Strategic Improvisation: Lessons in Leadership from the Grateful Dead

Years ago I had a friend tell me a story that has obviously stuck for one reason or another. He was working a summer job at RFK Stadium in Washington, DC as a local roadie. In essence, he and his crew set up and tore down the stage for a series of large concerts. One such concert featured a well-known band (that will remain nameless) and the Grateful Dead. Now, as I understood it, the local crew set everything up to specification the day before the concert and then notified the bands who showed up separately (at designated times) to conduct sound checks.

In my friend’s story, the “Nameless Band” showed up first. The gates opened and a series of stretch limousines rolled through. The band was escorted out of their limos and on to the stage. They walked by the local roadies, took the stage, grabbed their instruments, played a few notes, sang a few bars, retreated to their limos and exited. The total time lapse was somewhere in the neighborhood of 15 minutes.

Sometime later the Grateful Dead showed up. The gates opened and three or four recreational vehicles (RVs) appeared on the horizon. I distinctly remember my friend’s description of the RVs: “anything but nice.” A door opened and Jerry Garcia literally stumbled out of the lead vehicle. His parents (not a misprint), girlfriend, kids, other band members, etc. also made their way onto the field.

When he got his bearings, Jerry Garcia approached my friend with a question, “Do you think it would be cool if we played a little Frisbee football?” My friend (at this point the self-appointed “lead representative” of The RFK Stadium Executive Management Team) replied by saying, “Sure.” Then, Mr. Garcia came out of nowhere with a follow-up question, “You guys want to join in?” Since my friend was on a roll, he stayed “in-character” and responded almost immediately, “SURE!” Then my friend, five or six other RFK roadies and a couple of security guys joined the Grateful Dead crew for a two-hour “Frisbee Football Fest” they would never forget.

When it was time to go (in all likelihood because it was getting dark and nobody knew how to turn on the stadium lights) the band took pictures with everybody, said goodbye and fired the RVs back up. No one associated with the band even looked at (let alone approached) the stage. The next night, both bands delivered killer concerts that were ridiculously well received.

I thought about that story as I made my way through a book I came across recently, “Everything I Know About Business I Learned From the Grateful Dead,” by Dr. Barry Barnes

The first chapter is entitled “Mastering Strategic Improvisation.” The essence of the message highlights the benefits associated with “staying in the moment.” Every business (not unlike every band taking the stage) needs a plan. The problem becomes the shelf life of the plan, in the context of the pace of change, in combination with the emerging circumstances not addressed in the plan. For example, the Grateful Dead never had a pre-determined playlist for any of their performances. Their plan consisted of the fact that they were a band, cash paying customers were going to show up to hear them and they were going to play songs they had written. Everything else was going to be an in-the-moment decision that reflected “the vibe” of the band, the audience and that particular evening.

The risks associated with this sort of approach to leadership (and life) are self-evident, but the benefits are undeniable. It is so tempting to “get out of the limo, do your sound check and move on.” It’s another thing altogether to play a little Frisbee football and create a cadre of lifelong fans.



  1. Read Dr. Barnes’s book.
  2. Reflect on the amount of time you spend as a leader executing a pre-determined plan versus responding in a genuine manner to the nuances of the moment: