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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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We unpack transactional leadership—why it feels natural, where it works, and when it fails—and show how to pair it with relational styles so people and performance both thrive. Clear goals help, but autonomy, mastery, and purpose keep teams engaged and growing.
• definition of transactional leadership and its roots in school rewards
• where transactional systems fit: scale, sustaining growth, clear metrics
• strengths: clarity, consistency, fast runway for new hires
• weaknesses: micromanagement, pressure, shallow incentives
• autonomy, mastery, purpose as durable motivators
• pairing transactional with servant, transformational, and democratic styles
• co‑creating goals versus top‑down mandates
• producer‑to‑leader shift and ambition with boundaries
• organization‑first vs team‑first bias and how to balance
• whole‑self leadership and avoiding the pizza‑party trap
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Chapters
1. Setting The Stage: Freedom & Flow (00:00:00)
2. From To‑Do Lists To Leadership Pivots (00:01:42)
3. Defining Transactional Leadership (00:02:50)
4. School Rewards And Early Conditioning (00:05:40)
5. Where Transactional Fits In Organizations (00:09:05)
6. Systems, Scale, And Clear Expectations (00:12:40)
7. When Incentives Miss Motivation (00:15:45)
8. Autonomy, Mastery, Purpose Over Money (00:18:05)
9. Pairing Styles: Transactional Plus Relational (00:21:10)
10. Goals You Co‑Create Versus Mandates (00:25:05)
11. New Hires, Runways, And Micromanagement (00:28:10)
12. Selling Cars And Measuring What Matters (00:31:20)
13. Ambition, Boundaries, And Mentors (00:34:00)
14. Promoted Producer To People Leader (00:37:20)
15. Know Your Bias: Org Or Team First (00:41:10)
16. Avoiding The Pizza‑Party Trap (00:44:00)
17. Career Fit And Leadership Identity (00:46:40)
18. Whole Self Leadership, Not Silos (00:49:40)
19. Series Wrap And Community CTA (00:53:00)
175 episodes
