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U P D AT E D JAN. 10, 2023

10 Impressive Questions to Ask in a Job Interview

By Alison Green,
the Cut’s workplace-advice columnist

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Photo-Illustration: by The Cut; Photos: Getty Images

At the end of every job interview, you’re likely to hear, “Do you have any questions I can
answer for you?” As someone who has interviewed hundreds, if not thousands, of job
candidates in my career, I’m always taken aback by how many people respond with “No.” After
all, you’re considering spending 40-plus hours a week at this company … surely there’s
something you’d like to know.

The problem, I suspect, is that people worry the invitation to turn the tables is a trap — just
another way for interviewers to judge them. They’re worried their queries will seem
demanding or out of touch, or they wonder if they’re supposed to pick questions that will
somehow burnish their image as the most highly qualified candidate. Or, especially common,
they have no idea how to tactfully ask the things they most want to know. Things like “What
are you really like as a boss?” and “Is everyone here miserable?”

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So what should you ask when it’s your turn to interview your interviewer? Here are ten strong
questions that will get you useful insights into whether the job is right for you.

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Questions About the Position
1.
“How will you measure the success of the person in this position?”

This gets right to the crux of what you need to know about the job: What does it mean to do
well, and what will you need to achieve in order for the manager to be happy with your
performance?

You may figure the job description has already laid this out, but it’s not uncommon for a job
description to be the same one an employer has been using for the past ten years, even if the
job has changed significantly during that time. Companies often post job descriptions that
primarily use boilerplate language from HR, while the actual manager has very different ideas
about what’s most important in the role. Also, frankly, most employers just suck at writing job
descriptions (which is why so many of them sound as if they were written by robots rather
than humans), so it’s useful to have a conversation about what the role is really about. You may
find out that while the job posting listed 12 different responsibilities, your success in fact
hinges on just two of them, or that the posting dramatically understated the importance of
one of them, or that the hiring manager is battling with her own boss about expectations for
the role, or even that the manager has no idea what success would look like in the job (which
would be a sign to proceed with extreme caution).

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2 .
“What are some of the challenges you expect the person in this
position to face?”
This can elicit information you’d never get from the job description — like that you’ll have to
deal with messy interdepartmental politics, or that the person you’ll be working with most
closely is difficult to get along with, or that you’ll need to work within draconian budget
restrictions on your program.

It can also create an opening for you to talk about how you’ve approached similar challenges
in the past, which can be reassuring to your interviewer. I don’t recommend asking questions
just so you can follow up with a sales pitch for yourself — that’s annoying and usually pretty
obvious — but if asking about challenges leads to a genuine discussion of how you’d approach
them, it can be useful for you both.

3.
“Can you describe a typical day or week in the job?”

If the job description mentioned a combination of admin work and program work, it’s
important to know whether 90 percent of your time will be spent on the admin work or if the
split is more like 50/50. Or you might find out that the part of the job that you were most
excited about only comes up every six months. Even barring major insights like that, the
answer to this question can help you better visualize what it will actually be like to be in the
job day after day.

Tip: Some interviewers will respond to this question with, “Oh, every day is different.” If that
happens, try asking, “Can you tell me what the last month looked like for the person in the job
currently? What took up most of their time?”

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If nothing you try gets you a clear picture of how your time will be spent, that might be a sign
that you’ll be walking into chaos — or a job where expectations never get clearly defined.

4 .
“How long did the previous person in the role hold the position?
What has turnover in the role generally been like?”
This is important to ask because if everyone has left the position after less than a year, that
could be the sign of a horrible manager, unrealistic expectations, or something else that’s likely
to make you miserable too. If just one person left quickly, that’s not in itself a red flag. But if
you find there has been a pattern of quick departures, that should prompt you to ask your
interviewer what they think led to the high turnover.

Of course, if the position is brand-new, you can’t ask this question. In that case, ask instead
about what the turnover on the team has been like.

Questions About Your Success in the Position
“What are you hoping this person will accomplish in their first six
months and in their first year?”
With this question, you’re listening for what kind of learning curve you’ll be expected to meet
as well as the general pace of the team. If you’re expected to have racked up significant
achievements in your first, say, six months, you’re not going to have a lot of ramp-up time.
That may not be a problem if you’re coming in with a lot of experience and you know the
expectations are reasonable. If not, it may rightly give you pause.

The other advantage of asking this question is that it can elicit details about key projects that
you wouldn’t otherwise hear about, which can help flesh out your understanding of the work
you’ll be doing.

6.
“Thinking back to people you’ve seen do this work previously,
what
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A job candidate asked me this years ago, and it may be the strongest question I’ve ever been
asked in an interview. The thing about this question is that it goes straight to the heart of what
the hiring manager is looking for: Hiring managers aren’t interviewing candidates in the
hopes of finding someone who will do an average job; they’re hoping to find someone who will
shine. And this question says you care about the same thing. Obviously, just asking doesn’t
guarantee that you’ll do extraordinary work, but it does make you sound like someone who’s at
least aiming for that — someone who’s conscientious and driven. Those are huge things in a
hiring manager’s eyes.

Plus, their answer can give you more nuanced insight into what it’ll take to truly excel in the
job — and whatever the answer is, you can think about whether it’s something you’ll be able to
do.

Questions About the Company
7.
“How would you describe the culture here? What type of people
tend to thrive here, and what type don’t do as well?”
Sometimes hiring managers are pretty bad at accurately describing the culture on their teams
— in part because they have a vested interest in seeing it a certain way, and in part because
they have an inherently different vantage point than their reports do. For example, I’ve heard
incorrigible micromanagers tell candidates that they like to give people a lot of independence
and autonomy. And they probably believed that about themselves! So take managers’
descriptions of culture with a heavy grain of salt (and confirm anything that’s important to
you with people who are not the manager). That said, there’s value in hearing what they do
and don’t emphasize. You’ll often learn what that manager really cares about in their
employees, or which traits will set you up to clash with them, or who’s likely to bristle at their
management style.

8.
“What do you like about working here?”

You can learn a lot by the way interviewers respond to this question. People who genuinely
enjoy their jobs and the company will usually have several things they can cite, and will
usually sound sincere. But if you get a blank stare or a long silence before your interviewer
answers, or the answer is something like “the paycheck,” consider that a red flag.

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9.
Ask the question you really care about.
It’s understandable to want to impress your interviewer, but interviewing is a two-way street
— you need to be assessing the job, the employer, and the manager and figuring out whether
this is a position you want and would do well in. If you’re just focused on getting the job and
not on whether it’s the right job for you, you’re in danger of ending up in a place where you’re
struggling or miserable.

So before you interview, spend some time thinking about what you really want to know. When
you imagine going to the job every day, what are the things that will most impact whether
you’re happy with the work, with the culture, and with the manager? Maybe it’s important to
you to work in an informal setting with heavy collaboration. Maybe you care most about
working somewhere with sane hours, where calls and texts on the weekend or in the evenings
are rare. Maybe you’ve heard rumors about the stability of the funding for the position and
want to see if they’re true. Whatever you’ll need to know to decide if you want the job, think
about asking it now.

That said, you shouldn’t take your interviewer’s word for it. You should also do due diligence
by talking to people in your network who may have the inside scoop on the company’s culture
or the manager you would be working for, by reading online reviews at places like Glassdoor,
and by talking to others who work there. (Here’s how to do that.)

Questions About Next Steps
10.
“What’s your timeline for next steps?”

This is a straightforward logistics question, but it’s useful to know when you can expect to hear
back. Otherwise, in a few days you’re likely to start agonizing about whether you should have
heard back about the job by now and what it means that you haven’t, and obsessively checking
your phone to see if the employer has tried to make contact. It’s much better for your quality of
life if you know that you’re not likely to hear anything for two weeks or four weeks or that the
hiring manager is leaving the country for a month and nothing will happen until she’s back, or
whatever the case might be.

Plus, asking this question makes it easy for you to check in with the employer if the timeline
they give you comes and goes with no word. If they tell you that they plan to make a decision
in two weeks and it’s been three weeks, you can reasonably email them and say something like,
“I know you were hoping to make a decision around this time, so I wanted to check in and see
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if you have an updated timeline you can share. I’m really interested in the position and would
love to talk more with you.”

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the
Rest of Your Life at Work here. Got a question for her? Email [email protected]. Her
advice column appears here every Tuesday.

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