Why We Ditched Trello (and What Happened Next)

I'm going to be honest with you: I was a Trello defender for years. Like, the annoying kind who would bring it up in every tool discussion. "Why would we need anything else? Trello works fine."

And it did work fine. For a while.

The Cracks Started Small

We're a team of 14 engineers spread across San Francisco, Berlin, and Singapore. When we were 6 people in the same office, Trello was genuinely great. You could just tap someone's shoulder if you needed context on a card. The board was more of a visual reminder than a source of truth.

But then COVID happened, we went remote, and slowly hired people in different time zones. The problems weren't dramatic—they were death by a thousand paper cuts.

Here's what actually happened day-to-day:

• Ghost updates: Someone would move a card, and three hours later, someone else would move it back because they didn't know it had been updated
• Lost conversations: We'd have entire conversations in card comments that half the team never saw
• Meeting bloat: Our "quick sync" meetings ballooned to 45 minutes because we spent the first 20 minutes figuring out what everyone was working on
• Morning confusion: The Berlin folks would wake up to a completely reorganized board with no context

The Search (That I Really Didn't Want to Do)

I'll admit it—I dragged my feet on this. Tool migrations are painful, and I'd seen enough of them go sideways. But our PM finally sat me down and said:

"Marcus, we spent 11 hours last sprint just on coordination overhead. That's almost two full days."

She was right. So we made a list of what we actually needed:

1. Real-time everything. Not "refresh to see changes" real-time. Actual, see-your-teammate's-cursor real-time.
2. Integrated communication. Some way to communicate without leaving the board. Our Slack was becoming a graveyard of "see the Trello card" links.
3. Timeline view. For sprint planning. We were maintaining a separate spreadsheet for this, which is embarrassing to admit.
4. Reasonable pricing. We're a startup. $20/user/month adds up fast.

We tried Monday (too busy, felt like a spreadsheet cosplaying as a project tool), Asana (good but expensive for what we needed), Linear (almost, but we're not purely engineering), and then Gryphin.

The First Week Was Weird

I won't pretend the switch was seamless. The import from Trello worked fine—that part was actually surprisingly painless. But there's always that adjustment period where everyone's a little slower, a little more hesitant.

The board chat took longer to catch on. Old habits die hard, and people kept going to Slack first. We eventually made a team rule: if it's about a specific card or board, it goes in Gryphin. If it's general team stuff, Slack. That helped.

Three Months Later: The Honest Assessment

What I Didn't Expect

The biggest change wasn't any single feature—it was that people started treating the board as a living workspace instead of a static to-do list. There's something about seeing your teammates' presence that makes the tool feel collaborative rather than administrative.

Would I Do It Again?

Yeah. Without hesitation.

Look, Trello is still a good tool for certain teams. If you're small, co-located, and don't need a lot of coordination, it's hard to beat for simplicity. But for distributed teams? The gap between "technically functional" and "actually built for remote work" is bigger than I realized.

If you're on the fence about switching tools, my advice: don't wait for a catastrophic failure. The accumulated friction of a tool that's "fine" is insidious. You don't notice it until it's gone.

And if your team has shipped the same feature twice, maybe don't wait as long as we did.