Dead50ChicagoI spent four, kick-ass days in Chicago over the 4th of July weekend for the Fare Thee Well Grateful Dead shows, the last 3 shows the Dead will ever play. It was incredible. Seventy-five thousand people at Soldier Field, and another twenty-five thousand around the field who couldn’t get tickets but came for the community and the experience. (The show broke the Ticketmaster internet sales record. All three Chicago shows sold out in minutes, and according to Marketwatch, they grossed 55 million dollars in one weekend) The shows were mind blowing, and it was the best people watching experience you could imagine! I couldn’t help but be impressed by the legacy of the Grateful Dead, and I learned some great leadership lessons along the way.

“Great leaders know that the best ideas can come
from the most unexpected places.”

So what can you learn about leadership from one of the most influential bands in history? Here is what I was able to learn from speaking with so many of the great people I met over the weekend.

  1. Don’t lose site of the goal

    The goal of the Grateful Dead was to provide a high quality experience with high quality music. They wanted to play great music for people who were really into music. There were choices they could have made along the way that, while more profitable, would have meant abandoning their true goal. Great leaders are clear on what they want to accomplish, and they make deliberate choices based on that vision. All the other stereotypes you typically read/hear about are just that, stereotypes. The band was always about making great music for those that were willing to go on the journey with them.

  2. Leadership is Subtle

    The Dead built an entire community and cultural phenomenon slowly, over time. They didn’t wake up one day and have millions of people enamored with them, but it happened nonetheless. They were never in your face. They did what they loved, and their passion spilled over to others. Great leaders don’t announce, “I’m here! Follow me!” They build a loyal following over time. They stay true to their vision, and adapt or adjust when necessary.

  3. Lead Like Nobody’s WatchingFareTheeWell (Day 3) 6419

    Each time the Dead played, there were tens of thousands of people dancing. No one cared if it was good dancing! It’s about self-expression and having an experience. Some have even compared it to being at church and having a spiritual experience. Had I not experienced it myself, I wouldn’t believe it. There were concert goers spanning generations, and everyone felt free to be themselves. Leadership requires courage, and also letting go of some fear. Sure, it’s easy to play it safe, but great leaders are bold and brave. They dismiss the naysayers and focus on the strengths of their followers.

  4. Be Inclusive

    I would have thought that all Dead concert goers were hippies; until I went to the shows. I’ve been blown away to find doctors, lawyers, celebrities, and yes, hippies. You didn’t know if the person sitting next to you was a millionaire or a pauper and it just didn’t matter. I met some incredibly intelligent and really cool people. If you believed in their music, you were welcomed with open arms. Great leaders know that the best ideas can come from the most unexpected places. They are humble and treat others with respect.

  5. Leadership is about the Followers

    The Dead wouldn’t have grown to experience the success they had without followers. They stayed true to their desire for great music with an audience that was willing to take a journey with them to find it. When Jerry Garcia was asked if he still got nervous in front of audiences, he said “Of course I do. You can’t count on an audience loving you. It’s a bad idea to take a crowd of 30,000-40,000 people for granted”.  The interviewer followed up with “It just seems like the their ready, they’ve accepted you”. Garcia’s quick response? “I think that’s a convenient illusion”.  Ha!  Great leaders don’t make it about themselves, and they don’t take their followers for granted. They treat their followers as equals. While there will no longer be Grateful Dead shows, their legacy of building an entire culture will remain forever. They became what they were because they led like nobody was watching. They were true to themselves, their music, and most of all, their fans.


  1. Great takeaways from the Dead Concert. Thank you Anne. Just heard you speak today at Foodmaxx in Northern Ca. EXECELLENT job and connection with our team. Charla Giles

Leave a Reply

Your email address will not be published. Required fields are marked *

Post comment