Good talk. I thought it was interesting what you said about student principle because I have a counterpoint to it. Which is that not carving out time day to day to tackle tech debt (via sand bagging) means the treacle gets thicker and harder to run through and the volume of bugs increases which leads to corners being cut to get features out at the old pace.

So the argument to over-estimate or sand bag, and fold in better solutions with the boy scout principle seems to me the best way to make a brown field site green again.

I’ve had one experience of this which totally worked. Time to implement features went from weeks to hours. I’m currently trying to apply the same method again with mixed results