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85 Best Questions to Ask in an Interview: The Reverse Interview Strategy

Leon Intelligence 10 min
Leon Verified
85 Best Questions to Ask in an Interview: The Reverse Interview Strategy

At the end of almost every job interview, the script flips. The interviewer stops grilling you and asks: "Do you have any questions for us?"

Most candidates treat this as a formality. They ask two generic questions about "culture" or "next steps" and call it a day. This is a massive mistake.

In 2026, where AI-driven screening and high-volume applications are the norm, this 10-minute window is your only chance to perform a "Reverse Interview." It is the moment you stop being a "candidate" and start being a "consultant" evaluating a business problem.

The goal is not just to look smart. The goal is to uncover the "hidden job description": the real problems, the team friction, and the management style that will determine whether you actually enjoy the next two years of your life.

Here are the 85 best questions to ask in an interview, categorized by what you need to uncover.


1. The "Reverse Interview" Strategy: Why You Ask

Before we get to the list, you must understand the strategy. You are looking for Information (to decide if you want the job) and Signal (to prove you are a high-level thinker).

  • Lower-level candidates ask about benefits, PTO, and "what a typical day looks like."
  • High-level candidates ask about business goals, technical debt, decision-making frameworks, and how the team handles failure.

2. Questions About the Role (Assessing the "What")

These questions help you understand if the job matches the description and if you are set up for success.

  1. What does "extraordinary success" look like in this role 6 months from now? (This is better than "What are my goals?")
  2. What is the single biggest challenge the person in this role will face in the first 90 days?
  3. Is this a new role, or am I replacing someone? (If replacing, ask: "What did the previous person do well that you want to maintain?")
  4. How much of my time will be spent on new projects versus maintenance/support?
  5. What is the one thing I could do in this role that would make your life significantly easier?
  6. How does this role contribute to the company's "North Star" metric right now?
  7. What is the most common reason people struggle in this specific position?
  8. What tools/software are non-negotiable for this role, and what is flexible?
  9. How are priorities set when everything feels like a "Priority 1"?
  10. What is the budget/resource situation for this role's specific projects?

3. Questions About the Team & Dynamics (Assessing the "Who")

You spend 40+ hours a week with these people. You need to know if they are a high-performing unit or a group of individuals.

  1. How would you describe the team's "operating system": how do you actually get work done?
  2. What is the balance of seniority on the team right now?
  3. How does the team handle a missed deadline or a project failure?
  4. What is the team's biggest win in the last quarter, and how was it celebrated?
  5. How do you integrate new hires into the team's social and technical workflow?
  6. What is one thing the team is currently doing that you hope I can do better?
  7. How often does the team meet for non-work reasons?
  8. If I asked the team what their biggest frustration is right now, what would they say?
  9. How are cross-functional conflicts (e.g., between Product and Engineering) resolved here?
  10. What is the "vibe" of the team during a high-pressure week?

4. Questions About the Manager & Leadership (Assessing the "Boss")

People do not quit jobs; they quit managers. These questions filter for toxic or micromanaging leaders.

  1. What is your management philosophy in three words?
  2. How do you prefer to receive updates: async (Slack/Email) or sync (Meetings)?
  3. Can you tell me about a time you supported a team member's growth, even if it meant they eventually left the team?
  4. How do you handle underperformance?
  5. What is the most important thing I should know about working for you?
  6. How do you give feedback (Real-time, weekly 1:1s, or quarterly reviews)?
  7. What do you do to protect your team from "scope creep" or upper-management distractions?
  8. What is your go-to method for resolving disagreements with your direct reports?
  9. How do you stay connected to the day-to-day work of the team without micromanaging?
  10. What is one thing your best employee does that you wish everyone did?

5. Questions About Company Strategy & Stability (Assessing the "Why")

In 2026, market stability is key. You need to know if the company is growing or just treading water.

  1. What is the company's biggest competitive threat in the next 12 months?
  2. How has the company's strategy changed since the rise of [relevant industry trend/AI]?
  3. What is the most significant pivot the company has made in the last two years?
  4. How transparent is the leadership team about financial health and roadmap changes?
  5. What is the one thing the CEO is obsessed with right now?
  6. How does the company balance short-term profitability with long-term innovation?
  7. What is the company's retention rate for this department over the last two years?
  8. If the company achieves all its goals this year, what does that mean for this team specifically?
  9. How does the company decide which new markets or products to enter?
  10. What is the "moat" that keeps customers from switching to a competitor?

6. Questions About Culture & Values (The "Red Flag" Filter)

Every company claims to have a "great culture." Use these to find the truth.

  1. What is something that happens here that wouldn't happen anywhere else?
  2. Who is the "hero" in this company, and what did they do to earn that title?
  3. How does the company's stated mission actually show up in daily decisions?
  4. What was the last "unpopular decision" made by leadership, and how was it communicated?
  5. How does the company support deep work versus the "always-on" culture?
  6. What kind of person typically fails or leaves within the first 6 months?
  7. How does the company handle diversity and inclusion beyond just hiring metrics?
  8. What is the policy on "side projects" or community involvement?
  9. How are "soft skills" or "culture adds" rewarded here?
  10. What is the one thing about the culture that you would change if you had a magic wand?

7. Advanced Questions for Technical & Engineering Roles

Since Leon is a technical agency, we prioritize these for our candidates.

  1. How do you balance "shipping fast" with managing technical debt?
  2. What does your CI/CD pipeline look like, and what is the typical "code to production" time?
  3. How is the "on-call" rotation handled, and how often are people paged outside of work hours?
  4. Can you walk me through the decision-making process for a recent major architectural change?
  5. How does the engineering team influence the product roadmap?
  6. What is your approach to automated testing and documentation?
  7. How do you handle "Gold-plating" or over-engineering?
  8. What is the most interesting technical problem the team solved this month?
  9. How do you stay up-to-date with new technologies without chasing every "shiny new object"?
  10. What is the ratio of engineers to product managers/designers?

8. Questions About Professional Growth & Career Pathing

  1. Where have the last three people in this role gone within the company?
  2. What is the budget for professional development (courses, conferences, books)?
  3. How does the company handle internal mobility and promotions?
  4. What is the path for someone who wants to stay individual contributor (IC) versus management?
  5. How often are career pathing conversations held?
  6. What is the biggest skill gap on the team right now that you hope I can fill?
  7. How do you measure "growth" for this role?
  8. Are there mentorship or coaching programs available?
  9. How does the company support people who want to lead a new initiative from scratch?
  10. What does the "Senior" or "Lead" version of this role look like?

9. The "Closer" Questions (Wrapping Up)

  1. What is the timeline for the next steps in the process?
  2. Is there anything in my background or our conversation today that gives you pause?: Ask it to address concerns immediately.
  3. Who else will I be meeting with in the subsequent rounds?
  4. What is the best way to follow up with you?
  5. What was your favorite question I asked today?: A great way to end on a high note.
  6. How do you feel about the current team's ability to hit the upcoming milestones?
  7. What is the one thing I should prepare for the next round of interviews?
  8. Are there any specific case studies or projects I should review before our next talk?
  9. How many other candidates are you currently considering for this final stage?
  10. What is the planned start date for this position?

10. The "Bonus" High-Impact Questions

  1. "What is the one question I haven't asked that most people ask?"
  2. "If you could redo your first 90 days at this company, what would you do differently?"
  3. "What is the 'unofficial' requirement for this job that isn't on the JD?"
  4. "How does the team handle 'invisible work' like refactoring or mentorship?"
  5. "Why do you personally stay at this company?": The ultimate culture check.

Pro-Tips: How to Ask These Questions

Do not interrogate. An interview should be a conversation. Pick 3-5 of these questions and weave them into the talk as it happens. If they mention a project, ask Question #54 right then.

Watch for non-verbal cues. If the interviewer pauses for a long time when you ask about "unpopular decisions" (Question #44), that tells you more than the actual answer.

Take notes. It shows you care about the answers.


FAQ: Interview Questions to Ask

How many questions should I ask at the end of an interview?

Usually, 3 to 5 is the sweet spot. If you have more, ask if you can email them or save them for the next round.

Can I ask about salary in the first interview?

Generally, no: unless the recruiter brings it up. Save the deep compensation talk for when you have more leverage. See our Salary Negotiation Script for more details.

What if the interviewer already answered all my questions?

Do not say "I don't have any." Say: "I actually had a list, but we covered X and Y already. I'd love to go deeper on Z..." or use Question #81.

Should I ask different questions to the recruiter vs the hiring manager?

Yes. Ask the recruiter about process, timeline, and general company facts. Ask the hiring manager about the role, the team, and the "how" of the work.


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Written by Leon Intelligence

Career & Talent Advisors

Leon is a highly specialized team of career consultants, talent agents, and technical hiring advisors. We provide exact, real-time data on interview response times, compensation transparency, and salary negotiations to help top-tier professionals secure highly competitive offers.