Preparing to be bold in the moment

Vienna Opera Backstage, Austria

Avoiding risks can be a sneaky head game. I started McGee’s Musings as part of a class I had designed at the Kellogg School. The class routine created a rhythm for the blog that gradually led to maybe 1500 subscribers and a smidgen of internet visibility. But then I let it languish. I was in a new environment with different rhythms, there were fixes and improvements that I ought to make before I wrote the next post. Habit killers. Risk avoidance masquerading as good intentions.
The argument is that you must summon your courage, be bold, and face your fears and your risks.

Maybe.

But it might be easier to cheat; to arrange your circumstances and your environment so that boldness becomes the path of least resistance.

In my second year in college I was the stage manager for a large musical play, written and performed by fellow students. The group had hired a professional director from Off-Broadway. Tony was probably in his late thirties or early forties. I was twenty.

It was 7:30, the curtain was going up in 30 minutes for an invited audience to the final dress rehearsal before opening night. Behind the curtain, was what looked like chaos. Carpenters were putting the finishing touches on one set piece and repairing another that had broken. Electricians were on ladders tweaking the focus of one of the lights. Costume designers were fixing a hem. Tony was standing center stage with hammer in one hand, nails in the other, screaming that we weren’t going to be ready. I was trying to do my job which was to make sure that the curtain did go up on time. Without conscious thought I walked up to Tony; “Tony. You’re not helping. If the curtain doesn’t go up at 8, then you can fire me. Until then, get off of my stage.” Tony dropped the hammer, tossed the nails aside, and stormed off.

I was bold and the curtain went up on time, right?

The curtain did go up on time, but it’s a mistake to think that I was bold or brave. You can choose to describe it that way afterwards, but that misses something more important. I did what I did because it was my job. Said so right on the business card I didn’t have—stage manager. Ages of theater tradition backed me up. It was MY stage and it took no boldness to lay claim to it.

If bold action is called for, then strategy must design for it in advance. To know what behavior will be called for and to build that into the environment and the structures where the action will transpire. It is not enough to simply paint a picture of the desired future; the strategist must understand the journey well enough to prepare and equip the team for the obstacles that will arise. You can’t simply prepare for any and every contingency. Nor can you rely on an inventory of particular skills and knowledge, “just in case”.

The management challenge is to delve into this middle space of the journey. Pointing at the peak looming in the distance translates into breaking the journey down into daily treks, rest and replenishment stops, forays into the next leg of the terrain. Imagining the journey in that next level of detail is where you anticipate decisions that might have to be made and options to be weighed. Understanding the likely terrain and the possible options is where you prepare now to do what will look like bold then.

Reflections on reflection

When I was in high school, the most revelatory book I read was whatever I had just finished. Its insights were my insights and I shared them with whoever was in my vicinity. This annoyed my father for certain and likely most of my classmates, friends, and family.

As I acquired a bit more life experience to go with the words on the pages passing before my eyes, my assessments became more cautious. Any book can produce a moment of insight. What I’ve come to value is a book whose influence is more lasting and pervasive. This influence reveals itself as I find myself adopting new frames and pushing a title on my friends and colleagues. When a book gives me a new lens on the world and I find myself looking through it more routinely, I know that I’m on to something.

On that score “The Reflective Practitioner: How Professionals Think In Action” by the late Donald Schon ranks among my top ten. I stumbled on it in the late 1980s during the early days of my Ph.D. studies. The title caught my eye in Wordsworth, a bookstore that occupied a prominent spot in Harvard Square and in my household budget. It offered a label for what I was becoming and provided a bridge for a gulf I was trying to cross.

The essence of Schon’s argument is that professionals operate by building theories of practice of how their corner of the world works. Like good scientists they test their theories against the real world they operate in and on.
The best professionals do this explicitly and mindfully. They make the time to both do their work and to reflect on their work. Reflective practitioners acquire experience and actively engage in making sense of that experience.

This process allows two things. It offers a way to introduce new knowledge and ideas into practice. New ideas and theory become important when we aren’t satisfied with accepted practice. Second, it makes clear that what happens in practice determines whether new knowledge and ideas stick. Reflective practice is a way to achieve both/and possibilities instead of treating theory and practice as an either/or question.

This notion has become a unifying thread in my own work and practice since then. We generally get better at whatever we do through the accumulation of experience. Rather than simply accumulate experience, however, we are more effective if we develop parallel skill at actively making sense out of our experience.

From systems building to systems thinking

I once believed in systems. I believe in systems now. It’s what happened in between that I want to look at.

I started my career building information systems; after summer jobs as a programmers, I knew that I wanted to be a consultant. I didn’t understand what that meant, ignored wise advice about what I ought to do, and talked my way into a job with the consulting arm of Arthur Andersen & Co.—long before it morphed into Andersen Consulting and later Accenture.

I designed and built information systems that massaged accounting data and produced reports meant to lead to better management decisions. I became pretty adept at annoying my supervisors with questions about how my programs connected to the broader business. It’s possible that some of the information my programs produced may have contributed to marginally better analysis and decisions by some middle managers. I was absorbed with the intricacies of making computers do what I told them to do.

That led to an MBA on the theory that what I needed was to understand the big picture; how did all of the pieces fit together? If I wanted to build more effective information systems, I needed to understand business as a system. How did strategy and finance and operations interact? I jumped from the weeds to strategy and the CEO’s perspective. From there it was back out to the consulting world.

I now had the systems tools I needed to design solutions that would have real impact. The flaw in my brilliant plan was that the people I was designing and building systems for seemed to have little interest in actually changing how they worked or thought. I’m fundamentally a nerd so my solution was to go back to school again; clearly I had missed something in my previous studies. If the intended users of my systems insisted on being too dumb to recognize how clever my designs were then I needed to learn how to do better designs.

I started a Ph.D. program in management information systems. Fortunately, Ph.D. programs give you access to very clever people with lots of perspective. They began to gradually eliminate the stupid and replace it with some deeper insight. The first order analysis, of course, was that thinking of users as stupid wasn’t a winning strategy. I was young—younger anyway. The second order answer was to build a knowledge base in organizational theory. The quest since then has been to develop a better synthesis; exactly of what is an evolving target.

This isn’t a new quest. It’s often framed as an either/or choice between people and technology. A more intriguing path is one of both/and. That isn’t a new thought either. But it is worth a revisit.

Exploring the messy middle

Why is the middle ground between strategy and tactics so difficult to travel? Over the next month I will be writing about and around that question.

Trying to understand my successes and mistakes in this middle ground is the through line for much of my life. While I’ve chipped away at it, I haven’t done a sustained push to make sense of the journey or its trajectory. That kind of push needs some help, hence this exploratory visible effort.

What is this middle ground? In college I was part of a theater group that wrote a Broadway scale musical from scratch and staged it in the Spring. I was the production stage manager, which meant that I coordinated all rehearsals for the director and worked with the set designers, lighting designers, technical director, and musical director to make sure all of the pieces came together for opening night. I was also a student studying mathematics and taking a course about the math underneath managing complex projects.

Perfect opportunity.

I could take what I was learning in class, apply it directly to my extracurricular life, do less work, and get myself an easy A. You can guess where this ends. I squeaked out a C by admitting that I couldn’t figure out how to apply the technology to the creative chaos of producing an original show. And the curtain went up on opening night with the collective efforts of all of the cast and crew.

That was an early step on an exploration of how you mix people, processes, and technology to go from a germ of an idea to opening night. Opening night might involve actual curtains; it might also involve launching a new information system or an entirely new organization. What holds my attention is that middle space between the idea and its realization.

What I’ve learned is that there is a middle in this middle.

We know a lot about big ideas; we call it strategy in business and organizational settings.

We know a lot about the details of user interfaces, and writing code, and designing procedures, and arranging finances, and all of the tactics that go into a working organization.

In the middle, it gets fuzzy. As we move along that path from grand idea to final result, there is always an area of mysterious transition where we turn from grand thoughts to dirty work. We all know this. Some of us learn how to get across that transition; others seem trapped on one side or the other. Is there a way to eliminate or reduce the mystery and magic in the middle? This promises to be a messy but fruitful exploration. Stay tuned.

Review: WTF-What’s the Future?

Cover Image - WTF. What's the Future

WTF?: What’s the Future and Why It’s Up to Us.  Tim O’Reilly

Tim O’Reilly has had a backstage pass to the technology change we have been coping with for the past three decades. WTF is his effort to make sense of what he’s seen and offer some counsel about what it may mean for the next decades we’ll be living through. While some cynics and skeptics might view this as no more than O’Reilly’s attempt to hit the speaker’s circuit, there’s value here to those of us with a more restrictive view of the show. Can O’Reilly offer the rest of us valuable insights even if he may have been mostly a combination groupie/roadie for the more visible performers on the stage? My assessment? This is one smart roadie with insights worth paying attention to.

What makes WTF work is that O’Reilly is an unusual blend of techie, communicator, and entrepreneur. In ethnographic terms, he’s been a participant/observer throughout this unfolding process. Most of those reporting from the new territories are one or the other; they are participants either too busy or too biased to offer dispassionate analysis or they are observers too removed from the action to see the really interesting stuff.

One of the early battles was between open vs proprietary strategies. Eric Raymond labeled this as a choice between the Cathedral and the Bazaar. Today it is evolving into the emergence of networked platforms as one of the next arenas being contested. O’Reilly frames this continuing evolution as a requirement to differentiate between value creation and value capture. Organizations that focus on capturing all the value that they create do not prosper as abundantly as those who focus principally on value creation. Those who focus on playing positive-sum games do better—both for themselves and for the rest of us—than those who choose to play zero-sum games. This is a countercultural if not a counterintuitive strategy. The rhetoric of Wall Street and VCs is anchored in a zero-sum mentality; the winners in this new world, however, are playing a deeper game.

What I find especially intriguing about this line of thought is how it makes strategy and organizational design tightly coupled and how it then shrinks the differences between how things work inside the organization and how they work outside. One of the curiosities of large, traditional, organizations is that they cling to the worst practices of centrally planned and managed economies internally as they celebrate the value of the free market outside their walls.

At heart, what O’Reilly is arguing in WTF is not only that this is a hypocritical debate but that it has become a dangerous mindset as well. As he puts it “Amazon Web Services was the answer to a problem in organizational design.” O’Reilly reports on an interview with Jeff Bezos talking through the origins of AWS;

“Four years ago is when it started, and we had enough complexity inside Amazon that we were finding we were spending too much time on fine-grained coordination between our network engineering groups and our applications programming groups. Basically what we decided to do is build a [set of APIs] between those two layers so that you could just do coarse-grained coordination between those two groups.”

Working through this logic is anything but intuitive. Learning how to do so consistently may be the central skill for thriving, or possibly even surviving, in what is to come. O’Reilly has come in for some criticism in his perspective on Uber and its evolving working relationships with its drivers. I think the criticism is overblown and misses the nuance that O’Reilly is attempting to call attention to.

This goes to the heart of what WTF tries to do. Looking at a sample of successes, failures, and yet to be determined experiments, O’Reilly is trying to understand the strategic logic of the world we are brining into existence in a way that would let more of us contribute to that logic. I’m less interested in whether he has worked out the answers than I am in learning how to think along similar lines.

Strategy and organizational design in a crowded ecosystem

When I teach organizational design, I start with the observation that organizations survive because they’ve struck a balance with their environment. That environment is now an ecosystem teeming with other organizations seeking their own balance. One consequence is that you cannot separate organizational design from strategy. A second is that both must operate from a deeper understanding of the ecosystem.

Ecosystem has become a popular way to think about the competitive environment. Some of this is simply evolving language preferences; terms go in and out of style. But there is a deeper and more significant rationale for this evolution in terminology. The appeal behind talking about ecosystems lies in the adage that “everything connects to everything else.” While that has always been true, it wasn’t terribly relevant until recently; “everything” didn’t add up to very much. For a long time, organizations had to only pay attention to a well-defined set of customers, a small handful of suppliers, a small handful of competitors, and a handful of other factors that impinged on their freedom to act.

Wouldn’t it be nice to have that sort of environment today? Not only are there more players to consider in every category, those players bump up against one another more tightly. It’s easy to cross an empty room to get to the bar; in a crowded cocktail party it can be hard to move just a couple of feet. You need to think and manage differently if you need to cross that crowded room. To further complicate things our hypothetical room is surrounded by a balcony full of people shouting conflicting, contradictory, yet potentially essential advice.

The temptation is to put your head down and bull your way through the crowd toward your destination. If you’re a bull and you’re in a china shop, this strategy will get you to the other side. You might also think it acceptable that the floor is now littered with broken china. On the other hand, if we are indeed in an ecosystem rather than a china shop, then we trample at our own risk and as risk to others in the broader system. Are we trampling over a future food source? Predators? Poison? Future mates? Risks to others might be ignored; but many risks are to our own future existence.

It’s a popular notion that today’s environment calls for innovators to move fast and break things. If that environment is as tightly packed as today’s actually is, what may end up broken is the ecosystem itself. That’s a contest with no winners.

Smart people doing smarter work

For today’s organizations, success depends on the effective care, feeding, and management of smart people. This is not the same thing as managing the ideas these smart people produce, which is where too many organizations get stuck. Ideas may be the basic output of the knowledge economy but you can’t manage by focusing on these outputs.

In an industrial economy, you focus on outputs and the game is to optimize the faithful replication of outputs. Organizations lavish attention on standardization, process, uniformity, and predictability to produce identical outputs. It is tempting to equate ideas with products because we know how to do and manage replication. Software behemoths like Microsoft were built on taking one expensive first copy and figuring out how to distribute that copy as far and wide as possible. There was so much money to be made in the replication and distribution of the copies that there was little need to think, much less worry, about the economics of creating copy number one.

Professional service firms, advertising agencies, and other knowledge intensive organizations pay more attention to the economic importance of ideas. But their management focus and attention ignores the hard problem of the gestation and delivery of new ideas. Instead they apply the techniques and mindsets of industrial models to standardizing the irrelevant. They industrialize support processes and functions. In the best cases, they make an effort to streamline and support the work of the creative core. But their principal managerial strategy is what Tom Davenport accurately characterized as “hire smart people and leave them alone.”

How do we systematically enable smart people to do smarter work? Where are the effective leverage points if industrial models aren’t the answer? First, it helps to look at individual knowledge workers and groups separately. Second, we need to focus on effectiveness over efficiency.

I’ve written elsewhere about the challenges of looking at knowledge work–Managing the visibility of knowledge work – McGee’s Musings. An excellent recent example of this kind of observation of work practice and its value comes in a recent blog post by author Steven Johnson, “Why Writing Books Is More Than Processing Words – Workflow – Medium,” where Johnson reflects on how he approaches his work. To improve the effectiveness of knowledge work we have to go into the wild and study what practitioners are actually doing.

What I’m suggesting is the value of “reflective practice.” Donald Schön, late of MIT. argued that management–and knowledge work–is characterized by the need for practitioners to formulate and build theories of their work and their environment as an ongoing component of doing their work. “Practice” and “reflection” are both necessary to becoming effective in complex knowledge work settings.

This is more demanding than simply thinking about knowledge work in terms of productivity and efficiency. It asks you to think at multiple levels of analysis in parallel; to be adept at both cognition and meta-cognition. Most damning, perhaps, is that this course of inquiry appears to be overly abstract and academic to most managers.

We need to build better insight into how knowledge work gets done and how smart people are attempting to systematically improve their practices. That means going into the wild and studying what practitioners–effective and ineffective–are actually doing. For knowledge intensive organizations, this is an effort that can potentially yield substantial gains in knowledge work effectiveness.

Free and cheap technology is killing organizational effectiveness

Technologies supporting knowledge work are deceptive, especially for knowledge work shared among groups and teams. The ease of getting started obscures the challenge of learning to be effective. We focus on the details of particular features and functions at the expense of ignoring the cognitive challenges of deep thought and collaborative work.

I’ve been participating in a Slack team with a loose group of colleagues scattered across two continents. I was off the grid for about two weeks and found myself lost when I returned to the conversation that had continued in my absence. My first hypothesis was that Slack was the culprit and that some magically better UX would eliminate the problem. Slack, of itself, isn’t the problem but it is emblematic of the deeper issue that should be tackled.

In trades and crafts, the most experienced and effective practitioners would never invest in cheap tools or materials. Learning to use those tools and materials effectively is the work of years of deliberate practice. The strategy shouldn’t be any different if you are manipulating ideas than if you were manipulating clay. But the marketing and deployment of software rejects these hard won lessons. Software fame and fortune is built on promises of simplicity and ease of use, where ease of use has been interpreted as ease of getting started and minimally productive. We’ve all become facile with learning the first 5% of new tools and services. We’ve been led to believe or we pretend that this is enough. Few among us are prepared to invest in pushing further. Fewer still belong to organizations willing to support this investment.

The payoff from even this 5% has long been sufficient in terms of personal and organizational impact. We’re reaching the limits of the return from this minimalist strategy–it’s even more acute when we shift focus from individual knowledge workers to teams and groups.

To go beyond the 5% we need to modify our expectations and approaches about how we blend powerful tools with powerful practices. We need to adopt the attitudes of those who think in terms of craft and expert practice. Organizationally, we need to provide the time, space, and support to design and invent this new craft.

My hypothesis is that there are models to look to and borrow from. In particular, I believe that the world of software development has the longest and richest experience of dealing with the individual and group production of the thought products of the knowledge economy. Further, there are individual expert knowledge work craftspeople in various other fields; their tools and practices are also worth understanding and reverse engineering.

I don’t have this all figured out yet. Nonetheless, I ‘d like to get a new conversation going about how to improve on this train of thought. Where are good places to look?

Repeatable Processes and Magic Boxes

There is a trap hidden in most efforts to create repeatable processes and systems that try to guarantee predictable results in doing knowledge work. To avoid that trap, you must learn to recognize and manage the magic box.

The promise of repeatable processes is to identify, design, and sequence all of the activities that go into producing a specified output. It is the core of industrial logic. For industrial logic to turn out uniform results with predictable quality, craft must be transformed into proven systems and repeatable processes. Variation must be rooted out and eliminated. To do this, all of the design thinking necessary to produce the product must be extracted from the process and completed before any further work can be done. You get the prototype product done right and then you churn out a million replicas. For this strategy to work, all of the magic must take place before the first process step ever occurs.

Knowledge work cannot be forced into an industrial straightjacket. The essence of knowledge work is to produce a bespoke result. I have no interest in the strategy McKinsey developed for its last client; I want the strategy that applies to my unique situation. I do not need the accounting system tailored to GM’s business; I need an accounting system matched to my organization. And therein lies the rub. I may want a bespoke accounting system, but I’m not willing to pay for it. Forty years ago, in fact, I had to pay for one anyway because off-the-shelf accounting software didn’t exist. All software development was custom; as was all consulting work.

Consultants and software developers are not stupid people. They could see that, despite the necessity of producing a unique product at the end, much of their work had elements of the routine and predictable. To increase the quality of their work, to train new staff, to improve their economics, and to better market their cumulative experience, knowledge work organizations worked to transform their practices into repeatable processes and methods. New industries were created as software developers redesigned their code to segregate what needed to be customized from what constituted a common core.

In this effort to apply industrial logic to what was fundamentally creative work, most organizations were sloppy or short-sighted about managing what was a fundamental tension between industry and craft. What was big, and shiny, and marketable was the packaging of cumulative experience into a consulting methodology, or a software development process, or a customizable software product.

What could not be eliminated, however, was the essential craft work necessary to employ the methodology or to customize the product. What happened was that this craft work was pushed into a box somewhere on the process map or into a line item in the standard workplan.

This is the “magic box.” Whatever its name or label, it is the step where the necessary creative work takes place. This is work that cannot be done until the moment arrives.

Why does it matter to identify which boxes in the process require magic? Because they determine the quality of the final result. The other boxes only matter to the extent that they set you up to succeed in the magic box.

How do you recognize the your are dealing with a magic box? What are the clues that differentiate it from among all the other boxes? Sometimes you must approach this by process of elimination; many boxes—“conduct field interviews”, for example—are more easily identified as not possibly containing magic. As for positive identifying features, look for language that suggests design thinking steps or analysis that isn’t tightly specified. “Develop market segmentation approach”, or “design chart of accounts” are examples of possible magic boxes.

Understanding which boxes are which in a process is essential to managing the process effectively. Regular boxes can be estimated and managed more tightly than magic boxes. Data collection, for example, is usually straightforward; analyzing it, requires more flexibility and adaptability. Collapsing these related, but distinct, activities into a single step would be a poor project management decision. Just because creative work cannot be controlled in the same predictable way as industrial work does not relieve managers of their responsibility to make effective use of limited resources. Being clear and isolating the magic boxes from the ordinary ones is essential to making those resource deployment questions.

Repeatable processes are often marketed and sold as “proven approaches” that eliminate the trial and error that the uninitiated risk if they strike out on their own. This has enough truth to be dangerous. Traveling in new terrain is safer with an experienced guide. The guide may help you get to where the underlying geology is promising, but cannot guarantee that you will strike gold. Honest guides will emphasize the distinction. But it is a distinction that is only meaningful to those who can hear it.

Trial and error is an unavoidable feature of creation. A serendipitous error is often the seed of a creative solution. Understanding where the magic needs to occur helps you distinguish between unproductive and potentially productive error. Unproductive error is an opportunity for learning and process improvement; it should be carefully reined in. Potentially productive error must be permitted and encouraged. That can only be done effectively by understanding where the magic needs to occur.

Some related links: