Deprotonation of (cAAC)BH2(CN) provided clean access to the stable boryl anion, (cAAC)BH(CN)−. Whereas the addition of soft electrophiles occurred at the nucleophilic boron center, harder silyl electrophiles added to the harder terminal cyano nitrogen. The resulting (cAAC)BH(CNSiPh3) species behaved like a silylium boryl nucleophile as well as a neutral silylisonitrile borylene. Whereas the salt metathesis of soft electrophiles with the (cyano)hydroboryl anion (cAAC)B(CN)H− occurs at the nucleophilic boron center, comparatively harder silyl electrophiles add to the harder terminal cyano nitrogen. The resulting (cAAC)BH(CNSiR3) species behave as both zwitterionic silylium boryl and neutral silylisonitrile borylene, a BI compound accessed through simple deprotonation and salt metathesis. cAAC=cyclic (alkyl)(amino)carbene.