Spinal fixation with rigid pedicle screws have shown to be an effective treatment for many patients. However, this surgical option has been proved to be insufficient and will eventually fail for patients experiencing osteoporosis. This failure is mainly attributed to the lack of dexterity in the existing rigid drilling instruments and the complex anatomy of vertebrae, forcing surgeons to implant rigid pedicle screws within the osteoporotic regions of anatomy. To address this problem, in this article, we present the design, fabrication, and evaluation of a unique flexible yet structurally strong concentric tube steerable drilling robot (CT-SDR). The CT-SDR is capable of drilling smooth and accurate curved trajectories through hard tissues without experiencing buckling and failure; thus enabling the use of novel flexible pedicle screws for the next generation of spinal fixation procedures. Particularly, by decoupling the control of bending and insertion degrees of freedom (DoF) of the CT-SDR, we present a robotic system that (i) is intuitive to steer as it does not require an on-the-fly control algorithm for the bending DoF, and (ii) is able to address the contradictory requirements of structural stiffness and dexterity of a flexible robot interacting with the hard tissue. The robust and repeatable performance of the proposed CT-SDR have been experimentally evaluated by conducting various drilling procedures on simulated bone materials and animal bone samples. Experimental results indicate drilling times as low as 35 seconds for curved trajectories with 41 mm length and remarkable steering accuracy with a maximum 2% deviation error.