Properties of monodromy of a fibration? Sorry for a loaded question.
I'm not an expert on those things, but I do know that a fibration gives rise to the representations of pointed fundamental group of the base on the cohomology of the fiber.
What are the properties of this map for different classes of fibrations? I think it's known what the image of this map can be. And the local properties are governed, at least in the complex case, by what type the manifold is.
And, most importantly, there is something about uppertriangularity. What exactly is that? 
 A: For the last question: at least in the algebro-geometric case, the monodromy is always quasi-unipotent (i.e, some power of is unipotent). There is a beautiful argument due to Grothendieck that proves this by reducing to the p-adic case, and using the action of Frobenius on the (tame) inertia group of a p-adic field. 
A: A small clarification on bhargav's answer: in algebraic geometry we only have quasi-unipotency of the local monodromy in one-parameter families (which is what bhargav is talking about); or in multi-parameter families but only near a normal crossing point of the discriminant. Global monodromies are reductive and local monodromies near bad points of the discriminant can be more general.
For concreteness look at a projective morphism $f : X \to B$, where $X$, $B$ are smooth complex projective varieties. Let $D \subset B$ be the discriminant divisor of $f$, i.e. the divisor where the differential of $f$ is not surjective. The global monodromy of the smooth fibration $f : X - f^{-1}(D) \to B - D$ is always reductive by a theorem of Borel. That is: the Zariski closure of the monodromy in the linear automorphisms of the cohomology of the marked fiber is a complex reductive group. If we take a small analytic ball $U \subset B$ centered at some point of $D$, and if we know that $D\cap U$ is a normal crossings divisor in $U$, then the monodromy of the local fibration $f : f^{-1}(U-D) \to U-D$ is quasi-unipotent as bhargav explained. Note that the normal crossings condition implies that the fundamental group of $U - D$ is abelian, so the quasi-unipotency condition makes sense here. 
If however $U\cap D$ does not have normal crossings, then $\pi_{1}(U-D)$ need not be abelian and the monodromy of $f : f^{-1}(U-D) \to U-D$ need not be quasi-unipotent. An easy example is to look at a generic projective plane $\mathbb{P}^{2}$ in the $9$ dimensional projective space of cubic curves in $\mathbb{P}^{2}$. This plane parametrizes a family of cubics which degenerates along a discriminant curve $D \subset \mathbb{P}^{2}$ and under the genericity assumption $D$ has only nodes and cusps. The cuspidal points of $D$ correspond to cuspidal cubics, and near a cusp of $D$ the local fundamental group of $U - D$ is the amalgamated product of $\mathbb{Z}/4$ and $\mathbb{Z}/6$ over $\mathbb{Z}/2$ and so is isomorphic to $SL_{2}(\mathbb{Z})$ the local monodromy representation near the cusp, i.e. the representation of $\pi_{1}(U-D,u_{0})$ to the linear automorphisms of the first integral cohomology of the cubic corresponding to $u_{0} \in U - D$, is an inclusion, i.e. has image $SL_{2}(\mathbb{Z})$. In particular it is not quasi-unipotent.
