Since the heat equation for 1D time-dependent conduction is $$k\frac{\partial^2 T}{\partial x^2}=\rho c\frac{\partial T}{\partial t},$$
the hand-wavy way to derive the characteristic time is to replace partial differentials with finite differences and note that the thermal diffusivity $D=k/\rho c$:
$$D\frac{\Delta T}{(\Delta x)^2}\approx\frac{\Delta T}{\Delta t}$$
$$\Delta t\approx\frac{(\Delta x)^2}{D}$$
But note that $L^2/D$ is not an exact time for anything to occur—it's just an estimate. In your example, the bar never reaches its steady state; it only asymptotically approaches it. (In practice, random fluctuations would soon hide any difference.) For a given geometry and material, the progress in reaching this steady state (e.g., the middle of the object is now halfway to its steady-state temperature) will scale with $L^2/D$.
You can often assume that the process of reaching equilibrium is well on its way after time $L^2/D$ has passed and that the process is nearly complete after several time constants have passed. However, I emphasize again that this is just an approximation, one that depends on the nature of the boundary conditions (e.g., constant temperature vs. constant flux), for example.