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The Leadership Podcast

The Leadership Podcast

Why do we do this?

We interview great leaders, review the books they read, and speak with highly influential authors who study them.

How we do this?

#1 We interview great leaders.
#2 We review the books great leaders read and write.
#3 We have fun!

Oct 2, 2019

Brigadier General Cindy R. Jebb, 14th Dean of the Academic Board at U.S. Military Academy, West Point, joins the show this week. Cindy is the first woman to hold the prestigious position, and she graduated from the Military Academy in 1982. She has served at the National Security Agency, and has authored and co-authored three books. Cindy provides a masterclass in leadership this week, including what can and cannot be taught, the importance of character, and the need for trust. Cindy also talks about what it is like to be the first female Dean at West Point, and the five characteristics of leadership that have been critical to her success. 


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The Leadership Podcast is proud to announce a new initiative with thoughtLEADERS to provide very short podcasts called “chalk talks.” They’re “bitesize” hacks on common (but challenging) leadership issues. 


You can only access the Chalk Talks by subscribing to our mailing list at The Leadership Podcast


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Key Takeaways 

[3:46] BG Jebb is extremely grateful for the people she gets to serve with, and acknowledges them as a huge part of her personal success. 

[4:18] West Point is known for developing leaders through the four prong approach of: 

  1. Character
  2. Academics
  3. Military
  4. Athletics

Cindy has found that character is the most important of these prongs because it involves people counting on your word, your everyday habits, and the ability to demonstrate excellence. 

[7:09] Cindy is the first female Dean at West Point. Not only is this a huge step for women, but Cindy also has extra pressure in her role because of the Presidential appointment. 

[10:23] At West Point, despite the high demands and expectations, it is all about everyone supporting the mission and continuing to breed a mutual trust between society and the military. 

[18:10] Charisma is hard to teach, but learning presence and positive energy can be developed. Experiential learning also provides great experiences and resources for character building, but is something that can be worked on and shaped throughout someone’s lifetime. 

[25:24] Real development occurs outside our comfort zone. This is where we learn about ourselves and our limits and develop confidence. 

[29:42] Cindy and her team at West Point are aware that future leaders need time to reflect, think deeply and develop who they really are. 

[34:25] Five characteristics of leadership Cindy has found helpful: 

  1. Subtle discipline. Doing routine things routinely.
  2. Invest in your field and write/talk/read about it. Become an expert. 
  3. Have humility and understand that you don’t always have all the answers. 
  4. Embrace the struggle. Don’t shy away from performing outside comfort zone. Don’t be afraid to make mistakes.
  5. Cultivate relationship. Acknowledge vulnerability and develop empathy for fellow humans. 


Strategic Partner


Beyond the Uniform offers over 300 free episodes to help military Veterans succeed in their civilian career. This includes overviews of potential career paths, deep dives on necessary skills to succeed, and reviews of other free services that support the military Veteran community. You can find more info at


Quotable Quotes 

  • “We look at making sure that we are developing leaders of character that are going to live honorably, lead honorably, and demonstrate excellence.” 
  • “Humble minds are open minds.” 
  • “Investing in others is also an investment in yourself.” 
  • “Substance wins the argument.”
  • “Mastery requires and facilitates preparedness.” 


West Point 

Brigadier General Cindy R. Jebb 


Ep #051: Leadership is Hard Because Character is Hard 

Ep #095: Leadership Requires Solitude 

American University article - president protected from adversity 


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