Learning to fail

I grew up in the Midwest. It is as flat as advertised. Snow meant days off from school, snowball fights, and snow forts. Mountains were something I visited in the summer. That they sometimes had snow on top was of photographic interest only.

Life brought me to the East Coast and children brought me to ski lessons in my 40s. When I was 48, my youngest took up snowboarding and I decided to follow along. You don’t learn to ski or snowboard in a classroom; you do it on the slopes. So, you fall down a lot. Then you fall down less. What makes it work is instant feedback. That’s what good instructors offer. One of the best pieces of feedback I got was to accept that a snowboard run was nothing more than a connected series of controlled recoveries.

If you weren’t on the edge (figuratively and literally) of falling down you weren’t doing it as well as you could. Learning and doing were inseparable.

The world of efficiency pretends that you can separate learning and doing. If you control enough of the variables, you can get away with this strategy for chunks of time. If you stay on the bunny slopes, you can control the variables. But only at the expense of learning. If you avoid the edges, you never get better.

You can choose to stay away from the edges. The problem is that the edges keep moving. Often in your direction, despite your best efforts. Better to accept the world as it is and develop ways to operate with that reality.

Effectiveness is the shorthand I’ve adopted for this spot. More than anything else, it depends on accepting that you can’t separate learning and doing. It’s an accident of history that we’ve been able to pretend otherwise.

Sure, you can find guardrails while your doing is clumsy. But you have to be seeking out the edges where things get scary. The best way to manage the scary is to find others looking for the edges.

Our edges and our comfort zones never align. Collectively we know more and can do more than any one of us can individually.

Effectiveness depends on community

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

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

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

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

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

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

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

Making Art Happen

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

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

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

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

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

Looking outward

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

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

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

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

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

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

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

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

Book Smart and People Stupid

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

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

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

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

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

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

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

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

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

Asking better questions

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

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

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

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

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

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

Inventing Sails

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

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

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

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

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

Things you can’t teach

In high school, our younger son rowed crew. More specifically he was the coxswain charged with managing and navigating the shell with eight rowers in front of him. It was his first race ever after several weeks of learning the basics.

We drove to Toledo to watch the regatta. Not only was Derek a novice rower, we were novice rowing parents. We found our way to the river and, with the help of other parents, figured out which boat was Derek’s as it proceeded along the 2000 meter course. This was a “head” race, which meant that the boats were racing against the clock rather than against each other. You could see boats strung along the course all rowing furiously.

As Derek’s boat passed by at the 1500 meter mark they came up on a buoy marking the course in the river. The rower in seat 2 caught the edge of the buoy with his oar, popping the oar out of its oarlock, and stopping the boat dead in the water. Somehow, Derek and the rowers restarted the boat, now with only seven oars working, and finished the race. Working our way down to the finish, we learned that the boat had managed to finish in third place. The rower in seat 2 eventually needed ten stitches in his forearm but the crew was thrilled with the results of their first ever race.

After the race, I was talking with another dad, whose son was a couple of years older. Kris’s comment has stuck with me;

“We can teach Derek not to hit a buoy. What we can’t teach is the presence of mind to settle everyone down, restart the boat, and finish the race.”

A few years later, that boat won a national championship.

I sometimes think that effectiveness hinges on understanding things you can learn but can’t teach.

Solve the Right Problem

I’ve spent a lot of time in and around theaters, most of it behind the scenes. Everything you do is about the experience you want to evoke from the audience.

There’s no point to paint the back of a set.

If the audience can’t see it, it doesn’t exist. You often spend a good bit of time figuring out “sight lines.” Can everyone in the audience see what you want them to see? Not see what you want to conceal?

This is at the heart of learning to be effective. What is the end effect you want to accomplish.

I went to business school long enough ago that Fed Ex was still a relatively new company. We had a case study in our marketing class about the rollout of a new service called the Courier Pak (Yes, this was a long time ago).

Someone in the class thought it would be a clever idea to send a Courier Pak to our marketing professor. It would contain items from earlier case studies. We went to the local Fed Ex office to arrange to send the package and have it delivered during the next day’s class session.

The manager of the local Fed Ex office was a very smart person. Rather than send the package through the Fed Ex system and risk a late delivery, they stored the package in the safe overnight and delivered it personally to class the next day. We got our joke and Fed Ex protected its image. Actually sending the package was an unnecessary risk.

The first step is always to work out what the problem actually is.

Playing a bigger game

Back in the mid-1980s I was running an internal project for the consulting arm of Arthur Andersen & Co, before it split off to morph into Andersen Consulting and then Accenture. We were creating a system development center to provide all of the tools and facilities to support large scale systems implementation projects. This was in the day when serious development was done on mainframe computers and setting up an environment for productive work could chew up a lot of time and fees without adding value for Andersen or its clients. The centers turned out to be a successful venture for several years.

Setting up the first one was a large scale project management problem in its own right. There were some challenges in creating a work plan and work breakdown structure for something that hadn’t been done before, but nothing out of the ordinary.

One odd conversation from that effort still sticks with me. It was Monday morning, well before 8AM, and I was parked in a partner’s office. I had learned that the only way to guarantee Mel’s attention was to catch him before he got wrapped up in anything else. He rolled in a short time later and the conversation unfolded like this:

Me: I’ve been going over the project plans for the development center. We’re on track, but I’m worried about the scheduled install of the mainframe next month.

Mel: So?

Me: Do we deal with it now or wait until it’s a full blown crisis?

Mel: Wait until it’s a crisis

You need to understand that Mel was an excellent manager and leader.

I was greatly puzzled.

Isn’t management supposed to be about anticipating problems and dealing with them before they get out of hand?

Working out why Mel was right and I was missing a bigger picture took me back to graduate school and eventually a Ph.D. in organizational design and innovation. It isn’t enough to have the right answer for the problem at hand. The right answer, deployed at the right time, gives you the opportunity to continue to play the game. Eventually, it may give you the opportunity to shape the game to make it a better game.