Fantastic Questions (And When To Ask Them)

What to ask your interviewers when it’s your turn to ask questions

Joe Goldberg
May 21, 2019 · 6 min read
Semi-trucks in a row, at TA Truck Stop. North Bend, WA

Interviewing with a new company is like a dance between you and the prospective employer. Both parties are learning about each other to get a sense of fit in each direction. Of course you’ll be asked plenty of questions at each step in the process, but interviewing is also a chance to have your questions answered.

Since the time allotted for you to ask questions is limited, you should carefully practice in advance, just as you’d prepare to design a system on the whiteboard, or answer a STAR style interview question.

The earlier you get good answers to your key questions the better, as it gives you information on aligning your strengths with the company, and helps you determine whether you should move forward with the interview process.

Here are some sample questions to ask, and some general tips on how to make the most of your time spent interviewing.

Fantastic Questions (And When To Ask Them)

This section is organized into different topics. Pick a few questions that resonate with you and add them to your metaphorical toolbox of interview preparedness.


  1. “If you had a magic wand and could wave it to change one thing about your company, what would you change and why?” This is my all time favorite question. It’s a riff on the classic “What’s the worst thing about working here?” but invites the other person to dream big and think of audacious improvements. If you ask this to multiple people, you can triangulate the answers to build a picture of the most important problems the company is facing, so you can position yourself as the ideal person to solve them.
  2. “Why’d you choose to work here? And what keeps you here?” This is a good question to ask of quiet interviewers since it gives them a chance to talk about themselves, their tenure at the company, and their history at previous orgs. Also a good question for people who’ve been at the company a long time. Listen for what’s changed since they started, and whether their motivations are similar to yours.
  3. “What’s your favorite value of the company?” These days, most companies have corporate values that they’re happy to share with candidates, so it’s interesting to see what the company prioritizes, and if it’s a match for you.


  1. “What’s the ONE thing that must be done in the next 6–12 months, to ensure that your company (is / continues to be) a success?” A lack of consistency in this answer signals that the org lacks clarity/alignment in their priorities (one of the 5 Dysfunctions of a Team). It also gives you data on their most important problem (See the “Magic Wand” question above)
  2. “Tell me about your company’s competition.” Ask this to a PM or someone in Product, Sales, or Senior Leadership. Listen for a balance of “we know what our competitors are doing” but “we’re not over-indexing on it,” and some sense of introspection about their product/market fit. A serious red-flag is “We don’t have any competition, this is so innovative, etc.” that’s usually either untrue or a sign that the company is building something of low business value.
  3. “How does your company stay close to users?” A company needs product-market fit to become (or stay) successful. To do so, it should have some system or process in place to help route feedback from users back to those who are designing and building the product.
  4. “How do you handle technical debt?” This is a great question because you get data on two levels: on the surface, you get to hear about how the org balances new-feature development with maintaining existing systems. But it also serves as a proxy for a more general question, “How do you make tradeoffs?” Bonus points for interviewers who can couch their answer to the first (narrow) question inside an explanation of a reusable “meta system” used to answer the second (broad) question.

Fit for role

  1. “Paint me a picture of the platonic ideal of a perfect [job title you’re interviewing for]?” This is a take on the “What are the traits of the best…?” but since this is a vision of perfection, you’ll get a lot more aspirational info. The interviewer will likely describe a unicorn-ish combination of skills rarely found inside one single human. Regardless, you can see how well the description fits with your skills and motivations, and position yourself as a person with these qualities (if that is true!). A fun take that combines a couple of these questions is “What are the projects this company thinks are really key to its future, and how would a motivated person go about getting on them?” (hat tip to patio11 for this one)
  2. “How does your org handle [a specialty you’re interested in]?” Be open to the fact that the company you’re interviewing for might not approach the problem-space in the same way that you’re used to, since they’re solving an industry-wide problem but in the unique business context they find themselves in.
  3. “What’s your tech stack? What’s your software development lifecycle? Why did you choose these?” Ask this to engineers, managers, and PMs. The final question is the most important. Different languages, technologies, and processes are all tools in a metaphorical toolbox, to be pulled out when they’re the best fit for the problem at hand. You want to see that a company has chosen them intentionally, but isn’t dogmatic about their choices since things are bound to change.

General Advice on asking Questions

  1. DO ask the same question to multiple people. You need to get multiple data-points about a question in order to triangulate and get to the truth about a particular topic. It’s the same reason why a company has multiple people interview you.
  2. On the other hand, DON’T ask the same exact questions to everyone. You should tailor your questions based on the role, tenure, and personality of the interviewer. The hiring team will talk about what questions you asked during the debrief, so pretend like every interviewer is in the room for every part of your interview.
  3. Try to make it more like a conversation than a survey. Familiarize yourself with your questions ahead of time, memorizing them if possible. While it’s alright to read from prepared notes, it always comes across better if you can naturally speak to the other person conversationally.
  4. Take notes when the other person is speaking. Even if you have a photographic memory, you should respect the other person by taking notes, which shows that you’re listening to them and care about what they have to say. If notetaking really isn’t your thing, brush up on “active listening” so you’ll have other ways to let the interviewer know you’re engaged in the conversation.
  5. Be sure to manage time in order to get your questions answered, but also feel confident to go “off script”: ask follow-up questions, skip questions that got answered by this interviewer’s previous responses, etc. You might only get one question answered but spend 10 minutes in a deep conversation about something really interesting where both parties learn something new. That interviewer is more likely to walk back to their desk thinking “we gotta hire that candidate.”
  6. If you can’t get a critical question answered, follow up via email. You should at least have the contact info for a recruiting coordinator, and you can go through that person to get the question in front of the relevant interviewer. Not only does this get your question answered, but it also demonstrates your tenacity.


I’ve had a lot of success getting signal about the importance placed on Diversity & Inclusion (D&I) at companies by asking one of the above questions, “How does your org handle D&I?” I want to see that a company is taking D&I seriously, and they either have an existing group I can plug into, or they’re open to letting a newcomer take the reins. When I asked this while interviewing at Convoy, I was impressed with the transparency they exhibited in measuring their current state, and at how much thought they’ve put into iteratively improving.

Mathematically speaking, the Q&A portion of your interview is almost 20% of the total interview experience, so spend a commensurate amount of your time preparing for it. Don’t go overboard but don’t neglect it.

Ready to try out some of these questions? Convoy is hiring!

Convoy Tech

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