Questlove and the Art of the Sideproject

For a few weeks now I’ve been meaning to preform a close reading of a review I read on Pitchfork because (and this is going to sound a little bit odd*) I think it contains some great lessons for leaders, teams, and organizations.

The review is part of the new Sunday series that Pitchfork offers, wherein they break from their weekly pattern of reviewing newly released music and write a review of an important or classic album from the past. The album they reviewed back in August was Things Fall Apart by The Roots.**

In the review, writer Marcus J. Moore recounts a story about Roots drummer and bandleader ?uestlove.  Apparently, ?uestlove was drifting; his focus was moving outside of The Roots, which had been his central project.  He was, according to Moore, “more concerned with recording D’Angelo’s Voodoo and Common’s Like Water for Chocolate than he was with his own group.”  And, as often happens in these moments, his teammates, The Roots, resented him and “questioned his focus.”  This questioning, for me, is where the learning begins for organizations and their leaders.

If a star player — like ?uestlove — begins to drift away from your organization to explore outside interests, what should you do?  If others, within the organization are growing resentful, how do you handle it?  If such a loss of focus hurts you in the near term, how long should you create a buffer around it? How long should you gamble on it? What’s the possible upside?

I think you have to begin by trying to understand what your teammate is doing, and why he’s drifting.  The story of ?uestlove’s drifting offers some excellent perspective.

Again, according to Moore… While ?uestlove’s bandmates were resenting him, ?uestlove was actually working for them: “He was spending time with . . . engineer Russell Elevado, learning new ways to manipulate sound to give his own music a more granular, less studied feel. He wanted to be a heralded producer like DJ Premier and J Dilla, but his band’s work felt remarkably clean—even sterile—in comparison.”

So ?uestlove’s main band had become a bit formulaic, in part because he himself had become a bit formulaic.  In order to help The Roots, ?uestlove had to help himself first, had to change himself first.  Such change, such growth, required looking elsewhere: “Realizing he needed to improve as a producer, ?uest learned how to play drums ‘dirty,’ taking Dilla’s lead and dragging his percussion just a bit to make the beat seem off-kilter.”

Read the rest to see how things fell together on Things Fall Apart:

The genesis of Things Fall Apart can be traced back to a hangout ?uest had with Premier, Dilla, and D’Angelo, where he played them a rough version of a Roots song called “Double Trouble” and got disinterested head-nods in return. Determined to bolster the track, ?uest recorded drums to two-inch tape, looped it back through the soundboard, and tweaked the EQ to give it a feeling of distance. “It was a turning point in my understanding of my own career,” ?uest wrote in his memoir. “I knew that the other guys respected me as a drummer… but I also wanted them to respect me as a producer and a songwriter.” In its finished form, “Double Trouble” is arguably the centerpiece of Things Fall Apart; rapper Black Thought finally had a hard-charging instrumental to match his verbal dexterity, and guest Mos Def matched him bar-for-bar.

Things Fall Apart is where the Roots figured out who they were—it wasn’t “just another Roots record,” and if the group was going to fail, they were going out their own way. “Table of Contents (Part 1)” illustrates their new willingness to take risks: The breakbeat is messy and the mix is intentionally pinched and lopsided, but the track’s feeling of chaos is an ideal table-setter, opening the record on a tense and uncertain note. On “Step Into the Realm,” the drum loop fades in and out, but the rhythmic instability makes the rappers’ audibly distorted vocals sound even more urgent. If the Roots’ first three albums mastered the meeting point between jazz and rap, this was the first time the band went psychedelic, opening up new possibilities sonically and lyrically.

D’Angelo’s 1995 album Brown Sugar and Erykah Badu’s Baduizm from 1997 were the blueprint for new-school soul music, and Things Fall Apart applied those ideas to hip-hop proper. In this aesthetic space, artists with different approaches could find new ways to be creative together, and a new movement was being born. “You Got Me,” the lead single from Things Fall Apart, found a crooning Badu next to rapper Eve from the Ruff Ryders over a lilting guitar figure and strings. The classic arrangement and eclectic mix of voices, paired with ?uestlove’s typically propulsive and cutting backbeat, sounded both old and new, looking backwards and forwards simultaneously. The Roots were pushing the limits of their sound, establishing a lane for D’Angelo, Common, and Badu to do the same. By building a musical community and mastering the art of collaboration, they figured out how to cross over and keep their soul intact.”

Okay, now for a risky move of my own — a forced leap between The Roots and Andy Grove’s book High Output Management, widely touted and devoured in Silicon Valley.  When I read about, and digested, ?uestlove’s exploratory side projects, I thought immediately of the manner in which Andy Grove defines leadership, or in his word’s management:  “A manager’s output = the output of his organization + the output of the neighboring organizations under his influence” (page xxiii in my copy of his book).  ?uestlove fits this definition perfectly because of his willingness to use side projects as an instrument for his own learning and to bring such learning back (first) to his band and (second) to his “industry.”

His method — of looking far and wide for the next innovation to his craft — is instructive, too, and seems to be wired into his DNA.  His latest book is a series of interviews with . . . chefs.


(If that’s not a great cover, I don’t know what is.)

Not a chef himself, ?uestlove sought out chefs because he felt that they were producing the most exciting and innovative work, day after day and year after year.  The book is a masterclass in the kinds of struggle, contemplation, experimentation, frustration, joy, and seeking that leads to truly original and personal work — the work of artists and the leaders willing to learn from them.

*Actually, if you’ve been reading my work over the years, this shouldn’t seem odd. One consistent lesson I’ve learned — and tried to teach, including in this blog post — is that you never know where you’ll learn your lessons. Focused study is important, once you are drilling down into the problem you want to solve or the discipline you want to study. But unfocused study is also important.

**You can read the full review here:

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