What is Most Thought Provoking Interview Question You will Ever Ask?

What is your favorite interview question? You know….the one that engages the candidate in the most thought provoking conversation.  The one that reveals the most about them and can help you assess whether they are a fit for your organization or not.  I have one that reveals a lot about a candidate and helps you connect with them almost instantly.  What is it you ask?  All will be revealed in a minute...but first...let's set the stage.... (cue the psychedelic time travel music) 

Early my career I embarked upon my first real leadership position. This meant not only managing a team of about 15-20 software engineers, working with challenging Fortune 100 clients but also interacting with senior leadership within our own organization.  I was full of passion, energy and a “take the hill” attitude.  At the time….I was sure I was destined for greatness well beyond my years, experience and capabilities.  As a result…I often found myself very “wound up” and almost frantic at times when I approached someone on the leadership team to share good news…bad news…or to ask for assistance.  Upon reflection…..many years later….it is clear to me that part of that “wound up” nature was also due to my nervousness and desire to impress them…to be accepted into the “inner circle”.  It should also come as no surprise to you…that this approach had the exact opposite effect in those critical moments.  Even though I knew I was a bit “rough around the edges”….I was certain that my high employee satisfaction ratings from my team…the high client satisfaction rating and my ability to get things done far outweighed any “overwhelming” interactions the leadership team had with me.  As is turned out…this was not the case….

That first performance review with the consulting firm….I was sure there would be many accolades for all that I and the team had accomplished. How I had grown the business faster than most…showed great passion and potential….how I was destined for promotion.  As it turned out….the majority of the review was spent talking about how I was rated low in communication skills (a competency I counted among my great strengths) due to my passionate approach in critical interactions with the leadership team.  To say that I was crushed by this feedback would be an understatement.  It caught me off guard and I was unprepared to process it.  I think I welled up a little and fought back some tears as we navigated the meeting.  How could something that was a strength of mine be so misunderstood or undervalued?  My reaction at the time….not uncommon for most I believe…was to fight it…to convince him he was wrong and how he needed to see my intent…not what others perceived of me.  As you can imagine…this was a fruitless act…and in the days to follow….I spent a disproportionate amount of time mumbling to myself and others how wrong he was and how he just needed to take the time to see things my way.  The idea that I had to change really didn’t cross my mind.

I have used this story often over the years as a defining moment in my life and career as my “Humbling Experience”   It was the first time I came to the realization…after numerous follow-up discussions with my boss…that perception is reality.  You can’t spend your whole life and career trying to convince people to see you the way YOU want them to.  Only YOU can change and adjust your behavior so their reality and perception more closely matches the YOU that you want them to see.  This takes not only great self-awareness…but a support system of “compassionate truth tellers” to help you adjust in the moment or give you feedback in critical situations when you may not be at your best.  So you can understand your triggers and what you need to adjust to continuously improve.  Many years later….I am grateful beyond words for this feedback.  It marks the beginning of my quest for continuous improvement and self-awareness…..one that is a journey…not a destination.

SO…when I ask the magic question question…

”What is your most humbling experience?”

I share a little of my own story to set the context of what I am expecting. I also ask the candidate to describe the following:

• What were the circumstances or story leading into your humbling experience?
• What were the two or three things you took away from it that you carry with you today?
• Knowing what you know now…what are the two or three things you would do differently?
• What tools have you put in place today to ensure you don’t fall into that trap again?

I am always in awe and humbled when others share their story with me. I also learn a lot about them as follows:

• How self-aware they
• How good they are at connecting the dots between their strengths/weaknesses and their impact on others
• How open they are to accepting feedback
• How authentic they will be when they face difficult situations
• How likely are they to ask for help

I have also had a few situations where the candidate has “soft balled it” and tried to give a situation where it was actually a strength that they try to mask as a weakness. I completely understand why someone would do this in an interview…after all…they have never met me before…they don’t know my intent and they want to put themselves in the best light possible.  In 9 out of 10 cases I have been able to redirect the candidate to share with me a humbling experience where they truly learned something about themselves.  In the rare cases where the candidate has not been able to come up with one or just doesn’t have one…..I pass on them for the role I am interviewing them for.  Having said that….if they are an internal candidate…I make it a point to offer up several leadership and personal development opportunities to start them down the path of self-awareness….to support them in their journey…..just like it was done for me….many years before.

So….why does this come to top of mind? I’m glad you asked!  I was travelling on business last week and had some time in Boston airport as I waited to board my flight home.  While surfing the Linkedin updates a notification popped up that I had been endorsed by someone.  To my delight and surprise it was from the boss that had given me that very difficult review many years ago.  He had endorsed me for Leadership!  With a smile on my face…I messaged him right back and said “I just had to ask if you endorsed the right person or if you are drinking?”  I went on to say – that in all seriousness meant a lot to me…more than he could know.  What it represented for me was several things….

• Feedback is a gift whether you choose to accept it is up to you
• It takes courage for someone else to care about you enough to tell you something no one else will so you can improve and grow
• It takes an investment in time for that leader to not give up on you and help you in your journey if you are willing to accept that help
• This experience is not only impactful for the mentoree but also for the mentor. When done right you both grow in the experience
• You can change the paradigm…the way others see you…but it takes personal development and investment in yourself. You CAN have others see you differently….it’s never permanent…it just takes time

SO after our exchange….I took the time to write a recommendation on Linkedin to the person who gave me the most crushing feedback of my career…with the intention to…in some small way….repay him for believing that I was worth it. A note I could never imagined writing at the time….and now knowing….I could not be the person I am today without it.

Leadership Questions of the week for YOU: “What is your favorite interview question and what do you hope to learn about others when you ask it?”  “What do you think of the humbling experience question and what it can tell you about a candidate?”  “What is YOUR humbling experience?  Take a few minutes to think about what you learned and how it impacts you today”  “Have you taken the time to reach out to the person that was a part of your humbling experience and thank them?  If you haven’t…what’s stopping you?”

Thanks for reading….and remember…YOU make a difference!

Please continue the conversation by liking…commenting or sharing this article.  Follow me at