Peter Senge's Fifth Discipline is great. Related, I would also recommend "Thinking in Systems" by Donella Meadows and "An Introduction to General Systems Thinking" by Jerry Weinberg.
Also recommended in this reply
Typographic jacket · original cover not fetched
FROM THE SHARED SHELF · 2006–2026 SAMPLE
Topics are model-inferred labels.
THE WORD OF MOUTH
Original Hacker News comments, in the readers’ own words.