From time to time, I have people ask me for advice on how to kill their job interview.
One thing I never get asked is: “What questions should I ask the interviewer?”
This leads me to believe the majority of professionals are looking at job interviews all wrong.
Jobs are mutually beneficial relationships; therefore, you need to interview the company just as much as they’re interviewing you.
Any seasoned job seeker knows you’re supposed to ask questions at the end of the interview.
I used to ask just any old questions to make sure I was meeting this requirement in job interviews, but after working with a few bad seeds, I take those questions very seriously now because I never want to work for a bad boss or in a bad culture ever again.
You should follow my lead because your boss and internal culture have a massive effect on your happiness, even when you’re not at work.
In this post, I share all the most pertinent questions to ask that will help you make sure the company and role you’re interviewing for is actually right for you.
The 3 People You’ll Speak With
You’ll likely speak with three people, who could all be the same person, depending on the size of the company.
Have questions ready for each of these people. You may want to consider repeating the question to different people to see if their answers match up.
No answer is necessarily right or wrong. They’re just giving you insight into the people, processes, and culture of the organization so you can make an informed decision for you.
Questions for Coworkers
Note: Customize these questions further based on the team you’ll be on and what the prospective role will be doing.
1. How do you decide what to work on each day?
2. What tools do you use regularly?
This answer will obviously be different for every industry, but it’s an important question to ask. You’ll be spending a massive amount of time in different software and apps to do your job, so make sure you actually enjoy using them.
If you have a tool preference, keep this in mind. Will you be miserable every day if you’re forced to use a buggy, custom-built CMS as opposed to WordPress? Or do you really not care?
A few years ago, I was interviewing for a marketing position at a small startup, and I let this one slide when I shouldn’t have.
The team was run by engineers, so everything was custom-built—even the email marketing system and the CMS. I knew this before going in, and it didn’t turn out well.
They didn’t see a problem with their tech stack, and I was miserable every day because I couldn’t effectively do my job without proper marketing tools.
If they mention a tool you’re not familiar with, google it, sign up for a free trial, and ask the interviewer how they like using it.
Good tools = good team. A team’s toolbox can tell you things like how much the team knows about its industry and how much leadership values the team.
3. How do you collaborate at work?
This is another big one for me.
I (and many other remote workers) have come to hate real-time messaging apps like Slack because they leave you constantly interrupted and living in an always-on hell.
In particular, I like to know if they have specific hours they typically work and what the expectations are around being online.
Are you expected to respond to messages in a certain amount of time? How late is too late?
How would you describe the work environment here?
Is the work typically collaborative or more independent?
4. What do you like about working here?
A long silent pause is a bad response here.
“It pays the bills.”
“There isn’t a lot of pressure to deliver.”
Instead, you want to hear answers like…
“I enjoy what I do.”
“I have fun at work.”
“I love working with smart, driven, open-minded people.”
“The company values [your department/what you do].”
Every team member doesn’t need to gush over the company, but you definitely want more good answers than bad.
Side note: Glassdoor could also help demystify this question for you as well.
5. What do you measure?
I prefer teams that measure what they do because:
I want more epic case studies for my portfolio.
It proves my worth, which can easily be quantified, in the case of layoffs, etc.
I can’t speak for other teams, but for content marketing, I like to hear metrics around unique visits, time on site, conversion rates, referral sources, etc. But those are just a few. I’m basically hoping they don’t just say stuff like, “impressions” and “reach.” Those alone are vanity metrics and pretty useless.
If they aren’t measuring, they’re not improving, which will mean you won’t be improving either. Or if they don’t seem to place value on measuring stuff in the first place, it’s usually a sign of laziness or inaptitude, both of which are negative. It’s pretty hard to change cultures like this, in my experience at least.
On the opposite end of the spectrum, if the interviewer has a good answer to this question, it’s a great sign that they’re a high-caliber team.
A good follow-up question is: “Why are you measuring X?”
If the answer is bloated and vague, be leery. They should have a good reason for why they’re measuring what they are, and if they don’t, you might be in for a rude awakening when it comes time to starting work.
Metrics should always yield actionable insights.
What is the overarching success metric for the entire company?
What is your source of truth? (i.e. Google Analytics, Facebook, Intercom, etc)
6. What teams do you collaborate with the most?
The bigger the company, the more cross-collaboration.
If you haven’t worked at a big company before, then you’ll likely be weirded out by how many people must buy into what you want to do, even when those people aren’t experts in what you do.
For example, as a marketer, I often work with the product team, the engineering team, and the design team, to name a few.
Usually, the marketing website—companies’ No. 1 public facing assets—are controlled by engineers because back in the day, only developers could make websites because technology was not very advanced.
Today, in a world where WordPress exists, there’s no excuse for marketers not to have control over the website.
Unfortunately, many legacy systems still exist, so I always ask: “Which team (and which stakeholder) has the final say when it comes down to it?”
Ideally, this question will unearth the politics at play when making decisions at this organization. Does it make sense?
Which team/leader has the most influence in decisions usually?
Which team do you like working with the best? Why?
Which team do you like working with the least? Why?
Questions for Manager
I’ll admit, I’ve had my fair share of bad managers.
At first, I thought it had to be me, and at times, I’m sure it may have been. But then I started reading.
I quickly learned that most people do hate their bosses, which dramatically decreases their happiness, even outside of work. It’s also the No. 1 reason people quit/switch jobs.
Reflecting back on my own work experience, I realized I was the most miserable at times when I had a horrible boss.
“Who you work for is exponentially more important than the work you do. If you want to accelerate your career, spend a little more time finding a great boss.”
Managers should be more than just someone you’re able to stomach.
It doesn’t matter what the job description says, when you work for a great boss (and do great work) you will inevitably find yourself working on high impact projects. You will find doors opening. You will feel yourself growing. A great boss is a mentor, but with the added benefit of holding influence with the “higher-up’s.” They see the success of the people who work for them as a direct reflection of their own success, and because of that, they invest crazy amounts of time in the people who work for them…this will often continue even after you no longer work for them.
Now do you understand why these questions are so important?
If you’re not exactly sure what you’re looking for in a manager, here’s a good list of starters via Lantz:
Is this a person that you respect and trust?
Are they great at something? And is that a thing you want to be great at?
What kind of jobs do their direct reports get after working for them? Are they making lateral moves? Are they moving up in the company? Are they switching to new companies with big title changes?
Do they make an effort to get to know you and understand what motivates you?
Do you leave conversations with them feeling motivated, challenged, excited?
Onto the interview questions…
1. What did you do before this?
Hopefully, their background and experience will sound interesting and exciting to you because that will lead to respecting and trusting them.
Is there something they’re particularly good at that you’ll be able learn from them? If so, that’s a great sign.
The other insight you can glean from this question is how much they know about how to do your job (or how much they think they know about how to do your job).
If they don’t have experience in this role (e.g. a non-technical engineering manager), then it’ll likely be harder to communicate and sell them on why you should use a specific tool or method, for instance.
2. How did you become a manager?
You want to understand why your prospective boss is a manager in the first place.
Were they forced into it? Or do they genuinely enjoy helping (and mentoring) people?
My favorite bosses have:
Impacted my career by trusting me with big assignments.
Genuinely cared about my professional success as well as the team’s success.
Protected and supported me.
Made my work life significantly better.
You want a boss that does all of the above, so try to determine how much they actually enjoy their job as well.
3. Who do you most enjoy working with and why?
If you get a good answer for No. 2, then you’ll want to ask this one because if your boss doesn’t like you, it’s unlikely she’ll want to go above and beyond to help you.
This question gives you a feel for the traits they value in the people they work with.
You must assess whether or not you have those traits or want to develop them because you’ll need them in order to be successful in the position.
4. How does your team know what to work on every day?
Compare the answer she gives with the answers provided in your coworker interviews.
It might be good to ask this question to coworkers too to see if there’s disconnect, another sign of dysfunction.
6. How will you measure performance for this role?
First, I’m trying to see how hands-on they’re going to be (i.e. how much trust and autonomy they’ll give me).
If they have very specific KPIs, with no reason for picking these metrics, I’m leery, and I begin to lose respect.
If they are looking for this person to make a recommendation for their KPIs, I like that answer the most. I believe KPIs should be mutually agreed upon, not forced down someone’s throat. I want to know if they think something is a bad KPI and if they have a compelling reason(s) why X would be better.
Last but not least, I’m interested in how performance is tied to raises and/or bonuses. That’s why I like to agree to specific, high-impact KPIs that I’m pretty confident I can deliver on in a specific time frame so I increase my paycheck.
7. Are there annual performance reviews?
I am not a fan of annual performance reviews. People often don’t take them seriously, so they can be a useless waste of time, or peers try to sabotage top performers with poor reviews.
I prefer managers who give me feedback whenever I need it. I trust them, so it can be direct and not hurt my feelings. (It’s called radical candor, and it’s amazing!)
Whether they use an informal tool like 15Five or on an as-needed basis in private, I don’t care.
Candid, respectful feedback accelerates your career because it’s pushing your skills (hard or soft) to the next level.
The way you word this question will depend on the interviewer’s previous answers and the size of the company.
If it’s a startup question, I’d ask the question I listed above, because it’s easier to negotiate competitive, stretch goals and what you get when you reach each one. The faster you meet them, the faster you get a raise.
A more corporate company will most likely tie annual performance reviews to annual pay raises, which are only scheduled once or a few times a year. In that case, ask: Do you do annual salary increases?
Your wages should be adjusted to match your contribution, and it should be reviewed at least once a year.
What was last year’s median raise on your team (in percent)?
How much salary increase could I expect one year from now? Best case, worst case?
Questions for Leadership
Depending on the role, you may or may not get to speak with the company’s leadership.
Don’t worry if you don’t. You can probably find most of the answers by doing a little bit of googling and/or searching Crunchbase.
(You may be wondering why I’m suggesting questions that could be easily researched. It’s because you’ll likely get hidden gems of details/information that someone online got wrong or misconstrued, etc.)
1. Is the company profitable?
I hate to burst any bubbles here, but there are a lot of “unicorns” that aren’t profitable. They just have an obscene valuation. Valuation and profitability are not the same things.
If they’re not profitable, what’s the plan for becoming profitable? Or do they not care and want a fat exit or IPO in the future?
A more important question is: What’s your runway? How long could the company operate before raising more capital?
If they’re a SaaS company, a great question to also ask is: What is your churn rate? This tells you how fast people are deleting their subscriptions.
A high churn rate is not good. It means people are deleting their accounts at high rates, usually because the product sucks.
2. How would you describe the company culture?
You’re looking for answers that tell you how the company operates and what it values most.
It might be helpful to get the coworker interviewers to answer this question as well, to see if there are any discrepancies.
Sometimes leadership is out of touch with how things work for their employees. Or they just talk the talk and don’t walk the walk, so pay attention to very different answers from employees and leadership here.
Side note: A lot of companies have culture decks today. Google “[company name] culture deck” or “[company name] internal culture.” Or just visit their “about” page, or scroll to the footer and look for pages like “mission,” “values,” or “culture.”
The company values should not only match your own, but they should also be in the same order of importance, only if you want to steer clear of conflicts, of course.
3. Why did you start/join this company?
Is there a greater purpose for working here? Is there a meaningful story?
I care more about their demeanor than their specific answer here.
I can get excited about pretty much anything if you have a good story and are compellingly passionate about why you are doing something and why I should be doing it too.
With passionate people, you’ll usually just “feel” this amazing energy. They make you feel really excited about solving an interesting problem that affects a lot of people.
4. Tell me about your reporting structure.
It would be ideal to see an org chart here.
While there’s no right or wrong chart or answer, it’s nice to know who’s who in the decision-making arena so you can make an informed decision.
Interviews are a two-way street.
Not asking *good* questions in a job interview makes you look desperate.
Jobs are mutually beneficial relationships. Start treating them as such.
Know what you’re worth, what you want, your values (prioritized), and who you want work with on the reg. This will help inform your decision once you get the answers to the above questions.
Here are a few tools I use to research before interviews:
Crystal Knows: This freemium tool provides insight into people’s personalities who you haven’t met before based on their online presence and other data they collect.
LinkedIn: Great for finding information about people’s career paths and strengths.
BuiltWith: Shows you all the tools a website is using.
SimilarWeb: Free marketing report on the company’s website over the past six months.
Blind: Anonymous social network where you can get all the juicy details about big companies, in Silicon Valley specifically.
What meaningful questions do you ask in interviews? Any research tools I forgot to mention? Either way, make sure to drop a comment below. =)