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The Quiet Workflow Revolution

Starting a few years ago, ads for a web-based software start-up called began to show up everywhere online. A subsequent S.E.C. filing revealed that the company spent close to a hundred and thirty million dollars on advertising in 2020 alone, which worked out to over eighty percent of their annual revenue. By the end of this blitz they had generated more than seven hundred million views of their YouTube-based spots — an audience larger than the preceding four Super Bowls combined.

As I report in my most recent article for The New Yorker, had good reason to make this aggressive investment:

“ claims to help knowledge workers collaborate better: ‘Boost your team’s alignment, efficiency, and productivity by customizing any workflow to fit your needs.’ This objective might sound dry in our current moment of flashy social apps and eerie artificial intelligence, but helping organizations manage their workflows has proved to be surprisingly lucrative. Trello, one of the early success stories from this category, was launched in 2011 as a side project by an independent software developer. In 2017, it was purchased by Atlassian for four hundred and twenty-five million in cash and stock. Another workflow-management service, named Wrike, subsequently sold for $2.25 billion. For its part, went on to leverage the user growth generated by its advertising push to support a successful I.P.O. that valued the company at over seven billion dollars.”

This sudden shift in the business productivity market away from tools that help you better execute your work (like word processors and email clients), and toward tools that help you better organize your work, is important.

As I’ve long argued, one of the major problems in knowledge work is the haphazard way in which we organize our efforts, allowing the chaotic decisions of individuals to somehow aggregate into an ad hoc equilibrium. We give everyone an email inbox and a Zoom account, outline “clear” objectives, and then just tell them to “rock n’ roll.” The result is frenetic overload, exhausted brains, and, ultimately, burn out.

We can’t fix what we dislike about these jobs until we first get more specific about how they actually operate. And this will require clearly specified workflows. As I conclude in my New Yorker piece, if flashy new software services like help push toward this realization, then we should welcome their ascendency.

“It’s in rethinking how we organize our work, not just in how fast we can accomplish it, where the real improvements are to be found,” I write. “Perhaps we’re finally ready to learn this reality.”


In other news:

  • On the most recent episode of my podcast, Deep Questions, I shift my attention from the short-term to the long-term, investigating what habits you can put in place now to ensure you’re satisfied 5 to 10 years in the future. I also answer listener questions and discuss a new mathematical theory that explains how social media traps us in its misery-inducing web. (Watch | Listen)

7 thoughts on “The Quiet Workflow Revolution”

  1. Cal: Great expose on the new world of Information Management and Collaboration software. There is a plethora of new SAAS packages out there, and a growing movement of geeks and technical experts trying to wrap their head around the possibilities of automating information, making more seamless connections and communication with co-workers and clients, and making the management of information easier. You should check out the movement of Notetaking apps, CRMs, Database Organizers that have turned into powerful collaboration online and URL based tools, and gained a tremendous following of users as well as developers. Products like NOTION (my favorite) and OBSIDIAN are providing even greater flexibility for workflow, collaboration, website development, dashboarding and effective information organization (and also add AI features to make them effectively a Second Brain).

  2. Cal, have you ever looked into the Theory of Constraints (TOC)?

    I believe, and highly recommend it. I think it’s your next gold mine when it comes to
    focus, building work flows.

    Started in manufacturing, it has proven worthy in project management as well.

  3. As someone on the front lines, I’m not as hopeful about the advent of tools like Monday, Notion, and Trello.

    Leadership teams are purchasing these tools to “check the box” and prove that they’re helping improve employee workflows. However, without properly implementing these products, they just become another distraction.

    There’s still a lot of work to be done on leadership teams and *how* they use these tools.

  4. Hey Cal,

    I really enjoyed your books like Deep Work, Digital Minimalism and So Good They Can’t Ignore You, and lately I subscribed to your newsletter.

    Just writing to express that this blog post, and quite many in the recent past, in conjunction with the podcast, feels like in a conflict with your teachings.

    This is clearly a promotional post, and many posts start to feel shallow, with a purpose of engaging rather than educating your audience.

    As a really passionate reader of your modern “philosophy” about living a less digitally cluttered life, I find this a bit saddening, though I empathise with the fact that what you are currently building is a business rather than a movement.

    Of course, everybody decides what to read, and we can avoid listening to the podcasts, and reading your emails. At the end of the day, as a role model for me, I would expect that you practise what you preach!

    All with love

  5. Software engineers have known about this for years. Huge open source engineering projects have been rapidly built by globally distributed, asynchronous, not-in-the-same-company teams by using issue trackers like wrike. emails scale terribly for communication, as write once read once. issues scale well, as write once read many times, with the benefit of being editable, and with each post timestamped there is an implicit versioning of knowledge. Add in roles, task assignment, and automation plugins and it is incredible how quickly things can happen. Browse through the issue tracker on the popular software projects on GitHub to see how they do this. For example

  6. With sites like Trello and Monday (I personally use Asana for project management) I definitely agree that it’s a push in the right direction for knowledge work and team management overall.
    I also agree with Anonamoose, in that if there isn’t an intentional integration and training just having the tools might not be enough. There has to be some more effort placed into making the tools fully useful for our team needs.
    I’m hopeful for the use and creation of these tools, and I certainly imagine that with the increased need for technology in the workplace there will be a good chance of all of us being able to level up our work flow.


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