May 2018 - McGee's Musings

A Swiss Army Knife for Project Management

I’ve carried a pocket knife since my days as a stage manager/techie in college. A handful of useful tools in hand beats the perfect tool back in the shop or office. Courtesy of the TSA I have to remember to leave it behind when I fly or surrender it to the gods of security theater but every other day it’s in my pocket. There is, in fact, an entire subculture devoted to discussions of what constitutes an appropriate EDC—Every Day Carry—for various occupations and environments.

I’ve been thinking about what might constitute the equivalent EDC or Swiss Army Knife for the demands of project planning and management. We live in a project based world but fail to equip managers with an appropriate set of essential project management tools.

Like all areas of expertise, project management professionals build their reputations by dealing with more complex and challenging situations. The Project Management Institute certifies project management professionals. PMBOK, the Project Management Book of Knowledge has reached its sixth edition and runs to several hundred pages.

The complexities of large-scale project management push much training and education into the weeds of work breakdown structures, scope creep, critical-path mapping, and more. The message that project management is a job for professionals and the amateur need not apply is painfully clear. But we’re all expected to participate in project planning, and often we must lead projects without benefit of formal training in project management.

Recently, I looked at the need for project design before project management. The essential problem is to use a picture of where you want to end up to lay out a map of how to get there from wherever you are now.

The end is where to begin. Until you can conjure a picture of where you want to go, you have no basis to map the effort it will take to create it. Imagine what you need to deliver in reasonable detail and you can work backwards to the steps that will bring it into being. If you have a clear sense of where you are, you can also identify the next few steps forward.

Working out the steps that will take you from where you are to where you want to go can be done with two tools and three rules.

Tool #1: A calendar. If you can do it all without looking at one, you aren’t talking about a project.

Tool #2: A messy outline. An outline because it captures the essential features of ordering steps and clustering them. Messy because you can’t and won’t get it right the first time and the neat outlines you were introduced to in middle school interfere with that. (Personally, I’m partial to mind maps over pure outlines, but that is a topic for another time.)

Three rules generate the substance of the outline:

Small chunks
First things first
Like things together

“Small chunks” is a reminder that the only way to eat an elephant is in small bites. There are a variety of heuristics about recognizing what constitutes an appropriate small chunk of a project. Somewhere between a day and a week’s worth of work for one person isn’t a bad starting point. Writing a blog post is a reasonable chunk; launching a new blog isn’t.

Generating an initial list of small chunks is the fuel that feeds an iterative process of putting first things first, grouping like things together, and cycling back to revise the list of small chunks.

The art in project management lies in being clever and insightful about sequencing and clustering activities. Here, we’re focused on the value of thinking through what needs to be done in what order before leaping to the first task that appears. That’s why an outline is a more useful tool at this point than Gantt charts or Microsoft Project. An outline adds enough structure over a simple to do list to be valuable without getting lost in the intricacies of a complex software tool. An outline helps you organize your work, helping you discover similar tasks, deliverables, or resources that can be grouped together in your plans. An outline gives you order and clustering. The calendar links the outline to time. For many projects that will be enough. For the rest, it is the right place to start.

The point of a project plan is not the plan itself, but the structure it brings to running the project. The execution value of widespread project planning capability in the organization is twofold. First, it adds capacity where it is needed: at the grassroots level. Second, it improves the inputs to those situations where sophisticated project-management techniques are appropriate.

Trust, Verify, and Triangulate

“Trust but verify” is no longer an effective strategy in an information saturated world. When Ronald Reagan quoted the Russian proverb in 1985, it seemed clever enough; today it sounds hopelessly naive. If we are reasonably diligent executives or citizens, we understand and seek to avoid confirmation bias when important decisions are at hand. What can we do to compensate for the forces working against us?

It’s a cliché that we live in a world of information abundance. That cliché, however, has not led to the changes in information behaviors that it implies. We still operate as though information were a scarce commodity, believing that anyone who holds relevant data is automatically in a position of power and that information seekers depend on the holder’s munificence.

As data becomes abundantly and seemingly easily available, the problem for the information seeker changes. (It changes for the information holder as well, but that is a topic for another time.) The problem transforms from “Can I get the data?” to “What data exists? How quickly can I get it? How do I know I can trust it? How do I evaluate conflicting reports?” It is no longer simply a question of getting an answer but of getting an answer whose strengths and limits you understand and can account for.

The temptation is to fall into a trust trap, abdicating responsibility to someone else. “4 out of 5 dentists recommend…” “According to the Wall Street Journal…” “The pipeline predicts we’ll close $100 million…”

There was a time when we could at least pretend to seek out and rely on trustworthy sources. We counted on the staffs at the New York Times or Wall Street Journal to do fact checking for us. Today we argue that the fact checkers are biased and no one is to be trusted.

Information is never neutral.

Whatever source is collecting, packaging, and disseminating information is doing so with its own interests in mind. Those interests must be factored into any analysis. For example, even data as seemingly impartial as flight schedules must be viewed with a skeptical eye. In recent years, airlines improved their on-time performance as much by adjusting schedules as by any operational changes. You can interpret new flight schedules as an acknowledgment of operational realities or as padding to enable to reporting of better on-time performance.

If we are a bit more sophisticated, we invest time in understanding how those trusted sources gather and process their information, verifying that their processes are sound, and accept their reports as reliable inputs. Unfortunately, “trust but verify” is no longer a sufficient strategy. The indicators we once used to assess trust have become too easy to imitate. Our sources of information are too numerous and too distributed to contemplate meaningful verification.

Are we doomed? Is our only response to abandon belief in objective truth and cling to whatever source best caters to our own bias. Fortunately, triangulation is a strategy well matched to the characteristics of today’s information environment.

In navigation, you determine your location in relation to known locations. You need at least three locations to fix your current position. Moreover, you need to account for the limits of your measurement tools to understand the precision of your fix. In today’s world of GPS navigation, that precision might well be very high but still imperfect.

In organizational (and other) settings where you are attempting to make sense of—or draw useful inferences from—a multitude of noisy and conflicting sources, the principles of triangulation offer a workable strategy for developing useful insights in a finite and manageable amount of time.

In navigation, the more widely and evenly dispersed your sightings, the more precisely you can fix your position. Focus your data collection on identifying and targeting multiple sources of input that represent divergent, and possibly conflicting, perspectives. Within an organization, for example, work with supporters and opponents, both active and passive, of a proposed reorganization or systems deployment to develop an implementation strategy. When evaluating and selecting a new application, seek out a wider assortment of potential references, vendors, and analysts.

Triangulation also helps counteract the simplistic notion of balance that undermines too many narratives. Triangulation is based on living in a three-dimensional world; it cannot tell you where you are with only two fixes. We should be at least as diligent when mapping more complex phenomena.

A data collection effort organized around seeking multiple perspectives and guidance risks spinning out of control. Analyzing data in parallel with collection manages that risk. Process and integrate data as it is collected. Look for emerging themes and issues and work toward creating a coherent picture of the current state. Such parallel analysis/collection efforts will identify new sources of relevant input and insight to be added to the collection process.

Monitoring the emergence of themes, issues, and insights will signal when to close out the collection process. In the early stages of analysis, the learning curve will be steep, but it will begin to flatten out over time. As the analysis begins to converge and the rate of new information and insight begins to drop sharply, the end of the data collection effort will be near.

The goal of fact finding and research is to make better decisions. You can’t set a course until you know where you are. How carefully you need to fix your position or assess the context for your decision depends on where you hope to go. Thinking in terms of triangulation—how widely you distribute your input base and what level of precision you need—offers a data collection and analysis strategy that in more effective and efficient than approaches we have grown accustomed to in simpler times.

Chaos players: knowledge work as performance art

Stage - Auditorium. Photo by Monica Silvestre from Pexels

All the world’s a stage, And all the men and women merely players; They have their exits and their entrances, And one man in his time plays many parts
As You Like It, Act II, Scene VII. William Shakespeare

I’ve been thinking about the role of mental models for sense-making. While we do this all the time, I think there is significant incremental value in making those models more explicit and then playing with them to tease out their implications. Organization as machine is a familiar example, one that I believe is largely obsolete. Organization as ecosystem or complex adaptive system has grown in popularity. It has the advantage of being richer and more sensitive to the complexities of modern organizations and their environments. On the other hand, that mental model is a bit too appealing to to academic and consulting desires to sound simultaneously profound and unintelligible. It fails to provide useful guidance through the day-to-day challenges of competing and surviving.

Organization as performance art or theatrical production offers a middle ground between simplistic and over-engineered. It appeals to me personally given a long history staging and producing. It’s my hypothesis that most of us have enough nodding familiarity with the theater to take advantage of the metaphor and model without so much knowledge as to let the little details interfere with the deeper value.

The goal of theater is to produce an experience for an audience. That experience must always be grounded in the practical art of the possible. This gives us something to work with.

Let’s work backwards from the performance. We have the players on the stage and an audience with expectations about what they are about to experience. If that is all we have, then we are in the realm of storytelling. Storytelling demands both the tellers of the tale and the creator of the tale itself. Our playwright starts with an idea and crafts a script to bring that idea to life and connect it to all of the other stories and ideas the audience will bring to the experience. We now have a story, its author, storytellers, and an audience with their expectations.

Theater takes us a step farther and asks us think about production values that contribute to and enhance the experience we hope to create. Stage and sets and lighting and sound can all be drawn into service of the story. Each calls for different expertise to design, create, and execute. We now have multiple experts who must collaborate and we have processes to be managed. Each must contribute to the experience being created. More importantly, those contributions must all be coordinated and integrated into the intended experience.

This feels like a potentially fruitful line of inquiry. It seems to align well with an environment that depends on creativity and innovation as much as or more than simple execution. How deeply should it be developed?

Going behind the screen: mental models and more effective software leverage

I’ve been writing at a keyboard now for five decades. As it’s Mother’s Day, it is fitting that my mother was the one who encouraged me to learn to type. Early in that process, I was also encouraged to learn to think at the keyboard and skip the handwritten drafts. That was made easier by my inability to read my own handwriting after a few hours.

I first started text editing as a programmer writing Fortran on a Xerox SDS Sigma computer. I started writing consulting reports on Wang Word Processors. When PCs hit the market, I made my way through a variety of word processors including WordStar, WordPerfect, and Microsoft Word. I also experimented with an eclectic mix of other writing tools such as ThinkTank, More, Grandview, Ecco Pro, OmniOutliner, and MindManager. Today, I do the bulk of my long-form writing using Scrivener on a Mac together with a suite of other tools.

The point is not that I am a sucker for bright, shiny, objects—I am—or that I am still in search of the “one, true tool.” This parade of tools over years and multiple technology platforms leads me to the observation that we would be wise to spend much more attention to our mental models of software and the thinking processes they support.

That’s a problem because we are much more comfortable with the concrete than the abstract. You pick up a shovel or a hammer and what you can do is pretty clear. Sit down at a typewriter with a stack of paper and, again, you can muddle through on your own. Replace the typewriter and paper with a keyboard and a blank screen and life grows more complicated.

Fortunately, we are clever apes and as good disciples of Yogi Berra we “can observe a lot just by watching.” The field of user interface design exists to smooth the path to making our abstract tools concrete enough to learn.
UI design falls short, however, by focusing principally at the point where our senses—sight, sound, and touch—meet the surface of our abstract software tools. It’s as if we taught people how to read words and sentences but never taught them how to understand and follow arguments. We recognize that a book is a kind of interface between the mind of the author and the mind of the reader. A book’s interface can be done well or done badly, but the ultimate test is whether we find a window into the thoughts and reasoning of another.

We understand that there is something deeper than that words on the page. Our goal is to get behind the words and into the thinking of the author. This same goal exists in software; we need to go behind interface we see on the screen to grasp the programmer’s thinking.

We’ll come back to working with words in a moment. First, let’s look at the spreadsheet. I remember seeing Visicalc for the first time—one year too late to get me through first year Finance. What was visible on the screen mirrored the paper spreadsheets I used to prepare financial analyses and budgets. The things I understood from paper were there on the screen; things that I wished I could do with paper were now easy in software. They were already possible and available by way of much more complex and inscrutable software tools but Visicalc’s interface created a link between my mind and Dan Bricklin’s that opened up the possibilities of the software. I was able to get behind the screen and that gave me new power. That same mental model can also be a hindrance if it ends up limiting your perception of new possibilities.

Word processors also represent an interface between writers and the programmer’s model of how writing works. That model can be more difficult to discern. If writer and programmer have compatible models, the tools can make the process smoother. If the models are at odds, then the writer will struggle and not understand why.

Consider the first stand-alone word processors like the Wang. These were expensive, single function machines. The target market was organizations with separate departments dedicated to the production of documents; insurance policies, user manuals, formal reports, and the like. The users were clerical staff—generally women—whose job was to transform hand written drafts into finished product. The software was built to support that business process and the process was reflected in the design and operation of the software. Functions and features of the software supported revising copy, enforcing formatting standards, and other requirements of a business.

The economics that drove the personal computer revolution changed the potential market for software. While Wang targeted organizations and word processing as an organizational function, software programmers could now target individual writers. This led to a proliferation of word processing tools in the 1980s and 1990s reflecting multiple models of the writing process. For example, should the process of creating a draft be separate from the process of laying out the text on the page? Should the instructions for laying out the text be embedded in the text of the document or stored separately? Is a long-form product such as a book a single computer file, a collection of multiple file, or something else?

Those decisions influence the writer’s process. If your process meshes with the programmer’s, then life is good. If they clash, the tool will get in the way of good work.

If you don’t recognize the issue, then your success or failure with a specific tool can feel capricious. If you select a tool without thinking about this fit, then you might blame yourself for problems and limitations that are caused by using a tool that clashes with your process.

Suppose we recognize that this issue of mental models exists. How do we take advantage of that perspective to become more effective in leveraging available tools? A starting point is to reflect on your existing work practices and look for the models you may be using. Are there patterns in the way you approach the work? Do you start a writing project by collecting a group of interesting examples? Do you develop an explicit hypothesis and search out matching evidence? Do you dive into a period of research into what others have written and look for holes?

Can you draw a picture of your process? Identify the assumptions driving your process? Map your software tools against your process?

These are the kinds of questions that designers ask and answer about organizational processes. When we work inside organizations, we accept the processes as a given. In today’s environment for knowledge work, we have the capacity to operate effectively at a level that can match what organizations managed not that long ago. Given that level of potential productivity and effectiveness, we now need to apply the same level of explicit thought and design to our personal work practices.

Design projects before worrying about managing them

I’m gearing up to teach project management again over the summer. There’s a notion lurking in the back of my mind that warrants development.

We would do a better job at managing projects if we spent more time designing them first.

We turn something into a project when we encounter a problem that we haven’t tackled before and can’t see exactly how to solve in one step. The mistake we make is to spend too much time thinking about the word “management” at the expense of the word “project.”

Suppose our problem is to improve the way we bring new hires on board in a rapidly growing organization. There’s an obligatory amount of HR and administrative paperwork to complete, but the goal is to integrate new people into the organization. Do you send them off immediately to new assignments? Do you design a formal training program? There’s a host of questions and a host of possible ideas so you now have a potential project.

Given the pressures in organization to “get on with it” the temptation is to grab a half-formed idea, sketch a a plausible plan, guess at a budget, pick a deadline, and start. If we have some project management practices and discipline, we’ll flesh out the plan and develop something that looks like a work breakdown structure and a timeline.

What we don’t give sufficient attention to is the design thinking that might transform this project idea into something that might add meaningful and unexpected value to the organization. We don’t give that attention because we don’t view a project as something worthy of design.

What would it mean to design a project? Two ideas come to mind. The first would be to generate ways to increase the value of the effort. In our on-boarding example, one objective was to offer new employees practice in preparing client presentations. Rather than develop a generic presentation skills module, the project team came up with a better idea. We asked teams in the field for research and competitive intelligence tasks on their to do lists and transformed those into assignments for the on-boarding program. This allowed us to accomplish the presentation skills training, contribute to actual client work, and build bridges between new employees and their future colleagues.

A second design thinking aspect would be a more deliberate focus on generating multiple concepts and approaches that would evolve into a work breakdown structure. My conjecture is that more projects are closer to one-off efforts than to executing the nth iteration of a programming or consulting project. Project management personalities are tempted to standardize and control prematurely. But standard work plans and templates aren’t relevant until there are enough projects of a certain category to warrant the investment. Doing this kind of design work calls for expanding the toolset beyond the conventional project management toolkit that is focused on tracking and monitoring the sequence of tasks.

This is a notion in development. It isn’t fully baked but my instinct is that it is worth fleshing out. Some questions I’m curious to get reactions to include:

Is making a distinction between project design and project execution worth the trouble?
How do standard project management tools—Gantt charts, project management software such as Microsoft Project or Primavera, or spreadsheets—interfere with early stage idea generation and creativity?
How might you/do you expand the toolset to support better design thinking?

Review – Scrum: The Art of Doing Twice the Work in Half the Time

Scrum: The Art of Doing Twice the Work in Half the Time. Jeff Sutherland and JJ Sutherland

There’s a rule of thumb in software development circles that the best programmers can be ten times as productive as average programmers. This is the underlying argument for why organizations seek to find and hire the best people. There is research to support this disparity in productivity. There is similar research on the relative productivity of teams. There, the range in productivity between the best and the rest is closer to two orders of magnitude; as much as a 1,000 times more productive.

Jeff Sutherland makes the case that the practices that collectively make up “Scrum” are one strategy for realizing those kinds of payoffs.

Sutherland is a former fighter pilot, a software developer, one of the original signatories of the Agile Manifesto, and the inventor of Scrum. This is his story of how Scrum came to be, what it is, and why it’s worthwhile. The particular value of the book is its focus on why Scrum is designed the way it is and why that matters.

Scrum’s origins and primary applications have been in the realm of software development. Sutherland builds an argument that Scrum’s principles and methods apply more broadly. Although he doesn’t make this argument directly, this wider applicability flows from evolutionary changes in the the organizational environment. Changes in the pace and complexity of organizational work simultaneously make conventional approaches less effective and Scrum more so.

Scrum is a collection of simple ideas; it’s a point of view about effective problem solving more than a formalized methodology. That’s important to keep in mind because like too many solid ideas, the essence can get lost in the broader rush to capitalize on those ideas. There appear to be an unlimited supply of training courses, consultants, and the usual paraphernalia of a trendy business idea; you’re better off spending time reading and thinking about what Sutherland has to say first. That may be all you need if you’re then willing to make the effort to put those ideas into practice.

Sutherland traces the roots of Scrum to the thinking underlying the Toyota Production System. He also draws interesting links to John Boyd’s work on strategy embodied in the OODA Loop and to the martial arts. Scrum is built on shortening the feedback between plans and action. It is a systematic way of feeling your way forward and adapting to the terrain as you travel over it.

Sutherland draws a sharp contrast with more traditional management techniques such as Waterfall project management approaches and their well-worn trappings such as Gantt charts and voluminous unread and unreadable requirements documents.

Understanding the managerial appeal and limitations of these trappings is key to grasping the contrasting benefits of Scrum. Waterfalls and Gantt charts appeal to managers because they promise certainty and control. They can’t deliver on that promise in today’s environment. In the software development world, they never could and in today’s general organizational environment they also come up short.

Understanding that appeal and why it is misplaced clarifies the strengths of Scrum. There was a time when managers came from the ranks of the managed. They had done the work they were now responsible for overseeing and were, therefore, qualified to provide the direction and feedback needed to pick a path and follow it. Management was primarily about execution and not about innovation.

The illusion in waterfall and other planning exercises is that what we are doing next is a repeat of what we have done before. If we have built 100 houses, we can be confident of what it will take to build the 101st. If we are building a new road or a new bridge, then what we have learned from the previous roads and bridges we’ve built can provide a fairly precise estimate for the next.

This breaks down, however, when we are building in new terrain or experimenting with new designs. The insights and experience of those who’ve built in the past don’t transfer cleanly to this more dynamic environment. The world of software has always been new territory and we are always experimenting. The terrain is always in flux even when the technology is temporarily stable. Now, it is those who are doing the work who are best positioned to plan and manage as we move into new territories and terrain.

Scrum comes into play when we are moving into territory where there are no roads and are no maps. If you are moving into new territory you can only plan as far ahead as you can see. There are no maps to follow. Sutherland puts it thus:

Scrum embraces uncertainty and creativity. It places a structure around the learning process, enabling teams to assess both what they’ve created and, just as important, how they created it. The Scrum framework harnesses how teams actually work and gives them the tools to self-organize and rapidly improve both speed and quality of work.

There’s a terminology and a set of techniques that make up Scrum. Sutherland covers the basics of such notions as scrum masters, product owners, backlog, sprints, retrospectives, communication saturation, continuous improvement, and stand up meetings. But he’s no fan of turning these into dogma.

Scrum runs the risk of being viewed as no more than the latest management fad. Sutherland is a true believer and has evidence to support his belief. There are lots of true believers but only a few are willing to bring substantive evidence to back up that belief. That earns Sutherland the right to offer his own closing argument:

What Scrum does is alter the very way you think about time. After engaging for a while in Sprints and Stand-ups, you stop seeing time as a linear arrow into the future but, rather, as something that is fundamentally cyclical. Each Sprint is an opportunity to do something totally new; each day, a chance to improve. Scrum encourages a holistic worldview. The person who commits to it will value each moment as a returning cycle of breath and life.

The heart of Scrum is rhythm. Rhythm is deeply important to human beings. Its beat is heard in the thrumming of our blood and rooted in some of the deepest recesses of our brains. We’re pattern seekers, driven to seek out rhythm in all aspects of our lives.

What Scrum does is create a different kind of pattern. It accepts that we’re habit-driven creatures, seekers of rhythm, somewhat predictable, but also somewhat magical and capable of greatness.

When I created Scrum, I thought, What if I can take human patterns and make them positive rather than negative? What if I can design a virtuous, self-reinforcing cycle that encourages the best parts of ourselves and diminishes the worst? In giving Scrum a daily and weekly rhythm, I guess what I was striving for was to offer people the chance to like the person they see in the mirror.