Photo: The Cut

As someone who has interviewed probably thousands of job applicants throughout my career, I’m always surprised by how some candidates handle the part of the interview where it’s their turn to ask questions. A strangely large number of people don’t have many questions at all – which is hard to understand when they’re considering spending 40+ hours a week at this job, and when it’ll have an enormous impact on their day-to-day quality of life.

To be fair, a lot of people worry about what questions are okay to ask. They’re concerned about seeming demanding or nitpicky or that their interviewer will draw unflattering conclusions from the questions they ask. It can be hard to elicit the information you really want to learn (like “what are you really like as a manager?” and “am I going to go home crying every day?”) while still being reasonably tactful.

And other people are unclear on the purpose of the opportunity to ask questions. Rather than using the time to suss out the information they truly want about the job, the manager, and the company, they instead try to use it as a chance to further impress their interviewer and pitch themselves for the job. That ends up leaving them without the info they need to decide if the job is right for them or not. (It also tends to be pretty transparent, and will annoy interviewers who don’t appreciate having their time wasted that way.)

So, what should you ask when it’s your turn to question your interviewer? Here are 10 really strong questions that will get you useful insights into whether the job is right for you.

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 might figure that the job description 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 last ten years, even if the job 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 like they were written by robots rather than humans), so it’s useful to have a real conversation about what the role is really about. You might find out that while the job posting listed 12 different responsibilities, your success really just hinges on 2 of them, or that the posting dramatically understated the importance of 1 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).

2. “What are some of the challenges you expect the person in this position to face?”

This can get at 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 transparent — but if asking about challenges leads to a real discussion of how you’d approach them, it can be genuinely 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 actually only comes up every six months. But even barring major insights like that, the answer to this question can just 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?”

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?”

If no one has stayed in the job very long, that could be a red flag about a difficult manager, unrealistic expectations, lack of training, or some other land mine. If just one person left after a few months, that’s not necessarily a danger sign — after all, sometimes things just don’t work out. But if you hear there’s been a pattern of people leaving quickly, it’s worth asking, “Do you have a sense of what has led to the high turnover?”

Questions About Your Success in the Position

5. “What are you hoping this person will accomplish in their first six months and in their first year?”

This question can give you a sense of what kind of learning curve you’re expected to have and the pace of the team and organization. If you’re expected to have major achievements under your belt after only a few months, that tells you that they likely won’t give you a lot of ramp-up time. Which might be fine if you’re coming in with a lot of experience, but it might be worrisome otherwise. On the flip side, if you’re someone who likes to jump right in and start getting things done, you might not be thrilled to hear that most of your first six months will be spent in training.

This question can also draw out information about key projects that you wouldn’t otherwise have heard about.

6. “Thinking back to people you’ve seen do this work previously, what differentiated the ones who were good from the ones who were really great at it?”

A job candidate asked me this question years ago, and it might 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 excel at the job. And this question says that you care about the same thing. Sure, it doesn’t guarantee that you’ll do extraordinary work, but it makes you sound like someone who’s at least aiming for that — someone who’s conscientious and driven, and those are huge things in a hiring manager’s eyes.

Plus, the answer to this question can give you much more nuanced insight into what it’ll take to truly excel in the job — and whatever the answer is, you can think about whether or not it’s something you’re likely able to do.

Questions About the Company

7. “How would you describe the culture here? What type of people tend to really thrive here, and what type don’t do as well?”

If the culture is very formal with lots of hierarchy and you’re happiest in a more relaxed environment, this might not be the right match for you.

Similarly, if it’s a really competitive environment and you’re more low-key, or if they describe themselves as entrepreneurial and you prefer structure, it might not be an ideal workplace for you. If you don’t have a lot of other options, you still might decide to take the job anyway — but you’ll usually be happier if you know what you’re signing up for, and aren’t unpleasantly surprised after you start.

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

You can learn a lot by the way people respond to this question. People who genuinely enjoy their jobs and the company will usually have several things they can tell you that they like about working there 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.

9. Ask the question you really care about.

Sometimes people use their turn to ask questions in an interview solely as an additional chance to try to impress their interviewer — asking questions designed to reflect well on them (by making them look smart, thoughtful, or so forth) rather than questions designed to help them figure out if the job is even right for them in the first place. It’s understandable to want to impress your interviewer, but interviewing is a two-way street — you need to be assessing the job and the employer and the manager, and figuring out whether this is a job 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 job 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 work at the job every day, what are the things that will most impact whether you’re happy with the work, with the culture, with the manager? Maybe it’s important to you to work in an informal culture 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. Whatever’s important to you or that you’d want to have answered before you could know if you’d really want the job, think about asking it now.

Of course, you shouldn’t rely only on your interviewer’s answers about these things. You should also do due diligence by talking to people in your network who might have the inside scoop on the company’s culture or the manager you’d be working for, reading online reviews at places like Glassdoor, and talking to other people who work there.

Questions About Next Steps

10. “What’s your timeline for next steps?”

This is a basic logistics question, but it’s useful to ask because it gives you a benchmark for when you can expect to hear something back. Otherwise, if you’re like many people, 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 if you have an updated timeline you can share. I’m really interested in the position and would love to talk more with you.”

Got something to Ask a Boss? Send your questions to askaboss@nymag.com.