Ah ok, I got the directions mixed up. So, to see this formally, say the point is a regular point. $f\circ\gamma$ is a strictly increasing function, so $df\vert_y(\gamma^{\prime}(t))=(f\circ\gamma)^{\prime}(t)>0$ ($t$ the time s.t. $\gamma(t)=y$). $df\vert_y$ vanishes on a hyperplane and $\gamma^{\prime}(t)$ lies on the positive side of that hyperplane. In order to read positivity off of the angle with $\gamma^{\prime}$, we want that $\gamma^{\prime}$ is orthogonal to that hyperplane.
This is plausible geometrically, but I don't quite see it.