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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!

Jan 22, 2020

This is an episode Jim and Jan have never done before! They are featuring a previous episode with General Stanley McChrystal because they will be interviewing the General along with author Dan Pink live on February 7th. After listening, let Jim and Jan know if you have questions you’d like them to ask Dan and Stan! 


General Stanley McChrystal shares his thoughts and insights on leadership and service in the modern era. General McChrystal is the best selling author of Team of Teams, and Co-Founder and Managing Partner of The McChrystal group. He talks with Jim and Jan about the importance of a classical education, the sacrifice leaders must make in their lives, and why it’s up to the government and business to create challenging opportunities for the younger generation. He shares his unique perspective on the similarities and differences of leading and teaming in business and in the military. He concludes with his thoughts on national service, education, and his recipe for more constructive discourse.


Key Takeaways

[1:20] There’s going to be some exciting live content with General Stanley McChrystal and Dan Pink this February 7th! Do not miss it!

[2:55] Jim and Jan offer their thoughts and insights after listening to this episode for the second time.

[6:15] Regarding millennials, the talent is there! What’s different is that our community bonds have grown smaller and are more self-focused, making it difficult to find a clear path of how and where to make a contribution.

[7:40] Although we are in a time where much service is needed from young people, only 30% of younger people in the United States are qualified and eligible to enlist in the military.  General McChrystal poses the thought of government and business sharing the responsibility to create opportunities for the other 70% of those that still have a desire to contribute.

[8:40] The Civilian Conservation Corps of the Depression Era was a program created to give young men the opportunity to make money, earn confidence, and get a sense of self-satisfaction. Many of those men went on to serve in World War II.

[9:25] General McChrystal feels it is his generation’s responsibility to create opportunities for youth through funding, education, and business. At the McChrystal group, they value service and community involvement. If you have completed a year of national service, your resume gets a more detailed review.

[10:50] General McChrystal discussed how we must create an incentive for businesses to hire employees based on their potential and values — rather than just looking for professionals who already have the skills and need little training.

[12:50] In addition to General McChrystal’s famous ascetic lifestyle, he is still learning, growing, and studying every day.

[13:10] People skills and a strong work ethic as two of the benchmark qualities that make for a good business leader.

[14:45] General McChrystal had preconceived notions of the business world, while his colleagues had assumptions about working with someone from the military. They both found out that in each world there are opportunities and challenges not so different.

[15:45] His newest book due this fall 2018, Leaders: Myth and Reality, is inspired by Plutarch’s life and studies of notable people. They took the findings of this work and crafted it into modern-day profiles to compare leaders throughout history from all walks of life, and learn the nuances of different leadership styles.

[17:50] In pairing founders and leaders, General McChrystal finds it isn’t a one-size-fits-all approach to success and fulfillment. He did find the common threads to be a commitment to the choice to lead and accept responsibility in an authentic and self-assured manner.

[21:20] Possessing an absolute commitment and dedication to the cause comes at a cost.

[23:50] Classical and liberal arts education that roots us in philosophy provides a common language that connects us both with our values and to each other.

[24:30] James Stockdale, United States Navy vice admiral and prisoner of war for over seven years, was a strong proponent of a classical education as a way to connect us to ourselves and each other.

[27:25] As politics pervade our culture, and the absence of civility rises, it is crucial to listen more and welcome different points of view.

[28:30] We could benefit from thinking more long term and focus on building sustainable relationships that remain solid in the future. In a business world, that means treating your clients in a manner where long-term relationships are fostered.

[33:00] People think demonstrations of courage are usually reserved for the battlefield, but it is beneficial to recognize it in the workplace, as well.

[34:00] General McChrystal is a great believer in experiential leadership for individuals and groups. At The McChrystal Group, they offer adventures for the team to succeed, become familiar, and push one another.

[36:50] The military uses its advantages of patriotism and extra time for training to shape them into leaders. On the battlefield, you need to make life or death decisions, where in business, there are laws and bureaucracies and it’s harder for people to be decisive. Oftentimes, businesses will skimp on or cancel their leadership development programs due to a lack of budget or manpower.

[41:00] In an organization with timid leadership, they will see the problem and take a conservative approach while rationalizing to do very little, or not enough. Making strong decisions is like a muscle you must continue to work.

[42:50] General McChrystal names the two biggest current security challenges we are facing in today’s climate:

  1. Education lagging behind the progress of the rest of the world.
  2. Inability to make rational political decisions.

[49:00] As General McChrystal has a strong relationship with his grandchildren, he believes in balancing work with getting outside for adventure, continued education, and family.


Quotable Quotes

  • We’ve got to create opportunities where people can do the kinds of service that gives them a sense of satisfaction and a challenge.
  • Begin rewarding service in your home, school, and community.
  • When you enter the military, nobody is already a soldier, airman, or marine.
  • College doesn’t prepare you for what you are going to do, it prepares you to be prepared for what you are going to do.
  • Everything is simple, but the simplest is difficult.
  • Leadership is this complex weave of factors.
  • Possessing an absolute commitment and dedication to the cause comes at a cost.
  • Classical and liberal arts education that roots us in philosophy provides a common language that connects us both with our values; and to each other.
  • It’s a willingness to sacrifice for the cause when they decide to lead.
  • Strong leaders are themselves.
  • Learn to think long-term.
  • There’s got to be some long-term consequences for dishonesty.
  • Do everything today to protect what you can do in the future.
  • If you do something challenging with strangers, you rarely end up as strangers.
  • It takes courage to make great decisions.
  • When things get hard, it’s a time to show courage.
  • Don’t promise to do more than you are willing to do.
  • Leaders make decisions that others are reluctant to make.


Resources Mentioned


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