From Business Case to Enlistment Pitch

I’m a fan of case studies–both as a teaching tool and a research tool. They’re often disparaged. And caricatured. I certainly had my own reservations when I first encountered them. Why couldn’t somebody just lay out the problem and get on with solving it? What was the point of all the arguments and background and history and politics?

As I’ve written about before, I was eventually invited into the process and became a case writer. Now I was inside the mess and searching for the threads I could weave into something coherent. What had seemed unnecessarily complex as a student was a deliberately crafted simplification of the actual situation.

There’s an old maxim that the best way to learn a subject is to teach it. Writing stories about it is a close second.

In organizational settings becoming a competent performer is a process of learning the important stories. In most organizations that was largely an oral tradition. It was also an oral tradition that largely took care of itself. Most of us could sit back and gather round the watercolor while older and wiser heads clued us in to what was important and what was passing fancy.

That’s not so true anymore. Organizational and environmental change continues to accelerate. The people who might have the perspective to recognize and craft the relevant stories may already be gone or at the tail end of shortening tenures. What was once an organic outgrowth of routine organizational activity now has to be recast as an intentional and designed practice.

I think it has also become a more democratic and decentralized practice. In effect, we must all become case writers about our organizational environments. Resources and power flow to those who can weave the most compelling stories.

It can be tempting to interpret this as an indicator of organizational decay. A better view is that the most coherent stories warrant the organization’s resources. Learning to craft stories that are the right balance of threat and opportunity, tradition and innovation, and process and people becomes the new form of a compelling business case. The business case evolves from being a recitation of facts and figures to a story that enlists the right team of rivals.

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.

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…”

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.

Matching tool to task: mindmaps and project design

I’m fundamentally lazy so I’m always looking for tools to simplify whatever task I’m trying to accomplish. I’m currently teaching a course in project management and we’re working through how to build good project plans. In project management circles, there seems to be an infinite set of options for software tools to support project execution. Tool support for earlier stages receives less attention.

Most project management tools presume that you already have a plan to manage; how you create that plan is an exercise left to the reader. The tools treat the capture of phases and tasks as a data entry problem not a creative one. I see a project plan as an outline of tasks arranged and organized into a sensible order.

Creating that sensible order, however, is not an orderly process. It’s a thinking and writing task that of necessity proceeds in fits and starts, where order emerges only gradually. You don’t write a project plan starting at step one and marching along to step n anymore than you write a novel by starting with “It was a dark and stormy night…” and plowing ahead.

My preferred tool for the creative stage of project design and planning is a mindmap. Back in the day, I drew the initial maps by hand. Today, we’ve got software tools to make the process of creating and evolving plans smoother. I work primarily on Macs these days; my tools of choice include Scapple, Xmind, and MindManager.

There are plenty of other choices on every platform. Any of them is better than jumping straight into a tool built to manage project execution. And any of them is better than limiting yourself to a word processor or text editor.

I don’t worry about whether I am following the “rules of mindmapping” or have found the one perfect mindmapping tool. The key payoff is that I am using a tool whose fundamental design principles match the problem I am trying to solve.