Don’t Walk: Applying the Rules in a Volatile Environment

On days that I teach, I take the train into Chicago and then walk from Ogilvie Station up to the Loyola Watertower campus. Generally takes me about 30 minutes. Yesterday, as I was mulling over what to write here, I came to an intersection. The “Don’t Walk” sign was lit and several other pedestrians were waiting patiently. I looked both ways, saw that there was no oncoming traffic, and continued on my way.

It always strikes me as odd that Chicago pedestrians simply comply with the traffic signals and don’t adjust their behavior to the actual environment in the moment. I used to think it was simply because I learned to be an urban pedestrian in New York City, where getting from train station to office on foot was a blood sport.

I don’t think I can be accused of being a scofflaw; someone who is merely rebellious by nature. If anything, as an eldest child, I am a rule follower. Courtesy of my parents and a string of enlightened teachers, however, I also learned that rules are elements of larger systems. In good systems, there is a deeper logic; rules exist to advance the goals of the system.

One choice is to simply comply with the rules and assume that the goals of the system remain relevant and the design of the system matches the realities of its environment. In stable and slow-changing environments, that is a reasonable strategy. Waiting for the traffic signals to change doesn’t hurt, although it might slow the world down a little bit.

There is another choice, which is to look at the design logic driving whatever system you are engaged with. This is the dangerous path you set people on when you start teaching them how to program. Programs are the explicit rules for realizing the design goals of a bigger system.

The differences between a working computer program and a working organization are differences of degree not of kind. As you learn to see how rules, information, structure, and goals interact, you learn to see the commonality that unites systems across disparate environments. It can take time to work out the value and the limits of the analogies, but it gives you a path.

Things are the way they are because they got that way

I remember my parents as being light drinkers. One beer at a Saturday barbecue would be typical. I never thought too much about it, even as my peers began their introductions to alcohol.

Extended families became a larger element of my environment when we moved to St.Louis, where my mother’s siblings and their children all lived. Dad’s family was back East and weren’t part of my life. While it was never a specific topic of discussion, I eventually pieced together that my father’s move west was a very deliberate act. His two older brothers and his twin brother were all essentially functional alcoholics. Leaving that environment was his plan to avoid the same fate.

I think this must be one of the seeds of my sensitivity to context and the environment. The environment–social, organizational, physical–sets boundaries on what is easy and what is hard. And history shapes the environment.

Technology pretends to be ahistorical. We are here now and the future looks bright. There is nothing to be gained by wondering how we got here; press on.

Organizations are all about history. Jerry Weinberg was fond of reducing his insights into aphorisms or laws. There’s one he attributes to economist Ken Boulding;

Things are the way they are because they got that way

Understanding how things “got that way” is a necessary step to making things better. And that is true for organizations, technology, and their intersection.

[There’s a reason for the woodpecker but that is for another day]

Living the stories of astounding futures

My mom’s been gone for almost sixteen years now. I still marvel at how she managed to wrangle seven kids between the ages of 8 and 1. I recall one conversation about reading when my boys were young. I was the absolutely stereotypical bookworm. Getting my first library card at the age of 10 still ranks among my signal memories. On a recent visit to my home town, I actually stopped at the local library simply to thank the librarians for existing.

From time to time, my dad would grumble about getting my nose out of whatever book it was buried in and go outside. Mom, on the other hand, never once complained or pushed me to do something else. When I asked her about my relationship with books and why she sided with me rather than my dad she said,

You were compelled to read. I didn’t know what was driving you but I could see that it was something you had to do. I decided it was more important to let you follow your own curiosity than try to tell you what you ought to be doing.

I was pretty indiscriminate in what I would pick up. Early on, one vein that I started to mine was science fiction. I tore through the “age appropriate” material quickly and moved on to the grown up science fiction shelves in the library.

Muggles generally don’t “get” science fiction. But there is a core premise that has immense relevance in the world we’ve all grown up to live in. It has little to do with whether some author “predicted” cell phones or waterbeds or the internet. What science fiction makes you think about is the interaction between the relentless advance of technology and the equally relentless commitment to the status quo of groups and organizations. People are gonna people whether they travel by covered wagon or starship.

What science fiction encourages you to do is to think about how people will react in any kind of scenario. And, it gives you permission to imagine a much richer variety of possible scenarios beyond what history or contemporary society serve up.

There was a period in the 1980s, or so, when scenario planning was a popular technique in strategy circles. Turns out I had been studying scenario planning at the feet of much more accomplished story tellers than the strategy types could bring to the fight.

Technology change does trigger organizational change but the process is as human and messy as any other human system. Because it is fundamentally human, story is an essential entry point and vantage point.

Learning in a tool saturated world

Before my father became an engineer, he worked as a carpenter. When he worked on project around the house, it was a natural step to enlist his eldest as a helper. I was generally comfortable with basic tools by the time I left for college.

That offered an initial edge when I joined the tech crew in college. The interesting thing about tech crew in a university environment was that you couldn’t make any assumptions about prior knowledge. You had plenty of smart people but most equated learning with what went on in classrooms. What happened while you were helping to build or paint a set was work and was a break from class time. There were no teachers, just a handful of fellow students who got there before you did.

What you had was a classic blue collar apprentice environment hiding inside a competitive academic environment. After key safety lessons about working around power tools, you were expected to watch and learn from fellow students. You learned how to do the work by doing the work.

This, of course, was the way that most of humanity routinely learns. But it was out of sync with what most of us had practiced and absorbed as students up to that point.

That small initial edge my dad gave me led to important side effects. I was an apprentice, but an apprentice who could quickly be handed responsibilities to shepherd other apprentices. I was both teacher and student long before I appreciated that teaching was the fastest, and often best, way to learn. I learned how to protect myself from disaster before trying a new technique. Perhaps most fundamentally, I learned that not knowing was a temporary and correctable condition.

This last lesson might be most relevant in the technology saturated world we live in. The flow of new tools and technologies is continual. Learning to use what is new becomes a three step process. Protect yourself from disaster. Run the experiment. Incorporate the successful experiments into your routine. Repeat

Just because it’s cliched doesn’t make it bad advice

My time learning to be a stage manager contained my first lessons in managing something bigger than myself. If there are 40 people you can see dancing on stage, there were at least as many behind the scenes making it happen. Everyone has a very specific set of tasks to perform, it all has to sync up moment to moment, and it all has to serve a singular artistic vision.

This was during my university years, where I was usually at a rehearsal or work session when I should have been in class. Everyone in the group was a student with three exceptions. We paid for a costume designer, a choreographer, and a director. In my role, I worked with all three, but it was our director, Milt Lyon, who was the sources of the most lasting lessons.

Milt had been working with the Triangle Club for at least twenty years when I arrived. His job was to tease out the core of the artistic vision from the writers and composers and help the performers bring that to life on stage. Mine was to handle all of the mundane issues of time and space: rehearsal schedules, rehearsal rooms, copies of script updates, meeting schedules, agendas.

The details of the incident are lost to me but I had screwed something up that was throwing off the schedule and, therefore, messing up the plans and focus of a hundred other people. I was fumbling through an explanation of how we had gotten into this mess, which included the reasons for why it wasn’t actually my fault, when Milt held up his hand:


Milt was one of the three people on the planet who called me Jimmy.

“I’m not interested. Are we ready to start now? Good, then let’s get going.”

Afterwards, Milt did take a few minutes to talk me through ways to avoid the problem in the future.

Since then, I’ve acquired an expensive and extensive education in how complex organizations work. I’ve had business cards with C-level titles on them and budgets to match. But that moment remains one of the touchstones of my thinking. I’ve come to see it as one of the first moments where I saw what it meant to be a professional.

Are we clear on the goal?

Are we all in agreement about the goal?

Is there something in our way?

Deal with it.

Keep moving.

Eyes forward.

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 workDeveloping 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.”