Remote Work Time Management

The productivity paradox facing remote workers cannot be solved with technology. It’s a time management problem.

In 1987, Robert Solow, one of the leading economic theorists of the past century quipped, “You can see the computer age everywhere but in the productivity statistics.”

As information technology investment by businesses has seen explosive growth over the course of my lifetime, economists have been perennially puzzled by a paradox: that outside of the industries that manufacture computer equipment or provide IT solutions and services to businesses and consumers, there hasn’t been much evidence that investment in technology has increased productivity. This has caused such cognitive dissonance over the years that it called the prevailing economic methodologies into question. After all, can’t we all clearly see the benefits of computerized supply chain logistics, instantaneous global communication, mobile connectivity among knowledge workers, universal access to the world’s exponentially expanding knowledge, ever-growing data collection, its warehousing and more advanced computation to mine valuable insights from it?

Well, yes we can. But yet, the paradox persists and nobody seems to agree on a definitive explanation.

The field of economics is aware that it has problems with what it measures. Quality of life and a sense of purpose are better suited to other soft sciences like sociology or psychology. But even in the realm of cold hard economic data on GDP, CPI, average household income, GINI index, inflation and the like, all this investment in information technology has observable problems of lag, hedonic adaptation, energy consumption and that much of the net effect is potentially circular: technology eliminates jobs and displaces entire sectors, only to replace them with new industries that in turn create new jobs. We’ve been busy inventing and deploying mainframes, supply chain logistics networks, desktop computers, corporate networks, data storage systems, cloud solutions, mobile telephony systems and an untold number of software solutions for around 70 years, but every generation of those technologies are more complex, built on the shoulders of previous innovations, requiring an army of people to design, manufacture, market, deploy, train, maintain and effectively use them.

There’s the question of gross productivity, but then there’s the question of human effectiveness. Productivity hacks abound among the social media influencer community, as more people confront the confounding problem of navigating a world full of products exquisitely engineered to attract and retain your attention every waking hour of the day. There’s no question that a significant portion of modern post-industrial societies are primarily engaged in some sort of service, and a significant portion of that service labor is what’s often called knowledge work. Over the past 45 years, most of that labor has involved more and more interfacing with increasingly advanced technology.

To put it in simple terms, we’ve been engaged in an ongoing process of replacing inefficient, error prone human processors in our offices, factories and distribution networks with perfect and ever more powerful logic machines made of transistor switches. Oft-cited examples are roles such as clerks, routing dispatchers, typists, and filing secretaries.

Those jobs are obsolete, of course. Aren’t they?

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Starting in the 1980s, those office roles, once dutifully performed by a dedicated agent wearing the appropriate attire, were gradually replaced by a beige box that perhaps some scruffy guy plopped on your desk, featuring a screen, a keyboard and various wires coming out of it. Over time, it evolved, but the idea was that you used that box to do… well… everything. For the generations that saw that transition, it was difficult, slow and there was resistance to fire Brenda (because Brenda did far more than just type and answer phone calls), but by the 21st century, everyone was fairly comfortable handling all their own communication, typing, filing and so forth from that box that got upgraded every few years. The beige box changed colors, got faster, smaller, sleeker and easier to use, but in reality most of the so-called productivity software that we use today has been around for a long time.

For example, here’s what a typical networked computer in a modern office had on offer in 1990 (along with the year the paradigm first appeared):

  • Email (Ray Tomlinson 1971)
  • Word processing (Wordstar 1979)
  • Spreadsheets (VisiCalc 1979)
  • Realtime chat (yes, there’s clear evidence of chat dating back to 1973).
  • Network file system (Mainframes 1964, NFS 1985)
  • Inter Office Networking (widely implemented 1970s)
  • Database software for inventory, financial records, customer accounts data (1960s)
  • Databases and server file systems for central knowledge and documentation stores (1960s)
  • Fax (GammaLink 1985)
Mutt is an electronic mail client in a long lineage of command line programs since 1971

What’s notably absent from the list above is the Internet browser, but assuming that most of your work day is spent collaborating within your company, perhaps we can classify that as a feature, not a bug. With the rise of web-based software, the browser is an operating system or advanced network terminal for software you don’t own. Given the list of technology options above, it begs the question of, what the f*ck have we been doing for the past thirty four years? Well, moving all that same tooling from local networks to data centers (the “Cloud”) and accessing it over the Internet with “better” user interfaces — assuming the ISP is working. Oh, and not just the data, but the software itself — a curious reliance on a constant internet connection do do work.

Obviously the cloud has been a massive productivity boost for workers that must access information away from the office. Well, that’s not all that new, either. In 1991, my father brought home a 286 laptop computer running DOS and Wordperfect from my his corporate office that was deemed obsolete. It had a telephone modem. My brothers and I continued to use it as a backup machine to write papers for the next nine years. Why would a worker in 1988-90 possibly need a portable computer with a modem? Wasn’t that before the Internet? Well, before the Internet was a necessary utility in every home, corporate employees could connect to the office network and mainframe via a multiplexed phone line — from anywhere in the world — as long as the company would pay the bill. Local calls from home were a flat rate, of course.

We’ve been very successful in moving all our tools to data centers, and the Internet is ever faster, making remote access to large data and software as fast as local data was in the 90s. Since most knowledge workers were spending the vast majority of their time at the office working on a computer in an office or cubicle accessing data in the cloud over the fast Internet, people started asking a simple question, “why are we on site?” Aadanya in accounting was heard grumbling in the elevator that she got more of her monthly spreadsheets done when she called in sick and had plenty of time left over to get housework done and spend time with the family.

Then there was the great pandemic…

The pandemic was arguably one of the most turbulent chapters in recent human history, but it accelerated a series of long overdue social experiments that might otherwise have never happened.

Why do knowledge workers need offices?

Well, we’ve been wanting to try this remote work concept at maximum scale using this lightning fast Internet we were already using and talk to each other over video!

For people who don’t have jobs, and are thus poor, why don’t we just try giving them some money?

Ah, we’ve been wanting to try this idea of Universal Basic Income!

Why do we really even need to leave home at all?

Oh, well we’ve been meaning to test the latest logistics and delivery solutions at maximum scale to bring you everything you need!

As humans established herd immunity with the help of vaccines and weathered the storm, some of those experiments proved that there were viable alternatives to the old ways. Most of these experiments resulted in outcomes with major side effects. As large knowledge work organizations have confronted the post-pandemic landscape of managing time, information and resources in a distributed remote work environment, most have adopted a hodgepodge of software product solutions to collaborate. Online teams usually choose (or have foisted onto them) one of these products as their primary hub, attempting to connect it to other systems, linking references and files across these systems.

Unfortunately, the approaches we’re using don’t seem to be making us more productive. A joint international study by Michael Gibbs, Friederike Mengel and Christoph Siemroth for the IZA Institute for Labor Economics claim that remote workers during the work from home experiment are as much as 20% less productive, concluding:

“Time spent on coordination activities and meetings increased, but uninterrupted work hours shrank considerably. Employees also spent less time networking, and received less coaching and 1:1 meetings with supervisors. These findings suggest that communication and coordination costs increased substantially during WFH, and constituted an important source of the decline in productivity.”

Overall, research indicates productivity remained relatively stable in industries well-suited for remote work, but at the cost of longer hours, or less efficiency. When surveyed, WFH respondents knew that they were actually working more, but probably reported high levels of productivity and job satisfaction out of fear of losing their freedom to work in the location of their choice. Knowledge workers want flexibility.

Management theorist Peter Drucker, who coined the term, “Knowledge Work” in the 1960s, and every business productivity thinker from Steven Covey to Cal Newport has since reiterated an unwavering gospel that time management is by far the most important factor in productivity, and that any activity or behavior pattern that interrupts large continuous blocks of time is fundamentally detrimental to effectiveness.

Technology is now part of the problem, not the solution.

The medium is the message, or perhaps more aptly, in the scope of remote work, the medium often dictates the pace, quantity and quality of the message. Working via the web naturally tends toward the core paradigms of hypermedia that Tim Berners-Lee set forth in the 1980s: a word or object can be linked to another object. Most knowledge workers now expend a large part of their time managing this information. Many find themselves in a grueling series of communication loops via some flavor of threaded text discussion system (email or chat), attempting to consolidate information from a Babel of system sources. It’s not much different than crowdsourced blogging, or perhaps a professional version of an online Bulletin Board System.

Some well-organized colleagues and their teams may align on a preferred source of truth and consolidate information into a workable, agreed-upon filing system or knowledge base, but in the rush against deadlines — often behind schedule due to the ever-growing tax burden of messages and meetings delaying the actual execution of said work — the fatigue of context switching sets in and teams default to a “pump and dump” swarm pattern of message threads at the moment they need it, spamming across teams, departments and divisions, and hope to later find time to organize it or dig it out of history via a keyword search.

Once established, these habits are very difficult to break. Teams dig an ever deeper hole of technical debt in the form of chaotic and disorganized institutional knowledge on both systems and processes. This reinforces behavior as it’s a source of convenient job security for the individuals who’ve been around long enough to remember where to find a needle in a haystack, how something works or how a process should be conducted, and improbable to convey to a new hire. High value veteran cognitive workers find themselves increasingly unable to optimize their time to fit their strengths because they’ve become organic knowledge sources that everyone desperately needs constant access to.

Technological paradigm shifts happen in phases. Let’s enumerate five for the sake of discussion.

  1. innovation & introduction
  2. early adoption & evangelism
  3. widespread adoption & critical mass
  4. realization of second and third order effects
  5. selectivity, adaptation, optimization, elimination or replacement

The state of popular digital collaboration tools today is somewhere between phases three and four. Despite many attempts at a magical silver bullet in the form of a “software solution,” we’re not better off than we were in the email era.

The purpose of this writing is to explain how the rush to adopt solutions under the duress of the pandemic led to imperfect choices and a belief that the right technology could solve our problems. Organizations are only now beginning to observe the second and third order effects of the inherent design flaws of software on productivity. It’s time to evaluate the limits of techno-optimist assumptions and consider alternative strategies of techno-selectivism and even radical management approaches for a new remote/hybrid era.

Part 1: How Collaboration Software Is Counter-Productive

Every remote team needs a collaboration system. Most of the current post-pandemic solutions are a grab-bag of low-friction, real-time “professional variations” of social media apps: Slack, Teams and Zoom. New generations of workers who’ve been dopamine-primed for years by addictive social media mobile apps have led the widespread adoption of a collaboration paradigm that reflects the personal communication modalities they know and prefer.

The Five Fs of Popular Collaboration Tools:

  1. Fast – Users prefer the fastest, most direct option
  2. Familiar – Users engaged in collaborative activity default to the lowest common denominator solution that everyone knows.
  3. Flexible – Users prefer software with the fewest business or process logic constraints.
  4. Frictionless – Users prefer the solution that can be deployed and onboarded with the lowest effort.
  5. Fragmented – Users tend to break information into small fragments that are direct, impulsive, conversational and convenient but often lacking in holistic context.

This is why, despite decades of frustration among knowledge workers and IT administrators, email will never die. It’s easy to take for granted the tremendous elegance of email: a simple, system-agnostic public address protocol gives anyone access to interface with anyone, across teams, departments, divisions and business of any size anywhere on earth. It supports rich text, file attachments and CC group discussion. It’s still the most immediate and flexible means to spontaneously collaborate.

Anyone who’s worked in the modern knowledge economy since the 1990s understands how easily email spirals out of control and becomes a productivity sink. All it takes is one colleague’s misplaced CC thread including a VIP or key stakeholder to force every recipient into an implied obligation to respond with their two cents, and check that asynchronous loop – potentially for days, weeks or months until someone with enough expertise or authority intervenes with a conclusive solution, and usually that solution is a follow-up meeting to repeat the discussion that was already covered in the email. “Could have been an email,” is a popular cynical expression. More accurately, “Could have been a well-written proposal ahead of a well-organized working session with the right group of people who aren’t multitasking.”

When Slack skyrocketed into widespread user adoption as a solution to “the email problem,” many remote work veterans, myself included, felt a nauseating sensation of deja-vu. It was just the latest repackaging of IRC for Gen-Z: a software paradigm that has existed since 1988 (or even the 1960s if we count mainframe terminal messaging) and had been re-invented a dozen times with the same results whenever it attempted to scale beyond the scope of a project team: total disorganized chaos and constant disruptive interruptions.

When various technology critics pointed out the fact that this exact same pattern had been perennially tried and failed at scale, with innumerable studies underlining the problems with widespread misuse of electronic mail, the response from a new generation of evangelists was the familiar, “you’re just using it wrong.” Slack was the next edition of the same lazy, low-fidelity solution with no in-built guardrails for a new generation of users deeply addicted to a lifetime of instant messaging technologies. But don’t worry, if we can’t sort it out in chat, we’ll have a Zoom meeting.

Meeting Fatigue

Extensive research before, during and after the pandemic has shown that workers spend too much time in meetings that they feel are counterproductive. Microsoft’s own analysis of their product suite’s usage statistics indicate that video meetings have tripled since the pandemic with most users spending eight hours per week in meetings. For middle management and above, users are often spending 20 hours or more per week, and I know individuals in various large organizations who spend even more.

Image Credit: Htc Erl from Pixabay

The combination of video conferencing and real-time low friction chat solutions has been particularly disastrous for high value cognitive workers in large organizations. More companies are in the business of busy-ness than ever before. As Cal Newport aptly put it, when the pandemic hit and everyone shifted to remote work, it sent what he calls the “hyperactive hive mind” into overdrive. The root causes and their deleterious effects on productivity are easily explained: the shift to remote work removed all the rich visual context of office activity we took for granted. In a physical world, just wearing the right clothing, commuting to and reporting to work took effort and felt like it was worth something, even if someone was psychologically “checked out” for most of the workday. In a physical office we could see when people were having a meeting, one to one conversations, or were clearly busy (or pretending to be busy) focusing on a problem. Probably best to not bother Roberto right now; he’s clearly focusing. Humans have evolved advanced social situational awareness over the millennia. Gone were the not-so-chance discussions at the coffee maker or water cooler, where small talk between friends revealed valuable situational context across projects, programs and departments.

Perhaps most importantly, gone was the vital social friction of asking someone to do something in person, or the social capital cost of seeing someone after asking for something on an unreasonable urgent timeline. Now it’s just a 15 second friction-less DM on Slack or Teams to shove it off your plate.

Bjorn 3:16 pm: “Hey Jeanna, please see the attached report and enter in your team’s delivery dates. We need to get this to senior leadership by COB. Thanks! 😊”

The education system in the US was designed to condition people to be good industrial workers. That’s why we rang bells and moved from classroom to classroom on a fixed schedule. The result of shifting to remote work was a widespread “productivity paranoia” among users where the only means of “looking productive” was to engage in disruptive Slack conversations, email chains or peppering calendars with status meetings.

To channel the spirit of the late David Graeber, the thousands of people he surveyed who suspected that their roles were, as he charmingly describes, “bullshit jobs” had to find new ways to maintain visibility and justify their existence. Graeber described that in nearly every company, you’ll find well-intentioned, ethical, hard working people who feel guilty that they don’t really do anything and may unwittingly undermine the potential of focused teams with make-work and unimportant distractions. Graeber pondered this and posited that it may be acculturation, resistance to change, tenure, mismanagement, bad staffing decisions, lack of flexibility, lack of training, wrong fit, impulsive reorganization and good ol’ fashioned hierarchical politics. Jack Welch’s rank and yank strategy is no longer in vogue.

For knowledge workers with cognitively demanding problems to solve, such chaotic online workspaces can be a hellrealm of unscheduled interruptions and context switching, as more of their attention capital is annexed by communication and administrative overhead as management attempts to adapt to a radically different culture of trust without the physical walls and status signifiers that provided structure and context. Managers’ increased frequency of meetings throughout the day makes highly individualized time management needs difficult or impossible.

Thanks to the current generation of remote “productivity hub solutions,” the typical remote knowledge worker spends the majority of their day in a fatiguing battle of sifting through the constant barrage of information with no clear rules of engagement. The volume of data is often so overwhelming that more and more virtual meetings are scheduled to have a conversation about the immediate objectives instead of attempting to parse the information. Because workers have less time to prepare for them, those meetings are rarely well executed and become forums for committee decision-making where the average compromise wins, spawning a few circular action items to reorganize the information and inevitably a series of follow up meetings to review the same information again. For senior staff tasked with a combination of managerial responsibilities, analysis and providing guidance and training on institutional knowledge, more and more of their valuable time and attention capital is exhausted on context switching across many communication loops and more meetings resulting in longer hours and psychological burnout.

Part 2: Staffing

Peter Drucker noted that excessive meetings were one of the clearest indicators of mismanagement, overmanagement and overstaffing. The quantity of meetings is inversely correlated with the amount of work being done. It’s often management that perpetuates a culture of meetings.

A Work Index Report by Microsoft indicated Teams users saw a 252% increase in meetings between 2020-2022. Let’s be clear that meetings are not inherently a problem. On the contrary, well-organized meetings focusing on the right things are essential to a well-run business. Poorly organized recurring meetings are not. What contributes to an excessive meeting culture?

Overload & Productivity Paranoia

As we’ve touched on, the pandemic provided the perfect confluence of factors that exacerbated excessive meeting culture:

  • Productivity paranoia – Desperation to demonstrate productivity and contribute value in a low-friction virtual environment. Meetings signify busy-ness.
  • FOMO – what if a team has a meeting and makes a decision without me?
  • A lack of written communication skills – many workers may be highly effective communicators in person, but lack the skills or training on how to craft a concise written business communique. Even highly successful traditional leaders have struggled with this challenge, often relying on assistants or writing tools to bridge the gap.
  • Too many emails & messages – low friction, low quality, fractured communication tools lead to overload which in turn require more unplanned meetings to clarify things
  • Poorly organized meetings – Many individuals lack experience and training in how to set an agenda, prepare pre-reads, or lack the time to prepare for well-organized meeting
  • Lack of focus by attendees – Too many virtual meetings of low value contribute to multitasking during the meeting, which is much less common in person. A great meeting participant listens, takes notes and asks clarifying questions.

Put simply, some people wake up in the morning and don’t have enough to do. They feel a sense of duty and may even have a mandate enforced via software monitoring to work 40 hours but their job simply doesn’t require it. These roles have always existed in offices, and those people could look busy or collude with their staff to invent busy work. Work naturally ebbs and flows, often based on season, contracts or project stage. An independent contractor or entrepreneur doesn’t have this problem. They go do something else. Any modern company must have a reserve labor pool to provide reasonable functional redundancy, but an excessive imbalance of the wrong categories can be problematic.

Moreover, there’s a trend to recruit individuals with a lightweight “certification” with little to no hands-on industry experience into some variation of “soft middle management” with a vaguely defined job description as an overseer of an administrative process affecting aspects of a business unit they know nothing about and with no real authority. For example, Google and Facebook recently realized that over the past ten to fifteen years, as they invested in launching many new large products and services, an array of potentially redundant hierarchical administrative roles emerged: program managers, program project managers, project managers, product managers, product marketing managers, product owners, product analyst, product strategists, scrum masters, agile advisors, sales solutions engineers and so on. Once these product initiatives reached maturity, the maintenance phase of a production software system no longer required all these roles. Reassigning and retraining all this administrative talent proved difficult. Thus layoffs.

The labor marketplace has changed. In the 20th century, entry or mid-level job titles with obvious titles like, “assistant manager,” “secretary,” “invoicing clerk” or even “apprentice” were common. Modern companies invent vanity titles and job descriptions to attract entry-level candidates with the hopes of grooming them into valued long-term resources. The titles are designed to obfuscate rank, boost the hire’s morale, and contribute to a spirit of flat agile teamwork. Sometimes these positions are minted to provide a manager with an assistant staff, and when managed ineffectively, such roles with ill-defined and overlapping boundaries don’t really have a mandate to build anything themselves or perform cognitively taxing work. Lacking clear objectives, these individuals may find themselves desperate to demonstrate value, colluding in a cycle of meetings to contribute to collaborative decisions, involving powerpoints, roadmaps, flowcharts, gantt charts and vision boards, annexing more and more time of the overworked architects, subject matter experts, writers, illustrators, engineers and designers who are desperate to carve out the blocks of time needed to execute on the deliverables. These individuals need yet another daily status update summary or meeting that they then dutifully report up to their managers, who report up to their managers, who attempt to cram it all into a one page executive summary that overworked leadership may or may not have time to read. Their entire day may be to create an email that a leader glances over for 30 seconds. Send one of these administrators a question? They anxiously seek to get the problem off their plate, and immediately re-route it to one or many of the producers, bug them repeatedly until they get a response, and then route it back up the chain.

Everyone has probably seen a road crew where ten over-fed men are standing around one or two poor saps digging a hole — that’s the sorry state of many modern companies. Once established in a large remote organization it’s difficult to identify functional redundancies. Senior executives only see the managers, regardless of how much credit should actually be attributed to their staff who may be bending over backwards to “manage up” to potentially incompetent “organic” network chat routers. I know this because I’ve been guilty of falling into these same disruptive patterns that don’t add value.

With the current generation of collaboration tools, all this activity is extremely rich data. It can be streamed to a data lake and mined by AI and machine learning to extract not just crude (and arguably useless) productivity proxy statistics like average percentage of session time by various types of apps, but extremely powerful insights by implementing algorithms with weighted values for certain patterns of activity as productive or counter-productive, even evaluating the productive potential of a chat thread using an LLM. The problem is that high usage of video conferencing and chat applications may seem to indicate high engagement and collaborative productivity. Software vendors like this narrative. Look, our product is delivering value! AI has the potential to evaluate this with substantial nuance based on user-role and user profile analysis. Companies will pay a hefty price for it if it demonstrates the potential to save millions of dollars in labor costs.

For example, let’s imagine a “user M” profile that spends 35 hours per week initiating chat threads, sending out emails, scheduling meetings, and attending meetings. The productivity value of that pattern of activity is either high through the lens of management or low and disruptive through the lens of cognitive labor. There could be a “user P” profile who is a 10x software engineer, architect or graphic designer who is “optimized” and has little to no activity in meetings or chat but is delivering the core product of the company, spending 90% of their time in actual productivity applications like code editors, CAD applications, Adobe cloud, knowledge management systems, etc. If user M’s pattern of activity is primarily with other users M, and who’s also consistently interrupting users P with meetings and messages, the system could flag user M as potentially redundant, disruptive, and their behavior can be re-evaluated for training and intervention.

Chilling? Orwellian? Useful?

As capital markets have tightened in the past few years, large companies have been laying off workers, and since software companies usually have strong engineering cultures, they have rightly performed an analysis and focused on eliminating redundant middle and administrative management, support and junior contributor roles that don’t clearly demonstrate value. Nvidia’s lean org chart is a strong case in point. Apple has always been flat and lean — Steve Jobs made sure this culture was codified before he died. Facebook and Google have recently downsized after a long hiring binge and era of silicon valley “talent hoarding” when cash was cheap. Elon Musk’s companies are ruthlessly structured with a degree of recursive optimization that only a once-in-a-generation engineering and financial genius could achieve.

Drucker comprehensively outlined the principles and challenges of the knowledge worker in his celebrated writings that are as relevant today as ever. In his 1967 classic, “The Effective Executive,” he describes every knowledge worker as one who must effectively execute, and thus is an executive. He noted that in the life of a knowledge worker, time is the most precious resource. He writes, “One cannot buy, rent or hire more time. The supply of time is totally inelastic. No matter how high the demand, the supply will not go up. There is no price for it. Time is totally perishable and cannot be stored. Yesterday’s time is gone forever, and will never come back. Time is always in short supply. There is no substitute for time. Everything requires time. All work takes place in, and uses up time. Yet most people take for granted this unique, irreplaceable and necessary resource.”

In 1967, knowledge work was an analog world of typed memorandums, face-to-face meetings and telephone calls. Yet Drucker describes the same problems of ineffective time management we see today: too many meetings, reactive vs. proactive coordination, and perhaps most importantly, gross inefficiencies in time management at scale. He said that effective knowledge workers do not start with their tasks. They start with their time:

  1. They log and analyze what they are spending their time on.
  2. They manage their time by eliminating unproductive meetings, people, and activities.
  3. They consolidate their time into the largest continuous blocks possible to do quality work on what delivers the highest value.

This three step process is the foundation of executive effectiveness.

There’s no question that the “front office” IT revolution that Drucker championed much later in his books like, “Post-Capitalist Society” has been evolving at a rapid clip since the 1990s and has radically changed how we work. Titles and positions have changed, many outdated roles have been eliminated, but the problems remain the same.


History repeats itself. New generations of “wired workers” are often oblivious to the hard-earned wisdom of their forebears and are doomed to learn from the same mistakes. The highly effective and focused productivity cultures of the 20th century seem to have failed to cross the context shift of the digital divide, offset perhaps by the new “efficiencies.”

Information today is bigger and faster. Unimaginable quantities of data are gathered and mined for business analytics. Technologies have enabled companies to seem leaner and more dynamic. But yet we’re in the midst of a productivity crisis where workers are disengaged and chronically burned out.

Is it possible that there is a point of diminishing returns on humans interfacing with technology? Is there a threshold at which the quantity of information flow inversely correlates with effective organization and decision making? What if the leading technologies we’re using have serious side effects inherent in their designs? How much of a company’s implementation of advanced IT solutions masks the counter-productive effects of rampant overstaffing that Peter Drucker warned against 65 years ago?

When it comes to information, it would be heretical for the modern executive, division general manager, managing partner, department chair, or team leader to suggest that, when it comes to technology, less is more and slower is better.

But what if it was crippling the potential of your workforce? What if it was drowning your most valuable managers and talent in a state of analysis paralysis? What if it was handicapping 70% of your best and brightest minds in a swarm of digital disruptions without the autonomy or authority to stop it?

What if your managers struggle to coordinate cognitive capital using the tools and systems they themselves may have pointed to as the latest industry “silver bullet solutions” and convinced senior executives were essential?

Maybe we got it very wrong in the desperation of the pandemic. We grabbed what was easy. The evidence indicates it has failed.

But some companies are experimenting with radical new approaches. The most direct approach to forcing more effective use of time is to reduce the amount available, yet demand the same results. Cambridge University recently conducted the largest experiment in history involving a shift to a four-day workweek and discovered that participants were not only just as productive, but the longer people worked in new, more efficient ways, the shorter their workweeks became.

“We don’t have a problem, we just need a plan.”
-Timothy Leary

Part 3: Transforming Culture With Systems

Cal Newport’s last three books, “Deep Work,” “A World Without Email,” and “Slow Productivity” unpacked these problems with a fresh set of eyes from a systems-design perspective and crystallized them into a useful conceptual framework. Many find his analysis and recommendations extreme, but it’s because the challenges are unprecedented. All three books are excellent.

Newport’s second and third volumes in this productivity trilogy confront the uncomfortable reality that our attempts to solve the productivity problem with top-down, one-size-fits-all systematic approaches don’t scale well in knowledge work, usually resulting in a rigid, inefficient administrative bureaucratic apparatus, exacerbating the inefficiency with administrative overhead that limits the potential of a modern agile company to innovate. You hear this “cry for help” from individuals in every sector: academia, corporations, government and small to medium-sized businesses.

It took years of trial and error developing software architectures and managing teams for me to realize the trappings of what writer John Gall described in 1975 as, “Systemantics,” (sic) or that humans seem to be obsessed with grand systems as solutions, and that the more complex and comprehensive a system is, the more likely it will fail. See: Soviet command economies.

This principle can be applied at every level of an organization. For example, “cultural transformation” is leadership-speak for the C-Suite spending their valuable time and money on consultants that typically recommend a program that may have achieved results in one or two use cases that didn’t analyze long-term net impact, and often in a completely unrelated business sector. These consultants make a variety of recommendations:

  1. Adopt a comprehensive one-size-fits-few system of complex administrative processes
  2. Employee training programs to “transform culture”
  3. A reorganization strategy, often adapted from the private equity leveraged buyout playbook, which results in a reorganization exercise that disrupts or dismantles myriad invisible improvised arrangements and back-channel relationships that effective middle managers developed over the years when shit actually needed to get done. Global consulting powerhouse McKinsey’s own research suggests that only 23 percent of reorganizations are deemed successful.

All this to say, that the “man from the future,” Peter Drucker was correct in his prediction that knowledge work was going to be a new paradigm of managing and optimizing a different kind of capital, and to do so requires a radically new system of trust and accountability where individuals and teams should have the autonomy to self-organize to meet objectives. Senior leadership thus should focus not on command-and-control strategies of organizing their business with “big transformational initiatives”, but on tried and true approaches: surrounding themselves with advisors who deeply understand their departments and the people who run them, relentlessly simplifying by divesting or eliminating low-performing, non-strategic verticals and products, fostering cultural change by defining and constantly championing a clear vision for the future, investing time and attention in the training and grooming of the best people, and deploying the capital and incentives (both intrinsic and extrinsic) to the teams that deliver the best measurable results with maximum autonomy. And most of all, subtracting from the layers of your organizational structures to give the cognitive capital a seat at the table: take the time to build open relationships with promising talent at every level of the hierarchy to understand what’s actually happening “on the ground.”

If this sounds very familiar to those of us “from the 20th Century” it is, because it worked during a time of unprecedented change — arguably as great or greater than the rate of cultural and technological innovation we’ve seen thus far during the 21st century. A mere sixty-six years passed between the first powered flight by the Wright brothers to the Apollo moon landing, and it was only a few decades between the advent of the transistor at Bell Laboratories and the development of the UNIX operating system and ARPANET which were essentially the core technologies of the Internet we know today. What have we built in the 21st century? No doubt impressive high speed communication systems. But otherwise, it’s mostly been the smartphone, better entertainment and addictive social media apps. All distractions. Not very impressive, and all of it depends on massive amounts of low-cost energy with significant externalities.

Part 4: Friction

Cal Newport’s work can be seen as a continuation of Drucker’s philosophy. He understands the trappings of outdated bureaucratic approaches, and instead suggests that solving the problem of information flow and productivity falls to middle management and the individual producers using a set of basic principles that assume that change must happen from “the bottom up” in an organization.

Below is an interpolation of Newport’s three Slow Productivity Principles based on how they evolved as he elaborated on them in the context of his previous books across multiple interviews during his recent book tour.

  1. Do fewer things at the same time
  2. Work at your own pace
  3. Obsess over quality

It’s crucial to understand these principles in the broader context of Newport’s “Deep Work” time management philosophy.

Newport describes 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.”

Contrasted with Shallow Work which is, “non-cognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend to not create much new value in the world and are easy to replicate.

Sound familiar? He’s channeling Drucker (The Effective Executive) and Covey (Big Rocks) in a new high-distraction era.

Let’s expand upon these in an applied sense for an individual contributor/producer and team manager juggling many possible collaborative projects.

  1. Do fewer things at the same time
    Newport himself recommends that teams adopt agile-inspired methodologies. A team should align on a clearly defined set of goals within a given time frame, often called a “sprint.” The team should spend time at the outset of a sprint socializing a backlog of tasks and priorities. Tasks should be shared in a transparent, easy to understand system such as a team task list or Kanban progress board. Tasks are not “pushed” onto the team members by management. They are “pulled” by contributors when they have time available and are ready to focus on them.
  2. Work at your own pace
    Busy-ness is particularly anti-productive in knowledge work. It helps to unpack this in the context of Newport’s broader approach so as not to be misinterpreted as lazy, vague or overly-obvious. It’s not quiet quitting. Every contributor in a project is expected to work with their managers, teams and stakeholders to optimize their time management such that they can produce work of satisfactory quality at a pace that can be sustained without burnout. This means well-defined requirements, clear feedback and most importantly, minimizing unnecessary interruptions, meetings and communication so the contributor has the “space” to get the work done.

    Deep Work establishes a crucial truth that I’ve observed over the past twenty years: the more cognitively demanding a task is, the more autonomy the producer needs to block out their time in an individualized way that optimizes their performance potential. Everyone is unique. One size fits none.
  1. Obsess Over Quality
    This is the primary qualifier and driver for the other two. You’re doing fewer things at once and working at your own pace because if you’ve got a day packed full of meetings with dribs and drabs of 15-30 minutes of time here and there, you’re not doing anything but pushing information around and cannot effectively execute on cognitively demanding work.

In concert, these three principles deliver higher longitudinal productivity and better results.

Implementing Positive Friction

What may seem fast, fluid, busy, responsive, dynamic and flexible on the surface is really chaotic, disorganized, disruptive and self destructive. Many remote teams have to undertake a difficult transition to implement new norms, best practices and guardrails to reintroduce polite, intentional friction against disruptive tendencies that were taken for granted in a physical office.

Perhaps the most important concept of this transformation is a shift from an “assignment push” mindset to a “pull from queue” strategy. Anyone familiar with systems engineering will understand this paradigm.

The Person As Processor
Every person is essentially a process thread with an average rate of throughput that must be carefully managed and optimized.

There’s ample evidence emerging from the field of neuroscience that the human brain has evolved to optimally work on one task at a time. The more cognitively taxing that task is, the longer it takes to initialize the work. Any distraction that breaks concentration can take up to 15 minutes to resume an optimal state of concentration. Furthermore, even in shallow work activities, a high rate of context switching takes a significant toll, resulting in stress and fatigue that only worsens over time. The way we currently organize our remote workflow is counter to optimal performance.

Agile methodology was developed by software engineers who engaged in deep work and were familiar with the instruction set process thread architecture that is fundamental to ALL computer systems. Jargon aside, this is intuitive to the layperson. Everyone has to-do lists that represent things to be done. Many modern collaborative management methodologies are based on the queue worker paradigm: Lean, Scrum, Extreme Programming (XP), Kanban, Scrumban, etc.

Credit: O’Reilly

An effective manager has to first recognize the following:

  • A team and its contributors are fully optimized if they are working on one or few things at the same time
  • The work that needs to be done and its status should be visible to everyone
  • People should have the flexibility to PULL work in when they are ready and complete it at their own pace
  • The input priority must be continuously actively managed in short, efficient huddles every day.
  • All inputs (communications and meetings) that are not managed and scheduled are potentially disruptive
  • The collaborative approach and results achieved are evaluated and recursively optimized after each period of work (often called a “sprint” in Agile)

It’s simple: without shared visibility of workflow, there’s no way to effectively manage resource utilization.

Part 5: Solving The Visibility Problem

Cal Newport has recommended a collaborative optimization strategy that is so simple that it’s almost shocking in its elegance. If Agile queue workflow has been implemented so widely and effectively by teams throughout various sectors, then why not adopt it at every level? The primary issues we have with remote work are the constant status updates and meetings that are interfering with our management of time. We no longer have visibility of what people have on their proverbial plates. Agile teams typically use Kanban boards that everyone can see, so why not extend that simple concept to every contributor in the company using a publicly socialized task backlog queue, or “reverse to-do list” using one of many possible collaborative solutions?

For the sake of discussion, we’ll call this an Individual Public Request Queue or IPRQ (eye-per-queue). This doesn’t require some complex software solution, it’s simply a list of things that people have in backlog, prioritized, reasonably anonymized for sensitive requests and a status that everyone can see. It’s easily self-managed, serves as a unified personal task list and can be socialized in a shared document or spreadsheet.

When someone requests something from you, politely respond with, “I’d love to help you with this. I use a system for tracking my tasks and focus on a few things at once so I can execute them effectively. I’ve looked at my schedule and I should have time to complete this in two weeks. Does that work for you?”

Alternately, you can take the time to meet with them, understand the request and review your public task queue.

You haven’t said no — you’ve presented the requester with transparency and a choice to either accept your terms or look elsewhere.

Establish a quota system on predictable tasks and dynamic sense of workload based on something like “t-shirt” sizing. If you or the people you manage have too much in queue, point to the backlog and work with the stakeholder to redirect, reassign or manage expectations upward.

Prepare and refine a set of repeatable steps for intake. Seek to clearly understand the ask. Be clear that you’re not committing to something if you need time to evaluate and estimate it, which itself will be a potentially deep work task. Managers are often faced with an overload of estimation requests. Failing to evaluate them carefully only leads to failures.

When unexpected problems or complexities arise (what we call in software “blockers”), communicate them immediately. Ask your team every day if they have any blockers. Blocked processes are broken and cause backup.

To be clear, this isn’t a proposal for a software system. It’s an expanded agile management strategy. How it’s implemented is up to the team, and at minimum can be adopted by any individual who fails to persuade wider organizational adoption.

It will take time, diligence and consistency to help your colleagues get used to this pattern. You’ll have to respond to repeat requests for status updates with the link to your reverse to-do list, and depending on the requester, you’ll have to craft the response so they don’t feel slighted. Over time, your colleagues will come to appreciate the convenience of just opening the email that they were going to reply to anyway, and click the link. It will also serve as an invaluable tool to manage up, providing your manager with 24/7 access to your work and an opportunity to re-prioritize or remove things from your workload. The objective is to eliminate or at least reduce the repetition of loopback requests that has proven to be so disruptive to everyone’s time: the constant deluge of, “Is this done yet? What’s the status? When will it be done?” If you’re serious about time blocking, you can even schedule time on your calendar when you’re working on it and invite the stakeholders to the timeblock as a reminder event.

Relentlessly Protect Your Focus Time

No matter what your role is in an organization, everyone should reserve the right to block off a substantial section of their calendar day to focus without interruptions. My colleagues and I call this, “going dark.” I even change locations and leave my phone to reinforce and ritualize the context shift. This focus block is best when it’s predictable and aligned with your workgroup. Ideally, it would align across an entire department. Franklin-Covey trained organizations encourage focus days. Yes, an entire day. That requires trust. If you don’t trust your workers and feel that you must micromanage or see evidence of their productivity, you’re missing the point. Perhaps spending half of the day hiking or biking is precisely what that person needed to think about a problem or optimize their performance.

If you’re enabling a broken meeting culture by accepting meetings you can’t afford to attend, you’re part of the problem. You simply have to politely say no to meetings and recommend another time that aligns with your schedule. Stop trying to please everyone. Think of it like enabling an addict. Saying yes to the college buddy who regularly wants to skip out in the afternoon and hit the bar is just enabling his drinking problem. Three or four evenly spaced meeting invites throughout the day are enough to disrupt your productivity. Decline them and suggest a better time. Copy your manager and discuss it with them in your next one-on-one. It’s that simple. Just do it.

There will be situations where high value meetings require exceptions, and you will need to reschedule other meetings to shift your focus time to accommodate the important meeting. But no matter what, don’t let your calendar control you, control your calendar. Relentlessly optimize. Be honest and transparent about the fact that you’re busy during that time, because you are. That bi-weekly status meeting with the project/product/marketing clique can be effectively deferred using a well-crafted email or link to your project software. You’re making sure that you’re managing your time to deliver value to your organization. You’re applying the Pareto Principle. You’re focusing on the big rocks and pushing the small rocks off your plate.

What Team Managers Can Do

  • Ask each member of a team to keep a time log of their time for 2-4 weeks. Encourage honesty about breaks, family obligations, and even time spent walking or exercising, all which promote well being.
  • Ask team members to describe their ideal work-life time balance and discover what aspects of the team’s organization and communication they find frustrating.
  • Ask if they find their assignments poorly defined or lacking clarity.
  • Ask if there are any changes that could make them more productive and work to accommodate it.
  • Ask if and how often their work is interrupted and by whom. Intervene as much as necessary to eliminate the pattern and establish a clear intake process.

What Management Can Do

  • Discourage managers from enlisting work from other manager’s teams without their consent.
  • Coordinate focus blocks across teams, departments, or even the entire company.
  • Train and encourage managers to govern their teams use of Slack, teams and Zoom calls.
  • Establish and socialize predictable manager office hours to sort out issues in person.
  • Identity gaps in clarity of accountability on processes and tasks.
  • Build and socialize a procedural accountability map. Know who owns what when and why.