Leadership and Main

Bettering Others and the World You Live In

Wrestling With Questions

wrestling with questions

Wrestling with questions is a productive use of time for a leader.  Questions lead us in the direction of answers.  Towards a better place to make good decisions.  


Several of the last few blog posts have been anchored in the sport of wrestling.  As my son Grant wrapped up his freshman season, it created a lot of connections between the sport and leadership.  While wrestling is in the title this week, this one has nothing to do with the sport.

Women’s Leadership Summit

I had the unique experience this week to speak at the Georgia Recreation and Parks Association’s Women’s Leadership Summit in Kennesaw, Georgia.    

Two years ago, we hosted the event in Acworth.  The morning of that event, I dropped in to check in on the team.  They had just received word that one of their breakout session speakers couldn’t make it.  I volunteered to fill in with a leadership talk that I have given many times.

Since it was last minute, I didn’t feel the need to modify the presentation much.  The talk was what it was.  It apparently connected enough to get me an invite back to talk to the entire group this time.  I was honored.

When you speak to such a specific demographic, one that you do not belong to, it can be challenging to craft an effective message.  Honestly, it can be downright intimidating. 

The ability to connect with the audience is heavily dependent on quickly creating credibility (trust) and getting them to wrestle with themselves through questions.  I wanted to share two quick thoughts on how I attempted to do both:

Quickly Building Credibility

There were a few strategies that I employed to create a quick connection. 

First, I got there early, grabbed a cup of coffee and walked the room.  I visited tables, asked people their name, where they were from, and what their biggest takeaways from the conference were.  While I wish I could take credit for this strategy, I learned it by watching Dr. Tim Elmore

at a conference I attended one time.  I observed him working the room before his talk.  Each person talked to in advance of the presentation accelerates the connection.

Second, I built “Street Cred.” Yes, those were the words that I used!  I shared that my qualifications to speak at a women’s conference were grounded in being the son of Kathy, the husband to Shannon, and the father to Ashtyn.  I cited many examples as to why this made me qualified!   

Last, but not least.  I spent time talking about three women leaders in our organization that have had a significant impact on my leadership journey.  I celebrated their achievement as women, but ultimately shared with the group that those accomplishments as women had very little to do with why they were in the positions they were in.  I walked through defining characteristics of what made each one special and unique to me and our organization. 

Wrestling with Questions     

I wrestled with the question for weeks that I would have them wrestle with.  In full transparency to the audience, I told them I didn’t have an answer to it.  The answers to the two questions that I would ultimately ask them would rest within themselves.  THEY would have to wrestle with the answer.

Here was the question I asked them to wrestle with, “Are you a woman who is a leader or are you a leader who happens to be a woman?”  In fact, I asked it twice.  Once at the beginning and once at the end.  Never did I answer the question for them.

While it may not be what they paid for, hopefully each of them found their own, unique way to answer it.  An answer that would be found in deep self-reflection.  One that will be beneficial for their leadership journey.    


When you wrestle with questions, you wrestle with yourself.  There is an internal tension that is productive.  The process leaves the recipient of the message seeking the answer.  One that will get them where they need to be, on their own.

Towards the end, I left the answer in their court.  I confessed that I could not fully fathom what it is like to be in a leadership role as a woman.  Only they have experienced the challenges related to being in that position.  Therefore, they were best suited to take the content of the presentation and apply it to their worlds. 

I did leave them with some encouragement.  That each woman present had unique gifts to contribute to their organizations.  And however they answered the question, whatever their strategy was in leadership, they had the capability to achieve anything. 

When we wrestle with questions, we grow as leaders.  Win the match!    



Grateful for you taking the time to read this post!  Like what you read?  Share this post with your friends and followers with the icons provided below.  Are you interested in joining us on this leadership journey and having these posts delivered to your inbox weekly?  Subscribe here.  Would love for you to connect with us on social media via Facebook, Twitter, Instagram, and LinkedIn.

Share this post