Dear Businesslady: Advice on Uncomfortable Questions -The Toast

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Dear Businesslady,

My roommate is preparing for an interview for a position with a different team in the same large organization where he works. He met up with the person who referred him to the position, a former colleague, for coffee and learned for the first time that this very same person would be his supervisor if he were to get the new position. This understandably changed the tone of the conversation, and it turned out to be a bit of a pre-interview, even though the person will not be conducting the actual interview.

During their chat/pre-interview, the potential supervisor said to my roommate, “I need to ask you something. Are you planning on going to grad school next year? Because my supervisor will definitely ask you that in your interview tomorrow.” My roommate is considering going back to grad school eventually and may have said as much to this person back when they were working on the same team.

When I heard this, I had a gut reaction that this question in the context of an interview is absolutely inappropriate. In this country, ‘age discrimination’ as it applies to employment only covers people who are 40 or older. Still, employers also aren’t allowed to ask interviewees whether they’re married, have kids, live nearby. Those questions hint at whether a new hire is planning on sticking around, whether they have reached some point of stability in their life. Is it really okay for an employer to ask someone if they’re planning on going back to grad school? Am I overreacting? If I am, what is an appropriate answer to that question?

– Sympathetically Self-Righteous

Dear SSR,

I’m sympathetic too—to you, for being so upset on behalf of your friend. But I’m afraid you are indeed overreacting.

First and foremost, even those questions about marriage/kids/location (and others, like pretty-much-always-inappropriate questions about racial or ethnic background) are technically legal to ask in an interview. I know, right?? You can find more detail in this collabo post between Ask a Manager’s Alison Green (my hero) and Consumerist, but essentially the deal is this: it’s illegal to discriminate against someone based on marital status, race, and so on, which means it’s stupid for employers to ask applicants to disclose that information. But the law takes humans’ inherent stupidity/rudeness/capacity to place their feet in their mouths into account, and therefore focuses on actual discrimination rather than the tactless questions that might facilitate it.

That’s not even really relevant to what you’re asking, though. The above questions are out of line because they have absolutely no bearing on a candidate’s ability to do a particular job (okay, there may be extremely limited exceptions we could all hypothetically postulate, but that’s neither here nor there). If details about someone’s personal life come up in the course of the interview, that’s one thing, but hiring managers shouldn’t be evaluating people based on those factors.

In your friend’s case, by contrast, the “are you going to grad school?” question is just a more specific version of “how long are you expecting to stay in this position?” or “what’s your five-year plan?” I’ve been told in interviews, “we’d like to hire someone who can stick around for at least two years” and didn’t balk at that at all; it’s perfectly reasonable for employers to try to find candidates who will be in a position long-term. That longevity may be more essential in some positions than in others (such as those with an extended training period or highly cyclical workflow) but there’s no legal mandate for employers’ requirements to be rational—you might have trouble making a hire if you expect a minimum-wage cashier to commit to that job for at least three years, but you can boneheadedly try to make it happen if you want to.

The question of “how does this job align with your future plans?” is a pretty common one, and it often requires some delicacy of language and/or selective omission. You also have to try to read your interviewer and figure out whether they’ll find forthrightness refreshing and appealing, or unacceptable and appalling. And of course, the answer you give will depend on the relationship between the question and your actual reality. You have to titrate your ratio of “what I think the prospective employer wants to hear” to “actual truth” based on the particulars of your situation (as in, if you know it’s 99% likely you’ll have to move for your partner’s job within the year, you can’t just say “I’m completely committed to this job for at least three years but who knows what the fates might have in store”), but the balance you’re going for is “contextually appropriate honesty.”

Let’s say you’re considering going to grad school in the 2015–16 academic year and currently on the job market (like your friend). That’s a pretty vague set of plans, allowing room for “decided not to go to grad school,” “didn’t get into any programs [that I’d actually want to attend],” “got in but didn’t get funding and decided it wasn’t worth the student-loan debt,” “got in to dream program but in the meantime fell in love with someone local who can’t move and therefore staying put”—along with many others that wouldn’t preclude you from staying in a position for the foreseeable future.

I’m a big believer in the karmic ripple-effects of outright lying when there are real stakes involved, so a reasonable response to “Are you planning on going to grad school next year?” might be something like, “Well, I’ve always been interested in [field] and part of me thinks I’d get a lot out of pursuing an advanced degree. To be perfectly honest, I might go ahead and submit an application to one or two schools, just to see what happens. But there are so many other factors involved that I certainly can’t say it’s an inevitability. And I can imagine that once I settle into the groove of a rewarding job, I might decide against even applying.”

Now, if the grad-school-considerer above is being compared against an equally qualified candidate who discloses no grad-school aspirations, they might end up losing the position to the other person. That sucks, but it’s really no different from any of the other ineffable reasons that people don’t get job offers—any time you submit an application, the odds are always overwhelmingly against you actually getting hired (sorry, folks). And because it’s pretty rare for two people to have the exact same qualifications, there are ways an answer like that might work in your favor—it shows honesty, sincerity, a thoughtful approach to decision-making, and a vibrant intellectual life. If my top priority for the position was a minimum two-year tenure, I might not hire possible-future-grad-student, but if I’d be fine with them only staying a year as long as their work was good, I’d give them a shot (and perhaps enjoy the challenge of trying to lure them away from academia). And in either case, I’d be pretty upset if I hired someone who’d been all, “What? Grad school? Me? Ridiculous!” and then left within a year for a PhD program—regardless of whether or not I would’ve hired them if they’d been forthright about their plans, that type of move would undermine their integrity and basically destroy their chances of ever using me as a reference or networking contact in the future.

Job-searching is a lot like dating in this regard: sure, you’ll turn some people off by being upfront about your desire to have kids within the next five years/less-common sexual proclivities/chronic illness/ridiculously demanding work schedule/what-have-you, but that’s just inoculation against becoming emotionally invested in someone who’s a terrible match for you. Similarly, if a job wants someone who’d never consider leaving for a given length of time, and you’re someone who might be seduced by something else within that period, then it’s a poor fit and it’s just as well if they don’t make you an offer.

Staring moonily into the eyes of a person you find abhorrent might get you a second date, but that’s just one more date you have to spend biting your tongue and inwardly rolling your eyes. If you err entirely on the side of “tell employer what they want to hear,” it might land you a position, but it might not be one you actually want. And employers (like potential romantic partners) are perfectly entitled to ask questions that prompt answers they may not want to hear.



Dear Businesslady,

I’ve been in my current, essentially entry-level position for 5 years now. My role has expanded somewhat over the years—as I’ve gotten more efficient at everything I was initially hired to do, I’ve been able to take on more—but even the additional work is still mostly entry-level stuff, just different stuff than I was doing at first. I never intended to be here as long as I have, and for the past 2-3 years, I’ve been searching for another job, sometimes very actively and sometimes casually. In the beginning I was mostly looking at lateral moves and lately I’ve been looking for steps up. Obviously, I’ve been unsuccessful. A few interviews, no offers. My office is a good place to work, culture-wise and benefits-wise, but I am really, really bored by my job day-to-day. However, I appear to be stuck here, and I want to make the best of it. And by “the best of it” I mean “more money.” I’ve never gotten a raise in the time I’ve been here (also, I’ve never asked for one in my life). How much of a raise do you think it’s appropriate to ask for, given that if I left tomorrow they’d be able to hire someone else pretty easily to replace me, probably someone fresh out of college like I was when I got hired? I’m not at all indispensable, is what I’m saying. My salary is not exorbitant by any means but it is on the higher end for comparable positions in my field and city, or at least it was when I started out. Help?

–Possibly Stuck

Dear Stuck,

Like many “what am I doing with my [professional] life”-type questions, yours is complicated—but I’m going to try to answer it without going into an exhaustive list of possibilities. (If you’re thinking, “gee, this is way too concise,” you’ll find plenty more thoughts about job-searching and workplace self-advocacy in my second column…and the one before that, now that I think about it.)

If you’ve been doing the same job, with increasing success, for five years, that’s the perfect opportunity to make a case for a corresponding increase in pay. Sure, you risk seeming unreasonable if you request an enormous raise, but don’t sell yourself short: even if they could hire an unexperienced recent grad to replace you, I bet there’d be a steep learning curve for that person to perform at your level.

In an ideal world, you’d help figure out an amount by talking to coworkers about their salary. Yes, it’s awkward; yes, we live in a culture that’s deeply uncomfortable discussing money. But there are ways of doing this without grilling people about their paychecks. Asking other long-term employees if they’ve ever gotten a raise will help you determine how likely it is that you’ll get one; if anyone seems amenable to this line of inquiry, you can follow up with “do you mind telling me how much it was?”—after all, you’re asking for a percentage, not their actual income. People with comparable jobs/seniority will provide the most useful information, but your fact-finding may be limited by your office’s hierarchy and the extent to which you’re friendly with your colleagues. And you might breaking out in hives at the very thought of discussing this with anyone, which I understand.

So here’s another formula: at many workplaces, it’s common to get a 2% increase each year. (This is sometimes termed a “cost-of-living” increase, in that it roughly tracks with inflation—although true cost of living adjustments, or COLAs, are based on much more complicated and boring factors.) If you’d received a 2% raise each year for the past five years, your salary would be just over 10% more than it is right now. Depending on how generous you think your employer might be, you could pitch a higher amount and see where you end up as a compromise—or if you think 10% seems like too much based on your office’s culture, you could go lower and use “it’s less than an annual cost-of-living increase would’ve been!” as part of your rationale.

But I’m actually more concerned with the fact that you feel “really, really bored,” and with the fact that your job-searching efforts* haven’t been fruitful. Is there any opportunity for advancement within your current organization, where a pay increase could go along with a better title (which costs them nothing to give you!) or a new role entirely? If an internal promotion isn’t feasible, then you might want to double down on your job searching; getting more money is great—and you should definitely ask for a raise independent of looking for a new position—but it can’t fix a general lack of enthusiasm for your day-to-day work. Plus, you’ve been in the same role for half a decade, and if you’d ever like to do anything else, you’ll have to start that process somewhere.

This two-pronged approach—requesting a reasonable raise in recognition of your contributions, while also applying for any and all jobs that seem like a good fit—should give you the momentum that you’re looking for. If your current employer gives you a huge raise (and especially if they change your title), then you’re justified in staying put for a while longer, and if they tell you your salary is capped, you have all the more reason to find a new position somewhere else. Either way, you’ll be moving your professional life forward, and hopefully not feeling stuck anymore.


*P.S. If you’d like me to take a look at your resume and cover letter, I’d be happy to give you some feedback on how to make them more effective. You know the email address! (The same goes for other job-searching Toasties, although I reserve the right to rescind this offer and/or review things very quickly if I get an overwhelming number of responses.)

Businesslady is in her early 30s and somehow managed to find a rewarding career despite her allegedly useless degree in the humanities. Her job history includes everything from food service to retail to corporate nonsense, but she currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet.

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