected to things that I really enjoy, knowing that if I apply for the ED job it could have real, negative consequences on my current position, especially if I don't get it, but that could be a really rare opportunity to step into working around a longtime passion of mine. Oh, and I only would have until Friday to apply, so I'd need to jump on that pretty much tomorrow morning. I'm not used to having opportunities like this, and don't really know how to weigh them out.

What questions should I be asking myself? What questions should I be asking other people? Have you had similar choices?
posted by anonymous to Work & Money (3 answers total) 1 user marked this as a favorite
But getting together an impressive application package would mean getting references from people who — while they'll be absolutely glowing — would also let my current ED know I was looking at this position before I'd know whether I had a realistic shot at getting it.

Is your workplace really that backstabby? It isn't normal or professional to go tattling to the boss when asked to be a reference. If there really is nobody you can trust among your colleagues, how about getting a reference from someone who has left?
posted by Wordwoman at 6:13 PM on February 4, 2014

I'd be a little leery of this. The one time I took a job a friend recruited me hard for, I later regretted it: turned out the job kind of sucked. I realized afterwards that if it had been a great job at a thriving organization, they'd have had lots of applicants and the ability to run a proper search. Your friend may be recruiting you hard because the organization's kind of crappy, or because she has a personal agenda of her own (like, she doesn't like an alternative candidate).


* The majority of an ED's job is fundraising: would you enjoy that? Do you have any experience with it? You could ask the organization how much of the role is expected to be spent fundraising. Where does the money come from and what role does the ED play in bringing it in?

* You say what you're really interested in is publishing and editing. Ask how much of the ED job is spent doing that, versus admin, fundraising, accounting, HR, negotiating with vendors, working with the Board, etc. I'm guessing it's less than 25% and maybe zero.

* Definitely ask about the financial health of the organization. Ideally its revenues will be climbing year-over-year, faster than its costs. Ideally there will be a year's cash in the bank. (Six months would be okay. Less is bad. This is an important indicator of financial health, and will tell you if the organization is in trouble or not.)

* A trade group magazine is not the same as journalism or civil rights advocacy: it's more like conventional PR. Ask yourself whether you want to do that.

* If I've read your post right it's a very small organization: two people. Does that sound appealing to you? Ask if they expect or want it to grow, and if so how they plan to support the ED in doing that.

* ED's need to be people who really *want* to be in charge: do you? A typical (good) ED has a very high sense of personal responsibility, is intrinsically motivated, is a bit of a people pleaser with good emotional intelligence, and has some grit/backbone. Do you recognize yourself in that?

* For an ED job always always always ask a bunch of questions about the Board. Who selects Board members (hint: that is the stakeholder who you will ultimately be asked to satisfy). How long are Board member terms (for an ED longer=better, within reason). What's the relationship like between the Board and the ED? How did the last ED come to leave?

If I were you I wouldn't jump through a bunch of hoops by Friday to put together an awesome package: at this point you can't even know you want the job. If I were you, I'd consider writing a cover letter to accompany your CV, expressing that you find the position intriguing and would love to know more about it -- but stopping just short of actually throwing your hat in the ring. That would have the benefit of giving you deniability at your current organization because you'd just be talking about possibilities. Good luck.
posted by Susan PG at 7:33 PM on February 4, 2014 [3 favorites]

I just did this internally, moving from low man on the totem pole to running my very small organization. While I'm glad I did it, don't expect to get to do any of the things you like about your current job. Sure, you'll be an editor, but only maybe 10 percent of the time. The rest of your time will be consumed by fundraising, organizational management tasks (HR, accounting, insurance, etc.), and because this is a trade group, growing and managing your membership.

If that still sounds like something you want to do, go for it! The rewards of taking on something like this and succeeding (or even failing, in some cases) are significant. But be realistic about what it entails.

Oh, and I'd be very leery of supervising a friend. You can be a boss or a friend, but not both.
posted by postel's law at 5:29 AM on February 5, 2014 [2 favorites]

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