Stereochemistry of product in Grignard-Gilman addition reaction
I have supplied a diagram that is more legible than the small one you have provided. The cis stereochemistry of the product is a function of axial, but not equatorial attack of the reagent. The stereochemistry is established after the addition occurs. Structures 1 and 2 illustrate the "chair-chair" interconversions of the cyclohexene ring. As the C-C bond is being formed by axial addition in 1, the carbon bearing the red p-orbital will rehybridize from sp2 to sp3 during the transition state (TS) for bond formation. This transition state (TS) will lead to enolate 3 through a low energy, chair-like pathway. 
Alternatively, TS 2 would proceed through a higher energy, twist boat-like TS. Both routes occur through axial attack with 1 ---> 3 prevailing over 2 ---> 4. Enolate 3 is in equilibrium with enolate 5, which is unfavored by what is known as an allylic A1,3 interaction.1 The critical step is the kinetic protonation of enolate 3 on workup. Protonation of enolate 3 on carbon from the underside of the double bond (remote from the phenyl group) again occurs through a chair-like TS. Protonation on the top of the double bond would occur through a twist boat-like TS. This pathway is higher in energy and would have provided the trans isomer 9. Structures 6 and 7 are the two chair conformers of the cis-isomer. If one uses to vigorous a set of conditions upon workup, enolization of 6 and 7 can lead reversibly to enol 8 and eventually to the thermodynamic isomer 9.    



1) Johnson, F., Malhotra, S. K., J. Am. Chem. Soc., 1965, 87, 5492.