Lessons from the Sidelines with Tom Crean features great coaches across the sports landscape sharing their insights and experiences with the goal of inspiring those rising up the ranks of coaching. Upcoming guests include Baltimore Ravens Head Coach John Harbaugh, Los Angeles Chargers Head Coach Jim Harbaugh, longtime coach and Harbaugh patriarch Jack Harbaugh, former Green Bay Packers and Dallas Cowboys Head Coach Mike McCarthy and legendary basketball coach and Dallas Mavericks advisor Tim Grgurich.
Bobby Marks Sits Down with Tom Crean on NBA Roster Building, Draft Evaluation, and the Business of Basketball
In Episode 12 of Lessons from the Sidelines, Bobby Marks joins Tom Crean to break down how NBA teams are built through the draft, trades, and salary cap management. He shares insights from his time with the New Jersey Nets and ESPN, along with how elite organizations like Oklahoma City and San Antonio sustain success. The conversation also dives into player evaluation, focusing on intangibles like competitiveness, coachability, and response to adversity, plus stories from evaluating prospects like Kobe Bryant and AJ Dybantsa.
28 May 2026
Ben Herbert Sits Down with Tom Crean on Leadership, Accountability, and Building Elite Competitors
In Episode 11 of Lessons from the Sidelines, Tom Crean sits down with renowned strength and conditioning coach Ben Herbert to discuss leadership, discipline, accountability, and building championship-level culture. From his journey through Wisconsin and Michigan to helping shape the culture of the Los Angeles Chargers alongside Jim Harbaugh, Herbert shares lessons on trust, consistency, mental toughness, and getting the absolute best out of athletes. The conversation dives into player development, handling uncomfortable situations, creating buy-in, and why true growth comes from repeatedly doing the hard things at an elite level.
6 May 2026
Chris Caputo sits down with Tom Crean to talk NIL, Team Culture, and Building a Modern Program
In our tenth episode, Tom Crean sits down with George Washington Head Coach Chris Caputo to discuss NIL, the transfer portal, roster building, and the evolving landscape of college basketball. From managing locker room dynamics and player expectations to the importance of “friend-raising,” leadership, and community building, this episode explores what it takes to run a program in today’s game. Caputo also shares insights on player development, navigating team success, and why playing your best basketball late in the season is the ultimate separator.
27 Feb 2026
Nick Hostetler sits down with Tom Crean to discuss Scouting, Leadership, and the Art of Evaluation
In our ninth episode, Tom Crean sits down with Chicago White Sox Assistant General Manager Nick Hostetler to discuss scouting, player evaluation, clubhouse culture, and the balance between analytics and the eye test. From social media background checks to five-tool development and leadership lessons from baseball legends, this episode dives into what it really takes to build a winning organization — on and off the field.
13 Feb 2026
New York Giants Head Coach John Harbaugh, and his father, Jack Harbaugh, sit down with Tom Crean
In our eighth episode of Lessons from the Sidelines, John Harbaugh, newly named head coach of the New York Giants, joins his father, Jack Harbaugh, and Tom Crean to discuss John’s transition to New York, building a new staff, and his approach to leadership and quarterback development. They reflect on character, servant leadership, and balancing elite coaching with a strong commitment to family, emphasizing that great coaching starts with putting people first.
7 Jan 2026
Chris Hollender and Tom Crean Discuss Coaching, Analytics, and Finding an Edge
In our seventh episode, Tom Crean sits down with longtime college coach and Just Play Sports Solutions leader Chris Hollender to discuss coaching, leadership, analytics, and how teams find advantages by focusing on the margins that matter most.
18 Dec 2025
Fran Fraschilla and Tom Crean Discuss Leadership, Coaching, and Building Trust
In our sixth episode, Tom Crean sits down with longtime basketball coach and broadcaster Fran Fraschilla to break down leadership, collaboration, and why setting and living up to a standard of excellence matters in coaching, media, and life.
10 Dec 2025
Tim Grgurich Sits Down with Tom Crean to Talk Development, Daily Habits, and Coaching Impact
In our fifth episode, Tom sits down with legendary NBA and college coach Tim Grgurich — known for shaping stars from UNLV to the NBA — to discuss fundamentals, intensity, and the real lessons every coach and leader can use.
2 Dec 2025
Jack Harbaugh Sits Down with Tom Crean to Talk Family, Football, and the Heart of Coaching
In our fourth episode, Tom sits down with Jack Harbaugh to discuss the roots of the Harbaugh coaching family, the values that shaped John and Jim, and the lessons Jack learned through decades of leading teams and developing young players.
25 Nov 2025
Mike McCarthy Sits Down with Tom Crean to Talk Coaching Details, Development, and NFL Growth
In our third episode, Tom sits down with Super Bowl–winning Head Coach Mike McCarthy to discuss coaching creativity, developing young players, navigating today’s NFL, and why emotional growth matters as much as physical training.
18 Nov 2025
Jim Harbaugh and Tom Crean Discuss Coaching Toughness, Parenting, and Championship Culture
In our second episode, Tom Crean and Jim Harbaugh dive into the foundations of championship culture, breaking down locker room dynamics, building toughness, and the role parents and coaches play in developing young athletes.
6 Nov 2025
John Harbaugh Sits Down with Tom Crean to Talk Cut Day Emotions, Youth Sports, and Leading Through Conflict
In our first episode, Tom sits down with HCA founder and Baltimore Ravens Head Coach John Harbaugh to discuss the emotions of cut day, leading your kids through youth sports, what goes into teaching players and dealing with conflict.
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