Roots of Project Management

USS George Washington SSBN

I just wrapped up teaching an MBA level course in project management at Loyola University. I started doing project management in the 1970s and it has been an essential, albeit secondary, element of my skill set. During the course, I found it useful to look back to some of the origins of the field. Project management can be a second class citizen in many business schools; it feels too pedestrian next to courses on disruptive innovation or venture finance. I went looking for some interesting history to put these skills in broader context. 

In that search I came across several papers that offer important perspectives on today’s practices and conventional wisdom. You can track them down from these links:

The first two papers take a look at the U.S. Defense Department programs from the Cold War that created the Polaris submarine and also promoted a story of advanced management techniques that was a more complex mix of technique and internal marketing than we usually acknowledge. 

The third paper by Winston Royce is often credited as being the origin of the waterfall software development model that held sway for many years and is now ridiculed as often as it is praised. It’s revealing to take a look at what Royce actually said compared to what followed. 

I find it valuable to balance knowledge of particular tools and techniques with a more general sense of the history and organizational realities that shape our use and understanding of those tools.

Entropy and knowledge management

What does the second law of thermodynamics tell us about knowledge management? There’s some pretty complex mathematics around the laws of thermodynamics, but the poet’s version will do for our purposes:

  1. You can’t win
  2. You’re going to lose
  3. You can’t get out of the game

Life is a constant battle against entropy or disorder. Cars break down; they don’t repair themselves. Left to themselves, files, books, and ideas become disorganized. Organizations and the knowledge workers inside them are engaged in a constant, but doomed, fight against entropy; the order they bring is always temporary.

Knowledge management is one of many disciplines engaged in that fight. If entropy is destined to win, what does that tell us about how to carry on the fight?

It reminds us that perfection is the wrong goal. You can’t define a perfect taxonomy; 100% compliance with the documentation standards is wasted effort; there will always be something more pressing than the paperwork. This matters because the personalities attracted to the apparent orderliness of knowledge management tend to be seekers of this impossible perfection. You want to temper that predisposition, not feed it.

Surrendering to disorder isn’t a good strategy either. Let the reality of entropy shape our strategies and practices. There are things we should worry less about and things we might better do differently.

We should worry a lot less about perfection and completeness and strive instead for a standard of “good enough”. That requires more judgment and sensitivity to unique circumstance than most organizations—and many individuals—are comfortable with. Black and white makes for easier, albeit impossible, compliance standards and management.

If you are in a position to shift an organization in the direction of more gray, encourage that. If you are enmeshed in unrealistic organizational expectations, strive for only as much compliance as will keep the auditors and censors at bay. I’m not advocating open rebellion, or even mild “civil disobedience”; simply be comfortable that you have the laws of physics on your side while you quietly ignore stupider requirements.

If entropy is the law, how might you operate differently?

Learn where small efforts now postpone or eliminate major remediation efforts. Whatever you opt to do now, you are going to live with that choice later. Make your choices with that appreciation of a disorderly later. You are never going to go back later to add the appropriate tag, improve the name of the file, or reorganize the project team’s directories. Recognize the places and moments where a tiny injection of order now will pay lasting dividends. Don’t pretend that you can get organized after the press of the immediate has passed.

Entropy is inevitable. As a knowledge worker, your task is to create pockets of order out of the noise. As you create those pockets, don’t increase the noise everywhere else.

EntropyAndKidsHMP Comics

Carve out time and space for deep thinking


Deep Work: Rules for Focused Success in a Distracted World, Cal Newport

If your value to an organization depends on the quality and insight of your thinking, Cal Newport’s latest book, Deep Work, offers important insights about how to think about your thinking. The forces at work in our environment and in our organizations favor quick, shallow, and social over other forms of thought. That is generally adequate for much of the activity that fills our days.

Exceptional value, however, finds its roots in sustained, focused, individual thinking and reflection. Deep Work builds the case for this mode of thinking and offers paths to carve out the necessary time and develop the necessary mental muscles to engage in deep work more intentionally and predictably.

Newport defines deep work as

Professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.

The ability to think deeply is a skill, so it can be developed. Much of the book offers counsel on techniques and practices that can help you develop your skills at deep work.

Newport is an academic computer scientist. In his world the contrasts between deep and shallow work can be stark. His binary distinction doesn’t transfer neatly to organizational settings where it is more useful to think in terms of a spectrum of work with shallow and deep anchoring the extremes. With the pressure toward superficial and shallow, there is great opportunity for individual knowledge workers to become more proficient at going deep.

Newport does offer practical advice for how to make deep thinking more possible. That advice needs tuning and refinement to work well in most complex organizations. Newport sums up why that effort matters thusly;

A commitment to deep work is not a moral stance and it’s not a philosophical statement—it is instead a pragmatic recognition that the ability to concentrate is a skill that gets valuable things done. Deep work is important, in other words, not because distraction is evil, but because it enabled Bill Gates to start a billion-dollar industry in less than a semester.

What’s in a name? Unexpected demands on 21st century knowledge workers


I have over 49,000 files in the documents directory and its subdirectories on my computer. They span nearly thirty years of output writing, teaching, speaking, and consulting. These represent the knowledge assets that support my livelihood. I am willing to claim that this is likely to be typical of today’s knowledge workers. That means there is a knowledge management problem to solve at the personal level that precedes any organizational knowledge management requirement. The answer depends on being smart about naming things; in particular, about naming files.

This is a problem that snuck up on me; I muddled along for years before recognizing it and gradually crafting strategies to deal with it. At first, I thought of it as a problem of where to put things; a place for everything and everything in its place. The desktop metaphors of file folders and hierarchical directory trees fooled me into thinking that the answer was to replicate the practices of generations of file clerks and librarians. Wrong. The affordances of filing cabinets and bookshelves lead you in directions that create unnecessary problems and obscure the opportunities inherent in the digital realm.

The work of pioneering thinkers like Vannevar BushDoug Engelbart, Ted Nelson, and Tim Berners-Lee seemed to offer a way out. They painted a compelling picture of how knowledge work might flourish once everything was digital, reachable via clickable links, and cleverly indexed by the engineers and algorithms at Google. Progress, but these visions glossed over the question of how to create and manage all the digital goodies to be found at the other end of all those links. That’s the world that you and I spend our days in; a world of email, Slack, Dropbox, shared drives, and files. Lots of files; 49,000+ and counting in my case.

The choices you make the first time you save a file can either complicate or simplify your life tomorrow, next year, and five years from now. Here’s a file name I just pulled off my laptop from an old project;

Final Presentation v.3.31.ppt

I’m willing to bet that you have a similar file somewhere on your computer. In fact, I’m willing to bet that you have several files with that or a similar name. Now, you would be correct to surmise that this file was originally found in some project directory at the end of a path something like /Documents/CLIENT/CustomerServiceReview/. That doesn’t help you very much, however, without access to my computer. Things are slightly better if we are both working off of a shared drive or Dropbox folder. On the other hand, what if I need to email the file to a client whose IT department blocks access to Dropbox?

These are problems that occur when you share a file with an incomplete or ambiguous name. Weak file names also cause problems for the individual knowledge worker. While you will only name a file once, you will have frequent opportunities to decide whether to look inside a file based on its name. You will often be making that choice while scanning through a list of potentially relevant files—either a directory listing or the results of a search.

Over the last several years, I’ve evolved a set of rules or guidelines for choosing a file name. As a sort of meta-rule, I start from the perspective that I will write the name only once, while I will read the name and decide what to do based on that name dozens or hundreds of times over the course of a project or a career. Here are the names of two files from my computer:



The first is a journal article I want to have ready access to; the second contains the slides for a talk I gave to a networking group I participate in. Let’s dissect the names to see what they tell me. The first file name is straightforward; it identifies the names of the authors and the title of the journal article. It contains all I need to decide whether I want to open the file to read it or whether this is the particular file I’d like to share with a colleague.

The second takes a little bit more effort to decode, although I can decipher the code on the fly, which is my principal concern. If I share the file with you, the code might slow you down a little bit but you can still extract the necessary information with no knowledge of my system. Let’s breakdown the name into its components and see why its constructed the way that it is:

  • PKM-StrategyWhyAndHow- This is simply a descriptive name for the contents of the presentation. “PKM” is my shorthand for Personal Knowledge Management.
  • 2011-04-21-1104 This is a timestamp for when I created the file. When I created this file, I was using timestamps that included the time as well as the date. In my current practice, I only record the date. I use a keyboard macro program (TextExpander on my Mac, ActiveWords when I am working in Windows) to enter the time or datestamp.
  • NSC- This is a shorthand code for the organization I was part of at the time I wrote this talk. I’ve been affiliated with a number of different firms and institutions over the years and I find that who I was working for is a consistent memory trigger.
  • TLA- This is a shorthand code for the particular client I prepared this talk for. Another meaningful memory trigger.

There is a design logic underlying these names and a series of principles and considerations that have and continue to evolve:

  • Descriptive File Names: All modern file systems permit long file names. Use them. I choose names based on what they suggest about the contents and what will jog my memory later
  • Ordering of Name Elements: My basic ordering of name elements is Organization, Client/Project, Descriptive Name, and Datestamp. It’s basically a hierarchy to collect items in sorted lists
  • Shorthand Codes: I try to keep these codes at three letters each. I’ll deviate from that if something longer makes more sense. The codes are derived from the organization, client, project. etc. in a way that serves as a mnemonic for me. Three characters yields over 17,000 possible combinations so I’m not worried about running out. I don’t maintain an actual list; the code is a trigger for me to recall the actual organization. Here are some of the codes I currently use to offer a flavor of what I mean:
    • LOY – Loyola University Chicago
    • HCG – Huron Consulting Group
    • CMN – Collaborating Minds
    • NSC – New Shoreham Consulting
    • TLA – Technology Leaders Association
    • PKM – Personal Knowledge Management
  • Embedded Datestamps: Computer operating systems keep track of various file dates, so why bother to add a date to the file name? Because the operating system timestamps serve the operating system’s purpose and can change for any number of reasons. The embedded timestamp reflects a date that has significance to me. For example, it might be the day I delivered a particular talk.
  • Technical Considerations: Although most operating systems allow spaces in file names, I don’t use them. Instead I either capitalize each word (Title Case or CamelCase if you’re a wiki user) or use a dash to separate sections of the file name. I also try to avoid other punctuation characters to avoid potential problems in some operating system settings. Probably a holdover from my programming days.

This is a system that has evolved over time; much of it was not designed. I am not fanatical about any of it; utility today and tomorrow is the deciding factor. I do try to avoid the temptation to think any file is “only a temporary file.” I don’t try to be religious about any of this and keep the following passage from Jorge Luis Borges in mind:

These ambiguities, redundancies and deficiencies remind us of those which doctor Franz Kuhn attributes to a certain Chinese encyclopaedia entitled ‘Celestial Empire of benevolent Knowledge’. In its remote pages it is written that the animals are divided into:

(a) belonging to the emperor,

(b) embalmed,

(c ) tame,

(d) suckling pigs,

(e) sirens,

(f) fabulous,

(g) stray dogs,

(h) included in the present classification,

(i) frenzied,

(j) innumerable,

(k) drawn with a very fine camelhair brush,

(l) et cetera,

(m) having just broken the water pitcher,

(n) that from a long way off look like flies.

Paths to more effective knowledge work

There is no curriculum on how to be an effective knowledge worker although we live in a world dominated by knowledge work. We identify ourselves as knowledge workers. But what comes after that?

Peter Drucker observed that the defining characteristic of knowledge work and knowledge workers is that the first question is “what is the task?” (see Knowledge-Worker Productivity). In manual work, the task is a given. It is defined in advance of hiring the worker and its various inputs, outputs, and structures define who the appropriate worker is for each task.

All knowledge work begins with the question of what is it that I am expected to do. Nothing in conventional education or conventional organizational thinking prepares us to deal with this question. This goes well beyond questions of self-management or self organizing systems. It implies that we each have responsibility as both designers and executors of our work. It is not sufficient to understand the ins and outs of Microsoft Excel or Microsoft Word. If we have some responsibility for defining what the task is, then we have some responsibility to understand why the task is relevant and how it fits into the broader picture.

This complicates our lives as both individual knowledge workers and as members of larger organizations. This obsoletes conventional job descriptions. Every job now has components of project management, of strategic thinking, of analytic thinking, and design creativity. What does this imply for how we educate and develop ourselves to be effective as knowledge workers? Note that I’ve focused this question on our individual responsibilities. That leaves another set of questions for the educational institutions and training organizations that lay claim to preparing us for the environment in which we work.

Practice and Performance

Cpl. Derek McGee, USMC MEU15 TRAP 2013

How do you strike an effective balance between practice and performance? In many realms we draw a distinction between performing and preparing to perform. Actors and musicians rehearse. Athletes practice. Soldiers train before they fight.

In other, equally demanding, realms the boundary is fuzzy; at times non-existent. Where does a sales rep or project manager practice? Where does a brand manager practice market segmentation? When does an investment banker practice designing a deal?

The notion of an apprentice observing and mimicking a master is one proven model that blends practice and performance. What troubles me is that this model works best when it is explicit. There needs to be some recognition that some performance settings are about both performance and practice; some fraction of your focus and attention needs to be tuned to learning.

My sense is that we have abandoned the notion of practice built into apprenticeship and favor performance exclusively. If we substitute performance only in place of practice and performance, do we abandon the possibility of achieving peak performance? How do we recognize situations that call for effective apprenticeship models? How do we design organizations so that they meet their performance goals and provide the necessary practice opportunities so that tomorrow’s organization can perform as well or better than today’s?

DIY Learning Advice from Jay Cross


JayCross-real-cover.jpgJay Cross is at it once again. He’s launched the Real Learning Project, an exploration of DIY learning in today’s organizational environment. Here’s his description of the effort:

The Real Learning Project helps people who are taking their professional development into their own hands and shows them how to learn to learn.

My new book, Real Learning is for all those people we’ve made responsible for their own learning. This is the missing manual.

Real Learning explains self-assessment, setting goals, dealing with feeds and flows, improving retention, curation, working out loud, social learning, and more. Each technique is backed with a practical exercise.

Real Learning reveals how to:

• Learn from experience

• Take advantage of the latest findings from neuroscience

• Save time by accelerating how you learn

• Remember things faster, better, deeper

• Adopt sound learning practices as lifelong habits

• Form a sustainable, nurturing community

• Use shortcuts, cheatsheets, and rules of thumb

Real Learning is about how to learn for yourself. No classrooms. No instructors. No training department. Little in the way of theory. Just stuff that works.  (Although learning with your team is encouraged,)

The core focus is experiential learning and tacit knowledge. It’s learning to be all you can be rather than amassing more content.

This matters for two reasons. One, DIY learning is something we are all going to have to get better at. Organizations won’t have the time or the resources to invest in time-consuming formal training efforts. But the need to learn new things will only continue to increase. Two, Jay is one of the key people thinking about this problem in organizational contexts.

There are a number of resources to take advantage of with this effort:

The Real Learning Website

The Google Plus Community

• A blog that Jay describes as a Plog—A personal progress blog

I’ve purchased the e-book version of the book in its present beta form and hope to follow along and contribute as it evolves.

Insights Into Innovation: Peter Thiel’s “Zero to One”

Zero to One: Notes on Startups, or How to Build the Future Zero to One: Notes on Startups, or How to Build the Future Peter Thiel, Blake Masters

Peter Thiel’s Zero to One claims to be about startups, but that is too narrow a view of its value. Thiel explores the challenges of creating the risky new in an environment that prefers safe repetition. Startups are the favored example in today’s entrepreneurial environment, but we can all benefit if organizations learn to actually do the innovation they profess in their PR.

Zero to One is a book that bears rereading; there are insights throughout that are crisply expressed and presume that the reader is willing to think. I was hooked early on with this observation in the preface:

The single most powerful pattern I have noticed is that successful people find value in unexpected places, and they do this by thinking about business from first principles instead of formulas.

One of the values of the book is the focus on the difference between creating something new—going from zero to 1—and imitating or scaling an idea after it has been dreamt up. The U.S. is probably better than almost anywhere else at rewarding true innovation, yet most of us prefer the safety of copying someone else’s success.

One of the arguments Thiel develops is teasing apart whether we are optimistic or pessimistic about the future from our views about whether that future is “definite” or “indefinite.” Can we control what emerges tomorrow by what we do today? Or, are we at the mercy of a random and unknowable future? There’s an important insight here about striking a good (as opposed to the “right”) balance between having a definite perspective and adapting to new information as it becomes available. It isn’t a binary choice; like all important leadership challenges it’s about balance and perspective.

There is value in nearly every section of this book. Here, for example, is a list of seven questions that let you evaluate an idea for its entrepreneurial potential:

  1. The Engineering Question: Can you create breakthrough technology instead of incremental improvements?
  2. The Timing Question: Is now the right time to start your particular business?
  3. The Monopoly Question: Are you starting with a big share of a small market?
  4. The People Question: Do you have the right team?
  5. The Distribution Question: Do you have a way to not just create but deliver your product?
  6. The Durability Question: Will your market position be defensible 10 and 20 years into the future?
  7. The Secret Question: Have you identified a unique opportunity that others don’t see?

Elsewhere, you will benefit from Thiel’s musings on why you would just as soon avoid competition and opportunities to disrupt existing markets. Throughout Zero to One, Thiel hammers and chips at why the rules for going from one to many, which dominate conventional MBA programs and wisdom, are, at best, irrelevant and, more likely, misleading if you focus instead on creating something new.

If you’ve managed to create a billion dollars of value, you’re pretty much guaranteed a book contract. Whether you have anything useful to share in that book is a separate question. Thiel’s value creation skills extend to intellectual as well as financial capital. He’s clearly reflected on his experiences in a systematic way and we benefit.

Two spaces or one; change and persistence

Selectric-ElementI learned to type before I learned to drive; now nearly 50 years ago. I was taught that you put two spaces after a period at the end of a sentence. Eventually, I left typewriters behind and began to write with text editors and word processors. I learned a little bit about proportional fonts and typesetting and, at some point in the somewhat less distant past switched over to using a single space.

This morning, i came across the following link in my Facebook newsfeed – Space Invaders: Why you should never, ever use two spaces after a period. – posted by Andy McAfee. It’s an old item and it’s an old controversy (for example, see Why two spaces after a period isn’t wrong (or, the lies typographers tell about history)).

What I find interesting about this is what it reveals about change and habits. The very first comment in response to Andy’s post was from someone who had also learned to type a long time ago. In their view, the controversy was a silly waste of time and they intended to happily continue to insert two spaces until the end of time. I’m sure that if I went back to the thread. someone else will have weighed in otherwise. There will be yet another impassioned argument over a convention. How do you get new knowledge into an established system of practice? How do you get from new knowledge to new practice?

We are now three hundred years or so past the Enlightenment. How long do you think it will be before reason triumphs over tradition?


The importance of forgetting to creativity and innovation

Science fiction author Spider Robinson won the 1983 Hugo Award for Best Short Story with Melancholy Elephants. It’s a prescient take on an essential tension between creativity and commerce. Still worth reading. More worth contemplating.

Robinson explores where the boundaries of creativity might lie and what those boundaries might imply. There are tradeoffs to be made between the needs of artists and the interests of art as a whole. Those tradeoffs have artistic and economic consequences and striking the balance is by no means as self-evident as they might appear. Here’s the nub of his argument in his own words:

“I think it comes down to a kind of innate failure of mathematical intuition, common to most humans.   We tend to confuse any sufficiently high number with infinity.”  

For millions of years we looked at the ocean and said, ‘That is infinite.   It will accept our garbage and waste forever.’   We looked at the sky and said, ‘That is infinite: it will hold an infinite amount of smoke.’   We like the idea of infinity.   A problem with infinity in it is easily solved.   How long can you pollute a planet infinitely large?   Easy: forever.   Stop thinking.  

”Then one day there are so many of us that the planet no longer seems infinitely large.  

The ultimate bottleneck is this: that we have only five senses with which to apprehend art, and that is a finite number.

“Artists have been deluding themselves for centuries with the notion that they create.   In fact they do nothing of the sort.   They discover.   Inherent in the nature of reality are a number of combinations of musical tones that will be perceived as pleasing by a human central nervous system.   For millennia we have been discovering them, implicit in the universe–and telling ourselves that we ‘created’ them.   To create implies infinite possibility, to discover implies finite possibility.   As a species I think we will react poorly to having our noses rubbed in the fact that we are discoverers and not creators.”  

Go read the whole thing. It won’t take you long, But it will leave you thinking.