Rebalancing Planning and Doing: Seeking Knowledge Work Effectiveness

When I was first learning to be a project manager one of the mantras drummed into me was “plan the work, work the plan.” Hidden in this advice was a distinction between planning and doing. Today, we are immersed in doing; managing has been pushed to the margins. “Plan the work, work the plan” has shrunk to “work, work.”

Cal Newport, in his most recent book A World Without Email: Reimagining Work in an Age of Communication Overload, argues the case that email is the culprit. More specifically, the work style promoted and encouraged by email and other forms of instant communications. He labels this the Hyperactive Hive Mind, 

A workflow centered around ongoing conversation fueled by unstructured and unscheduled messages delivered through digital communication tools like email and instant messenger services.

Tom Davenport has often quipped that the default management strategy for knowledge workers is to “hire smart people and leave them alone.” This strategy can work if most knowledge work is independent; if your model of knowledge work is the individual data scientist, college professor, or computer programmer. 

Organizations, however, don’t exist to tackle problems that individuals can handle. They exist for problems whose scale and complexity exceed the capacity of any individual. We understand that for problems like churning out automobiles, breakfast cereals, or insurance policies. For those problems, organizations have learned to spend time to design processes that work at scale, spend time to deploy those processes, and then run those processes at scale. Running those processes at scale requires designing in the instrumentation and measurement to monitor and maintain compliance with the process. There is planning followed by doing.

Newport’s thesis is that email (and other channels of instant communication) disrupts this balance of planning and doing. The immediacy of message and response rewards one set of behaviors while concealing important costs.

This is where Newport’s and Davenport’s perspectives intersect. While we were deploying email and its cousins throughout the organization, we were also leaving all those smart people alone to figure things out on their own. We amped up the doing and left each knowledge worker to their own devices to do whatever planning seemed appropriate. 

While Newport is an academic computer scientist, he does manage to find his way to Peter Drucker’s work. Newport, Davenport, Drucker, and pretty much anyone else who’s thought about it, identify knowledge worker productivity as the problem to solve for modern organizations. Newport, however, does miss this observation from Drucker;

Whenever we have looked at any job – no matter how many thousands of years it has been performed – we have found that the traditional tools are wrong for the task

Email may not be thousands of years old, but it is the wrong tool for many tasks. At least in the way it is typically used in most organizations. 

The second half of Newport’s book works through several good approaches for attacking the problems he lays out so well. While some of his strategies can be applied unilaterally, most are premised on no longer leaving smart people alone. 

To achieve better overall outcomes, organizations need to rebalance planning and doing with respect to knowledge work. This is no longer a task that can be left to the individual knowledge worker. That leaves us trapped in a world of productivity hacks and the search for the magic shiny tool. We’ve all seen that that doesn’t work. Newport adds stronger evidence for why that approach can’t work and pointers on where to go next. The first step is to elevate the conversation to the organizational level; to put the topic on the agenda of those with the power to drive change. 

Planning to be Creative

When I was a very junior consultant, we were coached that there was one client question you were neither expected or allowed to answer, “how much is this going to cost?” A few years later, in the midst of getting my MBA, the one question you were trained to ask and answer was “how much is this going to cost?” Lately, I’ve been thinking about how much of my career has been spent caught between these two pieces of conflicting advice.

Nailing down answers to that question is a matter of nailing down assumptions. What materials from what suppliers? How many customers in each market? What’s the going rate for good sales reps? All reasonable questions; they all depend on knowing what you are doing. 

They are also generally impossible to answer when you don’t. Pretending to more knowledge or foresight than you have isn’t a recommended approach. As an individual manager, what do you do when faced with this dilemma? You’re being asked for answers to questions you are still trying to formulate. How do you work at articulating outcomes to drive planning when your fuzzy view of outcomes is what you are trying to address?

Too often, the default answer is to accept the brashest claim to knowledge in the meeting. “I have the answer” wins out over “let’s explore and see what we can learn.” We need to replace that default with approaches more likely to surface answers that we couldn’t know beforehand but outstrip the obvious, safe, and, ultimately, disappointing answers limited by what we already know.

You still have a project management task; organizations do not have unlimited resources even when the questions are open-ended. You are not simply executing, you’re also doing field research. The project management task is to thread a needle between systematically managing effort, tasks, and resources and what the phenomena in the field are revealing about how to adjust and redirect those resources and tasks. 

This marriage of exploration and execution is what agile methods are seeking in the realm of systems development. But the strategy extends to any setting where the destination has to be discovered or invented. With apologies to Gene Kranz, failure is always an option. It just shouldn’t be the only one.

The Promise of the Middle: Improving Knowledge Work Practices

Two years ago, I stumbled across Sonke Ahrens’ slim volume, How to Take Smart Notes: One Simple Technique to Boost Writing, Learning and Thinking – for Students, Academics and Nonfiction Book Writers. As a matter of practice, I am always on the lookout for potentially useful new ideas. The price of a book is a trivial cost and I only invest my time for as long as I’m learning something useful. I posted my review in March of 2019 [Unexpected Aha Moments \- Review \- How to Take Smart Notes \- McGee’s Musings). This is a bit of an interim progress report, although it feels more like a lament on just how hard change continues to be. Andy Matuschak’s recent observation that Note\-writing practices are generally ineffective hits way too close to home. 

Carving out an approach

Advice is always forward looking. The pretense is that you are starting from scratch. The reality for most of us is that we start somewhere in the middle. The problems of dealing with your existing bad habits and your existing body of work are left as an exercise for the reader.

One option is to pretend that you are starting from scratch. Ignore whatever artifacts and work in progress you’ve created to this point as well as whatever practices you’ve adopted. Start fresh with whatever your next project happens to be. Follow the proffered advice, practice new techniques, create new work products.

A second option—one that turns out to be a trap—is to believe that you need to fix or repair your history before you can move forward. It’s a trap I’ve fallen into. 

A middle approach that has evolved over time is to think of a knowledge work environment as a property that needs regular maintenance and remodeling plus occasional renovation. You do prefer to work with the materials already at hand, introducing new materials as needed. It’s also an environment that must support routine work; historic preservation is not the goal. 

Artifacts and Activities

My training and experience push me in the direction of organizing around projects and deliverables. I’ve begun reconsidering that (e.g., Deliverables and the downside of working backwards \- McGee’s Musings) and working toward a more nuanced view of knowledge work products.

There are some additional degrees of freedom to be found by shifting to more neutral terminology. I’ve started to think about what might be gained, besides alliteration,  if I start thinking in terms of “artifacts” and “activities.” 

Artifact encompasses deliverables but also extends to intermediate working papers. Anything that gets thinking outside of your head and into a representation that you can inspect and manipulate is worth considering. 

Some sequences of activity may be worth treating as discrete projects. But other sequences and patterns of activity may be worth incorporating into your repertoire and pairing with appropriate artifacts. 

Artifacts plus Activities Become Practices

The notion of “practice” has been floating around in my head for some time now. It isn’t something so structured as a process. Nor does it rise to the level of a project to be managed. But it does seem worthwhile to stay alert for stable patterns of artifacts and activities that yield insight. 

One implication here is that you should be attuned to two levels of thought. There is the ongoing work itself. And, there is a parallel level of the work of managing the work.In routine work environments, work and management are typically carried out by different players. In knowledge work, work and the management of work falls to the knowledge worker. I find it helpful to try to keep the two levels separate in my thinking. 

You never start from a blank sheet of paper

This train of thought appropriately brings me back to a piece I wrote some six months ago—Embrace the mess if you want to do better knowledge work. The trope about writing and writer’s block is the threat of the empty page or the empty screen. Unless you are at the absolute beginning of the path, this is an illusion. None of our work begins in the void; we’re always in the middle of one journey or another. Take advantage of wherever you are and start there.

Aspiring to Knowledge Work Professionalism

WorkstationIn April, 2003, the late Doug Engelbart gave the Keynote Address at the World Library Summit in Singapore; “Improving Our Ability to Improve.” The talk is an excellent entry point to one of his most powerful ideas. He also raises a specific question that I suspect wormed its way into my thinking back when I first encountered it. 

As an aside, I wish I could reconstruct the concatenation of events that led me to revisit the talk yesterday. I’m confident it was a revisit because I’ve been following Engelbart’s work for a long time and this piece was already in my systems. My note-taking and reading management systems are not so well-constructed, however, that I could do more than recall the essence of the piece. On the other hand, returning to old source materials can  pay dividends. The source may not change but my perspectives evolve.

Engelbart’s career was dedicated to exploring how information technology could augment human intelligence rather than displace it. He was especially interested in how that partnership could attack big, complex, problems. 

Shovels and bulldozers, to borrow and extend Engelbart’s analogy, both move dirt. If you have a lot of dirt to  move, a single shovel isn’t your best choice. If no one has managed to invent a bulldozer yet, you might be limited to shovels but you aren’t limited to a single shovel. 

Given a collection of shovels (and shovelers), you can organize the problem of moving dirt into a process. Process is an amplifier. With a layer of process in place, you can get further amplification by looking for ways to improve the process. Engelbart identifies one additional amplifier; improving how we do improvement. Engelbart labels these three amplifiers as A-activity, B-activity, and C-activity. It’s a simple enough model, but simple models can be very powerful. 

At the base (“A-activity” in Engelbart’s terminology), you have the realm of process; the monthly billing cycle, managing trouble-tickets at the help desk, the assembly line turning out Toyotas. The economy is built on transforming ad hoc practices into standard operating procedures and repeatable processes.

Repeatable processes that produce repeatable outputs open up the possibility of systematic improvement. What changes can you make to the process while holding the outputs constant? Process improvement (the “B-activity” in Engelbart’s model) is the realm of quality management, business process re-engineering, and continuous improvement. It’s an amplifier of benefits flowing from repeatable processes.

As an organization accumulates more experience with process improvement and more opportunities for process improvement surface, there’s another level of leverage in investigating how you can get better at those improvement processes (“C-activity”).

What Engelbart is doing here is employing a classic computer science problem solving strategy; adding a new layer of indirection or abstraction. Rather than attack a problem head on, step back from the immediate features and adopt a new perspective. Engelbart explores this three-tier model in more depth in Toward High\-Performance Organizations: A Strategic Role for Groupware \- 1992 \(AUGMENT,132811,\) \- Doug Engelbart Institute.

Returning to the keynote address, Engelbart launches into a bit of a rant about “ease of use” and letting the market decide what features and functions should be available. He isn’t a fan. As I was nodding along, Engelbart posed a question that grabbed my attention; 

Doesn’t anyone ever aspire to serious amateur or pro status in knowledge work?

If your answer is yes, then you have a problem in the context of the current information technology market and the purchasing preferences of most organizations. Those forces favor tools and services targeted toward beginner and intermediate levels of expertise. Think of the standard software installed on the typical corporate workstation. What training is provided on how to take full advantage of even those tools?

Reaching expert level performance in any field doesn’t happen by accident or by the simple accumulation of experience. It requires deliberate practice and a commitment to operate across multiple levels of perspective.

Start with a Bare Stage not a Blank Page

It was about 2am, the stage was bare, and the house was dark. Tech rehearsal had wrapped at midnight. There were four of us still in the theater–Producer, Technical Director, Lighting Designer, and Stage Manager. We were setting the lighting levels for each of the hundred odd lighting cues we would execute for each performance. 

Thos and Chaz–TD and Lighting Designer–were seated in the house about fifteen rows back. Steve and I were off stage left manning the dimmer switches that controlled the lighting instruments. Chaz shouts out, “can one of you go on stage? I need to see how this looks on skin.” Steve promptly takes center stage and moons Thos and Chaz. “Excellent! Jim, take dimmer 24 up two points”

Two in the morning is easier to face with collaborators. What makes a blank page so intimidating is that you feel alone. 

A bare stage promises a crowd. Even a solo performance presumes an audience. And a performance hints at a production crew lurking somewhere.

A blank page is a single entry point to creation. From a bare stage you can move in multiple directions. And you don’t have to move alone. 

Start there.

Where’s the Locus of Control?

Circular error probable - percentageOrganizations aspire to immortality. Few achieve it, but the mindset persists. I was thinking about this in the context of the various organizations I’ve worked for over the years. Many of them no longer exist; names changed, organizations shut down, organizations absorbed into other organizations. The life cycle of modern organizations is shortening.

One of the driving forces that took me out of the workforce and back to school for the third time was seeking to reconcile the rationality of technology and the irrationality of behavior in organizations. I needed to step away from the noise to see if there were patterns I could discern.

Midway through the process, I recall a conversation with my advisor. Had I revised my opinions about the irrationality of organizations? 

Herb Simon was a Nobel-prize winning economist who had explored this very question and had come up with perspectives that helped. Here’s what Simon argued. Organizations and the decision makers within them want to be rational but there are limits on their capabilities. Rationality is bounded by various limits on our capacity to process and make sense out of information. 

The mythology of business and economics is that decision makers seek optimal solutions. Business language is littered with superlatives; “best”, “fastest”, “cheapest”, “newest”. Mostly harmless in advertising and marketing circles where we presume a certain amount of puffery. Not so harmless in other settings. Simon’s argument was that decision makers “satisfice”; they make a good enough decision with the time and data available. You don’t give up on the goal of optimal choices. You do accept that they are a theoretical ideal, not, generally, an achievable goal.

This matters for knowledge workers because the mythology remains pervasive. Knowledge work feeds into decisions. Those doing the work recognize the limitations of their analyses that leave us short of ideal answers. Those making the decisions are too often predisposed to ignore those limits. It can take courage to be vocal about what you don’t and can’t know. 

Beneath the Magic

Despite how long ago it was, my university education was still an expensive proposition. Part of my financial aid package was an on campus job. In my freshman year, that job was working as a janitor in my dorm. Dealing with the bathrooms on Sunday mornings was not a pleasant experience. 

My second year, I moved on to much better pastures, working as part of the tech crew at McCarter Theatre, just off the southwest corner of the Princeton campus. I worked as a stage hand, carpenter, and electrician. 

McCarter is a Broadway-scale theater built in 1930 to house the Princeton Triangle Club’s operations. It stages multiple productions and concerts throughout the year. I built sets, hung lights, loaded touring shows in and out, ran follow spots, and pretty much anything else associated with the nuts and bolts of making the magic happen. A very blue-collar education taking place in parallel with the classical liberal arts education happening across the street on campus. There, I was studying Shakespeare alongside Regression Analysis.

This juxtaposition of manual and cerebral, art and engineering, practice and theory shaped my perspectives. Perspectives plural being the primary lesson. Classrooms have the luxury of taking narrow and precise focus on a question. A working theater is a laboratory for balancing and mixing competing claims and priorities to bring about moments of magic.

My first question after experiencing one of those moments is “what did it take to make that happen?” Seeking those answers enhances the experience. Finding answers leads to creating better experiences the next time.

Like may lenses ground in experience, I tend to look through them without noticing what they sharpen and what they distort. It’s worth taking a look at this particular lens as it applies to gaining a better understanding of doing knowledge work more effectively.

I find it useful to break this analogy between the players and the production.

The playwright and the audience bracket the collection of roles that contribute to creating an experience. Depending on the complexity of the piece, the number of participants in the chain can become quite long; 

  • producer 
  • director 
  • designers of multiple stripes (sets, lighting, sound)
  • performers (actors, dancers, musicians)
  • builders (carpenters, tailors/seamstresses. painters, electricians)
  • stage crew (grips, props managers, electricians, audio technicians)
  • front of house (box office, ushers)
  • marketers
  • managers (stage managers, crew chiefs, tech directors, business managers)

If nothing else, this is a reminder of how much collaboration goes into producing a designed experience.

There’s an equally complex mix of artifacts that can surround a piece of work. 

There is the script itself. But scripts do not spring forth from the brow of Athena or anyone else. Nor is a bare script enough if our goal is to create an effect or response from an audience; something too often overlooked based on the accumulation of dust gathering on ignored documents piled on shelves. 

Getting to a script is a journey of notes, outlines, drafts, notes, and revisions. Transforming a script into a production spawns multiple streams of subsequent artifacts. There are design artifacts, management schedules, calendars, plans, budgets, and more. These trigger the creation of still more artifacts; sets, costumes, props, promotional items, and more.

The risk of any analogy is to push it too far. If I step back from the precipice there are core elements that I keep in mind as I turn this lens on knowledge work. First, the goal is to elicit a response from an audience. The work doesn’t exist for itself, it exists for what it accomplishes. Second, you’re not alone; potential collaborators are everywhere, in multiple forms.

Finally, when the curtain goes up, what you get is what you see. There’s no point in painting the back of a set that can’t be seen by the audience. If the set collapses in the middle of the first act, however, you’ve got a problem. 

Make Your Own Space

Have you learned to have a healthy suspicion about “the way things are supposed to be”?

While I was in elementary and high school, my mother encouraged a certain fluidity about rules and regulations. She would happily grant me periodic “mental health days” if I thought a break was in order.

While I was in college, there was a lovely home about a ten-minute walk from campus. It belonged to the parents of a sometimes girlfriend; always and still a friend, occasionally something closer. I adopted them as a set of spare parents, more readily available than my own a thousand miles away. Over the years, I would take refuge there from time to time. No questions, no expectations, always welcome. Without models to guide us, we worked out arrangements fit to whatever moment we were in. 

This is on my mind as I try to work something out. I’ve noticed how often the advice I encounter about life and work has a certain implicit message of “everything you’ve been doing is wrong, here’s the right answer.” Whatever method or practice or tool or system is being pitched, the framing is that this is the solution to your problem. 

What’s missing from all of this advice is that your job is not to select from among the hypothetical solutions on offer. Your first task is to ignore the canned solutions and their canned definitions of the problem and work out your own definition of the problem. 

If it’s helpful, you are free to examine the solutions on offer, but what you want to do with those purported solutions is explore the underlying model of the problem they were built to solve. That can serve as additional input as you work to better define your problem. 

The key here is that knowledge work doesn’t fit into standardized models. How you solve a problem differs from how I attack the same problem. This is the fundamental promise of knowledge work. It is a search for the unique answer to the unique question at hand. If there were an off-the-rack answer, then we’re talking about standard operating procedures not knowledge work. 

There is an essential design component at the outset of any knowledge work effort. What features of the problem are salient? What tools and techniques are already at hand? Can you reorganize and redeploy the existing tools? Do you need to add in a new tool or technique (and figure out how to use it effectively in this context)?

There’s a hypothesis coming into focus for me here around the notion that any knowledge work effort begins with a design step. Analogies about work tend to be anchored around factories. The problem is that you design a factory once and run the same things through it over and over. 

I’ve spent considerable time in factories but I’ve spent more time in a place that provides a better analogy for knowledge work–the theater. No two productions of _Hamlet_ are ever the same; even with a known script the goal is to create something new and possibly unique.

Staging a production is a much more complex creative task. You start with an empty stage and you transform it into a magical space. That transformation may start with a script but it opens up to encompass sets, lights, sound, movement and more. Designing for knowledge work needs to be similarly expansive. It will require multiple perspectives and, often, multiple collaborators. 

Let’s see where this might take us.

Start at the Beginning

“I always get the shakes before a drop.”

That’s the first line of Robert Heinlein’s Starship Troopers, which I’ve probably read 20-30 times over the years. In science fiction circles, that line is the equivalent of “It was the best of times, it was the worst of times.”

I was probably about twelve or thirteen when I read it for the first time. There’s a problem with vacuuming up books that you’re too young to fully grasp. The folks around you are more pleased that you are precocious than aware that much is going well over your head. 

For the longest time, I naively assumed that the people who made up these stories started with the first line and simply plowed ahead until they reached the end. They had some magical talent that seemed far out of reach. It never occurred to me to voice my theories and my teachers were focused on issues of spelling, punctuation, and grammar. 

I had fallen victim to the “blank page” fallacy; the notion that the starting point for any writing project was an empty sheet of paper. It’s a myth that gets perpetuated in multiple forms. In school you deal mostly with toy problems; exercises that fit the constraints of lesson plans and grading. Examination books are nothing more than a collection of blank pages. 

It’s possible that you can move on to a world where you never run into a problem that’s big enough to reveal the limits of blank pages. A world of email and bullet points. 

More likely, you will eventually encounter a task that’s too big for a blank page. That’s when you need to see that the blank page is not the beginning; it’s a repeating phenomenon. It’s one of a series of blank pages to be covered with marks; words, phrases, arrows, boxes. 

Getting to a final deliverable (novel, consulting report, or something else) is a process. It’s your choice whether you design and manage that process or wing it. Regardless, it’s a process. The larger the deliverable, the more important the process. 

It’s helpful to separate thinking about the final product and the process of bringing it into being. One stream is about creating, the other is about managing. Two very different modes of thought, but you need both if the final destination is big enough or far enough away. 

Figuring out that first line could easily turn out to be the last thing you do.

Instigating Questions

It was the prototypical professor’s office. Book lined shelves, stacks of paper on most horizontal surfaces, ivy-covered walls visible across the courtyard. The day before, we had paid a visit to a potential case site. I was a newly-minted case writer meeting with my boss, Professor Cash. I was a former student and had left a lucrative consulting job In a quest to obtain a doctoral degree. 

Professor Cash would eventually become my thesis advisor, but we weren’t there yet. Cash had confidence in me; the admissions committee was more skeptical. Let’s just say that my academic transcripts displayed a significantly wider distribution of grades than they were accustomed to seeing. The compromise was to work as a case writer for a year and the admissions committee would take another look then.

We were meeting that morning to review our visit to the case site and discuss how to approach writing my first ever business case. As I student, I had read and analyzed on the order of 2,500 cases. This was the first time inside the sausage making. 

“Where’s your trip report?” was Cash’s opening question. The stupid look on my face would have terrified the admissions committee; Cash was more forgiving.

What he expected was to see my semi-legible, incomplete, and partial notes transformed into a coherent narrative of the previous day’s interviews. After spot checking my first few trip reports, Professor Cash didn’t bother to read them. They were for my benefit. If I was to create a case study that would work in the classroom, I needed to get my thinking out of my head and available for inspection.

This was the moment when I first began to grasp that thinking wasn’t something that happened exclusively inside your head. Most of the signals and clues we encounter encourage the notion that thinking occurs between your ears. Think of the penalties for referring to your notes during most examinations. 

The most powerful counterexample comes from a biography of Nobel-laureate Richard Feynman by James Gleick

[Feynman] began dating his scientific notes as he worked, something he had never done before. Weiner once remarked casually that his new parton notes represented “a record of the day-to-day work,” and Feynman reacted sharply. “I actually did the work on the paper,” he said. “Well,” Weiner said, “the work was done in your head, but the record of it is still here.” “No, it’s not a record, not really. It’s working. You have to work on paper, and this is the paper. Okay?” James Gleick Genius: The Life and Science of Richard Feynman

If Feynman depended on thinking outside of his head, it’s probably a sound strategy to adopt if you aspire to do meaningful work.