Interviewing for a Senior-Level HR Position? 50+ Questions to Ask

August 10, 2022

Contributed by Steve Cadigan, Founder Cadigan Talent Ventures

Interviewing for a Senior-Level HR Position? 50+ Questions to AskAre you interviewing for a senior-level HR position in the New Year?

Over the years I have coached dozens of HR professionals around the world on a whole host of topics. I’ve also received coaching from dozens of mentors, coaches, and friends on many matters both professional and personal.

While it’s hard to declare one subject area more important than another, I find the most challenging situations people face are those that involve deciding whether or not a new opportunity (in a new organization) is the right one!

This is especially challenging in the world of HR where there are so many critical elements that are important to choose from. For instance, a position on the HR team, in a new organization, that is nuanced and not easy to reveal in a standard interview process.

Assessing trust, culture, leadership style are highly challenging undertakings in this situation.

  • Does the organization really care about people and talent?
  • How do you know?
  • Is the HR function and team respected and where is their input really valued?
  • Does the company say, “people are our top priority” and do they really back that up?

More people know what they don’t want from HR than what they do want.

One of the sad realities of my experience in HR is that more people know what they don’t want from HR than what they do want. This means many companies and interviewers don’t know what questions to ask HR candidates, and worse, they come at the interview in a defensive frame of mind rather than bringing an open mind.

It’s really important to keep this in mind. It may be that the organization has never had access to great HR or maybe some people have had bad experiences with HR (or have misunderstood the profession). That said you need to bring your “A Game” to the table and be prepared to see it not just as an interview, but a chance to educate

Over the years, I have compiled a list of 50+ questions that have helped me and others assess new opportunities for HR roles in other organizations and I hope you will find them useful. I have attempted to categorize these questions into key areas, but the truth is many of them overlap and as you would expect one question may lead the respondent to answer 3 or 4 others.

These questions have been built to just be a guide to help you understand the company, the leadership team, the culture and their views of HR in the company and more generally. My intent in building this is that you have a framework to use to think about a new opportunity. I do not suggest that anyone ask all these 50+ questions in one interview.

As noted earlier, these questions are also designed to help the interviewer understand more about the scope and role of a high performing talent/HR function.  Take a look below and use the questions that make sense for you and for the opportunity. Some of them may not be helpful.

More specific advice on how to use these questions:

Note #1 – I strongly suggest you do not just roll through these questions and after they answer one move on to the next –and most of the answers you receive will suggest a follow-up question for you, so be prepared, dig in, and engage. How you drive the interview will tell them a great deal about your intellect and your HR savviness.  The organization will learn about you as a talent leader, someone who is a master of their craft and who cares deeply and has a passion for HR.

Note #2 – You also need to ask many questions about the business not included here. I suggest you always start with questions on the business first and then dive into some of the questions below.

Finally, in the spirit of giving back, if you have other questions you think will make this better, by all means, share them with me and others.

I would love your input.
Good luck!

Steve Cadigan, Founder Cadigan Talent Ventures –
For more resources and ideas on compelling talent, solutions visit my website:

Here are my 50+ Questions…

The Big Picture

  1. What is your personal view of HR’s role in a company? How did you come to this opinion?
  2. What is the company’s talent strategy?
    1. How do you measure the effectiveness of the strategy?
  3. How effective has the talent strategy been? Why?
  4. Have you ever worked in a company where the HR function was high performing?
    Please explain. If the answer is no or even if its yes then ask, “What does great HR look like to you?”
  5. Have you ever worked in a company where HR was awful? Please explain what awful looked like.

About Recruiting

  1. In the world of recruiting, who would you say is the primary owner of recruiting? The hiring manager or the recruiter?
    – What has worked the best in recruiting?
    – What is not working?
  2. When it comes to recruiting, what do you think is more valuable? A well-resourced recruiting team or having a great culture?
  3. How often do you survey employees here? If you do, what systems do you use? What has been the participation/response rate?
    What insights have you learned?
  4. What are the company’s greatest assets when it comes to recruiting? Explain your answer.

The HR Team

  1. (For CHRO role) What do you think are the most important elements that contribute to the success of a CHRO here?
  2. Where does HR report in the organization and why?
  3. What talent metrics do you measure?
    – Are there any talent metrics that you measure that have given you massive insights to help you improve the company performance?
  4. Do you think the HR/Talent team has been adequately resourced and funded?
  5. What is the brand of the HR team in the company currently?
    – What do they do well?
    – What can they improve?
    – Are there any issues or concerns with the team currently?

Company Culture

  1. Can you explain to me the formal and informal culture of the company?
    Is there someone who influences that more than others?
    Who is it and how do they?
  2. Where does “culture” fit in the priorities of the company?
  3. What are the best examples of culture in your company?
    – Who owns the culture in the company, if anyone?
  4. Who gets promoted in this company and why?
  5. What role does the senior leadership play with respect to culture?
  6. How are people treated when they are let go by the company? Do you have a practice and or policy you follow?
  7. What is the philosophy of performance management here? Do you do performance reviews? Explain your answers.
    – How does the process work?
    – How effective are you in this regard?
    – What system or tools do you use?
  8. Who owns ensuring the company lives up to it its values and culture?
    – Who are the most important relationships for the CHRO in this company?
  9. What qualitative and quantitative measures do you use to assess the effectiveness of the HR team in the company?
  10. Where do Diversity and Inclusion fit into the company priorities? How do you consider you are doing in this regard?
    How do you measure your effectiveness w/ D & I?
  11. Who are the people who are successful in this organization? Explain your answer.
    – Who are the people who are typically not successful in this organization? Explain your answer.

Communication & Alignment

  1. How often do you have all company meetings? Why? What is the goal of these meetings?
  2. How do you measure the effectiveness of key message delivery and absorption in the company?
  3. What you measure/track the most as a company and how is that shared with the organization?
  4. What are the toughest situations the company has faced in recent years and what role if any did HR play in these?
  5. How are conflicts seen in this company? Can you give me any examples of conflicts between Execs and how that played out?
  6. Can you explain the organization design to me and tell me why it is the way it is and why it’s working or not working?
  7. Can you share with me the level structure (i.e. do you have AVPs, SVPs, EVPs or do you just have VP)?
    – Can I get a sense of how you use and see titles in the company?
  8. How are promotions to Director and VP made? Do you have a consistent process for that?
    – Have you had any promotions to VP that in retrospect were a mistake? Explain your answer.
    – What did you learn and how did that shape how you do things differently now?
    – How did you recover from the mistake?

Demographics & Data

  1. What is the average tenure of employees? And which way is it trending? Why?
  2. Does the company curate relationships with former employees? Why or why not?
  3. In the technical departments, have you built an IC path as well as a management path?
    In other words, can people be rewarded here as Principal and Distinguished Engineers vs. at the same level, as a Director and VP Engineering can be?
  4. Do you do workforce planning here? If so, how far out are you looking? What skills do you think you need next year that you don’t have today?
  5. What are your turnover stats? Are they voluntary and involuntary? Do you have involuntary attrition targets?

Company Leadership

  1. Do you do succession planning here? If so, what does it look like? If not, why?
  2. How well does the executive team debate? Can you give me some examples?
  3. How would you measure the level of trust in this organization compared to other places you have worked?
  4. Do you think there is a strong degree of trust between leadership and frontline employees? Please explain your answer.
  5. Where and/or from whom do you receive coaching and mentorship to help you improve your performance?
  6. Most of us want to improve in some areas of our performance. Is there any area that you are working on?

Compensation & Benefits

  1. What is the compensation philosophy of the company?
    – How is it working?
    – How has it evolved or changed over time?
  2. How do you think the total rewards package here compares to your competitors for talent?

Additional Questions

  1. IF you could do over any organization decisions the past year what would they be and why?
  2. A year from now, what’s going to make you say “I’m so glad we hired you?”
    – In 6-9 months, if things aren’t working out with me in this role, what do you think the reasons will be as to why it didn’t work out?
  3. Do you have any pending litigation from current or former employees that I should be aware of?
  4. (If this position is replacing someone.) What did the person who used to have this role do well? What could they have done better?
  5. What administrative department in the company do you consider is performing the best: IT, Finance, Legal, HR, or Facilities?
    – How many of the executive staff members have worked and lived outside of the US (or another region if you are based outside the US) for an extended period?  Who are they and where did they work/live?

Share HR West 2018 Details! > HR in the most innovative place on earth! #HRWest18
Posted in HR BLOG and tagged , , .

One Comment

  1. Great set of question line up. I would add more under the sun-topic of demographics and data with a question on how do you measure diversity and inclusion? Are there set targets for the organization? Also, I would add a question for Compensation and Benefita for what do they see valued, compensation, benefits, retirement, work life balance, etc.? Thank you for pulling these together—very good to get these down on paper and available for all.

Leave a Reply