The mouse feels heavy, somehow heavier than it did this morning. It’s 4:45 PM, and Sarah is staring at the SynergyCloud dashboard. It’s offensively cheerful, all rounded corners and bright, optimistic progress bars that are telling her a story she knows to be false. She has 17 browser tabs open. Seventeen. Each one is a breadcrumb, a clue, a piece of data she’s trying to stitch back together into the coherent whole that SynergyCloud was purchased for $233,333 to provide. The old spreadsheet, the ugly, sprawling, universally-hated spreadsheet, is open in tab number three. It’s where she’ll get the actual answer, just as soon as she’s finished wrestling with the tool designed to replace it.

There’s a comfortable, easy narrative here. It’s the one the implementation consultants use, the one managers repeat in steering committee meetings. It’s called “user adoption issues” or “resistance to change.” It’s a story about people who are stuck in their ways, who don’t want to learn a new system, who can’t see the bigger picture. For a long time, I believed that story. I even told it myself. I’d watch teams struggle with a new platform and think, “They’re just not trying hard enough. The value is obvious.” I once blamed a 23-person team for failing to adopt a project management tool I had personally championed. I saw it as a failure of their mindset, not my choice.

I was profoundly wrong. It took me years to see it, but the problem isn’t that people hate change. The problem is that they hate being made incompetent. They hate having their workflow, honed over thousands of hours, shattered by a system that doesn’t understand the nuance of their actual job. They hate trading the fluid intelligence of a flawed-but-functional process for the rigid stupidity of a perfect-on-paper one.

It has Single Sign-On. Check. It has customizable reporting. Check. It has role-based permissions and a mobile app and integrates with 13 other platforms. Check, check, check. The buyer looks at the checklist, compares it to the proposal, and signs the check. They bought the solution. The problem is solved.

But Sarah’s problem isn’t solved. Her problem has been multiplied by 43. The single click it took to update a status is now a three-click process through a modal window that takes three seconds to load. The intuitive color-coding she used in the spreadsheet is now an unchangeable, hard-coded dropdown menu of corporate-approved statuses: “In Progress,” “Pending Review,” “On Hold.” None of them capture the reality of her work, which is usually a messy combination of all three.

The software doesn’t solve her problem; it solves the manager’s problem of not having a dashboard. It solves the executive’s problem of not having a single source of truth to point to in a board meeting. It imposes a theoretical, idealized workflow on the messy, practical reality of getting things done. It sacrifices the user’s efficiency for the buyer’s fantasy of control.

The Checklist Gear Analogy

I have a friend, Omar K.-H., who teaches wilderness survival. He spends his life in uncomfortable situations, and he has a deep, abiding hatred for over-engineered equipment. He calls it “checklist gear.” The knife with 23 attachments, none of which is a decent blade. The backpack with 173 straps and specialized pockets for gear you’ll never carry. The solar-powered, GPS-enabled, emergency-beacon fire starter that fails if it’s a cloudy day. He argues that in a high-stakes environment, complexity is a fatal liability. A tool with too many features has too many points of failure. What you need is something simple, robust, and utterly dependable. His preferred knife has one blade. His pack has three compartments. His fire-starting kit is a ferro rod and a handful of cotton balls soaked in wax.

He once told me, “The person who buys the 23-function survival tool is buying the fantasy of being a survivalist. The person who is actually a survivalist buys a good knife.” The design philosophy behind his gear is about ruthless functionality. It’s built for the user in their moment of need, not for the buyer in the showroom. You see this same ethos in other beautifully functional things. It’s in the simple, perfect balance of a chef’s knife. It’s in the intuitive layout of a well-designed workshop. It’s even in things as seemingly simple as clothing designed for its real-world user, like the thoughtful snaps and soft fabrics you find in quality Kids Clothing NZ, created for the parent who is tired and the baby who needs to be comfortable. The function dictates the form, not a list of marketable features.

Enterprise software, in its current state, is almost entirely “checklist gear.” It is sold to the person imagining the survival scenario, not the person who has to live through it. We are equipping our most competent people with multi-tools that can’t cut, and then we have the audacity to blame them when they can’t get the job done.

The Humbling Realization

I made this exact mistake. I led the charge to adopt a communications platform that promised to unify everything-chat, email, project updates, file sharing. On paper, it was flawless. It had every feature you could imagine. For three months, my team tried to use it. Productivity dropped by what felt like half. Simple questions that would have been a 3-second conversation became a confusing odyssey of finding the right channel, tagging the right person, and then losing the thread in a sea of notifications. We were constantly fighting the tool. The tool wasn’t a bicycle for the mind; it was a straitjacket. One day, our lead engineer, a quiet woman who had put up with it all in silence, simply created a new group chat in the old, “inferior” app we were supposed to have abandoned. Within an hour, the entire 13-person team had migrated back. They didn’t ask for permission. They just wanted to work. I had a choice: enforce the rule or admit the tool was wrong. It was one of the most humbling moments of my career.

We abandoned the $73,000 piece of software.

That’s the unspoken cost. It’s not the license fees. It’s the thousands of hours of collective brainpower wasted by people like Sarah, fighting their tools instead of solving business problems. It’s the slow, grinding erosion of morale that comes from feeling like your company doesn’t understand or value the way you work. It’s the tacit knowledge and clever workarounds developed over years that get paved over by a rigid, one-size-fits-all system. The organization gets its clean data and its pretty dashboards, but it trades away the adaptability and expertise of its own people to get them. It’s a terrible bargain, made by people who will never have to use the software themselves.

The End of the Day

It’s dark outside now. Sarah looks at the screen. She selects columns A through G on the old spreadsheet. She copies. She pastes the data into an email. She adds a single sentence of analysis. It takes her less than a minute. She closes 13 of her 17 browser tabs. She leaves SynergyCloud open, a silent, glowing monument to a problem someone else thought she had. Then she shuts her laptop and goes home.