Guest Post by Barry Rush

Are you having fun with questions?

In the last eighteen months, I have thoroughly enjoyed engaging spontaneously with managers of restaurants when I am having a nice meal.  Once in a while I spot managers and ask them to help me out with a project I have been working on.  Then I ask,

“What would you say is your greatest challenge as a manager?”

Sometimes they are too busy to stay, so I tell them to think about my question and come back by our table.  At other times we have a three-minute conversation right then.

Last week my wife, a friend and I were at Outback Steakhouse and the manager, a young lady, was helping me with replacing a “tough” steak.  She was super helpful and patient.  She brought me a new steak that was absolutely juicy and perfect … and she made it complimentary since I had to wait.  As usual, I asked her what her greatest challenge was as a manager. The timing was perfect.  She had been a manager for only two days!  She said her greatest test was in being courageous in asking her workers to do things that needed to be done or correcting them to improve their work.  When she interviewed for the job, she told the hiring supervisor that this issue would be the greatest challenge. She talked us through her journey for about 20 minutes!

That conversation has been one of my greatest “aha’s” in this journey of talking with about fifteen managers.  Some of them actually sit down and talk with my wife and me about what is going on in their life and work.  The Outback manager told us that her husband is amazed at her challenge!  He said, “You don’t mind telling me what to do around here!”  She laughed as she shared this!

Another manager of a restaurant near our home, answered very passionately, “I am an introvert.  But every hour tonight until closing, I have to extrovert, extrovert, extrovert!  That is my greatest challenge!”

So what is the number one answer I have heard?   Drum roll please!  It is … “people”.  I consistently heard, “My greatest challenge is my people… helping them increase their effectiveness.”

For example, a Panera manager (with a young employee standing beside him) explained, “These young employees are very digital in their focus.  So when a customer walks up they make initial eye contact while saying, “May I help you?”, but then immediately fix their eyes down on the screen in front of them, instead of keeping eye contact.”  He said, “This seems simple but it is a difficult habit to correct!”

One of the things I am learning in this process is that when I engage with managers about their greatest challenge, it is often a unique and meaningful experience for them.  No one that day will be asking them how they are doing!  In some conversations we have the opportunity to show understanding and empathy for the challenges they face and communicate genuine care.

Most managers are giving a lot of energy “to others” and no one is bringing energy “to them.”  In several cases I came away feeling that, wow! this was actually an opportunity to appreciate this person’s leadership and encourage them in all they are doing as a manager.

So use this question when you meet managers (I know you eat out occasionally) and enjoy what happens!

“What would you say is your greatest challenge as a manager?”

And of course in the spirit of leading with questions always ask “the next question” … “Can you tell me more about that?”

Meeting and asking managers this one question “What would you say is your greatest challenge as a manager?” has helped me connect with those I would not normally connect with and it has helped me learn about leadership and management challenges in a fun and relational context.

And to top it all, I actually got two free meals from Tim at TJ’s Seafood as we both wanted to continue our conversation … oh, and it is really awesome seafood!

If you get some intriguing responses please email me:   Have fun!

Note from Bob:  Good News – Barry’s great question will actually help you connect with any manager in any industry!  All you have to do is to ask, “What would you say is your greatest challenge as a manager?” 


Barry Rush helped design the first EQ Workshop in 2003.  In 1998, he joined the Global Leadership Development Team and provided leadership development experiences and seminars for young leaders in Europe, North Africa, the Middle East, Central Asia, and in the U.S.  Over the last 10 years he has been a guest speaker for the Leadership Course at Palm Beach Atlantic University, Orlando.

He has led EQ workshops in Zurich, Bucharest, Moscow, Belgrade, Budapest, Almaty, Varna, Bulgaria and Amman, Jordan andAlexandria, Egypt (Sept 2012).

He graduated with a B. S. in Pre-Medicine and is a certified CRM (Creative Results Management) coach. He has certifications in the Hay Group Emotional Social Competencies Inventory, the MHS EQ-i Assessment, Core Clarity Strengths Finder and the TAI Pro-D Assessment. Barry lives in Orlando, Florida.



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