Front Office

Industry Insights

Winston Churchill, Bill Belichick, and Leadership Now

By Jamie Hancock
April 1, 2020
4 min

What we can learn about leadership from Michael Lombardi—NFL analyst, co-host of the GM Shuffle Podcast, and founder of The Daily Coach.


A message from LeagueApps President and Co-Founder, Jeremy Goldberg:


This week, I’ve invited Michael Lombardi to join our NextUp Town Hall on leadership. Along with two-time NBA champion Shane Battier and a group of leading sports organizers, we’ll be discussing what it takes to motivate and inspire during times of crisis. In advance of the event, we sat down to discuss his unique leadership strategies—honed over the years while working alongside iconic figures like Bill Belichick—and identify a few actionable takeaways for youth and local sports organizers.


One of our core values at LeagueApps is being a “Student of the Game”—celebrating the opportunities to learn from our successes and failures, and from everyone and everything. For me, this means spending time developing myself as a leader: drawing lessons from those who inspire me in the world of business and politics, and observing them in action. 


I find it particularly helpful to think about leadership through the context of sport. (If you’re a winning team, it’s likely connected to your leadership.) This is why we’ve developed a ritual of studying different champions at our bi-annual company offsite (we call them OTAs); most recently, we dove into FC Barcelona and their approach of “Mas Que un Club.” It’s also why I’ve become a “devotee” of the popular NFL Analyst Michael Lombardi, whom I first discovered as a recurring guest on Bill Simmons’ B.S. Podcast, and now follow through his own show, The GM Shuffle, and the daily newsletter he co-authors with George Raveling, The Daily Coach. I have also turned many times to his book Gridiron Genius, a lesson in leadership informed by the years he spent with legends like Bill Walsh, Bill Belichick, and Al Davis.


Lombardi has developed his theories on leadership and organizational culture from his unique experience working with coaching legends. To be sure, I’ve appreciated his prognostication skills (unfortunately for this Dallas fan, he’s been way too right about the performance of the Cowboys). But his ability to articulate why teams are winning or losing is what I appreciate the most—and it translates into how I think about building and leading a winning organization. 


Throughout the past couple of weeks, as the COVID-19 crisis continues to turn our world upside down, I have found myself reflecting on the lessons I’ve drawn from Lombardi and from sports more broadly. As I thought about the challenges that we’re facing at LeagueApps and that business everywhere are confronting, I knew I wanted to sit down with him for a discussion about leading during times of uncertainty and crisis. 


Below, you’ll find a few pieces of guidance and inspiration pulled from our conversation. For more, don’t miss our upcoming event this Thursday, April 2nd at 1 PM EST.  


In reflecting how great leaders like Belichick would approach leading an organization during unprecedented times like this, Lombardi offered three powerful ideas:


1.) Understand How to Create Hope


The current situation may feel overwhelming to your employees and to your customers. The idea of spending weeks more sheltering-in-place, with health and economic risks pervasive, is a recipe for paralysis. Lombardi referenced a recent piece he did on Winston Churchill’s leadership, offering this formula for how you create hope in difficult circumstances:


  • Lead with integrity
  • Be accountable
  • Convey empathy
  • Be practical under pressure


What Lombardi has seen is that the best coaches, and leaders, don’t just espouse hope: they create it through their actions.  


2.) See the Non-Obvious


Lombardi warned against the law of triviality, or getting caught up in things that don’t matter.  Rather, he said great leaders step back, recognize the biases and assumptions of the status quo, and look to understand what’s truly urgent and important. (I sometimes use a framework called the Eisenhower Box to spotlight those insights).


He shared the story of Belichick not calling a timeout in the Super Bowl as the final seconds ticked down with the Seahawks on the goal line threatening to score against the Patriots.  The obvious move was to call a timeout and set the defense. Belichick made the non-obvious decision to let the clock tick down and put the pressure back on the offense. His defensive back Malcolm Butler proceeded to knock down the pass to secure a Patriots victory.


3.) Self-Scout 


Use this time to self-scout—reflect on yourself as a leader and on your organization as a whole. What feedback can you solicit from your employees, coaches, parents, and players that can help you improve? 


[There’s a great leadership book by Marshall Goldsmith called What Got You Here Won’t Get You There that describes a process called feedforward, instead of feedback. Ask people for 1-2 things moving forward that you can do to be a better leader]. 


Lombardi also suggested that while things are ever changing, it’s important to reflect on the things that will stay the same in the next five years. Then, “work the hell out of being great” at the areas that leverage that sameness. 


While Lombardi and I may not agree on the Cowboys’ fortunes, we did align on the important role that sports will play in helping our country recover from this pandemic. As he observed, “the world now knows what it’s missing without sports. It’s going to come back and be appreciated like never before.”


With the right leadership in the youth and local sports industry, that’s not a hopeful wish—it’s an inevitability.


*This blog was first published on my LinkedIn.