The 4 R’s of Good Interviewer Questions

Sergey Piterman
Outco
Published in
8 min readJun 21, 2019

Over the years I’ve impressed more people with questions I’ve asked than with questions I’ve answered. Questions are how I gather information from other people. And I’ve learned that the better the questions I ask, the better the answers I get.

When I talk to people about interviewing, there seems to be an underemphasis on asking questions. Sure, an interview is essentially a test and you do need to come up with the correct solutions (especially in coding interviews). But unlike multiple choice tests in high school or college, where you get all or nothing for an answer and get no credit for your thought process, on an interview you are being judged on how you arrive at your answer.

Are you engaging? Are you methodical? Are you someone the interviewer would enjoy working with? Would they subject their coworkers to working with you?

A lot of those meta-skills get overlooked, but I can say from personal experience that my ability to learn has mattered much more than my domain-specific knowledge.

Which brings me back to the topic of asking good questions. Below I’ve outlined some guidelines for how to ask your interviewers better questions. These are the 4 R’s of Good Interviewer Questions.

One Caveat

I think it’s worth mentioning the importance of your intention. Don’t think about asking questions as something you do just for the sake of interviewing or as a way of “extracting” information. Think of it as a way to explore and discover new things. Be genuinely curious to learn more about the person and company you’ll be working for. Ask yourself, if you were to get an offer or get hired by this company, what kind of things would you want to know beforehand? What are the factors that will affect your decision making? These are good questions not only for the interviewer but for yourself. Some you’ll be able to answer on your own. And the ones you can’t, you ask.

1. Relevant

Make sure the questions you ask your interviewer are relevant to the company or role you’re interviewing for. This one should be obvious, but it’s one that’s worth mentioning. Some small talk is normally fine to break the ice, but remember that you have a limited amount of time and you want to leave an impression on that person.

So ask about your role or their role. Ask about the company’s public announcements, or product lines, or their roadmap. Ask about the tech stack, or what skills the interviewer has found to be most important in their role, and if there’s anything they suggest you learn or brush up on. And for god’s sake, don’t talk about the weather.

And it should go without saying that you should stay away from completely irrelevant topics or potentially inflammatory topics like politics or religion (unless you’re interviewing for a political or religious job). There is a time and place for those conversations/questions, and the interview is not it.

Why do you want this role? What insights can this interviewer offer you that will help you think about the role in a constructive way?

Think about the kinds of things you’d want to know if this interviewer had agreed to meet you for coffee and you were able to pick their brain. And then cut 90% of those questions because your questions not only have to be relevant, they have to be:

2. Reasonable

During interviews at big tech companies you’ll often only get a couple of minutes to ask interviewers questions at the end, and sometimes if things are running over you may not even get that.

For example, you would ask different questions at lunch vs during an elevator ride. There are many important differences between those two settings but most importantly there’s a difference in how much time you have together.

So with that time constraint in mind, you’ll have to scope your questions appropriately. Don’t ask big questions about the system architecture or highly detailed questions about specific systems. Odds are they wouldn’t be able to talk to you about that even if they did have the time to.

As an interviewer, sometimes I’d get really loaded questions that seemed highly specific and made a lot of incorrect assumptions. They took a long time to answer and were a bit off-putting because I’d have to choose if I correct those assumptions or kind of dance around them. A lot of times that’s because the person down a rabbit hole online or were trying to impress me with how much they knew. Don’t do that.

Instead, stay relatively high-level, and if time permits or if you have follow-ups feel free to go deeper. Asking questions is a BFS traversal, not a DFS.

It’s dangerous to take what you read on the internet as gospel or even truth. But that said, you have to know some things before going into the interview. So make sure your questions are:

3. Researched

Your questions don’t just have to be relevant to the job and reasonably scoped, they should be things you can’t easily have researched online beforehand. This point has some nuance but should be pretty intuitive.

Not doing your research conveys that you haven’t put much effort into preparing, and it leads to questions that aren’t very interesting for the interviewer to answer. They might just rattle off the company slogan or give you some generic answer that you easily could have learned either before or after the interview.

Usually, you should avoid stuff like trivia which can easily be searched for online(company’s CEO, mission statement, history, job description, what they do/how they make money etc.). They may give you the rundown again during the interview, but it’s good to be prepared regardless so you can ask the next level of questions.

Where this gets a little tricky is when it comes to public social media profiles. As a general rule of thumb, public profiles are fair game. Anything the interviewer has tweeted about publicly, any articles they have written, or any information they’ve put on their Linkedin profile should be okay to bring up.

But again, back to rule #2, within reason. Do mention if they went to the same school as you or someone close to you, or if they worked at a company you’re interviewing with, or if they wrote a blog post you enjoyed, mention it. Don’t bring up with they did last weekend on their Instagram profile (see rule #1). You don’t want to come across as a stalker, but someone who came prepared. It’s all about calibrating.

But the question of social profiles is really about being:

4. Relatable

To paraphrase a good friend of mine:

“Interviews are this weird setting where we’re both going to sit down together and judge each other for 30 minutes to an hour, but pretend like we’re not.”

Interviews are not a situation we normally find ourselves in during our daily lives because that’s an uncomfortable place to be. The closest analog I can think of would be dating and I think that’s why some people find it so painful.

So the advice I have for this part is to make the interview more personal. I don’t mean in the sense that you should take the rejections personally. There are a million reasons why a company might reject you that you are blind to, but are nevertheless affected by.

They might have just hired someone for the role who began interviewing a few weeks before you. They might have closed the role or not secured funding for it. It might not be the right skillset fit or it could just be that you got bad luck with a tough question or interviewer. Add to that the desire to find a job you love, and not screw up, and the high stakes of the interaction and it’s easy to get a warped sense of reality. This leads to all kinds of expectations that aren’t healthy. Just because an interview went well doesn’t mean you’ll get the job. Just because it went poorly, doesn’t mean you won’t. And that can feel like a crapshoot.

So what I’ve found helpful is to focus on was trying to relate to my interviewers as much as possible. I try to understand where they are coming from. Everyone has a story, and most like talking about it. And not only that, it’s an incredible way of gathering valuable first-hand information.

Searching for something online is very different than asking a source directly. They’ll be able to tell you things about their personal experience at that company that you wouldn’t be able to get otherwise. You could ask about how they got into the industry or that role. What they like about it and what they don’t. Some things they wish they knew before starting, or things they struggled with initially. What kind of things do people who are successful in this role do?

Remember, there’s a good chance you’ll be spending more time with your co-workers than with your family, so part of the decision to hire you, especially at smaller companies, comes down to culture fit. Are you someone they want to work with 40 hours a week? Are you going to be the kind of person who clocks in and clocks out or are you going to build relationships that extend beyond work?

Asking the right questions is a big part of how we relate to one another as human beings. Even though this advice is centered around technology companies where technical knowledge is essential, I seriously underestimated how big of a component the human element would be to being successful. Being able to ask a question, listen, respond and follow up seems like a very basic skill, but it’s taken me a long time to get good at it. And I still see a ton of people unable to connect with one another because they aren’t listening and just waiting to talk.

So don’t be that person. Ask questions that help you relate to the interviewer. Try to find that common ground.

So those are 4 rules of thumb I try to follow not just when asking my interviewers questions but in life. It’s always good to know what you’re talking about (research), make sure it fits the constraints of the situation (reasonable), not come out of left-field (relevant) and to try to understand and connect with the other person (relatable).

Because even if you don’t get that particular job, you never know when you might cross paths again. And if you leave a good impression on them, they are much more likely to recommend you to another position if they become aware of it. This won’t always happen, but asking good questions can definitely make a difference.

Hopefully, you’ll be able to apply these rules small ways throughout your life and have them not just lead to more successful interviews, but more interesting, constructive and empathetic conversations.

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Sergey Piterman
Outco
Editor for

Technical Solutions Consultant @Google. Software Engineer @Outco. Content Creator. Youtube @ bit.ly/sergey-youtube. IG: @sergey.piterman. Linkedin: @spiterman