McGee's Musings

Questions with power

“Julie! It’s 10th grade algebra!”

We were sitting in an MBA classroom along with the rest of our section and Peter, our professor explaining how he had derived a particular economic formula. Julie was stuck and Peter had walked through the equation for the 3rd time when I burst out with my unsolicited comment.

Julie had the flash of understanding that had escaped her and I patted myself on the back for my clever intervention. Until the women in the class rebuked me for my clearly sexist and misogynistic attitude and insensitivity to Julie’s plight. The fact that Julie and I were friends, that I knew Julie majored in mathematics in college, and that I knew my comment was the fastest way to break her out of her confusion were all for naught.

For someone who claims to be a smart guy, I can be a slow learner.

The beauty of mathematics and technology is that not only are there right answers but that any question is appropriate at any time. Throw people and organizations–that is, people in groups–into the mix and simplicity is gone.

In technical settings, facts have no feelings and no question is ever out of bounds. In organizational settings, some of the objects you would like to treat as objective facts are other people with their own feelings and agendas. Questions don’t simply elicit data, they provoke reactions. Learning to be human includes many lessons on the limits of how and when you can pose questions.

For most of us, most of the time, it is enough to learn the boundaries and opt to stay within the lines. If you want to change organizations, however, you have to learn how to set up and sequence your questions to provoke the responses and the reactions you are seeking.

Looking for the machinery behind the magic

stage manager at work Developing an interest in the interplay between technology and organizations isn’t something you know is going to happen when you’re in middle school. There’s no teacher or coach to emulate. There’s no hero’s quest to set out on. But there have to be roots.

One of the constant elements in my life has been live theater. Books come from some magical place and appear on a shelf. TV shows and movies arrive from somewhere else, appear for a brief time on the screen, and disappear.

When the curtain opens on a play, there are real people before you on the stage. They wander off into some hidden place and reappear moments later. Perhaps you catch a glimpse of someone in the wings and wonder what they are up to. If you are a curious sort, you start to look for how to get back into those hidden places.

The conventional route is to aspire to be one of those people performing on the stage. Another path is to find work in the wings, to learn how the magic gets put together. Which was the path I chose. I started working in various backstage roles in high school and continued on in to college. I built and moved sets, I hung and focused lights, I searched out and managed the props the actors used on stage. Much of this work took place while the performers rehearsed. During a performance, however, while the actors delivered their lines on the stage there was a crew in the wings making everything else happen on cue.

All of that activity was coordinated by one person with a three-ring binder in front of them and a headset covering one ear–the stage manager. The stage manager never seemed to actually do anything expect read the binder and talk with other people wearing headsets. But nothing happened until the stage manager gave the order.

Claire was the stage manager I apprenticed myself to to learn the craft. She taught me how all the pieces came together to create the magic that the audience experienced from their seats. How the technology that moved sets, illuminated actors, and amplified their lines was woven together in support of their performances and how all of that was focused on creating a specific emotional experience for the people sitting in the audience.

The magic depended foremost on the talent and craft of the performers. Done well, all the other elements of a production amplify the magic. Done poorly, any element can destroy it.

The seed that this planted was a hint of how the whole was greater than the sum of the parts. Watching magic from the audience was entertaining. Putting it together night after night was empowering and humbling.

Magic doesn’t happen. It gets designed and then it gets made. How can you not want to learn more?

Keep it simple is still an excellent strategy

My fascination with the space between technology and organization is something that grew slowly. When I went back to school to get an MBA, I fell into the group that understood the quantitative and structured material. I had spent the previous years designing and writing programs to count things up and calculate answers. Half the curriculum made sense.

The other half–about markets and organizations and people–often bordered on mystifying. But mysterious can also be enticing. The mystery eventually brought me back to school for the third time. I still wanted to understand how to take advantage of technology but the answers were buried in the intricacies of humans in organizations.

One of the things you learn dealing with technology is that technology does only and exactly what it’s told to do. When technology behaves in unexpected ways, then there’s a mistake in your programming. You have to examine what’s going on around you as you look for clues and never forget that you are also a key part of environment your are exploring.

This is an interesting perspective to bring over to the task of understanding organizations. While you’re engaged in deepening your grasp on how organizations work in the abstract, you are also embedded in a complex organization environment.

While you are trying to acquire the tools and concepts to make sense of structure and power and leadership, you are simultaneously engaged in a live-fire exercise with the institution you are a tiny piece of.

I recall a conversation with one of my thesis advisors about a fairly nasty tenure fight that was going on in her department. Rather than get sucked into a Machiavellian swirl of intrigue, her option was to be very clear and explicit on her plans and objectives and then do exactly what she said.

Simple and classic advice.

One of the things you learn with technology is to look for simplicity. There’s plenty of sources of complexity. Your job is to not add to the problem. Combine technology and organization and you’re now in the realm of combinatorial complexity. Don’t make things worse by trying to be clever. Be predictable.

From old expertise to new expertise

When my family moved back to St. Louis in 1964, our family of seven kids was reunited with another 24 first cousins. The 31 of us were spread across four families and separated by only a few miles. We saw a good bit of each other over the years. My uncles were bricklayers and electricians. My aunts had been nurses before they became mothers and housewives. Family and church and community were core.

Not only am I going to the top Catholic school in the city, I am planning on going to college and am about to leave for Princeton, a school so fancy and rarified that we all knew of it. My cousins were mystified that I would pursue such an exotic path. Why go to college at all when you could get a good job now? If you insisted on continuing with school, why not go to St. Louis University? It was a good Jesuit school and then you could become a teacher and get on with the important work of raising a family.

Maybe theirs was the better plan.

I stayed with the student route. That strategy was about doing well and going deep. Each lesson completed led to another of more subtlety and complexity. There’s a logic to this path just as there’s a logic to the path my cousins were on. But that logic is implicit. Whatever path you are on, there is an assumption that you’re absorbed the essential features of the path by osmosis from the environment you grew up in.

My environment contained nothing to osmose. I had no role models to look to, other than what I could glean from my teachers. They knew little of my background. All they could see was that I did well within the walls of their disciplines. My parents knew little of what went on inside my classes. My grades were just fine; no problems meant no need to intervene.

The structure of schools and education was organized into silos–it generally still is. Everyone stayed in their lane. Progress was a function of racing ahead as far and as fast within a given lane as possible. But the notion of staying in your lane was largely an implicit assumption. You knew that was what to do because you had already absorbed it from those who had gone before you.

I didn’t know that.

I didn’t know that the game was to crank through the syllabus and only the syllabus. I didn’t know that exploring connections and linkages between and across courses and disciplines was an activity reserved to designated specialists. I didn’t know that you weren’t supposed to pick up books that weren’t on the syllabus and wonder what they had to say about what you were learning elsewhere.

Doing these things upsets the power balance. You aren’t supposed to peek behind the curtain to see how the show is put together. You aren’t supposed to recognize that the curtain is even there.

All of those restrictions on what you are supposed to do make sense in a stable world. If the road is straight and clear, then staying in your lane is the fastest way to get to your destination.

We don’t live in that universe anymore. Deep expertise and specialization lose their power if you have to start building new lanes and new roads. If you’ve got power in the current environment, this kind of change is a potentially existential threat. The specifics of your expertise and specialization have been challenged and potentially undermined. Survival now depends on how readily your old expertise lets you build the expertise you need now. We all have to learn to look behind the curtain and build a new base.

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 image Start 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.