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How do I write my first company handbook without it becoming dead documentation nobody reads?
Write it as decisions and defaults, not policies. One living doc that answers 'how do we do X here' (leave, expenses, tools, how we make decisions,...
What tools does a 5 to 20 person startup actually need, and what am I overspending on?
You need far less than the SaaS ads suggest: one chat tool, one docs/wiki, one project tracker, one place for files, and one for money (accounting ...