Jerry Weinberg's classic Secrets of Consulting has tons of hard-won wisdom about this kind of thing. "No matter how it looks at first, it's always a people problem." - https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que...
He posted once to HN (https://news.ycombinator.com/item?id=1825352 - but start here: https://news.ycombinator.com/item?id=1813443)
Edit: There's also
Gerald M. Weinberg has died - https://news.ycombinator.com/item?id=17716098 - Aug 2018 (66 comments)