from Guide to the Job Hunt on Jan 22, 2023

What to ask interviewers in a job hunt.

Almost every interview ends with a time for you, the candidate, to ask questions. However, these questions aren't optional. Interviewers are looking for information in your question, just as you are looking for information in their answers.

Your questions at the end of an interview are telling for an interviewer — in particular, your questions can help the hiring committee determine your interests and fit. A research team is looking for impactful ideas, an engineering team is looking for product focus, and Tesla is looking for 24/7 workaholics. There are two main purposes for preparing questions:

• Collect a few reusable questions for everyone. I'll discuss some of my own concerns and questions for you to repurpose or even reuse verbatim.
• Your interview is with a senior leader in the company, and you're not sure what to ask. I will guide you through designing authentic questions.

This post will take you through both aims for preparing questions¹.

Know the taboo topics.

Before knowing what to ask, know what not to ask. Certain taboo topics are team-specific and dependent on your hiring manager's concerns. For example, let's say the team you're interviewing for is a small applied research team at a startup. As a result of their size and the company's stature, the team's impetus is to move fast, with a focus on research for its product.

If you're a graduating PhD student, one of the hiring manager's foremost concerns will be whether or not you're a fit for industry, given your background is in academia. There is one of three possibilities:

1. You are tired of academia. In which case, your questions are geared towards applications of academia to industry: "What is the pipeline from research to product?"
2. You're not sure about academia but still want to understand the team's stance. In which case, you may ask about their priorities: "How does the team prioritize projects that're near-term vs those that're longer-term?" Use their own definition of what is near term (a few days? Weeks? Months?) and long term to assess how quickly the team moves.
3. You are really looking for an extension of academia. In which case, you may ask about the teams willingness to participate in academia: "Is the team looking to publish its research?"

In this case, questions in the first category are more suitable, and any question will immediately convey which camp you're in. With that said, ask questions that honestly reflect your curiosities; if the team has no interest in publishing but you do, better to find out now in the interview than a year down the line after starting the job.

Aside from the hiring manager's own concerns, there are several company-wide taboo topics to watch out for. Here are several taboo topics for different companies, although your mileage may vary for specific teams:

• Tesla: Work-life balance doesn't exist, and tech-company perks (e.g., gym, free food, shuttles) are non-existent. Side projects outside of work are looked down upon, although not explicitly forbidden.
• Apple: Anything you do that is public-facing, even outside of work hours and off of work equipment, is heavily scrutinized. Many activities are forbidden unless approved by leadership — to be specific, anything that conflicts with Apple's business is forbidden, and the list of Apple's business interests is fairly long. As of time of writing, especially for locations other than headquarters in Cupertino, in-person attendance is a touchy subject. Asking about future products, even to understand what your future team is doing, is taboo.

It goes without saying that asking about perks in an interview is a big no-no, no matter the company. If you have friends at the company you're interviewing for, chat with them to understand which topics are taboo, as a result of the culture.

Concerns, then questions.

To maximize value from these questions, design questions around your concerns, at least subconsciously. Here were a few of my concerns during the job hunt and the questions I asked. In particular, I structure the following as a criteria, my thoughts around that criteria, and the questions for each.

1. I want a team that is grounded in reality. I don't want to work on imagined research agendas designed from under a rock. Instead, I want to work towards solving real-world problems plaguing production models.

   1. How would the product be worse off, without your work? Is this noticeable to end users, and if so, in what way?
   2. What is a real-world problem that academics are missing, that is critical to the product? What is the insight to solving this problem?
   3. What is one project you're working on now that you designed, and how did that idea come to be?

2. I don't want to burnout (often). I don't want to feel guilty signing off at 7 pm., as a few hours a day for side projects every day is a must. I'm perfectly happy working long hours if that's what it takes to finish a project, but I don't want unsustainable levels of work to be a minimum. It should at least be recognized as above-and-beyond. The way I phrase it is: The team should have the work ethic to pull long hours if need be, but also have the sanity to work regular hours on a day-to-day basis.

   1. Do you get weekends to yourself? Have you pulled any all-nighters for work, out of necessity or out of your own volition?
   2. Have you burned out at work, and how do you recuperate? What is the key to a successful recuperation?

3. I want "interesting" coworkers. I want coworkers that I can discuss high-level ideas with, contemplating not just project execution but whether a project should be done at all — this means strong architects and researchers as well as strong engineers. I don't want coworkers that watch TV all day outside of work. The more I learn about my coworkers, the more interesting they should be.

   1. What is your 5-year vision at your company? What legacy do you want to leave behind, if you left the company after 5 years?
   2. From Hamming's "You and Your Research", What are some of the most important problems in your field, and how is your work related? If it's not related, what holds you back?
   3. Who is someone on the team you really respect, and why? What have you or hope to learn from them? Anyone except your manager.

In the same way, I would suggest at least knowing your general desires in your job hunt, then designing or picking questions around those desires.

• Right now, identify a job-related desire of yours. You can pick one of mine above, or design a new one. If finishing "I want…" is difficult. Try "I don't want…". If you're really drawing a blank, skip to the last section for more in-depth guidance.

With a desire established, let's now work on creating questions that effectively assess each of your criteria.

Designing effective questions.

Your goal with each question is to assess a certain criteria. However, rephrasing your criteria as a question verbatim rarely does the trick.

As a example, say my desire is "Have freedom to pick my own projects". I could convert this verbatim to a question: "Do you have freedom to pick your own projects?". However, anyone pitching the company correctly will say "Yes," so here are several tips to maximize effectiveness of your questions.

1. Base the question on a concrete example. Instead of asking if something is generally true, ask about an existing project to see for yourself how true that something is. Continuing the previous example with freedom of choice, don't ask "Do you have freedom to pick your own projects?" Instead, ask "What is one project you're working on, and how did you come to work on it? How did the project start? Were any of your projects your top choice to work on?"
2. Do not favor an answer implicitly in the question. Some questions are clearly biased. For example, you may ask "What is the most important problem in your field, and why aren't you working on it?" Others may express what you're looking for. For example, "Does the team value work-life balance?" means the less work and the more chill, the better. Instead, ask "What is the latest you've worked? What are normal working hours?"
3. Make the question about others. Instead of asking if the interviewer has a certain freedom, privilege, or ability, ask if their teammates do. You can use this a proxy for your future self. For example, say you're asking about freedom of project choice, you may ask "Have any of your teammates designed and started a project that you find impactful?"

With the tips above and your list of desires, start translating desires into questions.

• Right now, design a question that checks one of your desires. Make sure your question is based on an example and does not favor a certain response, to elicit the most honest answer.

Now that you have your questions, know who to ask what kinds of questions.

Know who to ask what.

As a candidate, especially one with an offer in hand, you have the most access to all sorts of company leaders that you ever will. In many cases, skip levels and even senior leaders may be interested in speaking to you — both to understand your interests and to pitch their organization.

As these calls roll in, ensure you ask appropriate questions of each leader — the higher up the leader, the broader and the harder the questions. Most importantly, take these opportunities when you can. They are very rare.

In my own job search, I considered three sets of people: peers, managers, and leadership. I'll organize example and types of questions using these three sets. I suggest organizing your questions using these categories, as well:

1. Peers - Ask about day-to-day work, culture, and project execution. Get to know your future coworkers. Ask all questions about your manager and other peers, in this call.

   1. Having a 30,000-feet perspective, as I want to be able to discuss not just goals but also the merits and design of a goal: What is one project that is going sideways (that you aren't working on), and how would you fix the problem? What is your goal in the next year? In the next 5 years? Good if they start with the problem statement.

   2. Being a strong architect, knowing how to break down a complex goal into smaller parts. You can test this by asking the reverse — if they can relate their work to the bigger idea. Being a strong researcher, having qualities in What defines a "good" researcher?: What problem does your project solve, and why is this critical?

2. Manager - Ask about your future role, what defines your success on the team, and what a great year for the team looks like. Ask all questions about "you" in this call.

   • Your role and success: What does a successful first 6 months for me on the team look like? First year? What would be a slightly beyond-reasonable idealized goal for me?
   • Team growth: How will the team be different in a year? Bigger scope? More headcount? Pretend that all undesirable external pressure is gone, and you had the freedom to dictate direction.
   • Alignment with your goals: What is your team's goal, summarized in a sentence or two? How do you know if you've succeeded or are making progress a few years down the road?

3. Leadership - Ask about the company's vision and product, and get a sense of how the team or organization will evolve. Understand the trajectory of your team, in this call.

   • Company vision: How will the world be different if the company succeeds? How will you know that you've succeeded? What is the biggest bottleneck to progress today?
   • Future bets: What long-term bets are you making now that others are missing? How do you take calculated risks? What properties of projects and teams stand out to you as strong indicators of success?

At this point, you should have concerns, questions, and a rough idea of which employees to ask what. However, say you have an important call coming up with a senior leader, and you're not sure what to ask. All the trivial ones — culture, company, team — have been exhausted. Read on for guidance on designing authentic questions.

Don't know what matters to you in your job?

Your questions are ideally designed around your concerns. What matters to you in your future job? What ticks you off — and what do you not want — in collaborators? What do you want in a company? If you're preparing for a post-offer call with senior leaders, or even your own manager, follow these guidelines to design authentic, informative questions.

Naturally, discovering what you really care about is easier said than done. To find your own taste and preferences, follow these four steps. Notice the process starts off very similar to How to make New Year's resolutions. — namely "write, then organize," a process I'd recommend for any introspective process:

• Make a list of all job-related desires, beyond fame and fortune. Most important to only list criteria that speak to your strongly. Half-heartedly writing "independence" doesn't mean much, if you're not even sure what "independence" at work means. However, if you've previously been stifled by a top-down culture with micromanaging managers, then "independence" may hold more meaning for you. Be specific about your desires — you may write a desire as specific as "freedom to decide on projects to work on". Don't just write "products," if you know more: In my case, I want to be able to see and use what I've built. In other words, I want to work for "a company whose products I use". If a criteria is vague but speaks strongly to you, write it down anyways. Right now, list 3 job-related desires no matter how vague, broad, or petty. Write it all down.
• Find recurring themes and identify categories of criteria: Some example categories include: company size, work ethic, people, culture, interest, work-life balance, manager, leadership, location, and remote work flexibility. Any way to categorize your concerns in a few words works. Right now, find 1 recurring theme in your desires.
• Expand criteria by discussing categories with friends and mentors. Explicitly ask others about their categories of criteria: What do you look for in <category>? For example, what do you look for in company culture? in a manager? One tip is to ask the reverse: What do you not want in a manager? What is one company culture you didn't like? Using the responses, populate each of your categories with more desires, or questions for yourself. Right now, reach out to someone you can discuss the job search with. Ask them about your categories, to discover other facets of your future job that you care about.
• Translate criteria into questions. Take individual desires from your previous steps, and translate these into questions for your interviewers. Right now, convert a desire into a question.

For more examples of criteria and categories, see How to make big decisions. You should now have a rough idea of your job-related criteria and a list of questions to ask. Ask your questions, be interested in the response, and take notes as need be.

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