Self-tapping screws, used as efficient reinforcements or connectors for timber and glulam structures, tend to “stray” from the designated axis when long and slender screws are applied. To provide a highly precise installation, the predrilling of guideholes using laser radiation has been examined. While laser cutting is already common in machining thin wood-based panels (plywood, chipboard, etc.), laser drilling has not yet been applied for higher drill depths. Based on preliminary tests, pulsed fibre laser radiation was used to drill through glulam species in different angles to the wood fibre direction to examine the geometry and thermal modification of the boreholes. Thereafter self-tapping screws were installed in the laser-drilled guideholes and their pull-out resistance was determined in comparison to screws installed in mechanically drilled holes and screws installed without predrilling. The results of the tests show the high potential for further development of this innovative wood processing method in timber construction.