I'm not sure what would work for this individual, but I'd be tempted to turn this around, Jeopardy! style. That is, instead of being presented with a diagram and trying to compute its limit/colimit, take some construction and devise a diagram which naturally expresses the construction as a limit or colimit.

So for example, this might be too easy, but consider the construction $X/A$ where $A$ is a subspace of a topological space $X$. Is this naturally a limit or colimit? Well, it's a colimit, but of what? Again, this may be too easy since your friend is comfortable around pushouts. For extra credit: what is the sensible meaning of $X/\emptyset$?

Or, take the graph of a function like $y = x^2$. Can this be thought of as a limit or colimit? This time it's a limit, namely the equal-izer of two functions from $\mathbb{R}^2$ to $\mathbb{R}$. (There's a more general lesson to be learned here, that limits are generally loci of suitable equations.)

How about the localization $\mathbb{Z}[1/p]$ where we invert a prime? Perhaps a little harder, do the same for the localization $\mathbb{Z}_p$. Or (would this be too familiar?) how would you express the $p$-adics as a limit?

Or, come up with the condition that a presheaf over a space is a sheaf. This might be either too familiar or too abstract, however. It might be best to take more concrete examples like the ones above. These are all off the top of my head, though, and somewhat untested by me personally.