Given some observable $\mathcal O \in \mathcal H$ it is simple to construct a CP (completely positive) map $\Phi:\mathcal{H}\mapsto \mathcal{H}$ that conserves this quantity. All one has to observe is that $$ \text{Tr}(\mathcal O \, \Phi[\rho]) = \text{Tr}(\Phi^*[\mathcal O] \rho).$$ Therefore, if we impose $\Phi^*[\mathcal O] = \mathcal O$, then $\text{Tr}(\mathcal O \, \Phi[\rho])=\text{Tr}(\mathcal O \rho), \; \forall \rho\in \mathcal H$. That amounts to impose that the Kraus operators of $\Phi^*$ should commute with $\mathcal O$.

I'd like, however, to construct a trace-preserving CP map for which the expectation value of $\mathcal O$ does not increase for any $\rho \in \mathcal H$. More explicitly, given $\mathcal O\in \mathcal H$, I want to construct $\Gamma:\mathcal H \mapsto \mathcal H$ such that $$ \text{Tr}(\mathcal O\, \Gamma[\rho]) \le \text{Tr}(\mathcal O \rho), \; \forall \rho \in \mathcal H .$$

How would you go about that? Any ideas?