The concept of headwind comes from aviation. A headwind is a prevailing wind in the opposite direction of travel that results in an identical airspeed but a slower groundspeed.
This model is a useful way of thinking about progress of a team. A team may be performing as usual, but a force outside of their control is making progress much slower than if the force was not present.
Similarly, a tailwind is the opposite; an external force that allows lower effort for equivalent progress.
Finally, a crosswind is a force that creates a discrepancy between your heading and your direction of travel. In order to maintain a particular course, you may have to “correct” for the crosswind.
All of these models are useful when thinking about where energy is being spent, what prevailing forces are present, and how they are managed.