Case Research of Knowledge Work Practice

You can observe a lot by just watching.

Yogi Berra

I’ve long argued that invisibility constitutes a major impediment to improving the practice of knowledge work. What we need is to see more practice.

So, I’m setting out to collect and develop stories and case studies of knowledge workers doing their work. Right now, this is exploratory research to discover categories and concepts that might prove useful. My conjecture is there’s an underlying set of skills and practices common across multiple instances of knowledge work.

Further, I suspect these commonalities aren’t immediately evident or obvious. They are “hidden” within the craft elements of different knowledge work jobs (e.g. reporter, consultant, systems analyst, programmer, data scientist, media planner, teacher). The initial goal is to figure out productive questions.

A starting point is to examine accounts of knowledge workers who have shared their journeys in ways that we can extract insights about their methods and practices. For example, Tiago Forte’s Building a Second Brain presents his solution for a personal knowledge management environment. He does so by sharing a good bit of how he got to his answers. Regardless of whether you find his destination suitable to your needs, you can learn from his journey. Supplement the book with the materials he has shared elsewhere online and we can craft a useful case study.

There’s a decent collection of knowledge workers (authors, scientists, entrepreneurs, etc.) who have shared enough about their methods and practices to form an initial sample from which we can develop the outlines of a theory of knowledge work. Once that exists, we can reach out to other knowledge workers to explore their practices and elaborate a richer model.

Learning to do learning by doing better

I’m a believer in learning by doing – both as a learner and as a teacher. As a learner I’ve largely been content to hack away at things in the belief and lived experience that I do figure something out eventually. I’m a bit more disciplined and intentional when I put on my teaching hat. There, I make a more mindful effort to design doing with the intent of nudging learners to do things I expect will impart the lessons I intend.

If learning by doing is a powerful strategy, shouldn’t we make an effort to develop that skill? What might happen if I bring more of my teaching strategies to my own learning by doing?

Let’s start with one learning by doing strategy. “See one, do one, teach one” is a strategy that’s long been effective in medical education. While typically deployed in the context of a broader curriculum where you can make assumptions about prerequisite knowledge and coaches to keep the learners in bounds and out of trouble, can I adapt it to my individual needs?

My hunch is that that “seeing” is the trickiest part in this equation. I’ve asserted that one of the fundamental problems of knowledge work is that it is largely invisible. What can we do to make it easier to see our own work?

One prior element in making my work easier to see was to worry about the naming of things. Which helps at the later stages of knowledge work. How about earlier stages? I think this is the potential within the world of note-taking/note-making apps and environments.

Ideas are rarely so accommodating as to show up fully formed. Sometimes they arrive as a phrase or as a handful of words. Sometimes as a sentence or two. They’re often rude enough to intrude when I’m half asleep without a writing implement nearby. I’ve had to accept that many will escape before I can write them down. However, I have slowly gotten better at capturing a reasonable percentage before they disappear.

Way back when, I did much of this capturing by hand in notebooks. Now, I capture these evanescent items in Obsidian. I don’t generally know what I will do with an idea at that point. But, bits are cheap and better to have a record and decide to throw it away later than miss collecting a gem. (One of these days, I will have to do a piece on why I am suspicious of the notion of the collector’s fallacy).

Gradually, I’ve been building a collection of my ideas that I can “see” from something resembling a single vantage point. It includes everything I’ve posted to this blog since 2001, everything I’ve highlighted on my Kindle (via the excellent Readwise Reader), and my journals going back to 2019. It leaks. And, there are remaining pools of thinking and ideas worth integrating over time. For now, the view is still fuzzy and incomplete but it’s moving in a good direction.


Moving from Tools for Thought to Thinking as Craft

The notion of “tools for thought” is undergoing a resurgence from niche topic to something approaching a fad. Everyone’s got a new tool for making notes or a course on how to optimize their Zettelkasten. Too few of them seem familiar with the prior art fueling their work. You might want to start by adding Howard Rheingold’s Tools for Thought: The History and Future of Mind-Expanding Technology to your reading list.

The problem is that we mostly get trapped talking about tools in isolation. The folks marketing and selling tools focus on what sets their tool apart from others. People looking at a new tool are seduced into comparisons between individual tools. Discussion threads revolve around narrow questions of “how do I force this tool to behave like the tool I already have” or “how can I import my collection of left-handed, Gregorian chant, meditations”. We don’t appear to have a principled way to talk or think about how a new tool might fit into a collection of tools and how tools (plural) enable and support the craft of thinking. We slide past the phrase “tools for thought” without giving much thought to where that might take us.

There’s more to quality work than any individual tool. 4.0. My wife is a photographer. If you want to irritate her, suggest that she must use a very expensive camera. She takes better photos with her iPhone than I can with $10,000 worth of equipment.

The eye behind the lens matters more than the camera. Or the mind at the keyboard.

Talking about tools is easy. Thinking about craft is hard.

Working out how tools enable better craft is the nub. George R.R. Martin still writes with Wordstar. Anne Lamott was pushing yellow legal pads in a recent workshop. John McPhee was rearranging index cards on the floor. I don’t take any of this as recommendations to adopt their tools. But it does make me wonder how I ought to think about how tools and craft intertwine.

A starting point is to turn Sturgeon’s Law into a working strategy. Sturgeon’s Law asserts that “90% of everything is crap.” Churn out a lot of output and learn to distinguish the 10% from the 90%. Becoming a better photographer consists of throwing away most of your shots. Same for writing. Step one in getting better is producing something to critique. Over time, you can begin to wonder about producing things worthy of critique. To start, focus on pure production.

Two things become possible once we’re producing something. One, we can begin to compare our outputs with one another and with similar outputs out in the world. Two, we can pay attention to how we’re going about our production. Both of these can work as individual practices. With a bit of confidence, you can expand your comparisons to others.

I’m an average photographer at best. I haven’t put in the reps that my wife has. She’ll take a dozen shots of a scene and throw eleven away to get an image worth keeping. Most of what she throws away put my efforts to shame. Slowly, I’ve learned there’s a body of knowledge about what separates a good shot from a mediocre one.

I’ve put in more reps at writing than I have at photography. This blog post is about 600 words at this point. There’s another thousand words of notes in the window next to this one and I’ve probably thrown away another 1500-2000 so far. There’s an extensive body of knowledge about blogging in particular and writing in general. I’m familiar enough with both to know the rules and to be comfortable breaking them when it suits my purposes.

I’ve got plenty of output that I can assess and evaluate. The second development path to explore is the production process. The tools I employ are pretty easy to identify. Teasing out the process is trickier. Discerning where improvement opportunities lie is harder still. It is most definitely a work in progress.

I’m on record that knowledge work should be treated as a craft. Lately, I’ve been lamenting that there aren’t enough case studies of knowledge work in action for us to learn from. Let’s see if we can start to generate and collect some to see what we might learn from one another.

Efficiency ignores obsession

Came across an interesting piece from Smithsonian Magazine from 2012 (Teller Reveals His Secrets). In it Teller, of Penn & Teller fame, writes about magic and psychology. Teller writes, of course, because Teller is the silent half of Penn & Teller. (I first saw them perform when they were the hot ticket Off-Broadway in 1985.) Teller’s argument is that

Magicians have done controlled testing in human perception for thousands of years….Neuroscientists—well intentioned as they are—are gathering soil samples from the foot of a mountain that magicians have mapped and mined for centuries.

One element of that understanding sheds light on contrasting efficiency and effectiveness. It’s a safe bet to assume that our cognitive and perceptual systems are fundamentally lazy. Our senses and our brains work efficiently by taking shortcuts whenever they can. The field of behavioral economics grew out of the work of people like Daniel Kahneman and Amos Tversky exploring what those shortcuts were and why they worked.

Magic works by understanding and exploiting that laziness. Often, by investing a degree of effort well beyond any efficiency calculus.

Teller is an artist, not a scientist. He, and Penn, are prepared to obsess if that’s what it takes to achieve an effect. This is an element of effectiveness I hadn’t considered until now.

Effectiveness depends on community

My sister-in-law and her husband owned a retail business for 45 years in the town where they, and my wife, grew up. Conversations at their dinner table often revolved around people they went to elementary school with and still interact with.

This mystified me for years. When I married into that family, I had lived in over twenty different places. Outside of my immediate family, I had no connections to the people I had grown up with. I’m not sure I had the concept of having grown up with someone who wasn’t family.

I’ve heard it said that the vast majority of humankind is born, lives, and dies within 25 miles of their birthplace. I understood this as an intellectual datapoint. Not so much as an emotional anchor.

Charlotte and I have been married for coming up on 39 years. We’ve had multiple addresses over that span. Most recently, we’ve been living in Nazaré, Portugal.

The cliche here would be that we have each other as anchors. While there’s certainly truth to that, the more interesting observation is that we’ve been part of two church communities. Ten years in Boston, Twenty seven in Chicago. Mainline Protestant (despite, or perhaps because of, my Roman Catholic upbringing). Neither the theology or the liturgy are central. What is central is a commitment to making community work.

I’m pretty sure you can’t be effective without community. You need something that resembles the history and connections that my sister and brother-in-law take for granted. You have to be able to predict how others will react to the unexpected. It takes time and effort to build and maintain community. Organizations are reluctant to invest in the long slow work of building community and resilience.

Organizations prefer to deal with the unexpected by eliminating it. This is the false appeal of efficiency. Lock everything down and define every response. The universe, however, insists on being unpredictable.

Making Art Happen

In high school I started to do some work in theater. It was a way to meet girls. At an all boys school, there wasn’t any way to do that in the halls between classes. There were, however, joint productions with a sister school. I was much too shy to attempt any performing roles but there’s always a need for people willing to work backstage.

I got to Princeton in the early days of coeducation there. Perhaps three quarters of the students then were guys. During Freshman Week I was enticed into a performance of the Princeton Triangle Club by a cute blonde passing out flyers outside McCarter Theater. Knowing one end of a hammer from another made me more than qualified to join the tech crew.

Four years later, I had done pretty much any backstage job that went into putting on a live performance. From stagehand to electrician to production stage manager I learned what went into making art happen on stage. And what supported that art offstage.

There’s very little about staging a play that’s efficient. I’ve stood behind a set piece on stage to keep it from falling during a performance. Don’t be seen and fix it later. Gaffer’s tape is your friend.

“The show must go on” is a real thing. Internalizing that sets you up to keep your wits about you in the midst of chaos. Turns out that’s a pretty important set of life lessons and skills.

Looking outward

Our family moved to St. Louis in the Fall of 1964. I was 11. Mostly this was hugely disruptive for a bookish, introverted pre-teen. A year later, I was switched from the parochial school just up the hill to a private all-boys school, a 40-minute drive away.

One of the saving graces in all of this turmoil was my dad’s new job. He had moved to St. Louis to become one of the lead test engineers for the Gemini spacecraft built by McDonnell Aircraft.

How could it get any better for someone absorbing every science fiction title he could lay his hands on at the local public library? Everyone was following the space program. My dad was part of it. I had pictures of him working with the Mercury and Gemini astronauts. I was a nerd before there was a word for it.

All of this directed my gaze outward. Not terribly unusual for a young boy in that time and place. What I also had was a glimpse at the complexity behind the scenes. Everyone saw the show on TV. I saw the testing and rehearsal and adapting that happened before or on the side. I didn’t have the words or the concepts for it at the time, but these were the seeds that grew into my fascination with innovation and creation.

Efficiency is boring. It’s interesting only to those who like piling things (money) up. Efficiency is isolating and inward looking. It stops at the edge of the system. You can’t even begin to think about it until you’ve worked out all the hard (and, therefore, interesting) problems.

The first few times you try anything new, you have to settle for effectiveness. Did it work?

That means looking at the bigger picture. How does this new thing fit in with and interact with the larger system? Effectiveness is about constantly running experiments in the real world. Can you make some predictions about what might happen next? What potential catastrophes do you have to guard against?

To me, I’ve always been mystified by those people who settle for efficiency. Who are content to do the same thing once again. Where’s the fun in that?

Book Smart and People Stupid

You get the behaviors that you reward. A truism of management.

A quick glance at my resume would persuade most people that I’m book smart. I got rewarded for doing things that schools find easy to reward; taking tests, making the teacher look good, saying clever things (at the appropriate time and place). So I continued to do those things.

There’s an implicit (and unexamined) assumption that the things that get rewarded correlate with underlying knowledge and skills in a broader way. Doing well on the tests was taken as a marker that you were putting in the necessary work employing (and developing) the more general learning and study skills that would stand you in good stead later on. Not necessarily the case. I got a lot of things on raw horsepower rather than on good work habits.

Other elements of the surrounding environment are meant to provide guard rails. Study groups, working with fellow students on problem sets, socializing with the group who had ways to police those who varied too far from the norms. For a variety of reasons that don’t bear on this tale, those other elements didn’t apply to my circumstances. I wasn’t part of the “classes” that took place outside of the classroom. I was in front of a pack that I didn’t know existed.

For a long time, I found myself in settings where I could prosper operating inside of systems that I couldn’t see. I would hit speed bumps that I attributed to other people being stupid or to me not being smart enough to outthink the problem. I was glib enough to talk my way out of most of the problems I found my way into. I wasn’t insightful enough to see how many of those problems were of my own creation.

I started building a theory built around stupid people and how to avoid them. There is enough actual stupidity in the world to make this a dangerously seductive theory. Fortunately, as a scientist at heart, I was committed to following the evidence. Everyone else couldn’t be consistently that stupid. It wasn’t stupid people, it was me being people stupid.

There’s a longer version of the quest to follow this line of thought. For now, it’s enough to note that looking inward was the essential step. For all that I was a quick study in knowledge intensive settings, I was slow to grasp how to navigate this terrain. The tests weren’t something I could power my way through. Not alone. I had work to do on learning to balance my head with my heart. Complicating that was an additional factor; attention deficit disorder. We can save the discussion of whether ADD is over diagnosed or not really a disorder. What was important to me was learning that there were things others found easy that I found nearly impossible. Raw IQ points and a quick wit were not the answer to every problem.

I didn’t discover any of this until well into my career. Raw IQ points and a quick wit can take you a long ways. Just not all the way. I’m still working to develop skills and compensating techniques to deal with the limitations of my brain.

The essential step to dealing with any problem effectively is to be able to name it.

Asking better questions

Alan Kay has been one of my heroes for a long time. Feel free to Google him if the name doesn’t trigger anything for you. One of my favorite Alan stories comes from his early days at Xerox PARC. Xerox PARC comes from the days when smart organizations carefully walled off the crazies from the rest of the organization in search of new ideas.

Xerox PARC was situated in the heart of Silicon Valley, a continent away from Xerox headquarters in Connecticut. A team of executives was on site to review the work going on in Palo Alto. Alan and his team of software engineers walked through one of the research projects underway. Alan carefully explained that this was ongoing research; experiments were as likely to fail as to succeed and the goal was to learn something interesting that might lead to the next experiment.

The suit from Stamford nodded along in approval. His closing remark was “I understand, but you’re only running the experiments that succeed, right?” In his universe, “failure is not an option” was not a motivational challenge, it was a risk to be avoided at any cost.

If you commit to the path of asking questions, you also commit to the reality that you often won’t get answers. You’ll certainly get answers you don’t want.

The false promise of efficiency is that you can guarantee control. You carefully limit the questions and the answers to obtain that control. And, that can work for a time. If nothing important changes.

Reorienting from efficiency to effectiveness is, at heart, accepting that important change always happens. There are no guaranteed answers but you have to keep asking the questions anyway. Your only salvation is developing deeper skill at asking more effective questions.

Inventing Sails

My CEO and I were arguing as we drove north along Lake Shore Drive in Chicago. He was concerned that I was too focused on insight at the expense of execution. As he put it “95% of the people in organizations are just pulling on the oars, they don’t need insight.” My response was to ask where did sails come from if everyone was pulling on the oars?

New ideas are scary things to most organizations and to most executives. Managers like order. For all that we praise entrepreneurs in today’s world, we get very uncomfortable when too many ideas are floating about. Most of us are, in fact, pretty comfortable pulling on the oars as long as someone is pointing towards something that looks like a worthy destination. We all point and laugh at the person playing with tying a sheet to an old oar to see what happens. Until the oar turns into a mast and everyone wants one of their own (or says it was obvious all along).

The people who want to play with things to see what might happen are a source of constant anxiety for those who favor order. They are also the source of great rewards. Managing the balance between risk and reward has vexed those in charge for as long as there have been people in charge.

In a slow-changing world, you can manage this problem by carefully limiting and constraining those who like to play with things. Create an R&D lab and wall it off from the day-to-day operations of the business. Set up a new business development group or an innovation lab. Call it what you want. Just keep the crazies under control and out of the control room.

We don’t live in a slow-changing world. We all have to learn to live with a degree of craziness and take ownership of some level of control. There’s no way to simply pull on the oars and let someone else worry about how to steer.