Ask HN: Bold Digital Strategy

I work in a resource sector that’s been evolved through a hundred years of M&A, inheriting all kinds of legacy systems, processes, racking up technical debt. It’s 2020 and we haven’t even begun a digital transformation. Our IT operations are constantly asked to cut costs while requiring to support the growth of our business. Everyone treats us like second class citizens, etc. So much of our work is manual that doesn’t get recognize. Last week a task that I thought would take 30 mins took 1.5 hours. Staff is burnt out, etc etc.

Instead of being “proactive” about needing a transformation, is it bad to have a reactive one? Which you just mandate employees to work their 8 hours and don’t respond so the company can feel the pain? I feel like this is the best and fastest way to convince change. Am I just being negative?