Deep dives on project management, process, workflow, newsroom culture & more

In The Pleasures and Sorrows of Work, Alain de Botton interviews a number of workers at a biscuit manufacturing company and concludes, unsurprisingly enough, that the place is rather dreary. He attributes the poor work culture to a factory-style approach that breaks up the making of biscuits into a seemingly endless list of tiny, discrete, and disparate tasks, spread out over specialized workers, most of whom have little awareness or influence over each other. De Botton concludes:

An endeavor endowed with meaning may appear meaningful only when it proceeds briskly in the hands of a restricted number of actors and therefore where particular workers can make an imaginative connection between what they have done with their working days and their impact upon others. (80)

The difference between a happy home cook and our listless biscuit manufacturing employee comes down to what Ursula Franklin describes in The Real World of Technology as holistic versus prescriptive technologies. In a holistic technology, a single person or small group of people carry through an entire process, from inception to sweeping the crumbs off the floor, making their own decisions and adapting along the way. Pottery is a classic example of holistic technology, but many other kinds of work fall within the same rubric: cooking, of course, but also knitting, clothes-making, woodworking—all traditionally entail processes in which everyone involved can readily make an “imaginative connection” between their work and the final product.

Conversely, if you pervert traditional cooking methods into, say, something akin to an industrialized sweatshop, you’ve created a prescriptive technology: one in which the work is broken down into discrete, predetermined steps, each of which may be undertaken by a different person or group of people, often with unique expertise, and rarely with any creative decision-making authority. Franklin defines prescriptive technology as specialization by process, as opposed to holistic technology’s specialization by product. In a prescriptive technology, everything must be completed according to some master plan, such that each individual is constrained by the system to do things in a particular way. Prescriptive technology workers are not in control—they are under control.

As a product becomes more complicated, prescriptive processes can seep in where holistic approaches had been the norm. Two decades ago, website building was largely holistic—simple enough that one person, or a few people working closely together, could build and maintain a website absent any predetermined rules. In fact, the process of making websites then was so nascent that a prescriptive process would have been laughable. Gradually, though, the field evolved, and many people necessarily began to specialize in different areas of website making—design, front end, ops, and so on. In large organizations especially, separation between the different specialties and a lack of cross-disciplinary collaboration produced lifeless workplaces and cookie-cutter products.

Most of us have shifted away from that separation, and towards agile processes which encourage collaboration and communication and emphasize quick decision making by all involved. Often, this kind of process is described as “working like a startup,” invoking a particular speed and scale—eliminating bureaucracy and allowing a small group of people to rapidly take over bigger, lumbering industries. But I’ve come to believe that Franklin’s holistic framework—with its attendant associations of both agency and humaneness—is more instructive. Striving for holistic technologies guides us toward processes and products that respect everyone who makes and uses them.

The question then is this: how, in a rapidly changing field that requires increasing levels of specialization, do we foster and protect a holistic culture?

Documentation over Transparency

The ideal expression of Franklin’s holistic technology is one in which a single person performs every step of the process, absent any outside control. That’s fine for many creative endeavors, but is likely to crack when a technology becomes sufficiently complex to require a breadth of expertise difficult for one person to acquire. Franklin’s analysis doesn’t preclude activities that are spread out among several people, but she does identify an important constraint:

Using holistic technologies does not mean that people do not work together, but the way in which they work together leaves the individual worker in control of a particular process of creating or doing something. (11)

In other words, each person on a team needs to act autonomously, making their own decisions and choosing their own way.

That, naturally, leads to perhaps the most important ingredient of a holistic culture: documentation.

A lot of workplaces worship transparency as a means of subverting traditional bureaucratic hierarchies long since discarded as inefficient. But transparency is a result of specific organizational action, not the means. The means is documentation: rigorous, clear, and thorough documentation empowers people from all disciplines to contribute to a discussion, assess where they are needed most, and productively contribute absent prescriptive processes. It also lets the light in—not only on the results of a process, but into the process itself, where it can be shared, learned, and iterated over collectively.

Remote cultures naturally lend themselves to documentation, inasmuch as they privilege written over oral communication. But even more traditional office environments can benefit by adopting remote habits that encourage documentation: small steps like assigning note-takers to every meeting, documenting decisions and requirements, and sharing the process by which decisions were made go a long way. The best documentation also adopts plain language, jettisoning industry or field-specific lingo in an effort to provide the most clarity, for readers and writers of the documentation alike.

Collaboration over Competition

Documentation serves to communicate processes and results, both within a small team and outward to other teams or stakeholders. But that communication itself also serves another purpose: to foment collaboration, the second necessary ingredient in Franklin’s holistic technology.

In a recent expose about what goes on inside Amazon, the New York Times reveals a “bruising” culture that pits workers against each other via anonymous review systems and a regular culling process designed to create a Survivor-like environment among team members. This is both inhumane and stupid. Back-stabbing forces every worker to work primarily for themselves, prohibiting productive collaboration. And there’s plenty of evidence that unregulated competition serves to reinforce existing power structures and suppress contrary perspectives—the very attributes that innovative companies are supposed to value most.

Amazon’s culture is one that presumes naked individualism and hubris are necessary ingredients for taking big risks that, occasionally, pay off. And perhaps they do every once in a while—but only at great human cost. A smarter way is to set up systems and habits that promote collaboration and suppress unhealthy competition, simultaneously reducing the costs of failure and increasing the likelihood of success.

There are many ways to do this: define success on a team level; establish norms of peer review and constructive feedback; adopt “yes, and” discussion tactics; and, most importantly, ensure that no one on a team is disenfranchised.

This last point is especially important: a collaborative culture is by definition an egalitarian one. Unlike a competitive culture—which presumes there will be winners and losers and works to ferret out the latter—a collaborative culture trusts that everyone involved has something to contribute, and ensures that they can.

Generalists and Specialists

Specialization by process—the bane of holistic technologies—is nonetheless unavoidable for much work. The trick is to avoid the paint-by-number processes of prescriptive technologies by creating small, cross-functional teams within which a holistic process is possible. Those teams, usually of five to seven people, are most effective when they pair specialists with at least one generalist. The generalist serves as both translator—mapping specialized lingo back to a shared vocabulary so that members of different specialties can all understand—and as cross-pollinator, carrying ideas and principles to new fields where they can take root.

A team generalist can also serve as editor, gathering documentation on the team’s diverse processes and editing it into a coherent narrative, in which each member of the team can see their own contributions to the whole.

A generalist can’t do this alone, of course. While specialists must be steeped in their own fields, they must also possess a basic curiosity about adjacent specialties—a curiosity that serves as an extension of the necessary respect they hold for their teammates.

Life and Work

I shouldn’t have to say this, but here we are: work that is excessive, consuming north of 40 hours a week and without regular holidays, leads to burnout and reduced productivity, not to mention a toll on workers’ mental and physical health. We should build workplaces that encourage healthy work habits because we are not monsters, but also because we benefit from sane work cultures because they achieve better results.

With that out of the way, parental leave, holidays, paid sick time, flexible hours, and remote-friendly environments are all table stakes for a holistic work culture. Holistic technologies rely on the creativity and leadership of all parties involved—so they are especially sensitive to environments that engender fatigue. Too often, work cultures neglect the fact that workers have bodies, forgetting that food, exercise, and rest are design requirements.

In addition to long hours, push notifications arriving 24/7 and expectations that workers are “always on” are similarly dangerous. A lot of recent technology makes connecting with far-off colleagues trivial, but that’s both a boon and a responsibility. Team leaders have to set an example by promoting responsible time off policies and setting expectations that off time is off limits. Likewise, unlimited vacation policies are only a perk if workers make use of them.

Most importantly, the egalitarianism necessary for productive collaboration requires that we work to reduce the effects of structural discrimination—otherwise, not every team member will be able to contribute fully. We don’t—we cannot—live in a meritocracy, so habits and expectations that force workers to prioritize work over life silently privilege the young, healthy, wealthy, and childless. If we’re going to build diverse workplaces—and we’d better—then it’s critical that we support the whole life of every worker, regardless of the circumstances of their birth.

There’s one final point I’ll make about holistic technology: it need not be constrained to the work of making products, but can extend to the products themselves. Many of the products most in vogue today—Slack, GitHub, Trello, or any member of the somewhat misnamed category of content management systems—are themselves tools for collaboration. Which means those tools can also aspire to holistic processes, creating environments in which individuals can take control of their work rather than being controlled by it.

Franklin notes that the real danger of prescriptive technologies is that they lend themselves to a culture of compliance: that is, a prescriptive process teaches people that they must do things a certain way, and so instills in them habits of following the rules. She writes:

The acculturation to compliance and conformity has, in turn, accelerated the use of prescriptive technologies in administrative, government, and social services. The same development has diminished resistance to the programming of people. (19)

The programming of people. In other words, prescriptive technologies lend themselves towards systems and structures that treat people as automatons, diminishing both their talents and their humanity. If we want communities of creative people—that is, people who do not merely accept the way things have always been done but try to improve them—then we cannot afford to breed compliance, in either our workplaces or among our users. The Times expose of Amazon also notes, almost as an aside, that the inhumane culture extends all the way down to warehouse workers who are expected to operate under conditions better suited to robots. If we bristle at working under those kinds of conditions ourselves, what excuse have we for imposing them on others? Moreover, what makes us believe that the programming of people will be limited to those on the lower rungs?

We can’t hoard holistic processes for ourselves—we need to also imbue the tools and systems we create with those same principles. That is, we should encourage collaboration and documentation; anticipate needs for both synchronous and asynchronous workflows; create meaningful ways to denote time working and time away; and most importantly we should resist, at all costs, the temptation to build rigid, prescriptive processes that users must slavishly follow.

Holistic technologies represent better ways of working—and living. We should both enthusiastically adopt them and work to ensure they are the norm, not the exception.

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