In the mechanism of a hydroboration-oxidation, the oxidation part includes a nucleophilic attack of a hydroxide on a trialkyloxyborane ( $\ce{B(OR)_3}$ where $\ce{R}$ is an alkyl group).
It creates a tetrahedral intermediate consisting of a negative center of boron with four groups attached to it (the hydroxide nucleophile and the three alkoxides). This step is followed by the loss of an alkoxide as the leaving group. However, to my understanding, the alkoxide is a stronger base than the hydroxide. Thus, why doesn't the nucleophilic attack fail?
Edit: Is it because of steric comparisons between the size of the alkoxide versus the hydroxide (since boron is a relatively small atom)?