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.

Muddling through as smart strategy

There’s a certain subset of academic articles that are as, or more, famous for their titles as they are for their insights. Charles Lindblom’s “The Science of Muddling Through” has to be on that list. Lindblom’s field was public policy but his insights are more broadly applicable. 

He starts with a simple enough observation; administrators don’t behave the way that theory says they should. Textbook decision processes of carefully articulating objectives, developing options, and selecting solutions that optimally meet objectives don’t show up in the wild. Real managers “muddle through,” making incremental changes and nudging complex systems in directions they hope will prove “better.” 

Lindblom’s insightful question was to wonder whether administrators weren’t as dumb as they looked. Theorists have the luxury of pretending that history doesn’t exist; real managers always start from Ken Boulding’s observation that “things are the way they are because they got that way.” The real world always imposes real constraints. 

The simplifying assumptions that economists and model builders must use to make their work tractable can be acceptable for simple enough problems. It’s dangerous to believe that the techniques that work for suitably constrained problems scale. Problems up the ladder aren’t simply bigger, they are more complex. That complexity transforms tractable problems into wicked problems.

“Muddling through” is what actually works; the primary metric for practicing managers. 

Buying Time

Review: Time Smart: How to Reclaim Your Time and Live a Happier Life

I think my father made decent money, although I don’t have any concrete numbers. But, if you have seven children to feed, clothe, and educate stretching every dollar is sound practice. My mother did this with sometimes frightening skill. She would drive out of her way to save a few pennies per gallon on gasoline or milk, both of which we consumed in prodigious quantities. Frugal was a badge of honor. Mom lived “time is money” more than any business school professor I ever met. It was a source of friction between us from time to time.

Ashley Whillans is a Harvard Business School professor whose research makes the case that we have that mantra inverted; “money is time.” But, unlike a mathematical inversion, the direction you adopt makes a difference. Whillans research investigates the trouble we get into by accepting the conventional wisdom. That leads to solid advice on how to shift your perspective to prioritizing time over money in spite of the pressures to do the opposite. Appropriately enough, Whillans manages to compress all of the argument and advice into a compact package respectful of and worth your time. 

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.

Simple Questions that aren’t so Simple

“Where did you go to school?”

It’s an innocuous cocktail party question that pops up fairly early. You would think that the answers would be simple. Not necessarily.

In St.Louis, where I grew up, this is actually a question about where you went to high school, not university. The answer slots you pretty precisely along political, religious, and socio-economic dimensions. 

Elsewhere in the U.S. this is, in fact, a question about your university affiliation. For most people, in most situations, the answers are simple; “Michigan”, “MIT”, “Notre Dame.” There are two seemingly evasive answers that I am qualified to and sometimes do use; “in New Jersey” and “in Boston.” These are code phrases for “Princeton” and “Harvard.”

Why dodge a direct answer? Because a straight answer might not provoke a straight reaction. The explicit conversation isn’t always the most relevant conversation underway. What appears to be a simple inquiry and a simple, factual, response may be heavily freighted with hidden assumptions and expectations. 

This layering of conversations is present in most settings. My history may make me a bit more attuned to that. 

Which turns out to be of increasing importance and relevance in knowledge intensive settings. Organizations want to pretend that they are simple, straightforward, places. While I am open to a debate about whether that might once have been true, I wouldn’t operate on any of those assumptions today. 

The complexity is there. You can ignore it or you can accept it and factor it in.

Making Room for Change

Image by Anita Smith from Pixabay

My undergraduate years were dominated by the theater. Most of my free time and a substantial percentage of what should have been class time was spent working on some aspect of the Princeton Triangle Club. By the time I graduated, I had done most every job backstage that existed and been elected an officer of the Club.

Shortly after I graduated, I was elected a Trustee of the Club. Members of Triangle that you are likely to have heard of include Jimmy Stewart, Jose Ferrer, Josh Logan, and Brooke Shields. My four years flowed into an additional ten as a Trustee.

That continuity gave me some perspective about organizations that I might not have gotten otherwise. This perspective had to do with history, tradition, and time horizons. At that time the club was about 90 years old. We had lots of history and history implies traditions. But I discovered a curious thing about traditions. For most members of the club, history was whatever happened during their four years.

There was no way to differentiate between a tradition stretching back decades and an accidental string of events covering your undergraduate tenure. I was frequently bemused and amused by how often I heard undergraduates tell me “this is the ways it’s always been done” about something first done three years earlier.

I suspect this had a lot to do with my focusing on the interplay between innovation and organizational change. The part of me fascinated by technology seeks out change. What new way have we dreamed up to make some piece of technology obsolete? Who needs a bank teller when we have an ATM? Why bother with cash when you have Venmo?

The Triangle Trustee part of me that sees a tradition crystallized out of a short span of experience is sympathetic about those who’ve just figured out how to swipe their credit card and are tripped up by the new card with a chip instead of a magnetic stripe. Doubly confused, perhaps, when the new card has both a stripe and a chip.

In a sense, we’re all stuck as undergraduates. Whatever we encounter is always “the way it’s always been done” as far as we can tell. It takes time and deliberate effort to separate the threads of useful tradition and accidental stability.

Sleep Deprivation is a Bad Management Strategy

It was shortly after midnight. The cast was seated or sprawled in the aisles in the house. I was onstage, clipboard in hand, with the Director, Choreographer, Band Leader, and Tech Director. We had just completed Tech Rehearsal. We opened in four days. We were about to do “Notes”, where the Director and others would walk through all of the things that needed fixing or adjusting. As Production Stage Manager, I was poised to capture all of those to dos on my clipboard. 

Milt Lyons, the Director, had been working with the Triangle Club since 1955, two years after I was born. Scarcely his first rodeo. 

We had worked together before, but I was unprepared for his very first note.

He deputized two of the cast to escort me to my dorm and put me to bed. I turned my clipboard over to my assistant and left with Milt’s deputies. Fifteen hours of sleep later I was back on stage. A bit of quick arithmetic indicated that I had been working on three hours of sleep a night for the preceding week. Nor had any of my professors in any of my classes seen me that week. 

This intervention didn’t lead to any sudden epiphany; I continued to make poor choices about how I managed my time and energy. But it did plant an important seed. A seed that did take root and eventually led to more respect for balance in creative work. We talk about knowledge work in abstract, cerebral, terms. Bodies are simply transport systems for moving brains from place to place. 

When circumstances tempt me to pretend that my brain operates in splendid isolation. I remember that moment. There’s Milt announcing that the health of an entire production needed one foolish young stage manager to go get some sleep.