I was on a routine demo. The prospect started explaining their leave request process.
Employees fill out a paper form. They mail it. Through the actual mail. To another office. Where someone manually enters it into a spreadsheet. Then mails back a confirmation.
I thought I misheard. I asked them to repeat it.
They repeated it.
This was 2024. People were mailing paper forms to request time off. And when I looked around the Teams meeting, nobody seemed shocked. This was just how things worked. This was normal.
Picture it. You want to take your family to Mexico in March. Before you can even check flights, you need to dig up a paper form. Print it out. Fill it out by hand. Employee ID, department, manager name, dates requested, reason for absence. You're not sure if you have enough days, so you call HR and wait for someone to pull your file. Then you find a stamp, mail it, and wait. Days pass. Maybe a week. Eventually a letter arrives telling you whether you can book the trip.
That's an extreme example. Most organizations aren't mailing forms. But that doesn't mean they're pain-free.
As a salesperson, part of you loves hearing this. The opportunity is so clear. The before and after writes itself. But deeper down, I felt something else. The weight of what they'd been living with. Like a migraine during an important exam you just can't shake. You push through. You adapt. You stop remembering what it felt like before the pain started.
That's the thing about broken systems. Live with them long enough and you stop noticing. The clicking. The waiting. The entering the same information you entered last month. It becomes part of the job, like fluorescent lighting or bad coffee.
I've seen the shared spreadsheet that everyone's afraid to touch because someone broke it once in 2019 and nobody knows how it got fixed. The same employee living in three different databases, HR, timekeeping, payroll, and nobody can tell you which one is the source of truth. The integration that supposedly syncs them but runs overnight, so you never know if the change you made this morning has hit payroll yet. Or if it ever will.
Companies spend over $1 billion a year on employee engagement software. The market grows 16% annually. And most of these tools still feel like homework handed out by someone who doesn't have to do it themselves.
That's not a user problem.
That's a betrayal of what software is supposed to be.
Here's something I think about constantly.
The best tools in history have one thing in common. They vanished.
Not failed. Vanished. Became so essential, so embedded in how we operate, that we stopped seeing them entirely.
A sword in the hands of a master isn't a separate object. It's the arm, extended. The samurai doesn't think about the blade. The blade thinks with them. Centuries of martial philosophy come down to this single idea. Mastery begins when the tool disappears.
Your phone crossed that threshold years ago. You don't "use" your phone. You just live your life, and it's there, filling in the gaps between what you know and what you need to know. Memory. Connection. Access. Extension.
Dan Bricklin and Bob Frankston invented the spreadsheet. Most people have never heard their names. But those same people would quit their jobs before giving up Excel.
The inventors vanished. The tool became invisible.
That's not tragedy. That's triumph.
There's an ancient Chinese concept called Wu Wei. It translates roughly to "effortless action," but that undersells it.
Benjamin Hoff explained it best in The Tao of Pooh.
"When you work with Wu Wei, you put the round peg in the round hole and the square peg in the square hole. No stress, no struggle. Egotistical Desire tries to force the round peg into the square hole. Cleverness tries to devise craftier ways of making pegs fit where they don't belong. Wu Wei doesn't try. It doesn't think about it. It just does it."
Water is the classic metaphor. It doesn't fight the rocks. It flows around them, finds the lowest path, and over centuries carves the Grand Canyon. Not through force. Through persistence. Through surrender to the shape of things.
Most enterprise software is the opposite of water.
It demands you reshape your day around its logic. It forces you to translate your questions into its language. It makes you memorize its quirks, click through its menus, submit to its worldview.
That's not flow. That's friction.
That's a tool fighting against you instead of extending you.
Here's a test.
Can you describe using a tool without the word "use"?
You don't "use" your calendar. You check what's happening tomorrow.
You don't "use" your messages. You text your friend about the game.
The language disappears when the tool actually works.
HR software almost never passes this test. People don't "check their time off balance." They "log into the HR portal to access the leave management module and view their accrued PTO."
Read that sentence again.
That's a small tragedy. A moment of someone's life, swallowed by a system that should have gotten out of the way. Someone just wanted to know if they could take Friday off. Instead they got a maze. Or worse. They got a paper form and a stamp.
It's 2026. We put touchscreens on gas pumps. We made it easier to order pad thai at midnight than to find out how many vacation days you have left.
That's not a technology problem. That's a failure of imagination so total, so normalized, that we forgot to be angry about it.
I'm angry about it.
For software to become habit instead of homework, three things have to be true.
The feedback has to be immediate. If you do something and nothing visibly changes, your brain never connects the action to the outcome. Timesheets that vanish into a void feel like homework. Timesheets that instantly update your paycheck preview feel like cause and effect. Like reality.
The context has to already be there. If a manager has to open three systems to understand what's happening with their team, they'll avoid all three. If the answer lives where they already are, they'll look.
And then there's the big one.
The value has to flow backward.
Most enterprise software is extractive. The payroll team needs your timesheet. HR needs your emergency contacts. Compliance needs your certifications. You fill out the forms. You click the buttons. You get nothing back except the absence of nagging emails.
But when that current reverses. When the system gives more than it takes. Everything changes.
When it shows you your schedule before you think to ask. When it tells you your vacation balance the moment you're daydreaming about a trip. When it surfaces exactly what you need, right when you need it.
That's when homework becomes habit.
That's when a tool earns the right to disappear.
Let me tell you the truth about where we are.
We're not there yet.
Workzoom is massive. Twenty-five years of building an all-in-one system. HR, payroll, time and attendance, scheduling, talent management. Multiple countries. Different regulations. Enough capability to run a thousand-person organization from a single screen.
And honestly? The UI shows it.
There are menus. There are clicks. There's a learning curve. We know. We hear it. We feel it every time we demo to someone who's been burned before. You can see it in their eyes. The skepticism. The "I've heard this pitch" look. The quiet calculation of how much pain switching would cost versus how much pain staying would cost.
But here's what we got right. The thing that matters more than people realize.
The infrastructure.
One employee record powers everything. When data changes somewhere, it changes everywhere. No re-entry. No sync failures. No three systems pretending to talk to each other while quietly corrupting your data in the background.
The plumbing works.
That matters because you can't build effortless on top of broken. You can't create flow when the foundation is held together with duct tape and API prayers. Most "unified" platforms are just technical debt wearing a trench coat. Thirteen systems acquired over a decade, stitched together with bubblegum and hope, sold as "seamless integration."
We built different. And now we're making it feel different too.
Every release, the UI gets cleaner. Faster. More intuitive. Every release answers harder questions. The kind that used to require a consultant or a week lost to spreadsheets.
It takes a certain kind of genius to distill a user experience down to effortless flow when the product runs this deep. We're not pretending that's easy. We're not pretending we've solved it.
But we're closer than we were. And we know exactly where we're going.
Your phone became your digital extension.
It holds your memory. Your connections. Your access to everything. You stopped thinking of it as a device somewhere along the way. Now it's just part of how you operate. Part of how you think.
We're building Workzoom to become your people extension.
Your workforce, represented. Your organization's knowledge, accessible. Every question about who's working, who's available, who's qualified, what's owed, what's coming. Answered without friction.
Natural language changes the game entirely.
Instead of clicking through five screens to find out who's on vacation next week, you ask. Instead of building a report, you describe what you want to know. Instead of learning the system's logic, the system learns yours.
Picture a tool that knows your organization the way you wish you could. That extends your awareness across every employee, every schedule, every deadline, every compliance requirement. Not because you memorized it all. Because the system holds it and surfaces what matters when it matters.
That's Wu Wei.
Effortless action. Not because the system is simple, but because the complexity becomes invisible. The power is all there. You just don't have to fight to reach it anymore.
A sword that thinks with the arm that holds it.
A phone that knows what you need before you ask.
A platform that extends your ability to understand and lead your people.
Here's how you know you've built something people actually love.
They use it when no one's making them.
Picture an employee opening the app on a Tuesday morning. No reminder pinged them. No deadline looming. They're just curious.
What's my paycheck look like this week?
Did I get that Saturday shift?
How much PTO do I have left?
Let me update my goals before I forget.
Each question answered. Each interaction, a small hit of satisfaction. The feeling of your own work life. Organized. Visible. Under control.
That's not software.
That's dignity.
Most HR systems treat employees like data sources. Clock in. Fill this out. Submit that form. Go away. The system takes and takes. The employee tolerates.
But when the system gives back. When it genuinely makes someone's life easier. When it puts them in control of their own information. Everything inverts.
Adoption stops being a problem you solve with training sessions and passive-aggressive reminder emails. People just come back. On their own. Because humans return to things that make them feel capable.
That's the standard. Not "user-friendly." Not "intuitive design."
Does it make people feel like more than they were before they opened it?
Forget adoption rates. Forget training hours. Forget satisfaction scores.
One question matters.
Do people use the system when no one is watching?
Not because they'll get in trouble. Not because a report is due. Not because an audit is coming.
Because it's just what they do now. Because it's part of how they work. Because it extends what they're capable of being.
When the answer is yes, you've built something worth building.
When the answer is no, you've built expensive homework.
The best software doesn't demand attention. It deserves it.
It doesn't create work. It dissolves into work.
It doesn't stay separate from you. It becomes part of how you move through your day, so quietly you forget it was ever there at all.
Like water finding its way through stone.
Like a blade becoming the arm.
Like Pooh wandering into exactly where he was always meant to be.
No stress. No struggle.
Just the way things work when you finally stop forcing them.
We're not there yet.
But we know exactly where we're going.
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Matthew Woolley is a Technical Sales Executive at Workzoom, where he helps organizations simplify how they hire, pay, and grow their people. He thinks a lot about why work software feels like work, and what it would take to finally change that.
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