Good advice, messy systems, and invisible work—evolving from where you are

For the longest time, I had a theory that there was a secret class that I had somehow missed. This was the class that would make sense out of those elements of daily life that were a source of frequent confusion to me. Today, my inbox is filled to overflowing with offers to reveal whatever secrets I might wish to know. Setting aside the more obvious scams and promises to solve problems that don’t trouble me, I could fill my days and nights with well-intentioned solutions to challenges that I actually face.

Smart people invest immense amounts of time and effort to organize and package what they know into software tools, self-help books, conferences, workshops, online courses and more. I’ve benefitted from many of these over the years to the extent that a recent gift from my wife is a t-shirt emblazoned with the warning “Dangerously Overeducated”.

But that secret class concern continues to trouble me.

Why does that wealth of good advice not smoothly translate into equally good results? Where am I failing as a student? This continues to trouble me long after I’ve moved to the other side of the classroom.

If you’re designing a class or planning a textbook, one thing you must do is establish what knowledge your target students should already posess. What are the prerequisites? What knowledge and skills can you assume? Good designers will also consider what sorts of mistakes newcomers are likely to make.

Elsewhere, I’ve made the point that no one starts from a clean sheet of paper. Thinking through prerequisites is part of figuring out what you’d like to see on that sheet of paper.

The piece that gets forgotten or skipped over is working out what is on that sheet that shouldn’t be there. What do you think you know that just ain’t so.

I’m hard pressed to think of anyone designing courses or offering advice who takes this step. Who thinks about or worries about how their lessons will interact with whatever stupid ideas or messy systems you possess. This is a responsibility that no one tells you is yours.

We can be quick to mock those who cling to knowledge, theories, and skills that we’ve outgrown or abandoned, It’s quite a bit harder to recognize the same behaviors when they’re revealed in a mirror.

The perspective I am coming around to is that my systems and practices are messy. They’ve grown by accretion over the years. I strongly suspect that this is also true of many, if not most, of those offering their insights and advice. We are gifted with the final outputs of their messy efforts. Anne Lamott encourages us to write “shitty first drafts”. She talks less about what comes between that first draft and the final one. John McPhee takes us as far as Draft No. 4. But, the system as a whole conceals the mess. It is invisible.

This suggests that one path forward is to look for the mess. Embrace the messiness in your own practice. Seek out those who will share details of their messes.

Accepting Limits to Rationality

I try to be rational. I have decades of knowledge and experience about the ins and outs of rational decision making. I have decades of experience within complex, human, organizations and their sometimes tenuous relation with rationality (and occasionally with reality).

I recall a conversation with my thesis advisor. He wanted me to work out where I stood on the issue. Did I believe that organizations where rational or not? This is not a idle question in the realm of organizational studies. Herb Simon won a Nobel Prize in economics for pointing out that there were limits to rationality. The mythology in business was that managers were rational decision makers. We continue to make up stories about why our decisions make sense. Simon showed that our decision making was bounded. We might try to make a fully rational decision but there were always limits of time, budget, capacity, and the like that come into play. At best, at best, we can try to be intendedly rational. To address as many of the limits as we can. But decisions have to be made.

I have to continually remind myself that bounded rationality is the best we can hope for. I also need to remind myself that not all the actors in a situation aspire to even that standard.

Personal knowledge management is a design problem not a selection task

PKM is a hot topic on the Interwebs. Everyone is peddling an answer; doubly so if you count the resurgence of evangelizing about the magic of notes. Everyone has the answer. No one is asking the right questions.

The questions I keep seeing run along these lines:

  • Which software product is best?
  • Is this the right way to build my Second Brain?
  • Who has the best training course/YouTube channel/e-book?

All of these questions are on a level of “Will this be on the test?” They are anchored in an unexamined assumption that there is a right answer.

Personal means personal.

All of the answers out there are answers that started out as the solution to someone’s personal take on the answer to the questions they had. At the very least you need to figure out whether those questions bear any resemblance to the questions you have.

You need to back up and formulate your knowledge management questions first before you have any hope of assessing the value of what is out there. The other day I suggested four questions that could get you started. Those questions put you on a design path, not a selection path.

This is not an easy perspective to shake free of. We are trained and acculturated to seek out “right answers.” Most of schooling is set up this way. Much of contemporary schooling was designed to prepare its products (students) to operate in a factory world of meeting production targets for standardized outputs. Only a tiny fraction of the workforce was expected and permitted to think for themselves.

We’re not quite sure what to do with the responsibility to understand our work and our unique contributions. And then comes the task of designing and implementing the practices that will let us carry out that work effectively. There is valuable advice out there to make use of. But the value lies in recognizing that what is out there is not the answer but input for the design work that you must do.

Why solving for pattern makes more sense than connecting the dots for knowledge work

I’m on record that solving for pattern is a better approach to knowledge work than connecting the dots. Connecting the dots is pretty common usage. I don’t think it needs much elaboration. Except to point out that there is a presumption that someone else has already drawn the picture you are now expected to reveal.

It’s about locus of control. Connecting the dots grants you only the task of discerning what someone else has already done.

Solving for pattern puts the responsibility where it belongs; on you. I encountered the term in Wendell Berry’s essay of the same name (add link).

A few days back I picked on the notion that if something works for you 10,000 times you have license to assert you have proven something in a substantive way. Implicitly I was asserting that there is only one path to reliable knowledge—experimental and replicable science. Pretty arrogant for a former case writer.

What I was arguing, perhaps badly, was that you need to be careful about the claims you can make about what you think you know. Solving for pattern is a shorthand for the process of building explanations from the experience (first and second hand) that you accumulate and models of the underlying systems you are interacting with along the way.

Solving for pattern is an active process that never ends. Each new cycle through the pattern is an opportunity to try a new variation or to investigate how changes in the external environment tweak the outcomes you expect. You’re free to try any “proven system” you’d like. You’ve also learned to be appropriately skeptical about other people’s proof.

Four questions to begin your personal knowledge management practice

I’ve made the claim that effective knowledge management must be personal at its foundation. This led one colleague to ask the natural question of “how do I get started?”

If you’re a knowledge worker, understand that you are already doing knowledge management in some form. You have an existing practice, even if you may not give yourself credit for it. Understanding what you are doing now is the best way to make it better.

Here are four questions that will help you tease out your existing PKM practice:

  1. What deliverables are you expected to create?
  2. When and how do you reflect on how and what you create?
  3. Where do you feel most/least comfortable in your work?
  4. What are the edges you encounter in your work?

Developing answers to these questions will surface strengths you can build on and weaknesses you will want to shore up. As you develop answers, you will also want to assess what degrees of freedom you have to work with. What restrictions does your organization or environment impose that you will need to bypass or overcome?

There’s a lot of attention and interest in the PKM field now. So there is a wealth of information to tap into. But the best place to start is with what you are already doing to meet the current demands of your work.

Choosing innovation perspectives

Ghost light on a bare stage

We rolled the last road box up the ramp and onto the truck. We were done. The truck was on its way to Chicago, our next stop. The stage was now bare, empty of the sets, lights, and cast that had filled it a few hours earlier. I had one last task as Stage Manager before heading off to the cast party now in more than full swing.

My last responsibility was to make sure that the “ghost light” was on. The theater is replete with custom and tradition. You never wish a cast member “good luck,” it’s “break a leg.” It’s “The Scottish Play” never “Macbeth.” And, you never leave a stage dark; there’s always at least one light left on over the stage. They’ll tell you it’s a safety thing; you don’t want someone to walk off the edge of the stage by accident. But, it’s really to keep the ghosts away.

The thing about a bare stage is that it exists between an ending and a beginning. There are old stories to be told and new stories to create. Either is a worthy task; it’s a choice of perspective.

Suppose it’s a new story you would like to tell. Economist Joseph Schumpeter developed the notion of “creative destruction;” the idea that innovation depends on getting rid of the old to make way for the new. It’s easiest to see in the demolition of old factories to make room for new ones. It’s harder to suss out when we’re talking about shedding obsolete ideas.

This seems to be an unexplored aspect of knowledge work. How does what’s gone before connect to the new thing wanting to emerge? What are the questions that bridge from “remember when?” to “what”s next”?

Both corporate and personal knowledge management obsess with capturing and recording what has gone before in the hope that those lessons will somehow guide us going forward. Avoiding error seems pretty straightforward. How many corporate procedures and policies boll down to “don’t ever do that again”? But what of the new? What about innovation?

Science fiction might offer one answer. Not so much in its track record of successfully predicting new technologies. That’s the mistake some companies make when they invite science fiction writers to share their predictions.

It isn’t the predictions that are important. It is the process. Good science fiction starts with the presumption that human psychology and behavior will remain stable and predictable. Science fiction explores two different questions, however, starting from that baseline assumption about where stability lies. First, they ask “what if?”. How will a possible invention or event collide with that stability? Second, they explore “if this goes on?”.

Gordon Moore notices that engineers are managing to double the number of transitors they can cram into the newly invented integrated circuits and asks the simple question “if this goes on?” what can we expect? The Apple M1 chip powering the MacBook I am writing this on has approximately 16 billion transistors in 120 square millimeters. An immense amount of engineering talent and effort went into getting from there to here, but it starts with that fundamental question.

These are the better organizing questions to pick a direction and move. They start with that quiet moment when the only thing illuminating the stage is that light keeping the ghosts at bay.

Works for me times 10,000 does not translate to proven strategy

I’ve been working with the Ship 30 for 30 writing program. The price point was acceptable and I had enough recommendations/pointers from sources I trust to give it a try. I’m not the target demographic but concluded the cost/benefit tradeoff was positive nonetheless. Not the first time I’ve taken on a learning challenge with the full expectation that I would be adapting lessons to my own purposes.

The lesson at hand focuses on why I should adopt their model of headlines. At best, the title for this post is within the outer periphery of their recommendations. But it’s more of an assertion about why I object to their logic.

Their argument is that a headline should make a clear promise of what is to follow and that any headline that delivers on its promise is not clickbait. Unobjectionable. They assert that this advice is rooted in their extensive experience producing headlines in their preferred style.

Extensive experience is a better starting place than a shot in the dark. On its own, however, “extensive experience” is just another way of saying “it works for me”. String all the stories you want together and it still doesn’t add up to data. You need a theory of the case for how your collection of anecdotes leads to your recommended rules. Asserting a proven strategy is only the first of many steps on the path to knowledge I can trust; I haven’t seen those steps.

The recommended headline structures do, indeed, feel like clickbait to me. While I agree that delivering on the promise of your headline absolves you of the accusation of promoting clickbait, I also swim in a sea of clickbait. I’ve been burned more than enough times to be highly skeptical of any headline that smells of clickbait. When I have a choice between a clickbait headline and a dull headline from someone I trust, the choice is easy.

The question becomes how do I find sources I trust? How do I find people whose pointers are worth following? I had a phone call this morning from a colleague and friend I’ve know for close to forty years. Over the course of 45 minutes I came up with dozens of pointers to things I now want to read.

A decent headline might get me to click. What I’m really in search of is sources I can trust.

Evolving a more effective writing practice

I’ve written on deadline and assignment for much of my life. We all learn to do that in school. Add extracurricular writing activities, segue into a career in consulting, work as a case writer at Harvard Business School, write a dissertation, co-author two books, start blogging in 2001, and I think I can claim to be a practiced wordsmith.

What’s been troubling me lately is restoring consistency in getting across the finish line. The transition from writing to hitting publish seems to be acting more like a roadblock than a speed bump. I’ve had some success with various forcing functions that work for a while but haven’t proven sustainable. I need to develop better insights into what works well and what doesn’t in my writing practice.

“Practice” feels a more suitable term than “process.” It keeps the feel organic rather than mechanical. It reminds me to stay mindful of craft when the environment celebrates the mechanical and the technological. Don’t misunderstand. I am a fan of technology wherever it aids my craft. For example, I’ve created at keyboards for over half a century. My handwriting is atrocious. I used to transcribe interview notes as soon as possible after taking them (something I should have also done with lecture notes but that is a tale for another time). I was an early adopter of word processing software, outliners, mindmapping tools, and have experimented with multiple “tools for thought” as they’ve become practical.

I’ve found myself less enamored of templates and formulas. To me, they smack of industrial thinking. Again, I prefer the image of practicing my craft in a workshop over that of churning out product or content in a factory. I’m not striving for masterpieces of art but I’m not producing widgets either. I want what I create to be functional and pleasing to the senses at the same time.

One difference between a practice and a process that has been on my mind is that a process implies a set procedure; a fixed sequence of steps guaranteed to turn out a predictable finished product. A practice suggests a story behind each finished piece. Understanding and improving practice flows from inspecting both the finished pieces and their origin stories. What this has meant for me is that notes and chronology have taken a more central place in my craft.

Notes and note-making have been undergoing something of a renaissance in the last several years. I’ve been tapping into that creative stream. It’s a rich manifestation of something I was trying to articulete back in 2010 when I first touched on the notion of managing the visibility of knowledge work.

Owning your practice

I had an email exchange earllier this week asking what had soured me on the personal productivity space. “Soured” may be a bit too strong a term but I have become skeptical about most advice about personal productivity. It is not for lack of trying or familiarity with the domain.

A little history is in order.

I was a product of the parochial school system. Nuns had their methods for dealing with daydreamers. Getting caught at it bordered on a mortal sin. I mostly avoided getting caught. I was lucky to have one nun who figured out that a major piece of my problem was that I wan’t being challenged enough and channeled me to a private all boys school for middle school and high school. Turns out that Benedictine monks are even better than nuns at keeping you busy and focused.

Their tutelage earned me entry into Princeton. In retrospect, I should have brought one of the monks with me instead of my typewriter. I left behind a support system that was simultaneously invisible and essential for keeping me organized and focused. ADD was not a diagnosis that existed in the early 1970s.

Struggling with deadlines and deliverables was either a moral or a systems failure. I opted for the systems failure hypothesis.

I didn’t articulate it that way but I found my way to the first of many systems promising to provide the structure I needed. That first was contained in Alan Lakein’s classic How to Get Control of Your Time and Your Life, published midway through my college career. I bought DayTimers and Palm Pilots. I paid for David Allen’s workshops out of my own pocket. I’ve tried just about every piece of productivity and personal management software that’s reached the market. They would work for a while, then collapse.

The moral failure hypothesis was beginning to look more likely. On the other hand, I was getting stuff done even when it felt harder that I thought it should have. I convinced Harvard to give me an MBA and a doctorate in business. I had a series of successes and occasional catastrophic failures. What I was struggling to discern was an underlying pattern that didn’t hinge on my being a bad person (or on everyone else being out to get me).

My doctorate is in how organizations manage to innovate, particularly with technology and systems. I turned that lens into a mirror. I was successful when I was in an environment that compensated for my weaknesses and failed in environments that called for strengths where I was weak.

Part of the answer came when the world put a name to my particular collection of strengths and weaknesses—ADD. More recently, we’ve broadened that notion to the idea of neurodiversity. People’s brains work differently. By and large the world is uncomfortable with diversity. Organizations and markets want to find and address large, average, groups.

This is as true for productivity promoters as concert promoters. Wonderful if you are Taylor Swift and your art matches nicely with millions of fans. Less desirable if your art appeals only to left-handed guitarists.

We all have the same twenty-four hours available to us each day. We are all faced with more options for what we might do than will fit into those twenty-four hours. Productivity advice ought to be universal applicable. The unstated assumption is that we are all neurotypical and that we, therefore, treat hours and options in the same way.

Productivity advice assumes that one size fits all. All you need do is put on this particular productivity outfit and all will be well. Neurodivergence means that nothing fits right off the rack. The question isn’t whether the advice is right or wrong; the question is how to make it fit you.

It is safe to presume that productivity advice will continue to target the average neurotypical brain. If that is not you, then you have extra work. Work to understand and articulate how you diverge. What’s easier for you? What’s harder? Can you find a way to compensate? Adapt the recommendations to something better suited to your unique profile.

It’s nice if off the rack suits you. But you’ll do even better if you learn how to tailor things to minimize your weak spots and flatter your best features. True whether we’re talking fashion or work practices.


Knowledge is personal, manage it that way

Thirty years ago I was the Chief Knowledge Officer of Diamond Technology Partners, a consulting firm attempting to blend the perspectives of Accenture and McKinsey. Leveraging what we knew was the essence of the value we created for clients. With a total headcount at the start of 25 people, the title was more aspirational than practical.

Things got tougher as we grew to over 1,200 professionals over the next six years. The technology couldn’t do what we thought it needed to do. There were no playbooks for how to do knowledge management. Half of what we did had never been done before. We tried programs and practices with variable success.

One of the central challenges was persuading our consultants to share what they knew with one another. The consensus in the field at the time was that sharing was the problem to crack.

Pondering the question of what made knowledge sharing hard led to one of those shower moments where insight happens. Were our consultants hoarding their knowledge to preserve their rank and status? What incentives could we offer them to part with what they had learned for the benefit of the organization? Did we need to find more altruistic individuals who would share because it was the right thing to do? Could I be doing something to set a better example of what good knowledge sharing looked like? Had I done anything recently that was worth sharing more widely? What, in fact, had I learned recently that was of any interest or value?

I had found the culprit!

Knowledge sharing was failing because I wasn’t sharing knowledge with myself. Socrates had it right after all. Know thyself.

It’s hard to share what you don’t know that you know.

The starting point for effective knowledge management in organizations needs to be knowledge management at the personal level. If you are a knowledge worker, effective personal knowledge management matters regardless of whether your organization cares.

In the last several years, we’ve seen a surge of interest and attention to the problems of personal knowledge management. The technology environment has become more welcoming and robust. There are organizational barriers that continue to make this harder than necessary. Organizations still favor standardization and control in ways that clash with the needs of individual knowledge workers. This will resolve over time.

If you are an individual knowledge worker, you should be thinking in terms of your own PKM needs and environment. You may need to work around organizational limitations. Persevere. The improvements in your effectiveness will buy you degrees of freedom in enlightened organizations. If not, your organization may be less enlightened than you’d like.