Who’s Your Caddy?


This summer, I spent a weekend with some college friends playing golf in Pinehurst, NC.  Pinehurst is one of the true meccas of golf in the world, and we played on some amazing golf courses.  I played more rounds in those 3 days than I had in the last 18 months and had a blast doing so.  For those of you who know me, I graduated high school in Pinehurst as well and was able to spend some time visiting my mom while there.  I also had the opportunity to watch my niece, Kit, play in a USGA Junior event and was thoroughly impressed with her composure and her ability (at 12 years old she is a much better golfer than I am).

This was the first juniors golf event I have attended and during the round, Kit’s father was her caddy (which seems like a common occurrence for parents to caddy for their kids during tournament rounds).  Through the pre-shot plan of every stroke, to helping her determine the right club or the slope of the green, to encouraging and pushing her to be better, he assisted her to finish second in this tournament.  I wished I had a caddy helping me for the three rounds I played the previous 3 days.  From a professional perspective, it also got me thinking, “Who is my caddy in the professional world”?  As leaders of others, we all should have people in our business life that we are able to run through a pre-call plan with, someone to remind us of the tools we have to be successful, and lastly, someone to encourage us to be better when we have bad days, and continue to push us on the days where nothing can go wrong.


  1. Pick the right number of people to support and guide you. Just as you don’t want to have too many caddies giving you advice during a round of golf, limit the number of people you confide in or seek advice from to 3-5.  Network with as many people as you wish, but try to limit your true “Caddy” group to 3-5 people.  And don’t be afraid to change your group from time to time.
  2. Choose people with varying strengths than yours. The best “Caddy” I ever had was our Chief Financial Officer, whose leadership style and strengths were totally different from mine.  He challenged me to think through situations from a totally different perspective then I had ever used which has allowed me to avoid some mistakes in decision making.   Surround yourself with people you can learn from.   It’s easy to interact with people who share your same way of thinking….true growth comes from getting comfortable being uncomfortable and learning from people who are different from you.
  3. Set a goal and follow up action item for every meeting you have. The most frustrating meetings and conversations are ones without purpose or without a specific direction on what needs to happen after the meeting.  Make sure to set objectives for all interactions and more importantly, make sure you are setting up what needs to take place between this meeting and the next.  This will allow you to hold yourself and others accountable to detailed action items and make sure you are improving on the process or skillset originally discussed.

As we approach the end of my second year with this blog, I appreciate all of the well wishes I have received with this project.  It is truly humbling to think that people are referring to my thoughts or ideas to help them get through challenging leadership situations or using some of these experiences to make their leadership conversations more effective.  I have been fortunate to have worked with and learned from some great people throughout my career who have challenged me to be better than I am today.  The most influential and inspiring leaders care more about impressing the people they lead versus worrying about impressing their boss.   Be confident and courageous in your leadership and challenge yourself to “always be learning”…




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