Are estimation and release planning in software development fundamentally broken?

tl;dr IMHO, yes

...but let me explain.

We have a weekly team meeting called Wochenschau on Mondays (inspired by German TV news show Tagesschau), in which we share wins and opportunities of the last week, look at what’s up the current week, appreciate colleagues who received a “You just made my day card” - but I digress…

Yesterday we spoke about a presentation that was given to our leadership team including CEO Jamie Iannone. Our map view feature was shown, which was created for the eBay.de local experience. These folks are excited 🎉 and want to implement the feature across other areas of the eBay.de site. The expectation now is to estimate efforts and plan the implementation. So far so normal you may think.

However, we don’t know the dependencies to other teams, the seniority and skillset of the engineers, not to mention their holiday schedule or them being on paid Sabbatical.

❓How could you possibly estimate efforts?

• for something, you never did before,
• months in advance,
• without knowing the code base(s) and the teams,
• not knowing the skill set of the team members?

💡What do instead? Maybe we should try to simply invest and prioritize, and continuously check whether our customers enjoy our changes and pivot if needed.

PS: I get that people do want to timelines… 😏

Your help wanted: If you think, my post has no merit, please help me understand. 🙏

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