Empathy is an emotional intelligence skill that has been known to make significant impacts in various professional environments. Teachers have always been expected to work at high levels in the midst of difficulties. Educators are constantly inundated with increasing workloads, added responsibilities, ever changing expectations and regular mandates to remain sharp by elevating their professional practices for the overall benefit of student learning and growth while simultaneously battling against behaviors, learning gaps and the emotional traumas that exist in educational spaces. This then begs the questions; How are teachers doing? How are educators coping under the strain of constant demands? If teachers are supporting students, who supports teachers? This study aimed to shed light on the empathy practices of school administrators and how empathy modelling by school leaders impacted the daily experiences of teachers in the concentrated areas of stress and burnout as well as professional development. The qualitative case study focused on the workplace experiences of educators in Bermuda in conjunction with the empathy modelling practices of the school administrators and leaders they worked with in an effort to uncover how empathy can be a tool that is used to reduce teacher stress and burnout as well as improve attitudes and efforts toward professional growth. Empathy was found to be highly valued among the study participants. The lack of empathy modelling by administrators in the areas of relationship building, understanding, inclusion, and development was found to be largely influential to the increase of stress, stress related feelings and behaviors among participants. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]