James' World 2

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One of the most surprising things to me about interviewing people for jobs has always been how frequently candidates profess not to have any questions for me when prompted. After all, this is a job they’re considering spending a large chunk of their waking hours at for the next however many years, and it’s likely to have a significant impact on their day-to-day quality of life and progression in their career. Surely there’s something they’d like to know about.

Undoubtedly, part of the reason people tell their interviewers they don’t have questions is that they’re unsure of how to ask about the things they really want to know, like “Are you a nightmare of a boss?” or “Am I going to get work calls at 9 p.m., or be expected to work all weekend?” or “Is everyone here miserable?” They also worry that interviewers will read negative subtext into perfectly reasonable questions, for example, looking like a slacker if they ask about what sort of hours people work, or not appearing sufficiently interested in the position they’re interviewing for if they ask about advancement potential. But when you don’t take advantage of the opportunity to ask your interviewer questions, you risk coming across like you’re not that interested in the job or not thinking critically about whether it’s one you’ll do well in.

It’s true that some of the information you want to know is best sought outside of a formal interview (more on how to do that here), but you can still learn a lot by asking your interviewer the right questions. Here are ten 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 may think you already understand this from the job posting, but it’s not uncommon for employers to post the same job description year after year, 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 some are written by AI and so many more sound like they

were), 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 needs of the role are expected to change significantly in the next year, 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?”

Job descriptions usually just lay out a list of activities and responsibilities. But it’s also important to know what it really looks like to operate on this particular team and in this particular culture. Maybe you’ll find out that the role’s most important client is notoriously hard to please, or there’s been a sticky political history with partner organizations that will complicate the work you’d be taking over. You might find out there’s tons of organizational support for the role, or that it’s a battle to keep the position’s work funded. Things like that often aren’t listed in written job descriptions but can have a profound impact on what it’s like to be in the job and how happy you’re likely to be if you take it.

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