The short answer is probably because it's a people thing.
But, I feel like the tools themselves are lacking a basic understanding of the real problems in software development projects. They're all the same, whether it's JIRA, Linear, Clubhouse or any of the myriad other ones — just with different UIs that are a better spreadsheet.
What are your biggest pet peeves and frustrations? Here are mine and I'm curious what others think.
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Planning is hard. These tools throw a big backlog at you and grooming/planning is incredibly frustrating. They don't give me a good look into my team, their availabilities, or their capacity. It is also really hard to plan and estimate a sprint when you're just staring at a long list of tasks that are prioritized low/medium/high.
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Once a sprint gets going, there are no guardrails, and no easy way to assess the "health of a sprint". Consider JIRA's Active Sprint view. If you have 6 people on your team, that's a freaking overwhelming board. You really have to hate your life to work with it. It takes way too many gymnastics to assess how we're doing, what's falling behind, and how much more we can actually get done. I'm surprised none of them have a "resource view". I have to filter person by person to get a better look into a team member's tasks. As an engineering or product manager, it's hugely frustrating to not be able to have a better lens into the current state.
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No way for higher ups to get an insight into what's shipping and when. I've grown tired of answering the same question a hundred times – "when is X going to be ready?".
All of the above are based on my experience as a manager/lead, but it was no different as a developer. They didn't make my job easier.
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