When Simple Collaboration Becomes a 20-Minute Detour

Chris Terrell
Dec 5
3 min read

It was supposed to be simple. A few clicks, a quick bio, maybe even a profile photo if we were feeling fancy. Instead? Password purgatory. Forgotten logins. Emails that never arrive. Password managers are arguing with reality. The kind of nonsense that makes you nostalgic for typewriters.

The Comedy of Errors That Isn’t Actually Funny

Toby hits “Log in.” Wix says no. He resets the password. Wix asks him for the same email he’s already given. His password manager grabs the wrong password. Then the right password. Then the wrong password again. Meanwhile, I’m logged in just fine, trying not to laugh, which frankly makes it even funnier for me and more annoying for him.

All of this… to edit one line of text.

The absurdity is that this is the simplest kind of knowledge work — credentialing. A thing that should be as predictable as gravity. And yet it eats time, energy, and emotional bandwidth like it’s hungry.

But here’s the kicker: this isn’t rare. It’s the hidden tax we all pay when tools don’t behave the way we expect.

The Moment Everything Tilts

This is the part people forget: collaboration assumes stability. It assumes everyone can access the tools. It assumes the link works. It assumes the doc is shared correctly. It assumes your browser isn’t logged into your cousin’s Wix account from 2013.

But the moment one of those assumptions breaks, the whole collaborative flow collapses. You shift from working together to working around each other. Suddenly, the goal isn’t “update the profile” — it’s “figure out what the hell is going on.”

And that’s where the real process lesson lives.

This Is What Process Debt Actually Feels Like

Process debt isn’t always dramatic. It’s not always a giant workflow diagram gone wrong or a massive cross-functional project derailing.

Sometimes it’s tiny. Invisible. Irritating in a way that feels too small to complain about.

But it compounds.

That 20-minute login fiasco is the same reason:

Teams can’t find the “one true spreadsheet.”
Meetings start 12 minutes late.
Project handoffs drop into the abyss.– “Quick reviews” take three days.

Because when assumptions aren’t aligned — when the system doesn’t behave the way we think it will, humans stall. We go into troubleshooting mode. We backchannel. We improvise. And suddenly, the work we came to do is not the work we're doing.

It’s like my dad working construction: when he needs a two-by-four, he just picks up a two-by-four. There’s no “access denied.” There’s no “unexpected error.” There’s no shared folder buried three layers deep under someone’s maiden name.

In knowledge work, the materials are virtual. The problems? Very real.

And because they’re invisible, we mistake them for user error instead of process error.

Collaboration Isn’t Broken — Our Assumptions Are

The truth is, most collaboration issues aren’t about skill, motivation, or willingness. They’re about invisible process friction.

We think everyone knows the path because we do. We think the system is intuitive because we set it up. We think the login “should” work because it worked for us.

Then someone gets stuck, and we silently assume the issue is them, not the cracks in the system.

But here’s the hopeful part: once you see these cracks, you can patch them. Rituals help. Clear access patterns help. A shared agenda helps. Even something as small as aligning on “Hey, where does this document actually live?” helps.

Because reducing friction isn’t glamorous, but it makes everything else possible.

Process Debt Truth

Most collaboration doesn’t break because people fail. It breaks because the system quietly asks them to navigate problems no one prepared them for.