Habitual Struggles

One of my bad habits is obsessing about my deficiency of good habits. I know that good habits are important because the nuns and monks were relentless in telling me so; decades later their ambivalence about my academic success without suitable discipline still lingers.

I’m not devoid of good habits. Lately, I’ve had some success with Jerry Seinfeld’s keep the streak going/don’t break the chain trick (Jerry Seinfeld’s Productivity Secret), although Friday’s NY Times Crossword stumped me, breaking a 355-day streak. Two and a quarter years ago, I managed to reboot a journaling habit by starting a Morning Pages effort. 

Habits are on my mind lately for several reasons. Back in March, I finished Wendy Wood‘s Good Habits, Bad Habits: The Science of Making Positive Changes That Stick and thought it worth processing my thoughts into a post here. A bit slower than I would like, but not unusually so. 

More recently, I came across an interesting blog post from Eleanor Konik, The Difficulties of Teaching Notetaking » Eleanor Konik. I’ve been chipping away at improving my own note-taking practices and was toying with how and whether to incorporate any of that into my teaching. Konik’s argument is that no one implements good techniques simply because they’re good techniques. We’re all adept at cost/benefit calculations and the payoff structures for most “good” habits are hugely dependent on how heavily you weight the suasion of authority figures. For most of us, most of the time, the payoff for following objectively good practices doesn’t rise to the effort. 

This is where the accumulating research on habit formation comes in. Converting an activity from an invocation of willpower to automatic pilot effectively eliminates the effort and energy part of the equation. This is why Alfred North Whitehead’s observation continues to show up in discussions of habit:

 Civilization advances by extending the number of important operations which we can perform without thinking about them. Operations of thought are like cavalry charges in a battle- they are strictly limited in number, they require fresh horses, and must only be made at decisive moments. 

We know that thinking is expensive. As knowledge workers, thinking is a definitional component of your work. One of the highest returns on IQ points is reducing the demand for IQ points wherever possible. 

Woods offers an observation that I’ll close with; 

we repeatedly do the things we love doing. But we also grow to love the things that we repeatedly do.

The task then is to be more intentional about the practices whose repetition will lay down the habits that will free up the capacity for better “operations of thought” when those decisive moments arrive.

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. 

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. 

Leading from the bench: Abby Wambach insights on leadership

Wambach, Abby. 2019. WOLFPACK: How to Come Together, Unleash Our Power, and Change the Game. Celadon Books.

I am not the ostensible target audience for this book. Abby Wambach, one of the all-time best soccer players in the world, wrote Wolfpack following her commencement address at Barnard College in 2018;

She’s talking to women about leadership.

But I would be stupid not to take advantage of wisdom wherever I find it. I stumbled across Wolfpack courtesy of Brené Brown ([Brené with Abby Wambach on the New Rules of Leadership) who puts it on her “top five must-read leadership books.” She’s right.

Wolfpack is a short book. That’s because there isn’t any padding. The book resembles the game Wambach played; competition and cooperation stripped to its essentials.

She draws her title from the tale of how the re-introduction of wolves restored the ecosystem of Yellowstone Park. It’s a story about the complexity and simplicity of systems. I’ve written about it myself before; (Learning to see systems \- wolves and rivers). It’s worth your time to check that story out;

Wambach packages her advice in a handful of rules. One that stood out for me was “lead from the bench.” Perhaps it resonates with my experience as a stage manager operating in the wings. While I’ve had my share of leading from in front, I’ve seen the power of leading from wherever circumstances have put you. Wambach’s particular story stems from her transition from starter to substitute during the 2015 World Cup competition. Here’s her take on that moment:

You are allowed to be disappointed when it feels like life’s benched you. What you aren’t allowed to do is miss your opportunity to lead from the bench. If you’re not a leader on the bench, don’t call yourself a leader on the field. You’re either a leader everywhere or nowhere.

Wambach understands that leadership isn’t about the individual. One powerful statement of that level of insight shows up in this TV commercial with her;

One more quote from Wambach;

Leadership is not a position to earn, it’s an inherent power to claim. Leadership is the blood that runs through your veins—it’s born in you. It’s not the privilege of a few, it is the right and responsibility of all. Leader is not a title that the world gives to you—it’s an offering that you give to the world.

This is leadership worth emulating.

Choosing to say yes inside the organizational hairball

MacKenzie, Gordon. 1997. Orbiting the Giant Hairball : A Corporate Fool’s Guide to Surviving With Grace. US: Viking Pr.

I first encountered Gordon MacKenzie’s Orbiting the Giant Hairball during my time growing Diamond Technology Partners. I decided to revisit it recently. I’ve picked it up from time to time over the intervening 23 years (we’ll return to that notion in a bit). It wasn’t something that neatly fit my typical reading patterns. But it deals with a problem that has been central to my work. How do you reconcile creativity and organizations?

Maybe it was the image of large organizations as “hairballs.” MacKenzie’s point about larger organizations was that they accrete rules and standard operating procedures over time. Mostly, that is a good and necessary thing. You don’t want every worker on the line to decide which tires to attach to the axles today. But if you spend much time inside organizations, you learn that rules and rule-making can impose their own perverse logic. How many items in the standard operating procedures or the employee manual reduce to “never, ever, let Joe do that again?” Organizations are suspicious of creativity and people are full of it. A volatile combination.

MacKenzie worked inside Hallmark; he was a creative leader in an organization that depended on its creativity. Even there, the forces working to suppress creativity were powerful. MacKenzie puts it succinctly, ” it is not the business of authority figures to validate genius, because genius threatens authority.” His solution as he gained authority within Hallmark was appropriately creative. Genius is hard to discern before the fact. MacKenzie’s answer was to default to saying “yes.” If someone or some team approached MacKenzie with a proposal to try something, he gave them permission. He didn’t ask or worry whether he had any authority to do so. This mildly subversive act was often just enough to shake loose resources or convince others to let an experiment proceed. I adopted this strategy to good effect.

Fundamentally, Orbiting the Giant Hairball is about this tension between order and chaos. The proponents of order are loud and powerful. But the world depends on the balance between yin and yang. There are more than enough forces working against creativity in organizations; the creative spirit needs champions too.

One final observation. I pointed out at the start that I had elected to reread this provocative little book, Lately, I’ve been encountering a lot of well-argued, and certainly well-intentioned, advice about the importance of improving efficiency in processing new information. We’re assaulted with new inputs. But efficiency is the wrong metric. Managing inputs effectively should dominate efficiency. But effectiveness is much harder to assess. Many items on my reading list are worth no more than a single reading; some turn out to not be worth that. But the other tail of the distribution also matters. Certain books yield new insights when you revisit them with further experience. Don’t let a quest for temporary efficiencies block access to that additional value.

Review – Intertwingled: Information Changes Everything

Image of Intertwingled CoverMorville, Peter. 2014. Intertwingled: Information Changes Everything. US: Semantic Studios.

Intertwingled is not a practical book. It is not intended to be. Unfortunately, that will discourage those who could most benefit from its message and perspective. It’s an extended reflection by its author, Peter Morville, on the deep challenges of making information more easily accessible and impactful within organizations. Morville has written several of the essential books in the world of information design and architecture (Information Architecture,  Ambient Findability). Intertwingled is a more reflective exercise; an attempt to pick a broader vantage point on understanding both the technological and organizational environments we inhabit. Morville opens with an observation from Ted Nelson:

People keep pretending they can make things hierarchical, categorizable, and sequential when they can’t. Everything is deeply intertwingled.  – Theodor Holm Nelson

I’ve never been a huge fan of the term “intertwingled” – probably because I am generally suspicious of coining “cute” new terms. Ted Nelson, on the other hand, seems drawn to the practice. Nelson’s books, Computer Lib/Dream Machines and Literary Machines, were hugely influential in luring me into the field and Morville seems to have been similarly enticed.

I don’t think Morville makes me any more comfortable with the term, but the book and his arguments and observations are still  worth the time.

It’s beyond cliche that we live in an information economy. It’s easy to be distracted by the shiny stuff– apps, devices,  platforms, technology. Morville’s focus is on the peculiar notion of information. Information is a surprisingly slippery term and we are all well served by efforts such as Intertwingled that make us think about that slipperiness. Morville observes that

Access to massive amounts of conflicting information from myriad sources creates filter failure. We don’t know what to believe. So we fall back on simple ways of knowing. We trust experts and those in authority. We follow doctor’s orders. Or we reject expertise completely.

Lately, it seems that rejection has become the go to strategy in many settings. This is not, in fact, a new problem. Morville, for example, offers the following observation from computer scientist Calvin Mooers published in 1959:

Many people may not want information, and they will avoid using a system precisely because it gives them information. Having information is painful and troublesome. We have all experienced this. If you have information, you must first read it, which is not always easy. You must then try to understand it. Understanding the information may show that your work was wrong, or may show that your work was needless. Thus not having and not using information can often lead to less trouble and pain.

Morville’s goal with Intertwingled is to make you think. He succeeds admirably. Enough so that this will be a book I expect to return to.

Insight on Project Planning and Management: Review of Start Finishing

book cover imageStart Finishing: How to Go from Idea to Done . Charlie Gilkey

I suspect that diet books are the only non-fiction category with more titles than time management and productivity. Perhaps I would be better served if I shifted to reading diet books.

Like diet books, I once read these books in quest of the perfect system; the answer that would guide me waking and guard me sleeping. What I seek these days is much the same as I do with Compline[add link] ; reassurance that I am not alone in my struggles and the possibility of insights I can fold into my practices. Charlie Gilkey’s Start Finishing offers both in good measure. I think what got me hooked this time was this point of tangency with my thinking:

Most of what I read didn’t hit the target, though. The personal productivity literature was too nitty-gritty and focused on tasks, and the personal development literature focused on principles and big ideas. But my problem was in the messy middle where creative projects live.

I’ve been exploring this messy middle myself for some time. It’s where I keep running into trouble. There’s a scene in The West Wing where Leo shares the following story with Josh:

This guy’s walking down the street when he falls in a hole. The walls are so steep he can’t get out.

A doctor passes by and the guy shouts up, ‘Hey you. Can you help me out?’ The doctor writes a prescription, throws it down in the hole and moves on.

Then a priest comes along and the guy shouts up, ‘Father, I’m down in this hole can you help me out?’ The priest writes out a prayer, throws it down in the hole and moves on

Then a friend walks by, ‘Hey, Joe, it’s me can you help me out?’ And the friend jumps in the hole. Our guy says, ‘Are you stupid? Now we’re both down here.’ The friend says, ‘Yeah, but I’ve been down here before and I know the way out.’

Gilkey has solid insight and advice for finding the way out.

The two most useful elements of his approach are guidance on breaking projects down into manageable chunks and an interesting way to think about blocks of time at different scales. Gilkey repeats the fairly conventional advice that chunks of work are best described with a crisp combination of  verb and object; “analyze customer data,” “identify key competitors,” “draft report outline.” What he adds is a scheme for classifying action verbs in terms of the time span they imply. “Email” or “call” suggests a 15-minute task while “Research” or “coordinate” suggests an activity that might consume a week. I’m copying his lists of action verbs into my crib sheets.

Gilkey extends this notion of organizing actions by timescale to advice that you stay clear about what timescale you are thinking through at any moment. Are you thinking about blocks of time that you map into a week of work or are you thinking in terms of month or quarter long projects on the path to larger goals? Becoming mindful about which timescale is relevant and moving up or down timescales as you plan work are practices I intend to fold into my work.

There’s plenty of other useful perspective and advice throughout Start Finishing. This will be by my side as I work on my next round of planning efforts.

Developing Design Perspective

Monteiro, Mike. Ruined by Design: How Designers Destroyed the World, and What We Can Do to Fix It. Mule Books.

We live in an artificial world; most everything we interact with has been designed by another human. In Ruined by Design, Monteiro explores this territory from the perspective of a professional designer. His quest is to make the case that designers have an obligation to think beyond the immediate demands of making some idea come to life and to ask “why” questions that are going unaddressed. His claim is that

A designer uses their expertise in the service of others without being a servant. Saying no is a design skill. Asking why is a design skill. Rolling your eyes and staying quiet is not. Asking ourselves why we are making something is an infinitely better question than asking ourselves whether we can make it.

He builds a compelling case but I want to take his argument further. Asking why is a design skill. It is a design skill that we should all develop.

It is a powerful step to ask why. Children know the power of this line of inquiry. It is a power to develop not suppress, whatever the temptation as a weary parent.

Too much of our educational and organizational energy is devoted to fighting the power of “why” instead of developing and strengthening it. Monteiro’s concern is that designers have abdicated their responsibility. Mine is that we all have.

We live in a designed world. That makes all of us designers. Every choice we make about what technologies to use and how to use them is a design choice. Montiero’s target audience is professional designers; you are part of that audience.

Twyla Tharp on the Practice of Collaboration

Book cover for Twyla Tharp The Collaborative habitThe Collaborative Habit: Life Lessons for Working Together. Twyla Tharp. 2009. T

Collaboration is fundamentally an artistic process. That is easy to lose sight of in the organizational exhortations to be more collaborative and the mass of marketing literature touting the collaborative goodness of some new piece of software.

If you agree that attacking today’s wicked problems depends on effective collaboration, then the arts are a good place to look for insight. Dancer and choreographer Twyla Tharp has done us a great service in reflecting on and sharing her decades of experience as creator and collaborator in The Collaborative Habit: Life Lessons for Working Together. This is a book I’ve revisited many times since it was first published in 2009. I’m still learning from it.

Tharp concludes with the following advice:

In the end, all collaborations are love stories…Honesty and bluntness, but not to the point of pain. Mutual respect, but not to the point of formality and stiffness. Shared values, so the group’s mission can carry it over the inevitable bumps. And, of course, actual achievement, so the group is supported by an appreciative community.

This is not counsel that fits into a motivational poster in a conference room or into the menus of a new software application or service. Collaboration is a practice built over time out of snippets of behavior and interaction anchored in a supporting context.

Tharp shares the stories of her collaborations with fellow artists, institutions, and communities. As an aside, it is clear from her stories that Tharp has always been a reflective practitioner. Her earlier book, The Creative Habit: Learn It and Use It for Life, contains insights into her processes and how she documents them; it is equally worthy of your time and attention. The richness and grounding of her observations reinforces her point that collaboration and creativity are work; rewarding work but work nonetheless.

When we observe the end products of creative and collaborative efforts, we admire the grace and beauty of the art and the artists. By taking us back into the process and behind the scenes, Tharp reminds us of the intense work and discipline it takes to make it look easy. She also reinforces the essential truth in an old cliche that “the work is its own reward.”

Review – Alan Alda on Communications and Improv

Book Cover imageIf I Understood You, Would I Have This Look on My Face?: My Adventures in the Art and Science of Relating and Communicating. Alan Alda

I’ve been working through a line of thought about the growing importance of improv thinking to dealing with organizations and innovations in the current environment. In this book, Alda lays out  advice on how we might do a better job of communicating in our work and improv plays a central role.

Alan Alda’s rumination on communications grew out of his work as the host of the PBS series *Scientific American Frontiers*. As the host, Alda was faced with helping deeply technical experts explain what mattered about their work to mere mortals. Alda brings a perfect mix of a curious layperson’s perspective and a trained actor’s craft at communications. It’s also an entertaining and illuminating mix.

A naive view of acting and of communications is that the work involves learning and delivering a script. We learn our lines and recite them when the moment arrives. Alda dispenses with that illusion immediately; 80% of his advice involves listening and observation skills and techniques. The remaining advice talks about story telling, but that advice is rooted in how to tell stories that take advantage of how we expect stories to play out and not mislead the listener or reader. In other words, how do we put stories together that anticipate and raise the questions our readers will have.

Alda, of course, is a consummate story teller himself. There is no blinding flash of insight or advice that is startling or unexpected. What he provides instead is an artful example of how well his advice works in the hands of an experienced pro.