I want to take you back to a time when I was a young manager. A time when I thought interviewing was about being as challenging as I could be in an interview based on the questions I asked.

My first and earliest interviews weren’t really focused on expanding the conversation and getting to know the person applying for a job; they were focused on seeing whether a candidate could outlast the rapid-fire sequence of questions that I would pose.

How confused and misguided I was. The idea of asking questions was a good one, but my approach and interviewing style had a greater tendency to shut people off rather than getting them to open-up and allow me to learn more about them.

Thankfully, John, a leader I respected invested the time to sit in on several of my early interviews and offered this simple, yet profound, guidance. “The objective of an interview is to create an exchange in which the person being interviewed shares information that allows you to get to know them and how they think. In return, you share information that allows them to get to know you and how you think. They get to understand the leadership philosophy and culture of the company. You both get the opportunity to determine if there’s a fit.”

After three decades, hundreds upon hundreds of interviews and 20 years of advising family-owned and privately-held businesses, I have come to understand and appreciate this important thought:

The questions you should really ask in an interview are the ones that allow you to get to know the person you’re talking with and reveal their thought process. The key word here is person. An individual. Someone worth learning about and understanding. Determining mutually if the role, culture and mindset are a good fit that will bring success and allow them to maximize their capacity.

I’m an intense person. I live by the mantra that if you’re going to do something then do it well. Truth is that I don’t value mediocrity in anything and mediocrity tends to not enjoy spending time with me. My intensity, sometimes drill sergeant like in my earliest of interviews, could be seen as alienating the person being interviewed, rather than understanding them. What John taught me as a young manager was the importance of balance and understanding. Balance between my interviewing intent, approach and desired outcome. Between talking and listening. The ability to share thoughts in order to get thoughts. The understanding of what you may ask and what you aren’t  allowed to ask.

In the world of family-owned and/or privately-held business, every hire makes a difference. Why? Because typically, the size of the company or number of team members doesn’t allow for someone not to be a fully-engaged and contributive member of the team. The quality of the question impacts the quality of the answer. Poorly developed questions provide the potential for equally poor answers. That exchange provides for really poor understanding and connection. That’s a direct pipeline for poor choices on many fronts.

If you want to get to know the person you’re talking with in an interview, here are three types of questions you should really consider asking:

1.         Thinking and reasoning questions. In this sequence you want to know how thoughts are formed, decisions will be made, or leadership will be lived out. “Define a time when you had to…”, “When confronting a complex problem, how do you…”, “When learning something new, what are your first steps to…”

2.         Scenario based questions. In this sequence, you’re representing scenarios that are typically faced in the work environment and your objective is to understand how the person being interviewed would handle or respond to those situations. “How would you handle…”, “What would you do…” and “Walk me through your leadership mindset regarding…” are all phrases that expand the conversation in an interview.

3.         Individual understanding questions. In this sequence, you’re getting to know the person at a more one-to-one level. “Tell me about a time in your life when…”, What is the most important thing you learned from…”, “Who has had the greatest impact on…”

There is one important #Thoughtstarter for you to consider asking after each of the above question types have been answered. It is perhaps the most important question you should really ask and yet the simplest way to expand your awareness and understanding of a person you’re interviewing for a position in your company.

Could you tell me why? Made even simpler… Why?

Why? Because the understanding of a person being interviewed begins with an understanding between you and the person being interviewed.

Until Next Time,


P.S. What is your favorite question to ask in an interview?… Why? I’d love to hear from you in the comments!

NOTE: Each of these types of questions are open-ended and designed to bring understanding in a way that is consistently asked and equally appropriate to everyone being interviewed. If there’s ever a question as to whether a question is legal, or able to be asked, make sure you get with the person responsible for human resources within your company and clarify the question before it’s asked of the person being interviewed. There are clearly acceptable and unacceptable questions and approaches in an interview.