Thanks for recommending the link to Olsen's "Going Bedoin."  With 110 people and growing, we at Compumentor/TechSoup struggle with the balance of infrastructure vs. flexibility all the time. 

 As I read Olsen's post, though,  I kept thinking "But what about the liabilities that HR is expected to manage?" Workers comp issues come most quickly to mind--as an employer in California, we are held responsible for doing everything reasonably possible to prevent employee injuries--in our environment, especially repetitive stress injuries (RSI).  So we invest expertise (someone on staff to do ergonomic assessments), infrastructure (workstations, keyboards, etc.), and staff education to minimize the chance of RSI injuries.  And by the way, the law says that if an org encourages people to work at home, the org is responsible for the ergonomic setup of the employees' home offices! And I could tell similar stories about having to appear in aUnemployment Compensation Administrative Court over hiring contractors; the need for uniform and just hiring and evaluation practices; setting up and maintaining benefits packages for a multigenerational workforce,  etc.  None of this stuff is fun, and it all take investment in expertise, and often in systems and physical infrastructure.  Unfortunately, if an org gets very big, the Going Bedouin route isn't really an option in HR--there are government agencies and legislation that give responsibilty and accountability to employing organizations whether we want it or not.  And while one can contract out for some of HR management, we can't really contract out our essential responsibility for providing for our employees in ways that are in compliance with the rules defined by the state or the federal government.  So some of the forces of entropy as an organization grows seem unavoidable to me, imposed as they are by the larger society.    And some are important to keep our employees healthy and happy.

So I love the idea of a dispersed, flexible, easily mutating organization--and I have trouble applying it to some of the important aspects of running a nonprofit.  I'd love to hear what other people think about these issues.