I find one of the most difficult aspects of software is the very powerful "local minima" of effective (but not optimal) techniques combined with entrenched knowledge. People are so incredibly biased towards what they know well, and that bias is backed by objective evidence: when they do it X-way they are objectively faster AND better, and what's more, X-way has many objective benefits. This is the local minima in a vast multidimensional space of the benefits and tradeoffs of different possible technical approaches. The multidimensional problem of overall comparing X-way with Y-way is nearly impossible to accomplish, so we nearly always fall back to our intuition (aka bias) which nearly always leads us back to what we already know. And consequently most organisations are stuck in some version of a local minima that is very hard to escape, but ultimately represents a big disadvantage over time. But the question of when is the right time to move out of that minima - and incur the expense of navigating the hills between where you are now and the better minima - is really hard to solve.