How to make sense of any mess

Information architecture and what “messes” look like in practice

• Several commenters say the book’s framing matches their real-world experience, especially in large orgs (e.g., banks, hedge funds, legacy enterprises).
• A recurring theme: the “mess” is less about technology and more about misaligned definitions (e.g., many competing definitions of “user” or “retention”) and undocumented processes.
• People often disagree not on “what should we do?” but on “when do we want it?” — time, scope, and expectations are the real battleground.

Diagrams, dependency graphs, and underused tools

• Critical path / flow diagrams, swimlane diagrams, and dependency graphs are called “criminally underused” despite their huge value in clarifying serial vs parallel work and uncovering loops/dependencies.
• Simple live tools (Mermaid, yUML, Draw.io, yEd) are praised for making dependencies visible and revealing when systems are “spaghetti.”
• One story: just switching planning sessions from data-structure diagrams to data-dependency diagrams eliminated API loops and missed deadlines almost overnight.

Decision-making, data, and leadership behavior

• Some report leaders deciding first and then seeking data to justify it; others push back, saying they more often see hypothesis → data request → adjust (or not) based on results.
• On data: good leaders instrument early to enable before/after comparison; others “yolo” changes and only later ask for impossible metrics.
• Comments connect cognitive biases and “press secretary” self-justification with how orgs rationalize choices; references made to dual-process thinking and hidden motives.
• Military and aviation planning are cited as positive models: formal planning, risk management, and decision frameworks (OODA loop, pilot decision-making, checklists) are seen as transferable to product and org design.

Complex, interconnected messes and “garbage can” thinking

• The hardest problems are chained dependencies: fixing system A breaks B and C, and so on.
• One commenter links this to the “Garbage can model,” where organizations accumulate dumped projects and failures, sometimes as intentional scapegoats.

Website / hypertext design reactions

• Many find the site hard to read: narrow columns, excessive pagination, many links, and highlighted lexicon terms that disrupt flow. A few see it as almost “TimeCube-like.”
• Others appreciate the hypertext/lexicon concept and decomposition of the book into small web “articles,” though they agree the visual hierarchy and typography could be better.
• There’s meta-discussion about not letting complaints about formatting drown out discussion of the ideas.