The Cynefin framework can be really useful for having this conversation. https://lizkeogh.com/cynefin-for-developers/ https://lizkeogh.com/cynefin-for-developer

The Cynefin framework can be really useful for having this conversation. https://lizkeogh.com/cynefin-for-developers/ https://lizkeogh.com/cynefin-for-developers/ How well do the people executing the project know the codebase, data, and tech stack they're working with? How understood and confirmed are the requirements? The less those things are true, the less certain you can be with estimates. At the extreme, all you can do is poke the system and commit to providing feedback on what you've learned. At the same time, you should be trying to make the system more lucid, both for yourself and new joiners on the team, such that estimates can become more accurate. The more senior you are as an engineer, the quicker you should be able to do that.