A tool bit (5000, 6000, 7000) for use with a blade assembly of a grading machine, the tool bit (5000, 6000, 7000) comprising: a shank portion (5002, 6002, 7002) defining a longitudinal axis, a free end and a perimeter (5003, 6003, 7003), at least one anti-rotation feature (5012, 6012, 7012) on the perimeter (5003, 6003, 7003) extending to the free end and a cross-hole (5014, 6014, 7014) defining a cross-hole axis (A5014, A6014, A7014) along which the cross-hole (5014, 6014, 7014) extends through the shank portion (5002, 6002, 7002); and a working portion (5004, 6004, 7004) extending downwardly axially from the shank portion (5002, 6002, 7002); wherein the working portion (5004, 6004, 7004) includes a rear region (5016, 6016, 7016), a front working region (5005, 6005, 7005) defining a width (W5005, W6005, W7005) with a midpoint (MW5005, MW6005, MW7005), a first side region (5018, 6018, 7018) and a second side region (5020, 6020, 7020), and the first side region (5018, 6018, 7018) and the second side region (5020, 6020, 7020) define an angle of extension (y) measured in a plane perpendicular to the longitudinal axis, and the cross-hole axis (A5014, A6014, A7014) passes through the width (W5005, W6005, W7005) of the front working region (5005, 6005, 7005) when projected onto a plane perpendicular to the longitudinal axis; characterised in that the angle of extension (γ) forms a wider front working region (5005, 6005, 7005) than the rear region (5016, 6016, 7016) in a plane perpendicular to the longitudinal axis; the front working region (5005, 6005, 7005) includes a first angled surface (6006, 7006) and a second angled surface (6008, 7008) forming a first included angle with the first angled surface (6008, 7008) projected along the longitudinal axis onto a plane perpendicular to the longitudinal axis ranging from 130 degrees to 180 degrees; and the first side region (5018, 6018, 7018) or the second side region (5020, 6020, 7020) include a first surface (630,730) extending along a direction parallel to the longitudinal axis of the shank portion and disposed longitudinally adjacent the shank portion (5002, 6002, 7002). a shank portion (5002, 6002, 7002) defining a longitudinal axis, a free end and a perimeter (5003, 6003, 7003), at least one anti-rotation feature (5012, 6012, 7012) on the perimeter (5003, 6003, 7003) extending to the free end and a cross-hole (5014, 6014, 7014) defining a cross-hole axis (A5014, A6014, A7014) along which the cross-hole (5014, 6014, 7014) extends through the shank portion (5002, 6002, 7002); and a working portion (5004, 6004, 7004) extending downwardly axially from the shank portion (5002, 6002, 7002); wherein the working portion (5004, 6004, 7004) includes a rear region (5016, 6016, 7016), a front working region (5005, 6005, 7005) defining a width (W5005, W6005, W7005) with a midpoint (MW5005, MW6005, MW7005), a first side region (5018, 6018, 7018) and a second side region (5020, 6020, 7020), and the first side region (5018, 6018, 7018) and the second side region (5020, 6020, 7020) define an angle of extension (y) measured in a plane perpendicular to the longitudinal axis, and the cross-hole axis (A5014, A6014, A7014) passes through the width (W5005, W6005, W7005) of the front working region (5005, 6005, 7005) when projected onto a plane perpendicular to the longitudinal axis; characterised in that the angle of extension (γ) forms a wider front working region (5005, 6005, 7005) than the rear region (5016, 6016, 7016) in a plane perpendicular to the longitudinal axis; the front working region (5005, 6005, 7005) includes a first angled surface (6006, 7006) and a second angled surface (6008, 7008) forming a first included angle with the first angled surface (6008, 7008) projected along the longitudinal axis onto a plane perpendicular to the longitudinal axis ranging from 130 degrees to 180 degrees; and the first side region (5018, 6018, 7018) or the second side region (5020, 6020, 7020) include a first surface (630,730) extending along a direction parallel to the longitudinal axis of the shank portion and disposed longitudinally adjacent the shank portion (5002, 6002, 7002).