Refuse to choose sides

After church yesterday, I had a quick conversation with a relatively new parishioner. I had learned that Ben was from St. Louis, as was I. This was a perfect opening to ask the first question that always gets posed whenever two St. Louisans meet: “Where did you go to school?”

In St. Louis, this is actually a question about what high school you attended. The answer is meant to pigeonhole anyone precisely on a clutch of dimensions – religious, socio-economic, political, cultural. I got the one answer from Ben that I would never have expected. We had both graduated from Priory. We are separated by enough years, that his classmates were the children of my classmates.

The answer was unexpected because Priory is a Catholic, Benedictine, school and we were in an Episcopal Church. First pigeonhole broken.

I’ve been thinking about pigeonholes and sides. And the experiences from my middle school/high school years bounce off that quintessential St. Louis question in odd ways. The question is usually pretty reliable because St. Louis is a pretty reliably stratified environment. If you grew up in the environment, you knew where you fit. By the time you reached Priory at age 11, you knew where you belonged.

I was dropped into this environment as an outlier. We had only just moved to St. Louis and I had no previous connections or pigeonholes that mattered. I lived a fair distance from the school which complicated matters further. My classmates didn’t know where to pigeonhole me either. But I had to be categorized and sorted if I wasn’t to disrupt the natural order of things.

I grasp the fundamentally tribal nature of humans. I’ve spent a good portion of my professional existence dealing with it. But back then I was simply a piece on the board as others were choosing up sides in a game I was only dimly aware of.

I was in an environment where I had strengths that qualified me for multiple roles. I was bright. I was decently athletic. I was quick witted and fast tongued. I was valuable, albeit naively so, to multiple sides. Gradually, I learned to move between sides. What I discovered was how committed people were to fitting smoothly into a primary pigeonhole.

That commitment to fitting in one category often blinds us to the degree of commonality that actually exists between categories. We invent new language to emphasize differences and distinctions. The path to fame in many settings starts with inventing new terms for old ideas. It’s a temptation that is hard to ignore. There’s less reward for revealing shared concepts hiding behind language invented to sharpen differences. There’s deep wisdom hiding in the tagline to the movie WarGames; “the only winning move is not to play.”

Crossing the between: building more human organization in a digital world

“But, you’re not an asshole!?”

A client I was working with had just discovered that I have a Harvard MBA.

More recently, I’ve taken over a course from a colleague and I’m starting with his slides so that I can focus on delivering the material and not get bogged down in the details of course design. He had an opening slide with his academic credentials and I copied in mine. It’s causing the annoying problems I could have predicted.

I don’t hide my background but I’ve become guarded about what and when I reveal facts about myself. That guardedness causes its own set of problems.

I used to think the explanation was about belonging; about being on the inside or on the outside. I got into Princeton and Harvard because I did well on tests and in classrooms but I came from a different world. Big family, Midwest roots, Catholic boy’s school, technologically adept, socially awkward; not quite Eliza Doolittle but not a bad approximation.

Skip ahead several decades and the rough edges have become reasonably polished.

Belonging isn’t the right way to think about it.

It’s about being between; of sitting within the overlap of a Venn diagram and working to make the shared space bigger. Not just for me but for everyone. Making the between bigger is about building bridges, creating shared language, and committing to learning about the other circles in the diagram.

The primary circles that draw my interest are organizations where humans band together to pursue human goals and technology where tools amplify human capacities. I believe that there is an enormous amount of overlap to be found there. The counter-belief feels more like warring camps in trenches with a shell-pocked no-man’s land in between.

I know from personal experience that the overlap is real. What I intend to explore over the next several weeks is what it might take to traverse the between safely.

Knowledge work and stable intermediate structures

There’s a story of the two watchmakers that Herbert Simon tells in The Sciences of the Artificial to illustrate the relevance of intermediate structure and hierarchy. Here’s the story

There once were two watchmakers, named Hora and Tempus, who made very fine watches. The phones in their workshops rang frequently and new customers were constantly calling them. However, Hora prospered while Tempus became poorer and poorer. In the end, Tempus lost his shop. What was the reason behind this?

The watches consisted of about 1000 parts each. The watches that Tempus made were designed such that, when he had to put down a partly assembled watch, it immediately fell into pieces and had to be reassembled from the basic elements. Hora had designed his watches so that he could put together sub-assemblies of about ten components each, and each sub-assembly could be put down without falling apart. Ten of these subassemblies could be put together to make a larger sub-assembly, and ten of the larger sub-assemblies constituted the whole watch

Simon uses the story to illustrate why structure and hierarchy emerge in complex systems. Or why good designers build  intermediate structure into their systems.

One interesting aspect of this fable is that Simon talks of two levels of intermediate structure. This suggests that there are criteria to invoke when making design choices about the size and complexity of intermediate structures.

I’ve been thinking about intermediate structure lately in the context of how to be more effective in doing knowledge work. I’ve touched on working papers recently and I wanted to revisit the topic from the perspective of stability and intermediate structures.

I’ve been blogging for a long time and writing at multiple lengths–blog posts, teaching cases, articles, books. I use or have used all sorts of tools in the process

  • mindmaps (both by hand and by software),
  • outlines (again, both by hand and by software)
  • word processors
  • text editors
  • bibliographic/reference management software
  • wiki software
  • specialized note taking tools (Evernote, nvAlt, etc.)

The space between glimmer of an idea and finished product is what draws my attention now. Although I’ve been nibbling around the ideas of working papers, most of what I’ve discovered and examined has talked about writing process. Freewriting, shitty first drafts, mindmapping techniques. What’s starting to come into view is the structure side of the question.

For the longest time, I’ve worked and thought in terms of deliverables and working backwards from some vision of an end product. That works well enough for blog posts and most client reports. At the longer scales of a book, on the other hand, working backwards breaks down. You know that the outlines and mindmaps are  necessary but they morph as the process unfolds and as your understanding of the deliverable evolves.

The notion of a permanent and evolving collection of notes and treating those notes as “first class objects” that should be designed to stand on their own is a new to me. When I started blogging the idea of a commonplace book was one idea for an organizing container for developing ideas and lines of thinking. Jerry Weinberg’s Weinberg on Writing: The Fieldstone Method is an approach that I’ve worked to understand and adopt. I’ve certainly recommended it to many colleagues. More recently, Sonke Ahrens’s How to Take Smart Notes: One Simple Technique to Boost Writing,  Learning and Thinking drew me into the subculture of Zettelkasten.

All of these new ideas still focused mostly on process advice. They fell short on offering insight into the structure of the data and information that you created through the processes. They slide past the data half of the equation and I’m only know coming to see how that has been holding me back.

A collection of permanent notes is a handy thing to have around. But, without attention to intervening stable structures we are still fighting the problem of building a 1,000 piece watch in a single step.

There are some hints scattered in what I’ve found so far. The Zettelkasten sub-culture references the notion of special forms of structure notes, for example. In my own work. I’ve started to recognize the emergence of recurring themes and am trying to develop techniques to capture and track them.

I feel I am at the stage of recognizing that there’s a problem to be addressed. I can see the gap between a collection of random notes and the organized flow of a final deliverable. Now I’m looking to design or discover stable structures that can serve as waypoints where I can pause before I have worked out what the final deliverables might be. Is this a problem that others have also encountered? Are there concepts and structures I can learn and adapt?

What will the new year bring?

The time between semesters has turned into a bit more of a hiatus than I would have predicted. I’ve been doing a good bit of writing for myself but not in a way that unpacks easily into posts worth sharing more widely.

I’ve always been in the school of “how do I know what I think until I see what I say.” Often, when I say it for the first time, I’m still not sure I know what I’m thinking. I try to avoid inflicting those moments on everyone else.

There’s a quote that’s been on my mind lately. It comes from an interesting novel by Cory Doctorow called Homeland. In it, one of the characters observes:

Start at the beginning,” he said. “Move one step in the direction of your goal. Remember that you can change direction to maneuver around obstacles. You don’t need a plan, you need a vector.

When we get to the end of a journey, it’s always tempting to revise the story to make the journey seem more straightforward than it ever actually is. We’ll pretend that we knew where we were going all along; the goal was clear and the plan was good.

Doctorow’s formulation is more modest. A vector is movement and a direction. Movement without direction may be walking in circles or worse. Direction without movement is no more than gazing at some vague and hazy shadow on the horizon.

What I find intriguing about the notion of a vector is how it directs my focus away from that haze on the horizon to the terrain in front of me.It’s the terrain that throws up the obstacles that call for maneuvering.

The terrain that holds my attention is the space where technology innovation and organizational inertia interact. It’s tempting—and certainly simpler—to pretend that you can limit your focus to one or the other. But that requires lying to yourself about the world as it is. Never a wise approach. Nor an approach I intend to adopt.

Building systems intuitions

Heroes always need a Sancho Panza. Not for comic relief but for essential logistical support.

In high school I found my way into the theater, not onstage but in the wings. I had a friend who persuaded me to audition with her for her school’s upcoming production. I was horrible. That disaster became a path to working on the tech crew where I learned how much work went into creating the magic.

Even a one-person show has a multitude working out of sight. There are directors, producers, set designers, lighting designers, carpenters, electricians, stage hands, ushers, ticket takers, publicity managers, and the list goes on. I financed a chunk of my college education working in those roles. I met my wife working backstage in community theater.

The role I gravitated to was stage manager, which sits at the intersection of several streams. It is where the design work, preparation work, and backstage efforts come together to support the performance on stage. The insight I gained from that perspective was that excellence depended on blending all of the elements in play. You could get acceptable results from focusing on any one to two elements. But the best outcomes depended on taking advantage of all the components interacting.

They way I would explain that today is that excellence flows from systemic performance. For all that we talk of systems in today’s organizations, developing a true systems perspective runs counter to most of our intuitions. Russell Ackoff remains a source for replacing those intuitions with more principled understanding. The following video is longish but more than worth the time to work with and understand:

Insight on Project Planning and Management: Review of Start Finishing

book cover imageStart Finishing: How to Go from Idea to Done . Charlie Gilkey

I suspect that diet books are the only non-fiction category with more titles than time management and productivity. Perhaps I would be better served if I shifted to reading diet books.

Like diet books, I once read these books in quest of the perfect system; the answer that would guide me waking and guard me sleeping. What I seek these days is much the same as I do with Compline[add link] ; reassurance that I am not alone in my struggles and the possibility of insights I can fold into my practices. Charlie Gilkey’s Start Finishing offers both in good measure. I think what got me hooked this time was this point of tangency with my thinking:

Most of what I read didn’t hit the target, though. The personal productivity literature was too nitty-gritty and focused on tasks, and the personal development literature focused on principles and big ideas. But my problem was in the messy middle where creative projects live.

I’ve been exploring this messy middle myself for some time. It’s where I keep running into trouble. There’s a scene in The West Wing where Leo shares the following story with Josh:

This guy’s walking down the street when he falls in a hole. The walls are so steep he can’t get out.

A doctor passes by and the guy shouts up, ‘Hey you. Can you help me out?’ The doctor writes a prescription, throws it down in the hole and moves on.

Then a priest comes along and the guy shouts up, ‘Father, I’m down in this hole can you help me out?’ The priest writes out a prayer, throws it down in the hole and moves on

Then a friend walks by, ‘Hey, Joe, it’s me can you help me out?’ And the friend jumps in the hole. Our guy says, ‘Are you stupid? Now we’re both down here.’ The friend says, ‘Yeah, but I’ve been down here before and I know the way out.’

Gilkey has solid insight and advice for finding the way out.

The two most useful elements of his approach are guidance on breaking projects down into manageable chunks and an interesting way to think about blocks of time at different scales. Gilkey repeats the fairly conventional advice that chunks of work are best described with a crisp combination of  verb and object; “analyze customer data,” “identify key competitors,” “draft report outline.” What he adds is a scheme for classifying action verbs in terms of the time span they imply. “Email” or “call” suggests a 15-minute task while “Research” or “coordinate” suggests an activity that might consume a week. I’m copying his lists of action verbs into my crib sheets.

Gilkey extends this notion of organizing actions by timescale to advice that you stay clear about what timescale you are thinking through at any moment. Are you thinking about blocks of time that you map into a week of work or are you thinking in terms of month or quarter long projects on the path to larger goals? Becoming mindful about which timescale is relevant and moving up or down timescales as you plan work are practices I intend to fold into my work.

There’s plenty of other useful perspective and advice throughout Start Finishing. This will be by my side as I work on my next round of planning efforts.

Design and Craft

There’s been a recent cluster of articles on the productivity benefits realized from capping working days and working hours. Earlier this week Cal Newport penned an op-ed in The NY Times picking up on this theme.

Newport has been arguing that current approaches to complex knowledge work are poorly conceived. He argues for the importance of learning how to do “deep work” and advocates for the value of digital minimalism. Here he turns to a well-worn comparison. Manufacturing work did not realize meaningful productivity gains until Henry Ford made the transition from craft approaches to a carefully designed and engineered assembly line.

All too often the next move in this argument is to immediately conclude “craft bad/engineered process good.” I doubt that Newport would support that conclusion but this short circuit occurs often enough that I want to slow down for a moment and focus on it.

Concluding “craft bad/engineered process good” is the wrong answer to the wrong question. The lesson to be drawn from the Henry Ford is not that Ford found the right answer, it is that he found a better question.

That better question was “How do we design a process that will produce consistent, quality results?” His answer, in a stable and predictable environment, was an engineered process operating within tight tolerances to produce standard products of uniform quality.

We do not operate in “a stable and predictable environment.” Nor are we expected “to produce standard products of uniform quality.” How do we begin to answer that design question given those constraints?

We don’t do it by copying Ford’s answer.

I continue to believe that developing new answers starts by thinking in terms of craft. Recognizing that the goal is no longer “standard products of uniform quality” is a first step. I’ve talked about it as balancing uniqueness and uniformity.

The harder question is how to think about process without falling into the trap of engineered rigidity. I think getting answers to that questions needs to start in the field, watching how effective knowledge workers practice and think about their craft. I would like to get something more concrete than the classic consultant’s response to any request for advice of “well, it depends…”

McGee’s Musings turns 18; still curious, still exploring

This experiment is now old enough to enlist. Pretty sure that wasn’t something I anticipated.

The blogging software I was using at the time asked for a tagline to describe the blog. I chose a quote from Dorothy Parker that I always liked and that seemed to fit the spirit of blogging at the time:

“The cure for boredom is curiosity. There is no cure for curiosity.” – Dorothy Parker

I found it an interesting bit of serendipity that the New York Times ran an op-ed on Sunday titled “Why Aren’t We Curious About the Things We Want to Be Curious About?.” The core argument is that:

Across evolutionary time, curious animals were more likely to survive because they learned about their environments; a forager that occasionally skipped a reliable feeding ground to explore might find an even better place to eat.…But it’s good to know about your environment even if it doesn’t promise a reward right now; knowledge may be useless today, but vital next week. Therefore, evolution has left us with a brain that can reward itself; satisfying curiosity feels pleasurable, so you explore the environment even when you don’t expect any concrete payoff.

The article offers insight into the mechanisms of curiosity, their payoffs, and a little bit of guidance about nudging curiosity into less frivolous paths.

It’s pretty clear to me that the environment we inhabit is increasingly in flux. Unsurprisingly, I’m in the school of thought that believes that curiosity about what is new and what is different is more relevant and important than ever. Hence, I continue to explore. I share traces of that exploring for two reasons. One, it forces me to make sense of what my curiosity dredges up. Two, it connects me to other explorers and their perspectives.

What’s the value of proven systems in a roll your own world?

I’ve often railed against the standard marketing trope of “here’s our proven system for solving problem X.” Proven systems pitches classify problems as simple to solve and, by implication, those with problems as either ignorant or lazy. My objection is that this offers little help for hard problems and we live in a world with lots of hard problems.

Suppose your interests lie in attacking hard problems? Call them wicked problems or management messes, these are the problems that constitute more of our agenda.

One answer is to acknowledge that answers to hard problems have to be custom crafted, with solutions tailored to the environment and the circumstances. Can we glean some value from the “proven systems” hawkers even as we recognize that our problems of interest don’t fit their premises?

MacGyver provides the essential strategy here. The point is to treat a proven system as design input to crafting a custom solution. To do this effectively, the first step is to reverse engineer the proven system. First, to understand the assumptions about the problem structure and environment driving the system design. Second, to extract the components and subsystems comprising the system. Third, to pattern match between the problem characteristics of the two systems—those of your problem and those built into the assumptions of the proven system. Fourth, to adapt and apply the subsystems that apply.

This approach depends on recognizing that you own the problem. That means rejecting an implicit premise of the proven systems perspective that you can transfer ownership and responsibility to the system.

Systems thinking and Improvement

A systems lens is one of the primary ways I seek to understand the world around me. No surprise, ten, that I’ve long been a fan of the work of Russell Ackoff. Here’s a short video of a talk by Ackoff on systems and improvement. He does two things here. One he provides a better description of a system than I typically do on my own. Two, he then shows why improvement programs in organizations generally disappoint because they fail to use that systems lens.

Well worth the fifteen minutes it will take you to find and watch.