Most modern knowledge work organizations treat individuals as general-purpose computers that execute a turbulent mixture of value-producing and administrative tasks—often unequally distributed, and not at all optimized for any particular big picture objective.
— Cal Newport ¹
It is the most incredible moment in sports that no one talks about. ²
Michael Jordan’s first six seasons with the Chicago Bulls created speculation: will Michael Jordan be the greatest NBA player to never win a Championship? Jordan was a bonafide superstar and, after the rookie signed a sneaker deal with Nike, the biggest name in pro sports. But despite all their talent, the late ‘80s’ Bulls had back to back to back losing seasons, three head coaching firings, and were twice swept in the first of the playoffs. ³
Then in 1988, things looked to be coming together. Jordan led the league in scoring. Scottie Pippen was emerging as the superhero’s sidekick. The Bulls ended the regular season 47-35 and knocked off two favored opponents in the first and second rounds of the playoffs. But then, they lost to the Detroit Pistons in the Conference Finals. And after one of the best seasons in franchise history, head coach Doug Collins was fired.
He was replaced with Jordan’s fourth coach, Phil Jackson, who led the 1989 Bulls back to the Conference Finals where, again, they lost to the Pistons. After back to back to back appearances in the Conference Finals, expectations for the 1990 Bulls were high. But on December 19, 1990, after a 21-point loss to the Pistons, the Bulls were sitting in ninth place in the conference, out of playoff contention.
The following day, Phil Jackson announced, and the Chicago Tribune reported, “The Bulls have named center Bill Cartwright a co-captain along with Michael Jordan, who had held the job by himself.”
In his eleventh season, Cartwright was, to many, a stunning choice for co-captain. Medical Bill, as some teammates referred to him (because he was always nursing some injury or another), played in just four games the season before he joined the Bulls. He didn’t score a lot of points, was good but not great at defense, didn’t say a whole lot, and always looked kind of sad. He wasn’t a paragon of leadership.
But the moment Bill Cartwright was named co-captain was the moment the Bulls became a championship team. As Sam Walker, author of Captain Class, said, “If you looked at the numbers, just purely the numbers and asked, what’s the moment the Bulls became a championship team? You would point to that day. It was that day. It’s clear as a bell.”
The Bulls didn’t lose another game that December, winning twelve of their next thirteen games. Then after 11- then 9-game winning streaks, they finished first place in their conference with a franchise-best 61-21 record. After sweeping the Knicks in the first round of the playoffs and knocking off the 76ers in just five games in the second round, the Bulls swept the Pistons in the Conference Finals. They lost game 1 against the Lakers then won the next four to win the 1991 NBA Finals.
Which brings me to the productivity puzzle.
In Why Things Bite Back: Technology and the Revenge of Unintended Consequences, the writer and historian of technology and culture Edward Tenner seeks the answer to a “productivity puzzle”: why has the advancement in workplace technology not been reflected by an advancement in workplace productivity? “Intuitively,” Tenner writes, “it is hard to believe that huge investments in improving the quality of anything will not pay off in the long run.” ⁴
But here are the stats. The economist Stephen Roach found that in a nine-year period in which the service sector increased investment in advanced technology by over 116 percent, workers’ output increased by only 2.2 percent. Two other economists from the Brookings Institution and the Federal Reserve, Tenner writes, “calculated the contribution of computers and peripherals as no more than 0.2 percent of real growth in business output.”
The explanation for this puzzle is what Tenner calls a “rearranging effect.” Technology made secretarial and managerial tasks easy enough that, technically, intellectual specialists could do them. So, figuring computers were essentially a tool making it possible for a smaller number of people to accomplish the same amount of work, companies en masse laid off support staff.
In 2009, the entrepreneur and tech investor Paul Graham wrote an influential essay on makers and managers. In it, he argues that the best types of workflows for makers (e.g. programmers and writers) are different than the best workflows for managers. Essentially, makers need large chunks of time where there are no interruptions, no meetings looming, and no expectations on their responsiveness. They need to be able to sharply point their focus at a singular attention target. Therefore, makers, Graham writes, “prefer to use time in units of half a day at least. You can’t write or program well in units of an hour. That’s barely enough time to get started.” ⁵
When the support staff is eliminated, makers have to absorb the secretarial and managerial tasks. They have to orphan the makers workflow and adopt the managers workflow. They need to be able to diffuse their focus at many attention targets. They have meetings and calls looming. Large chunks of time are shattered by daily barrages of emails and Slack notifications and calendar alerts and ad hoc requests. Tenner cites the research of Peter G. Sassone, who “concluded that computerization has helped reduce rather than promote the amount of time that these employees spend performing their highest and best work.”
Attention is a zero-sum game. When you are attending to the execution or facilitation of quotidian tasks, you are not attending to the production of valuable bottom-line-boosting work. So, it takes a larger number of makers to accomplish the same amount of work. But a company that won’t hire support staff probably won’t hire more makers. So overall organizational productivity declines. Sassone says this is an inevitable result of the “law of diminishing specialization.” ⁶
“Economic theory suggests,” Tenner writes, “the most rational way to deploy staff is to have the most skilled and specialized employees working as much of the time as possible at the highest level of specialization.” People who study productivity in the business sector refer to this as intellectual specialization, which says: you want your skilled specialists to spend more time focusing on work that creates value for your organization and less time on work that doesn’t. You want to makers making and the managers managing. In his book A World Without Email, techno-philosopher Cal Newport references the example economics textbooks use to illustrate the idea of efficient labor markets: though a great lawyer could also be her own typist, she’d be a fool to not hire a typist. If she bills $500 an hour and a typist costs $50 an hour, she’s clearly better off outsourcing whatever she can to spend more time on legal work.
In our expanding jobs ⁷, the work once divided among two or three workers has crawled onto a single worker’s plate. We’re the lawyer and the typist, the maker and the manager, the Jordan and the Cartwright. As an inevitable result, despite spilling work into all hours of the day and week, like Jordan and the late ‘80s’ Bulls, we’re not producing the first-class work we know we’re capable of.
In 1986, Richard Hamming gave a talk at his former employer, Bell Labs, on how to do first-class work. In mathematics and computer science arenas, Hamming is one of the all-time giants. The talk was informed by his observing and collaborating with Nobel Prize winners, interviewing the great scientists of his time, and studying the great scientists of all time. “Most of you in this room,” Hamming said, “probably have more than enough brains to do first class work. But great work is something else than mere brains.” ⁸
Hamming tells the story of a fellow with mere brains. “He took me into his office and showed me his method of getting letters done and how he took care of his correspondence,” Hamming says. “He was bragging about how marvelous it was and how he could get so much work done without the secretary’s interference.” He was bragging about being the maker and the manager and, as we’ve said and as Hamming told him, you have to be a fool to not use your manager. If you only work on what only you can work on while the support takes over the rest of the work, Hamming told him, you will go much farther.
“And, he never went any further,” Hamming writes. “[He] was not willing to recognize that you need the support.”
Jordan recognized it. He recognized that being an elite captain is a full-time job. As Sam Walker describes the job, “The captain is the figure who holds sway over the dressing room by speaking to teammates as a peer, counseling them on and off the field, motivating them, challenging them, protecting them, resolving disputes, enforcing standards, inspiring fear when necessary, and above all setting a tone with words and deeds.”
When Jordan was freed from having to attend to the tasks of a captain, Walker said, that’s when the Bulls became a first-class team. “That’s when Jordan became great—when he was allowed to be the star and someone else was taking care of the duties of management.”
“Without Bill Cartwright,” Walker writes, “it’s not clear Jordan would have won anything.” “Bill,” Jordan would add, “made all the difference.”
To do first-class work, Hamming says, “you don’t let anything else get the center of your attention.” You don’t try to be the scientist and the secretary, the lawyer and the typist, the maker and the manager, the Jordan and the Cartwright. ⁹ ¹⁰
Or if you do, as Graham said, “understand the cost.”
 A World Without Email: Reimagining Work in an Age of Communication Overload by Cal Newport
 Sam Walker: Author, the Captain Class
 The Captain Class: The Hidden Force That Creates the World’s Greatest Teams by Sam Walker
 Why Things Bite Back: Technology and the Revenge of Unintended Consequences by Edward Tenner
 Maker’s Schedule, Manager’s Schedule by Paul Graham
 Office productivity: the impacts of staffing, intellectual specialization and technology by Peter G. Sassone
 The Expanding Job by Anne Helen Peterson
 You And Your Research by Richard Hamming
 After a six-year study of twenty departments at five major U.S. corporations, Peter G. Sassone found that these organizations could immediately reduce their staffing costs by 15 percent by hiring more support staff and freeing up their professionals to produce more bottom-line-boosting work.
 “When you allow specialists to work with more focus, they produce more, and this extra value can more than compensate for the cost of maintaining dedicated support. Our rush to cut payrolls by having everyone handle their own administrative work through computer interfaces provided only the illusion of streamlining. These top-line numbers obscured the degree to which the cognitive gears that produce value in knowledge work began to grind and stick under these new demands. Returning to a culture that allows more separation between specialized and administrative work is crucial.” — Cal Newport, A World Without Email
Thank you to Greg Shildkrout and Katie McKenzie for reading drafts of this.