A series of titanate cisoid bis(chalcogenidos) (Ch = Te, Se, and S) complexes supported by the β-diketiminate ligand BDI- = [ArNC(CH3)]2CH (Ar = 2,6-iPr2C6H3) are readily assembled via treatment of the TiIII precursor (BDI)Ti(CH2SiMe3)2 with 2.5 equiv of elemental "Ch" source and 1 equiv of reductant in the presence of crown-ether. In the absence of the electride, Te or S addition to (BDI)Ti(CH2SiMe3)2 results instead in the isolation of a mononuclear tellurido-tellurolate [(BDI)Ti(=Te)(TeCH2SiMe3)] and the bridging sulfido-thiolate complex [(BDI)Ti(SCH2SiMe3)(μ-S)]2, respectively. In the case of Se, the rare selenido-perselenoate complex [(BDI)Ti(=Se)(η2-SeSeCH2SiMe3)] was isolated. In addition to crystallographically and spectroscopically characterizing all of the complexes, we demonstrate the latter species to be likely intermediates in the formation of [(BDI)Ti(Ch)2]- via the addition of electride.