By Alison Green
The Cut, January 9, 2018 —
Ask A Boss
As someone who has interviewed probably thousands of job candidates in my career, I’ve long been surprised by how many people don’t ask good questions when their interviewer gives them the opportunity. A surprising number of candidates don’t have many questions at all, or simply use the time to try to further pitch themselves for the job. To me, this is crazy — after all, this is a job that you’re considering spending 40 or more hours at a week, a job that might have a huge impact on your career and your quality of life for years to come. You should have questions!
But people understandably worry about what to ask. They stress about seeming demanding or nitpicky, or that they’ll be negatively judged for things they want to know. They also worry that they don’t quite know how to draw out the information they really want about the job or the manager or the company.
So here are the five best questions to ask a job interviewer when it’s your turn to ask the questions — to both impress your potential employer and help you get useful insights into whether or not this is the right job for you.
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?
Initially you might think 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, despite the job having changed significantly during that time. Organizations 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 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).
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. “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.
4. 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 fundingfor 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.
5. “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 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.”