Three things that 5+ years in enterprise tech taught — and one thing it didn't prepare anyone for

Hi community, I want to share some honest takeaways from a long stretch in enterprise software (mostly across APAC):

Lesson one: the technology is rarely the problem. The hardest part of any deployment is the conversation between the people who buy it, the people who use it, and the people who maintain it.

Lesson two: 'best practice' is a moving target. What worked five years ago is now a liability. What's working now will be a liability in three.

Lesson three: trust compounds slower than reputation. Reputation can be built in a launch. Trust takes years and three difficult conversations you didn't want to have.

What it didn't prepare for: how fast the ground would move under enterprise tech once AI agents showed up. The playbook from 2020 reads like a different industry now.

I am happy to hear what the community has been unlearning lately.