Interview Questions That Don't Suck

Most interview questions suck because they're polite questions asked by nervous adults trying to avoid asking about touchy subjects like salary while also trying to sound interested. Advice for those types of questions is often focused on telling candidates what to say to get hired. This is about what to ask so you don't regret getting hired. After all, you're interviewing the company just as much as they are interviewing you.

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"What's the culture like?" is useless. Every company answers with the same words and none of them mean anything. Honestly, if I hear about being a family, work hard play hard, or having an in office ping pong table (I do love ping pong) one more time, I'm going to lose my shit. If you actually care about culture, ask questions that force concrete answers.

About the company and your role

Instead of vague culture questions, ask about how work actually happens.

• How much autonomy will I have in this role? Can I be a god damn adult and do my work or will I be micromanaged to hell and back?
  Who sets priorities? How often are they changed? Can I push back, or is that a career-limiting move?
• What are postmortems like? Can I fuck up and not be persecuted?
  When something breaks, is the goal to fix the systems or assign blame? Can I mess up, learn from it, and still be trusted afterward?
• What does the deployment process look like? How much freaking red tape am I going to have to deal with?
  How many approvals, gates, forms, meetings, and rituals stand between me and shipping code? This tells you more about daily friction than any "fast-paced environment" ever will.

These answers reveal trust, maturity, and how much bureaucracy you'll be wrestling with on a normal Tuesday.

About why they're hiring

This one matters more than people realize: Is this role backfilling someone who left, or is it net new headcount?

If someone left:

• Why?
• What would they say was hardest about the job?
• What would you want the next person to do differently?

If it's growth:

• Is this a brand-new team?
• An established team?
• A mix?

Each option has tradeoffs. New teams flail. Established teams have history. Being the FNG in a tight-knit group can be great or miserable depending on how inclusive they actually are. Ask now, not three months in.

How information flows (or doesn't)

Is information treated as secrets that you have to pry from others hands, or is information openly shared?

• Are calendars generally shared or private?
  This hints at transparency and how easy it is to collaborate without ceremony.
• How do people get access to chat channels?
  Open to join or invite-only? Who decides? Gatekeeping here often mirrors gatekeeping everywhere else.
• When cross-team collaboration is needed, what usually happens?
  Do people just ping each other and work it out, or does everything start with a ticket and a wait?

None of these questions are about tools. They're about trust, accessibility, and how much institutional friction exists between "I need help" and "problem solved."

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Most interview advice is about performing well enough to land the job. This advice is about making sure the job is worth landing for you. Asking better questions is about being honest with yourself about what kind of work environment you can actually function in. These questions are designed to get at the real answers indirectly, because direct questions rarely get honest ones. Interviews aren't a test you pass, they're a mutual risk assessment. Ask the questions that help you make an adult decision, not the ones you think you're supposed to ask.