Why People Hate Jira

When pressure is on - deadlines are real, stakes are high, and ambiguity is everywhere - teams don’t want to manage tickets.

We want to think together.

Under real pressure, we need fast edits, prioritization without ceremony, partial thoughts that we can bookmark, rough language so we can move fast, and out-loud thinking.

Workflow tools are structured, typed, permissioned and schema-bound - constraints that create friction and resistance to fast, forward progress.

Thinking together is messy, nonlinear, and conversational - and that’s exactly why it doesn’t fit cleanly into tickets.

Where Relying on Jira Fails

Jira and its ilk are fundamentally state machines.

State machines work best when the work is already understood - when the main question is “where is this?” not “what is this?”

When the pressure is high, people don’t want to manage states:

  • To Do
  • In Progress
  • In Review
  • Done

… we want to think together - thinking vs tracking.

The Tools Assume Clarity That Does Not Yet Exist

The problem isn’t that Jira is bad, it’s that it assumes clarity: a known goal, stable scope, and an agreed-upon path forward.

But that clarity often emerges through conversation, not before it.

The deeper issue is timing.

Wrong Tool Because It’s The Wrong Time

There are two different moments:

  1. Figuring out the work - designing
  2. Executing the work - executing

Progress is experienced over time, not across columns.

These Tools Drift

Another problem is that the tools drift from coordination to surveillance. Over time, these platforms often become:

  • Reporting tools for managers
  • Compliance systems
  • Justification engines

Once a tool feels like oversight instead of support, we stop using it to think - and start using it to comply.

This is how drift shows up in practice.

I literally just created Jira tickets yesterday just to create a GitHub Pull Request to deploy a change to our stage environment.

What most teams are missing is a sense-making layer.

A place where work becomes understood before it becomes tracked.