5 Critical Interview Questions to Find your Leader of People and Culture

5 Critical Interview Questions To Hire The Right Leader of People and Culture

This is a post from Max Hansen, Chief Executive Officer and co-founder of Y Scouts.

Since starting Y Scouts in 2012 we have placed, worked with, and met thousands of incredible forward thinking People Operations leaders.  We are very fortunate to continue attracting more and more each day while deepening the relationships with the leaders we have worked with in the past.  

These leaders tend to have titles such as Chief People Officer, Chief Talent Officer, Chief Human Resources Officer, VP of Employee Experience, VP of Human Resources, and Director of HR.  In smaller organizations, the titles can vary accordingly. Regardless of their title, we recognize these are the HR Leaders of the Future. Or what Y Scouts calls Leaders of People and Culture.

I was recently working with one of our clients and we were discussing the most powerful interview questions for leaders—Which led to the discussion around the most important foundational questions we should be asking Leaders of People and Culture.

During our discussion, we came to an agreement that the most successful leaders in the world are good at creating strong relationships through quality interactions. Not just sometimes, but all the time. If you’re one of those people that need empirical evidence to buy into the importance of developing relationships, please watch the Ted Talk by Robert Waldinger on what makes a good life.  

In this TED Talk. Robert Waldinger discusses a 75-year-old study on adult development.  The data from the study is clear. People and leaders that develop strong relationships live longer, happier lives. Period.  Which leads me back to the most important thing you should know about your Leader of People and Culture before you hire them— After all, this is the person making all the strategic decisions around hiring, firing, and developing others.  The success of their job lies purely on their ability to develop, maintain, and mend relationships.

5 critical interview questions to hire the right Leader of People and Culture


Tell me about your 5 closest and strongest professional relationships to date.

This question is incredibly informative as to what type of person you are interviewing and who you can expect to show up once they are hired.  Let’s be real. If someone is going to be successful leading in any role around People and Culture they must have proven experience in developing strong relationships.  And they should have no problem telling who they developed relationships with, why, and how.

*Bonus points should be given if they can actually tell you who they should have developed stronger relationships with and failed to do so.  

What made the relationship with (Choose any one of the people they named) strong?

Hiring and developing people successfully in high performing companies requires someone that has good judgment.  I’ve heard some people say it’s not our job to judge others—What I say to that is bullshit. Judging people in managing a culture of people is so incredibly important.  Especially in hiring. And in order to have good judgment about others, one must maintain the balancing act of judging themselves. Aka self-awareness!

Describe to me what a good interaction looks like with X (one of the people on their list)

Having a leader describe what they view as a good interaction is so intuitive on so many levels.  The answer to this question ultimately let’s you see how they describe good character in their strongest relationships.  They are pretty much giving you their version of what good character means to them. Is this in alignment with how you and your organization judges good character?  If so, perfect, and if not, this is not the right leader for you.

If for some reason you didn’t get what you want out of those questions.  Ask the same ones but ask them about their strongest personal relationships.  I have come to believe Leaders / People that have not developed strong relationships in their personal life will not be strong at developing relationships in your organization.

Tell me about your biggest professional accomplishment. What did you learn from it?

This question is pretty cut and dry.  If you want someone to drive a culture of performance.  This leader must be able to drive results. And most importantly talk about it in a way that is not cocky but confident.  Driving results is one of the 3 elevated behaviors of exceptional leaders in the Y Scouts Leadership model.

Tell me about your most challenging professional relationship. What did you learn from it?

Every great leader of People and Culture should be able to answer this question well.  You should be able to hear and feel the genuineness in their answer. It’s vital that you see how they have dealt with challenging people they have either led with or led for in their past.  If they can not openly talk about challenging relationships they have had in their past organizations, this potential leader is not for you. Real leaders recognize challenging relationships and typically can talk about ways they mended them.  

Don’t be surprised if someone can’t give a good answer to this question. I have interviewed plenty of really accomplished leaders that can’t pull themselves to talk directly about these challenges. This is a red flag and means at this point in their life and career they are not able to be as honest as they need to be in order to have good judgment.

Y Scouts is a purpose-aligned, performance-proven leadership search and development firm focused on transforming how people and organizations connect to work that matters. When you’re ready to hire a new leader, Contact Y Scouts. If you are looking for your next leadership role within a purpose-driven, performance-focused organization, please join the Y Scouts Leadership Community.