In my experience everyone has a natural mode of working and the conundrum for management is do you try to get people to change (to become all-rounders) or do you develop people in the direction they are already headed and therefore encourage specialisation? In my experience it’s sometimes better to let people be the best “them” they can be, than to try and require them to change and lose their uniqueness.

I think most developers naturally become more cautious with experience (the bitter experience of debugging long into the night usually), while some never grok maintainability or documentation but can still be highly productive net contributors if you have a great testing team between their code and your customers

I agree. The most important quality I try to cultivate is what I guess many would call 'good judgment', and others 'intuition'.

I've worked as a freelancer, lead front-end developer, and contractor, and ranging from 'stuck in the nineties' to 'use whatever HN talks about for the front-end' companies. One of the most important lessons I learned is to use the right tool for the right job. Also to not let 'purity' or 'elegance' get in the way of getting it done (which is difficult for me). But also to never confuse 'getting things done' with laziness.