The worst questions you can ask your future employer in a job interview

Bethany Crystal
9 min readDec 21, 2018


So, you landed an in-person job interview? Good for you! You’re one step closer to getting a foot in the door someplace new (and hopefully better) than where you are today.

I’m sure you’ve already practiced and prepared a short list of micro case studies about yourself so you can speak to your previous experiences at work. And I’m absolutely positive you know all about STAR technique (situation, task, answer, response) as an incredibly helpful framework to answer questions.

So with all that in mind, I want to talk about that last part of the interview. You know the part I’m talking about — that very last moment when the interviewer lets you out of the hot seat and poses a single query back to you:

“What questions do you have for me?”

Oh shit. You did come in prepared, right?

Not so much? Eek. Remember: Interviews are two-sided, mutual decisions. This moment is your prime time as a candidate to decide for yourself about whether or not you even like this job, this company, and your potential future manager.

Asking the right questions here can help you crystallize the best and worst parts about this job and make your end of the decision-making process super easy.

And by the way, good questions also signal to your interviewer that you’re paying attention and processing information in real time. When I interview people, I always write down what questions they ask me: If someone doesn’t have any questions after an hour-long interview, I think twice about whether I’d want them on my team.

There are a lot of great questions you can ask in an interview, but the best questions here are customized and specific to that particular job. It’s impossible to list them all out here.

But as for the worst questions? Oh yeah, that part is easy.

And so, I give you my five least favorite questions to be asked in an interview, along with why I think they suck, and what you might ask instead.

Question 1: What do you like the most about working here?

Why it’s not actually that helpful:

I know what you’re thinking — “But this is my default question! I always ask it!” To that, I’d say, well, it’s time to up your game. This is a terrible default question because it’s far too subjective to be helpful. Just think about how easy it is to give a benign and generic answer to this question: “Oh, the people are so great!” or “The culture is really inclusive.” But what does that tell you, exactly? The best interview questions give you more data toward your pros/cons list about why you might want to work at that place. It’s very unlikely that you’ll get anything productive from a question like this.

One other point: Unless you’ve already determined that your personality, motivations, and desires are 100% aligned with your interviewer, it’s pretty unlikely that their favorite thing will also be your favorite thing.

What to ask instead:

“Tell me about a time when you felt really proud to work here.”

Yes, this question is still centered on the individual. (What makes you feel pride may differ from someone else). But I like this question for one main reason: You get to learn what the company values and what behaviors they incentivize. This is something that people often “tell” with core values posted on the wall, but hearing a story about a moment that a person felt proud to work in a place really brings a strong sense of authenticity to light. As an added bonus, you’ll also get a peek in learning a bit about what motivates your interviewer.

Question 2: What’s the work/life balance like?

Why it’s actually not that helpful:

Let’s be honest: Is anybody ever going to tell you that it sucks to work there? Don’t forget, you’re in an interview. This means that whomever you’re speaking with was pre-determined to be external-facing enough to both vet you AND sell you. Even if the work-life balance is terrible (but again, that’s also subjective depending on who you ask), you’re not going to get a straight answer from your interviewer.

The other reason this question is bad is because you give your interviewer the opportunity to answer it in a million different ways. I might say, “Pretty good! I never work on the weekends!” when in reality, that’s because I’m working until 11 p.m. every day during the week and everyone is just burnt out by Friday evenings.

What to ask instead:

“When do you unplug from work emails and calls?”

This is only one possible way to tease out better information about how much time people spend at work vs. in other life activities. The important thing here is to really think twice about what piece of information you’re hoping to learn here. Do you want to know about how late people work to see if a role here might suit your commute schedule? Whether or not you’ll be expected to reply to emails on the weekends? Or something else? Whatever you want to know, more specific is better. If you’re feeling super brazen, you might also inquire about the last time your interviewer took a vacation.

Question 3: What’s the company culture like?

Why it’s not actually that helpful:

Here’s one way I could answer this question: “It’s great! We eat lunch together on Thursdays, have all-hands meetings on Tuesdays, and I mean — ping pong in the office…so fun, amirite?!” But again — does this actually give you any information that might help you decide whether or not you want to work for this place?

The concept of “company culture” has become such a catch-all for “perks” or “fun stuff” that asking it in such a broad way is once again, only asking for a vague answer that’s probably not all that helpful.

What to ask instead:

“How do product or business decisions get made here?”

The truth is that any specific question is better than any generic question, so this is just one example. There are so many elements that factor into “culture” at work — from the people to the organizational design to the way you run meetings to how you celebrate wins. There’s no way you can tease all of that out with a blanket request for someone to tell you about their culture.

I’d encourage you to try really hard to avoid even using the phrase “company culture” in a job interview. Instead, challenge yourself to consider what exactly you’re looking to better understand. Do you want to know whether people have friends at work? Ask about social activities outside of work? Do you want to know whether it’s a meeting culture, an email culture, or a Slack culture? Ask where information lives and how decisions get made. Do you want to know if the CEO is a tyrant who micromanages everyone? Ask about the best example of cross-department collaboration and pay close attention to who was involved in the process. Truly, any question you can ask will be better than asking about culture. Do yourself a favor and reach for something deeper.

Question 4: What’s the team dynamic like?

Why it’s not actually that helpful:

To be clear, I think it’s so important to understand the team dynamic before going into a new job. I just think this is a terrible way to figure it out. A vague question like this again allows your interviewer to get off the hook with answering it in an equally vague way. Here’s one response you might get: “Oh, the vibe is great. We’re all really collaborative and everyone pitches in and pulls their own weight on projects.” But does that really give you what you’re looking for?

What to ask instead:

“What do you see as the strengths and weaknesses of the current team?”

This might be one of my favorite questions in the world that you can ask as a candidate because the answer you’ll get is so rich with information that can guide you on the rest of your questions. Let’s break it down a bit. First, by posing this as an opinion question (“What do you see…”), you cut your interviewer a little bit of slack by not expecting them to speak on behalf of the whole company. You’re more likely to get an honest answer.

Second, wouldn’t it be fascinating to understand where your future colleague or future manager sees great performance and blindspots before you come into an organization? You might hear what they are telling you and mentally clock, “Ah, got it. So we have a lot of strategic thinkers. But sounds like they need help with execution.” Then you can decide for yourself whether or not your perceived strengths might blend well into a group dynamic like this.

Last but not least, I love this question because you can ask it to every single person you meet. You can ask it to the manager, to a peer, to the executive. And now, as the candidate, you not only have multiple perspectives on the inner workings of where they excel and where they need help, but you can start to get your finger on the pulse with how much internal alignment and agreement you see going in.

Question 5: What does a long-term career path look like here?

OK. This one comes with a caveat: I *only* think this is a bad question if you’re applying to a job in tech or at a startup. I imagine larger enterprises and corporations are much more likely to have already designed pipelining programs internally, where this may be a very appropriate question. But startups and tech are where my experience lives, so that’s where my brain space is at for this one.

Why it’s not actually that helpful:

Because startups don’t know. Seriously. These early-stage tech companies barely know where they’ll be in 3–5 years, let alone where a potential future new hire could fit into the equation. Will there be 4 new offices by then? Two new products? An accelerated round of funding? A downsizing event? This is the last thing on their mind, so give them a break and don’t ask it.

And by the way, anybody who does give you an answer here (even one you like) is likely just setting you up for disappointment down the road. It’ll be really hard (if not impossible) for anyone to keep a promise like, “Well, if you do great as Director of Marketing, I can see you in C-Suite potential as our CMO in a few years.” Don’t sign up for a job because you want the thing they are dangling in front of you two or three jobs from now. That’s not fair to you or to them.

What to ask instead:

What does success look like for this company in five years?”

I know this seems very far away from a personal question about you and your career path, but hear me out. It’s really unlikely that anyone has considered a five-year career timeline for a future new hire. But I would really hope that someone (if not many people) have had long-term vision conversations about the company as a whole.

Asking this question gives you two key pieces of insight. First — have they thought it through? (And do they have a good answer?) Second — do you like what you hear? And can you visualize a future state world for yourself in whatever picture they paint for you?

If their future plan includes rapid expansion in Asia, does that pique your interest because you’ve always wanted to move there? Can you imagine a world where your future job is scaled out for even more responsibility to fit into a future-state of their organization?

If you remember only only thing from this blog post…

Specific questions are better than generic ones.

Yes, this means you need to do more work ahead of time to consider questions you care about. You need to think (I mean, really think) about what’s important to you going in. You also need to pay attention in real time as your interviewer is grilling you and be able to turn on a dime and jump in with thoughtful follow-ups.

This is easier said than done. But if you get it right, you’ll go into your next job with both a clear understanding of what to expect and better position yourself to land something that’s right for both of you.

Happy interviewing, everyone. Go get ‘em.



Bethany Crystal

A little bit web2, a little bit web3… Board @CompSci_High ; ex-USV, Stack Overflow, Bolster, Variant, Uniswap Foundation; alum of @Northwes