William Safire has penned an excellent piece regarding the phrase "Straw Man", in his New York Times "On Language" column, On Language - Who is a 'Straw Man'? - NYTimes.com:
"Accepting the Democratic nomination in a huge football stadium way back in the presidential campaign of ’08, Senator Barack Obama displayed his oratorical talent by using one of his favorite tried-and-true devices in argument: “Don’t tell me that Democrats won’t defend this country!”
Who was telling him that? To be sure, his opponents were claiming that a Republican administration would be stronger on defense, but nobody was telling him or the voters that Democrats preferred abject surrender. At the time, reviewing that speech, I noted the rhetorical technique: “By escalating criticism, he knocked down a straw man, the oldest speechifying trick in the book.”..."
Safire explains these fascinating origins of "Straw Man" in the context of political speeches. Those of us involved in technology and other business projects, know that a "Straw Man" can also be used in a business context, typically to refer to the first attempt at documenting a project's initial charter and/or requirements, or even a preliminary prototype of a proposed new or enhanced system's user interface.
As explained nicely on mindtools.com:
"When you begin a project or start looking into a problem, you often have incomplete information to work with. So you can spend time gathering facts and data until you are ready to build a really strong argument or plan, or, you can get going straight away and jump in with a not-so-complete solution, with the intention of finding a much better one, as you learn more and more.
That's the premise behind building a straw man - creating a first draft for criticism and testing, and then using the feedback you receive to develop a final outcome that is rock solid..."
A similar, and very concise definition of "Straw Man" can be found in J. LeRoy Ward's excellent Dictionary of Project Management Terms :
"Working draft copy circulated for comments or suggested changes."
Finally, I would like to suggest a connection between the idea behind a "Straw Man" in business and technology, to the very similar concept in Software Engineering, as originally explained brilliantly in the classic Fred Brooks work: The Mythical Man-Month: Essays on Software Engineering, Anniversary Edition (2nd Edition):
"The management question, therefore, is not whether to build a pilot system and throw it away. You will do that [anyway]."
Thus, Brooks suggests that one may wish to "plan to throw one away", since it is quite possible that you will, anyhow. And by building this "pilot system" into the plan as an explicit milestone, communication is simpler, and expectations are more realistic from the start.
So perhaps, although not identical, Safire's "straw man" and Brooks' "pilot system" are both trying to capture the same notion: That we sometimes need to start with something we know is imperfect, in order to be able to proceed from there to a truly excellent result.