When a submodule $N$ of a $R$-module $M$ is a direct summand of $M$?
There is not really any criterion (one significantly simpler than the definition) to spot summands in general. It all depends on the module structure of $M$. There is an important equivalent condition, though: $N$ is a summand of $M$ if and only if there is an idempotent homomorphism $e:M\to M$ such that $e(M)=N$.
or of $R$-module $R$?
At this point things are easier since the idempotent homomorphisms $R\to R$ are given by idempotent elements of $R$. So a right ideal $T$ is a summand of $R_R$ iff there is an idempotent element $e\in R$ such that $eR=T$.
For instance, if $M$ is semisimple then $N$ is semisimple, does this say that $N$ is direct summand of $M$ (or of $R$-module $R$)?
Well, yes, because a characterization of semisimple modules is that every submodule is a direct summand. I'm not sure which definition of "semisimple" you are using, so I don't know if you need help seeing this.