Six honest interview questions we should all be asking.
And why you should ask them
How much time do you spend prepping for job interviews by working through a list of questions that start with: “Tell me about a time when…”
Tell me about a time when you had to resolve conflict at work.
Tell me about a mistake at work you made and how you corrected for it.
Tell me about a time you had to fire someone, and how they handled it.
Questions like these start with the assumption that an experience at work is so universal, it’s not a stretch to ask people how they handled it (whether that’s actually the case is an issue for another Substack).
Most of us know the importance of showcasing our lessons learned. Having a good personal story is a skill that came up over and over again in my chats with with recruiters and hiring managers for Job Therapy. And so prepare for job interviews like contestants on Jeopardy. We start with 100 potential “tell me about a time when” questions, memorize our answers, and hope they pick our favorites.
But during this process, we often forget to construct our own questions. Questions which if asked properly, can make the difference between the landing the job and winding up in the top 10 pile.
I was shocked at how often people come up empty when asked by interviewers, “do you have any questions for me?” Exhausted yet still motivated to impress, our questions are often flipped versions of the ones we’ve been asked. “Tell me about the work that you’re doing?” is a common one I get during graduate school interviews. We go for generic, safe, and most importantly, won’t cause any friction.
Asking the right questions of your interviewer is a skill people look for, even if it’s not an advertised one. It shows that you’re thinking about long term fit. That you’ve researched this job and you’ve thought through what might get in the way of doing well at it. And it shows that you care about clear communication. All good things.
A good job interview, like a good date, shouldn’t be frictionless.
To build intimacy during the dating stage of a romantic relationship means asking questions that are a little bit uncomfortable (my husband Jay and I put each other through the gauntlet with these, which we made a questionnaire out of).
You want to learn things like a person’s beliefs around saving versus spending, how often they like to have sex (really), and if they snore. Asking can be awkward, but when it becomes a two-way street, the awkwardness will subside, and intimacy will take it’s place.
Job interviews should be the same.
So here’s a list of questions that you should be asking during job interviews. And if you’re worried these questions will rock the boat in the wrong way—offend the job interviewer or make you look ungrateful—don’t. These are all “job interviewer” approved, based on my research for Job Therapy.
Questions that get at whether the expectations for the job align with the reality of the job.
1. Who wrote the job ad? And did the person who I would report to weigh in on what’s in it?
Miscommunications about the expectations for a job start early, at the job ad creation stage. And when you show up for a job that isn’t what was promised, it’s often because you’re expected to take on roles or have certain skills that simply weren’t advertised.
How could this happen?
It happens when the person you report to wasn’t involved in the early stages of hiring, from the creation of the ad (which might have been done by Human Resources, or by an external recruiting company), to the early “sourcing” stage—who they get to apply, and what the qualifications are for this first batch of applicants. Job ads are living documents—they get taken down and put back up all of the time throughout the interview process. Sometimes it’s because the ad “asked for too much” in terms of qualifications, and they aren’t getting many applicants. This doesn’t mean those qualifications don’t matter—it’s just that they need to remove some of them to cast a wider net and get more people to apply.
Think of the job like a glacier. Above the water is what’s written down in the ad; below it, the qualifications and experiences you need to land the job and succeed at it.
Are there any additional experiences or qualifications not listed here that you think are important for succeeding at this role?
This question serves a few functions. First, it can soften the concern that you simply don’t trust the company to create an ad that accurately reflects the role. Second, it shows that you’re thinking about fit. You want to know what skills and experiences you should have, not advertised, to do well here. A savvy interviewer will respect this question, and will happily tell you what experiences “other people who’ve succeeded have had” that aren’t listed.
Can you tell me what the day-to-day of the job will look like, or connect me with someone who’s held this role before who can?
Job interviews, like dates, rarely get down to brass tacks until you’re pretty far along. Interviewers will say things like, “you will be doing a lot of client-facing work here,” and “we need someone who is open to new challenges” (whatever that means). It’s a bit like telling your date that you’re looking for someone who “loves new adventures” when you in reality you really just want to know if they’re a morning person, or if they’re going to snap at you anytime before 8 am.
Happiness at work often comes down to the day-to-day, from how often you need to have small talk and how many “not advertised” tasks your expected to take on, to whether your boss puts meetings on your calendar last minute. You want to get down to the nitty gritty of the job as soon as possible. And often the person interviewing you isn’t the one to tell you what that nitty gritty looks like.
Ask to speak to someone who is. Interviewers should be happy to connect you.
Questions that show you’re thinking seriously about long term fit.
I was surprised to learn that many people don’t seem to know much about the company they’re interviewing for—how many employees they have, how long people at the top have been working there, the names of people who’ve been promoted from within. A lot of these data are available on LinkedIn if you go searching for it (You can find the names of employees, and look at their work histories).
You can showcase that you’ve done your homework through a careful line of questioning. These are the exact types of questions that employers are looking for if they want to hire someone who is in it for the long haul.
Open up with your line of questioning with some data.
“I noticed that the C-Suite here has all been working for the company for 10 plus years (or whatever your nugget is). Can you tell me about the internal promotion trajectory here?” Sometimes, the point of a question is just to showcase your own knowledge. And you can add some details about your own history too, if relevant (e.g., “at my old job, most of my bosses were hired externally, and I’m really looking for a job with an internal promotion trajectory.”)
Among those who’ve been promoted, has anyone been surprised at the skills they needed to do well once they moved up?
This question is relevant for people who will eventually want to be internally promoted. If you’re worried about looking too eager or presumptuous, you can frame it around a boss at work (e.g., “have you found that anyone who was promoted to manager were surprised at the skills they needed in their new role?”).
It serves a few purposes. One, by framing it around surprises, it gets the interviewer thinking about unexpected barriers people faced once they were promoted that might not come to mind otherwise. Two, it frames the question in a way that doesn’t imply fault (it could be the organization’s fault for not filling them in, or the person’s fault, for not leveling up). Three, it shows you’re thinking long term.
And the answer matters. I’ve met people in sales who were surprised to learn that the network they needed to be a regional leader (deep and small, with a handful of repeat customers) was a totally different type of network that they needed to be a leader at the national level (wide and weak, with a lot of lose connections spread throughout the country) . But no one told them this, so they lost out to external hires.
What does it look like to fail at this role?
This is my favorite interview question. Losses loom larger than gains, and most interviewers have a few lessons they can share from what went wrong in the past. Ask this one of as many people at the company you can. You can ask what it looks like to succeed too, but failure answers are almost always more useful. They get at the unexpected things people did wrong that might be out of mind.
Your goal is to discover the hidden parts of a job that people don’t spontaneously think about. To get them thinking, “huh, I hadn’t thought about that. But now that you mention it…”
Want more job interview questions? The last stage in every chapter of Job Therapy has a list of interview questions, tailored to your particular needs.
