During a military patrol or infantry operation, the point man is a navigator who walks several meters out in front of everyone else and is likely to be the first one to encounter enemy soldiers.
[4] The concept seems to have been introduced to the American military at West Point by Professor Dennis H. Mahan, who taught most of the top officers on both sides in the Civil War.
In his Elementary Treatise on Advanced-Guard, Out-Post and Detachment Service of Troops (1861), he discussed the use of the column or V-shaped advance guard by the Greeks and Romans: Among the orders of battles among the ancients, that known as the wedge, or boar's head, is the most celebrated.
In this disposition, the point, or head, is formed of a subdivision of the phalanx of greater or less strength, according to circumstances; this being supported by two, three, and four subdivisions of the same force, one behind another.In the section on Advanced Guards and Advanced Posts, Professor Mahan introduced the definition of the point man to the future American generals: From these indications of the manner of distributing the troops of the advanced-guard, the following general dispositions, adapted to ordinary circumstances of locality may be gathered.
"Taking point" is often used in describing pathfinding behaviors in non-military situations, or simply to mean "lead the challenge", often in a business context.