Metal machining is one of the most important manufacturing processes in today’s production sector. The tools used in machining have been developed over the years to improve their performance, by reducing the cutting forces, the friction coefficient, and the heat generated during the cutting process. Several cooling systems have emerged as an effective way to remove the excessive heat generated from the chip-tool contact region. In recent years, the introduction of nano and micro-textures on the surface of tools has allowed to further improve their overall performance. However, there is not sufficient scientific data to clearly show how surface texturing can contribute to the reduction of tool temperature and identify its mechanisms. Therefore, this work proposes an experimental setup to study the tool surface characteristics’ impact on the heat transfer rate from the tools’ surface to the cooling fluid. Firstly, a numerical model is developed to mimic the heat energy flow from the tool. Next, the design variables were adjusted to get a linear system response and to achieve a fast steady-state thermal condition. Finally, the experimental device was implemented based on the optimized numerical model. A good agreement was obtained between the experimental tests and numerical simulations, validating the concept and the implementation of the experimental setup. A square grid pattern of 100 μm × 100 μm with grooves depths of 50, 100, and 150 μm was introduced on cutting insert surfaces by laser ablation. The experimental results show that there is a linear increase in heat transfer rate with the depth of the grooves relatively to a standard surface, with an increase of 3.77% for the depth of 150 μm. This is associated with the increase of the contact area with the coolant, the generation of greater fluid turbulence near the surface, and the enhancement of the surface wettability.