[rajacombinator]

Thanks for these insightful posts. I’m in a role that is exactly what you described above. (Perhaps prior to the “initial success” phase, due to political challenges.) It feels like I’m tilting at windmills in a management vacuum. Any general thoughts on how to detect in advance if these kind of projects are worth pushing through or if one should deftly sidestep them? Seems to be an unfortunate but necessary corporate skill.

[aprdm]

Yeah it's an interesting balance of asking per permission and pushing forward & begging for forgiveness. There's no true answer and it really depends on trust + culture + teams you're interacting with.

I've often error-d on the side of side stepping once I get a feeling that people have enough context on what I'm attempting and won't hate me for it :) even if not green-lit by upper management..