I Know Getting a Job Is About Your Qualifications. But I Suspect Another, Harder-to-Control Factor Is Holding Me Back.

Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!)

I’ve worked in public libraries for over 20 years. But over the last few years, moving into a new position has felt nearly impossible, leaving me stuck in a position I’ve outgrown with a manager I dislike.

Last December, I interviewed for an assistant manager position at another local system, expecting to hear back from them in a few weeks due to the upcoming holidays. Instead, I heard back the day after my interview that they were going with other candidates. Now, a year later, they have two new assistant manager positions posted, and I’m debating whether I should apply again. (They only keep a list of previous applicants for six months, so I’d have to apply to be considered.)

Would I just be wasting my time, since they clearly decided very quickly last time that I wasn’t a fit? Or is each hiring process different enough that I would come in with a relatively blank slate? My confidence is quite shaken from interviewing for several positions over the last four years and not receiving any offers. While I know in government work, it often comes down to qualifications over personality, it also certainly comes down to personality, too.

—Once Bitten, Twice Shy

Dear Once Bitten, Twice Shy,

Yes, please do apply for these positions. It’s common for someone to get a job, fellowship, award, grant, or other competitive opportunity on the second or even third try.

Now for the practicalities. Should you mention that you applied before? Yes. The hiring manager might recognize your name, so it’s impossible to hide that you’re a re-applicant (and you shouldn’t hide it). If they aren’t entirely sure how they know you, they will appreciate the reminder. You got to the interview stage last time, which is a good sign and should bump your application to the top of the list. In your cover letter, emphasize how you’ve grown professionally since the last time you applied. (It’s OK to put a shine on it.) Give some specifics about projects or skills you’ve developed since the last time you spoke, to give them an excuse to change their minds.

Thinking back on your earlier interview, did they have questions you weren’t able to answer well? Or did they seem enthusiastic about any other parts of the conversation? You must have learned about their organization through the interview process, and you should use that intel to tailor your resume and cover letter.

Try not to think of applying again as a sign of desperation. Instead, frame it in your cover letter and interview as a sign of your enthusiasm for the job. Thank them for meeting with you last time. Praise any projects or services they’ve introduced since then, as specifically as possible, to show you’ve been following their work and respect it as a peer. Talk about your own commitment to their mission and your eagerness to build on what they’ve already accomplished.

I know it feels like a rejection when you don’t get a job offer, especially after an interview. It is a rejection. But it isn’t necessarily a rejection of you. Think about this from the hiring manager’s perspective. Hiring managers typically have several candidates they wish they could hire, and they often regret the ones that got away. They hate telling people “no” (at least any manager you’d want to work with). You can ease any awkwardness by approaching the application and potential interview with no resentment or suspicion, just enthusiasm for having another chance at the job.

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My sister, “Jackie,” and I work in office buildings that are a couple of doors down from one another, so we try to get together and have lunch once a week. Most of my co-workers know who she is because we usually meet at my office. Recently, my co-worker, “Daniel,” approached me and asked if Jackie was single, and if so, if I would mind setting the two of them up. Apparently, they’ve chatted a couple of times while Jackie was waiting for me, and she made an impression.

I was honestly caught off guard, and I said I would have to get back to him. Here’s the thing that’s giving me pause (and maybe it shouldn’t, I don’t know!): My sister is a trans woman. I know this shouldn’t matter, but I think I would be remiss if I didn’t at least acknowledge that it does make the situation more nuanced. I need help understanding what my obligations are to my sister and my co-worker.

I’ve asked myself if Jackie were cisgender (male or female), whether I would hesitate to set her up with an interested co-worker. The answer is no, probably not. Daniel seems like a nice enough guy, although admittedly, I don’t really know him well enough to know where he is on the political or sexuality spectrums (we really have kept things professional). Our work does not overlap much; neither of us is in a supervisory role over the other, and if he were to date my sister, it doesn’t violate any codes or ethics explicitly stated in our employee handbook.

But I keep picturing worst-case scenarios. Obviously, trans rights and visibility are eroding. I really don’t want to create an awkward situation at work or jeopardize my job—or worse, my sister’s life—if something goes sideways. If I lie to Daniel, I would likely be found out if he and Jackie run into each other. Am I being overprotective? Should I give her Daniel’s number and let them figure it out?

How lovely to have a sibling who works close enough that you can stop by each other’s offices! Normally, people’s family and professional colleagues occupy different physical realms, so this sort of thing wouldn’t come up. This overlap can make sorting out your obligations tricky, as you’ve found, so let’s talk through it.

When it comes to potential dates, your loyalty should be to your sister (or other friends or family) above your co-worker. You owe Daniel whatever confidentiality and collegiality is appropriate to your shared employment, but you owe Jackie so much more. As her sister, you care about her happiness and safety, and your relationship should last your entire lives. Some work friends become friend-friends for life, but frankly, most don’t. So tell Jackie that Daniel asked about her, and offer to give her his contact information. Let Jackie decide whether she’d like to talk with him outside the incidental conversations they strike up when she visits your office. This advice stands whether your sibling is male or female, trans or cisgender. Jackie surely has strategies for figuring out who to trust and when or whether to discuss her history, but it might help to hear your perspective on what sort of a person Daniel is at work.

Your response to Daniel was perfectly professional. You didn’t promise to set them up or even pass along a message; you just acknowledged that his message was received. You were also smart to think through your professional relationship with him and check the employee handbook for any relevant prohibitions. Let Jackie guide you on whether you should tell Daniel you passed along his number, tell him she’s not interested, or just drop the subject.

As you’ve foreseen, making a connection between a co-worker and a friend or family member can get complicated. If they find true love and name a future child after you, that’s wonderful … but most relationships don’t work out. The best you can do is continue to interact professionally with the co-worker, never asking about their relationship or even acknowledging that you’re aware of it. (I’m sure you would resist asking, “How was your weekend?” and waggling your eyebrows.) Conversely, if you see your colleague socially through your sibling, try not to discuss work. And don’t let either one of them pull you into being a relationship counselor if the relationship falters. This kind of code-shifting keeps your relationships in their proper spheres and ideally minimizes the mess for you if the relationship blows up.

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It’s the beginning of the year, and lo and behold, I didn’t get a raise again this year. It’s been two years now without a significant bump. It’s hard not to get angry about it and look at these things logically: I like my job most of the time, I’m comfortable, and I probably make enough (though I know less than I should). How does one find the balance here? When do you stop waiting for a raise and look elsewhere, versus seeing if things change?

—Here We Go Again

Dear Here We Go Again,

Many employers will happily chronically underpay people who accept a low salary and don’t ask for a raise. Your question implies you’ve been seething about the lack of a raise, which is understandable, but that you’ve been waiting for one passively. If that’s the case, it’s time to advocate for yourself.

Make a list of your accomplishments over the past few years, with a focus on things you’ve done that have benefited your organization. This can include projects you completed, deadlines you beat, clients you brought in, new employees you mentored, and especially anything you did to improve productivity or profitability. Then schedule a meeting with your boss. Tell them you would like a raise, and back up your request with your list of accomplishments. Mention a few highlights in your meeting, and send the list as a memo to follow up. It sounds like raises are distributed at the end of the year in your organization, so your boss might not be able to get you a raise right away this year, but you can at least start the conversation.

Your boss should have been paying attention to their direct reports’ salaries and recommending raises all along, but some bosses don’t think about it, are reluctant to spend their budget, have to prioritize raises for “flight risk” employees who could get better offers, or were told that their division can’t afford raises this year. Whatever the reason, this conversation gives your boss a chance to explain the lack of a raise, which can help you think about your next steps. After you share your recent accomplishments, ask your boss if there are other things you could do to position yourself for a raise or promotion. If your boss at least extends some compassion about the lack of a raise, especially if there were budgetary constraints you didn’t know about, that might take some of the sting out and let you do your job with less anger. If your boss blows you off and doesn’t give you much hope that you’ll get a raise in the next budget round, let that encourage you to start looking elsewhere.

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