I hate project management software. Despise it. Refuse to use it—and if I can help it, even look at it. This does not endear me to people in my life who are more traditionally organized and process-driven.
That includes my dear husband, who I’m pretty sure believes this is my most toxic trait.
I’ve always been this way. But I used to grit my teeth and try to push through. Then, I realized that I couldn’t tolerate project management software because, by and large, it works on the assumption that projects are linear and discrete. The software design necessarily reduces work to tasks that can be named, ordered, and given a due date. It divorces the content of work from its form and purpose. In the user interface of project management apps, there is no such thing as the big picture.
Also, I just really hate being told what to do.
Almost everything I hate about project management software can be valuable and useful; they’re just not valuable or useful to me. They work against the way I work.
Once I saw how the software itself tried to force me into a way of relating to my work (and my working relationships), I couldn’t unsee it. And I hated it even more.
Now, don’t @ me with recommendations for different apps or hacks for working with Asana or Clickup or Trello. I’m not interested. If you love your project management software, I’m happy for you. If you find it useful, great!
My point isn’t to shame anyone into abandoning a system that works for them. Instead, I want to ask a simple question:
Do you see your software?
Do you see how it influences how you run meetings, brainstorm ideas, fulfill your responsibilities, and communicate with others? Do you see how its text boxes, radio buttons, tabs, search results, and menus train you to think? Do you see it, or do you just use it?
Keep reading, or listen on the What Works podcast.
An impossible dream
In October, The Verge‘s Nilay Patel did an episode of his podcast Decoder on the “impossible dream of good workplace software.” Patel and his guest, Verge editor-at-large David Pierce, discussed the promise of workplace software, putting it this way: “If everybody worked this way, it would be great.” That is certainly the promise of project management software. It’s been the promise of tools like Google Drive and Microsoft Office. It’s become the promise of apps like Canva and Figma.
However, Pierce argued that this promise could be an existential problem: “The idea that you’re going to get an entire large group of people to all understand a single system, and process, and tool for getting things done is borderline impossible.” He’s right. Yet more importantly, what Patel and Pierce reveal is that the value proposition of workplace software—beyond lower costs, beyond greater productivity—is conformity. It’s sameness. It’s predictability.
Engineering sameness and predictability into work patterns has been with us since at least the advent of scientific management. We gain efficiency when we simplify and standardize a complex task that can be done in various ways. This type of standardization also reduces the power of any one worker because the job requires less skill—let alone craft—to complete. It makes work less fulfilling while also limiting compensation.
In the pre-software workplace, workers could focus their dissatisfaction on the boss. It was the manager who insisted on sameness and predictability. You could get mad at the manager. You knew who they were and how they would respond if you didn’t do things the way they wanted. You knew others were in the same boat and could plan acts of resistance.
Now that software has eaten the world, many of us don’t know where to direct our ire or even why we might feel frustrated in the first place. Software mediates our experience of the work we do—quite often in ways that improve efficiency while also making work less satisfying. We end up angry at ourselves rather than the boss. And if we’re our own boss? Well, we might get doubly angry, ranting to ourselves about our lack of discipline.
We don’t see the software, so we don’t see how it alters how we work, what we perceive as productive, or how doing things differently becomes increasingly difficult to imagine.
When we change software, the software changes us
When we learn how to use a new piece of software, we learn a new way to work. When my husband decided to run our production agency on ClickUp instead of Asana, he had to learn the best ways to use the software, given the kind of work we do and the team we work with. At the same time, he and our team revisited our production and communication processes.
Learning the software and reevaluating our processes weren’t independent exercises. They overlapped in every way. Sean asked himself and the team (consciously or not), ‘Given this feature (or limitation) of ClickUp, how could we do this better?’ The feature or limitation is accepted as unchangeable. It’s the humans that end up changing to accommodate it.
We change in relation to resistant or unmovable forces all the time. I can’t change the bureaucratic hula hoops I have to go through to update my name on my passport or sign up for next year’s health insurance policy. I learn the process, follow the instructions, and act accordingly. The procedure is visible. If I want to do a thing, I have to engage with the procedure to do it on its own terms.
Software functions differently. We largely see software as tools of our own agency. The onboarding instructions, help docs, and customer support seem to exist to help us do what we want to do. In reality, they exist to shape our behavior to fit the tool. If we can’t change the code, we must change ourselves or our aims.
In a piece the political nature of AI chatbots and generative models, technology and culture writer argued that this form of artificial intelligence “is a tool of power that masquerades as a tool of knowledge.” Something similar could be said of project management software: these apps are tools of power that masquerade as tools of agency. Or, to expand our scope a bit, design tools like Canva and Figma are tools of power that masquerade as tools of expression. Meeting tools like Zoom or Google Meet are tools of power that masquerade as communication tools.
That these apps are all tools of power does not require us to stop using them. But we do need to be aware of the power they wield and how we adapt our behavior (or even worldview) to accommodate that power.
Software’s normative power
Any piece of software enables some actions and disables others. This is a normative process as well as a political one.
Consider early Twitter’s 140-character limit. The platform disabled long posts and enabled short ones. So early users learned to communicate 140 characters at a time. People who could state things succinctly with viral flair became power users. Because succinctness and viral flair don’t lend themselves to thoughtful, nuanced discourse, the users and messages that rose to the top tended to be overly confident blowhards—to put it not-so-nicely. As a result, those blowhards gained power and established new norms.
And that’s how we got… all of this.
The mass adoption of Zoom in 2020 also highlights these normative and political effects. While work-from-homers like me had internalized Zoom’s norms years before, many new users were introduced to the software fresh. Teams needed to form new norms around meetings, collaboration, and participation. Discussion of these norms explicitly took the form of Zoom’s features: muting/unmuting, camera on/camera off, use the chat or speak aloud. Fortunately, some of these new norms also prompted conversations about accessibility, mental health, and the challenge of Zooming in the same place where your husky might get the zoomies.
All media influence how we think, socialize, work, and participate in society. Language mediates our experience of the other. The clock, first analog then digital, mediates our experience of time. The book mediates our experience of knowledge and narrative. The car mediates our experience of geography. Project management software mediates our experience of our work(load). Zoom mediates our experience of meeting.
The clock, the book, the car, and language are all media inventions that dramatically changed how we understood the world. Their arrivals reshaped our brains, our days, and our communities. Software has done and is doing the same—often in ways we don’t perceive if we’re not primed to notice. Note: I don’t mean the internet broadly. Obviously, the internet has had a world-changing impact. But the seamless ubiquity of software, along with its unremarkable integration into our lives and work, should be thought of as its own media phenomenon.
Software changes how we work—and changes us. Sometimes in very positive ways. And sometimes in harmful ways. Often the effect is somewhere between those two extremes.
Be a chooser rather than a user
If we want to experience the positive impacts of software more often and resist its harmful ones, then we need to see it. We must be consciously aware of what it enables and what it disables. We must be intentional about the norms we establish with its use. Most importantly, we need to ask what’s best for us and the people we work with before we consider software and its features.
In my previous life as a business coach, I would encourage small business owners to think about their software choices as if they were hiring an employee. First, take stock of what you need and the resources you have to invest. Next, write a job description. Then, recruit potential candidates and interview them to determine who was best-suited to the job. Yes, I had clients brainstorm exactly what they needed to be done, turn that into a job description, and then search for software options that fulfilled it. Interviewing could be doing a trial of the software before committing, attending a demo, or talking to a salesperson.
The assignment was really valuable for those who completed it. However, it was a big challenge for most people I gave it to. Software had already insinuated itself into the way people thought so that they had a hard time thinking about what they wanted done or how they wanted it done outside the software paradigm. They were much more comfortable starting with one set of features and comparing it to another—in other words, evaluating software on its own terms. As a result, they subverted their work and business priorities to those feature sets. Time and time again, they’d switch up their software looking for something “better”—but rarely “a better fit for me.”
There is no “right” or “best” software for X, Y, Z tasks. There is software that enables you to work the way you want to work and do the things you want to do. And there is software that doesn’t. If I start with cultivating awareness of my own needs and desires, I’ll have an easier time choosing software that works for me. I won’t use project management software because it enables all the wrong things for me. I’ll continue to use Canva because it enables most of the right things (albeit imperfectly).
Software, like books or clocks, isn’t going anywhere. Life and work will continue to be mediated by the apps we use. Instead of turning their feature sets into our standard operating procedures, we need to take the lead. Whenever possible, we need to see the software for what it is and decide whether its assumptions, biases, and incentives are the ones we want to incorporate into our lives and work. We need to be choosers more often than users.
