$tbcs — engineering & the business of building software

EP38 - Why estimating and planning is so hard

Episode 381 hr 26 min

Why planning and estimation are so hard — system and organizational complexity, process, portfolio planning, and whether AI can help.

Engineering practices

Topics and Takeaways

  • Why planning is so hard

  • We humans are just terrible at estimating

  • How does system and organizational complexity add to planning issues

  • Do we build in terrible planning in our processes

  • Do we pretty much guarantee bad planning with the way we do “agile” and portfolio planning?

  • If we are so bad at estimating… why do we do it?

  • We are trying to use AI for everything these days… can we use it to help with planning?