An apparatus and method according to one or more embodiments are provided for a tool that guides a drill in drilling a hole at an angle substantially perpendicular to a non-planar work surface. The tool may be implemented, for example, as a portable drill assist tool that rests unsecured on a non-planar work surface substantially perpendicular to a target hole formed within the non-planar work surface. In one example, an apparatus includes a main body having a through hole formed therein. The through hole is configured to receive a drill bushing and an alignment pin. The apparatus further includes at least three legs configured to independently translate relative to the main body to contact the non-planar surface and maintain the through hole substantially perpendicular to the non-planar work surface when the alignment pin is passed through the drill bushing and into the target hole.