Not every facilitation gig goes great. The kind of work I do – and this is probably true of many of you – is usually novel. It is new to the organization I’m working with and often times new to me too, because every organization’s context is different and we design to what is needed.

This means that I often find myself involved in processes that folks have never done before. Moreoften than not, if we’ve done our preparation work well and folks are well invited to the gathering, the process is fun, engaging, powerful and results in good outcomes.

And sometimes it doesn’t. Sometimes we get lost, don’t know where to start, flounder and find ourselves surprised. And at times like that I think about Tommy Flanagan.

Tommy Flanagan was one of the best jazz pianists who ever lived. His discography includes 40 solo recordings and some of the seminal jazz recordings of the 20th century: Sonny Rollins’ Saxophone Colossus, Kenny Burrell’s Swingin’, and numerous albums with Ella Fitzgerald, Coleman Hawkins, Milt Jackson, and JJ Johnson among others. Famously he appeared on John Coltrane’s 1959 album Giant Steps.

Now Giant Steps featured as its title track a now-classic tune of the same name which is diabolical in nature. Coltrane plays it very fast, and the chord progression is something that no one had ever seen before – embodying Coltrane’s radical approach to jazz harmony – with hardly any time to think between changes.

When Coltrane introduced the song to Flanagan a couple weeks before the recording session, he played it slowly so Tommy could get a sense of how the changes worked, and this left Flanagan with the impression that the tune was a ballad. Ballads are played at 60 beats per minute. When the band stepped into the studio to make the recording, Coltrane played it at nearly 300 beats per minute. Flanagan wasn’t prepared.

On the recording, you can hear Coltrane’s soaring solo of 11 choruses, before he drops and lets Flanagan comes in. Tommy Flanagan has five choruses to solo on and he starts scared and gets progressively more and more lost until by the fifth chorus he is just comping out some chords and probably thanking his stars he survived it.

His solo is perhaps the most famous example of a top jazz musician who tried something and failed. Lost, bewildered, out of ideas, but gamely getting through it.

Some days are like that. Folks loving using jazz as an example of what happens when teams of people really cook together, but they never seem to bring up Tommy Flanagan’s solo. Facilitation is like that sometimes too. You know you’re stuff, you are good at it, and then you find yourself in a context where things are not what you expected and you dry. It doesn’t mean you’re not good at your job. But, Coltrane’s recording of Giant Steps is perhaps the most relatable moment I can describe listening to jazz masters play.

Flanagan, by the way, had more than the last word on this piece of music. After Coltrane died he recorded a lovely version of it on a tribute album that has a solo that rivals Coltrane’s and is maybe even better for its lucidity and cohesiveness and swing.