The Ultimate Checklist: 25+ Insightful Questions to Ask a Hiring Manager

An interview is a two-way street. While the hiring manager is assessing if you are the right fit for the company, you should also be evaluating if the company is the right fit for you. The questions you ask at the end of an interview are your golden opportunity to do just that. They demonstrate your engagement, intelligence, and thoughtfulness, while providing you with crucial insights that a job description could never reveal.

Asking generic questions like "What's a typical day like?" is a missed opportunity. To truly stand out and gather the information you need, your questions should be strategic, insightful, and tailored to the role. This guide provides a comprehensive checklist of over 25 questions, categorized to help you probe into the areas that matter most: the role itself, the team dynamics, company culture, performance expectations, and future growth.

Why Asking Questions Matters

Before we dive into the list, let's establish why this part of the interview is so critical.

It Shows Genuine Interest: Thoughtful questions signal that you have done your research and are seriously considering the role, not just going through the motions.
It Helps You Evaluate the Role: This is your chance to uncover the nuances of the job. Is the role what you expected? What are the real challenges? What does success look like?
It Assesses Company Culture: The answers you receive can be incredibly revealing about the company's values, communication style, and work environment. Pay attention not just to what they say, but how they say it.
It Demonstrates Your Expertise: The right questions can subtly highlight your skills and experience. For example, asking about the team's biggest challenge with a specific technology shows you understand the domain.
It Establishes a Peer-Level Dynamic: Asking insightful questions shifts the dynamic from a simple interrogation to a collaborative conversation between two professionals.

Questions About the Role

These questions help you understand the day-to-day realities of the job, the immediate priorities, and what success looks like in the first few months.

Can you describe the key priorities for this role in the first 30, 60, and 90 days? This shows you are goal-oriented and want to hit the ground running. It also gives you a clear picture of immediate expectations.
What does success look like in this position, and how is it measured? This is crucial. It tells you what the key performance indicators (KPIs) are and how your performance will be evaluated.
What is the biggest challenge the person in this role will face? This question uncovers the potential pain points and shows you are not afraid of a challenge. The hiring manager's answer will reveal a lot about the team's current struggles.
Could you walk me through a typical project I might be working on? This moves beyond abstract responsibilities and gives you a concrete example of the work you'll be doing.
What is the level of autonomy versus collaboration in this role? This helps you understand if the role aligns with your preferred work style. Are you expected to be a self-starter, or is the work highly collaborative?

Questions About the Team and Manager

Your immediate team and direct manager will have the biggest impact on your daily happiness and success. These questions help you evaluate that dynamic.

What is your leadership style? An essential question for your potential manager. Look for answers that align with the type of environment you thrive in (e.g., hands-off, collaborative, mentoring).
What are the strengths and weaknesses of the current team? Where would I fit in? This shows you think about team dynamics and helps you understand how your skills complement the existing team.
How does the team handle disagreements or conflicting ideas? This is a great culture question. A healthy team sees disagreement as a path to better solutions, not as a personal conflict.
What is the communication style of the team? (e.g., async on Slack, frequent meetings, etc.) This is especially important for remote roles. It helps you understand the operational cadence and meeting culture.
How do you support the professional development and growth of your team members? This shows you are serious about your career progression and helps you gauge if the manager is invested in their team's growth.

Questions About the Company and Culture

These questions help you look beyond the specific role and understand the broader company vision, values, and work environment.

What are the company's biggest challenges right now, and how is this role expected to contribute to solving them? This connects your potential contribution to the company's high-level strategic goals.
How would you describe the company culture in three words? This forces a concise and often revealing answer. You can then ask for examples that illustrate those words.
What is the company's philosophy on remote work and flexibility? In today's world, this is a non-negotiable question. Understand their policies on in-office days, flexible hours, and async work.
How does the company handle feedback and foster transparency? Look for specific examples like all-hands meetings, employee surveys, or open-door policies.
Where do you see the company in the next five years? This question assesses the long-term vision and ambition of the leadership.

Questions About Performance and Growth

These questions show you are forward-thinking and invested in your long-term success at the company.

What is the performance review process like here? How often does it happen? This helps you understand the formal feedback loop and how you can expect to grow.
What are the opportunities for career progression for someone in this role? Is there a clear career ladder? Do they promote from within?
Is there a budget for professional development, such as courses, conferences, or certifications? This is a tangible indicator of how much a company invests in its employees.
Can you give me an example of someone who started in a similar role and has grown within the company? This makes the concept of career progression concrete and real.
How does the company support work-life balance and prevent burnout? This is a critical question about company culture and employee well-being. Look for specific policies or cultural norms.

Red Flag Questions (To Ask Carefully)

These questions can be very revealing, but they need to be phrased carefully to avoid sounding negative or confrontational.

What is the biggest reason why people have left this team or the company in the last year? A direct question about turnover. The answer (or hesitation) can be very telling.
If you could change one thing about working here, what would it be? This humanizes the interviewer and can elicit an honest response about the company's imperfections.
How has the company changed since you first joined? This can reveal the trajectory of the company's culture and growth.
What is the process for making decisions on new ideas or projects? This helps you understand if the company is bureaucratic or nimble.
What are the next steps in the interview process, and what is the expected timeline? A simple, professional closing question that shows you are organized and respectful of their time.

Frequently Asked Questions (FAQ)

Q: How many questions should I ask?

A: Aim for 2-4 well-thought-out questions. Quality is far more important than quantity. Have a few more prepared in case your initial questions are answered during the conversation.

Q: When is the best time to ask these questions?

A: The interviewer will almost always save time at the end and ask, "Do you have any questions for me?" This is your primary opportunity. However, if a natural moment arises during the conversation to ask a relevant question, feel free to do so. This can make the interview feel more like a natural dialogue.

Q: What if they answer all my questions before I get to ask them?

A: This is a good sign! It means the interviewer was thorough. You can say something like, "You've actually done a great job of covering most of what I was curious about, especially regarding the team dynamics and performance expectations. I guess my final question would be..." and then ask one of your remaining, more nuanced questions.

Q: Should I ask about salary or benefits?

A: It's generally best to save compensation questions for a later stage, typically with the HR representative or recruiter, rather than the hiring manager. The initial interviews are about determining a mutual fit for the role and culture. Once the company has decided they want you, you will have more leverage in salary negotiations.

By preparing a list of strategic questions, you transform the end of the interview from a formality into a powerful tool for evaluation and connection. You will not only impress the hiring manager but also walk away with the clarity you need to make the best decision for your career.